DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Priority
This application is a 371 of PCT/JP2020/048220 which claims benefit of JP 2019-239974, JP 2019-239975, JP 2019-239976, JP 2020-018910, JP 2019-239978, JP 2019-239979, JP 2020-006660, and JP 2019-239977 with an effective filing date of 28 December 2019 as reflected in the filing receipt mailed on 04 November 2022.
Status of Claims
Claims 1-5, 7-14, 21, and 22 are pending.
Claim 22 is new.
Claims 6 and 15-20 are previously cancelled.
Response to Amendments
Applicant’s amendments filed 26 January 2026 are acknowledged.
Applicant’s appear to have filed a non-compliant amendment, see MPEP 714 II.F. Claim 1 has been amended without the proper mark-ups and to not include all of the limitations “relative to the immediate prior version”, see MPEP 714 II.C., the claim objection below, and the 35 USC 112(b) rejection below.
Response to Arguments
Applicant’s arguments filed 26 January 2026 have been fully considered but they are not persuasive.
Applicant argues that Tsuji and Utsunomiya do not disclose the limitations as recited in claim 1. These arguments have been considered but are not persuasive for the reasons set forth in the response to arguments provided below.
In response to applicant's argument on pages 5-6 of the remarks filed on 26 January 2026 that “the reflux ratio disclosed in Utsunomiya is established to separate and remove 1,3-butylene glycol along with other impurities from the 1,4-butanediol” and “one of ordinary skill in the art, beginning with Tsuji's method, would have had no motivation to modify Tsuji's reflux ratio to Utsunomiya's reflux ratio, because the reflux ratio employed in Utsunomiya's distillation column (d) provides (i) refined 1,4-butylene glycol”.
“A reference is analogous art to the claimed invention if: (1) the reference is from the same field of endeavor as the claimed invention (even if it addresses a different problem); or (2) the reference is reasonably pertinent to the problem faced by the inventor (even if it is not in the same field of endeavor as the claimed invention).”, see MPEP 2141.01(a).
Tsuji is in the known prior art of “a butanol-containing distillate is separated from a 1,3-butylene glycol distillate through distillation; the butanol-containing distillate is subjected to distillation and a chemical treatment; and then the resultant distillate is further subjected to distillation to thereby separate low-boiling-point components and high-boiling-point components, thereby yielding butanol”, see Abstract, where the butanol to purify is selected from “a crude mixture obtained through hydrogenation of acetaldols”, see Para. [0029].
As stated on page 14 of the previous office action dated 26 September 2025 (hereinafter POA), “Tsuji teaches higher reflux ratios increase cost; but, does not “criticize, discredit, or otherwise discourage” the use of higher reflux ratios, see Tsuji, Paras. [0137];[0231] and MPEP 2145 X.D.1. On the contrary, Tsuji teaches if the reflux ratio is low, the amount of the removed low-boiling-point components is small, see Tsuji, Para. [0298].”
Utsunomiya is in the known prior art field of refining a “raw material 1,4BG-containing solution (in FIG. 1, the processing solution of the step (c))”, where step (c) is a hydrogenation reaction resulting in the refined raw material containing “1,3-butanediol, 2,3-butanediol”, and 1,4BG, see Paras. [0050];[0099];[0136]-[0137]; Fig. 1. This refined raw material is then purified in steps (b) and (d) to obtain the desired purified butanol, where 1,4BG is obtained from a side stream, the bottom stream, and the top stream in step (d), see Fig. 1; Paras. [0141];[0148]-[0149].
Tsuji is applied to teach the purification of the specific butanol 1,3-butylene glycol from a hydrogenation reaction product crude mixture. Utsunomiya is applied to teach the reflux ratio and recycle process steps in the purification of butanol from a hydrogenation reaction product crude mixture. Utsunomiya is not applied to teach the purification of the specific butanol 1,3-butylene glycol.
As stated on page 15 of the POA, Utsunomiya teaches “a final distillation step (d) at a reflux ratio of 0.01 to 100 to obtain refined butanediol with a purity of 99.5 mass % or more, see Paras. [0016]-[0022];[0148]-[0157];[0203], Fig. 1”.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Tsuji and Utsunomiya both teach the purification of butanol from a hydrogenation reaction product crude mixture, a person of ordinary skill in the art has good reason to modify Tsuji by relying upon Utsunomiya before the effective filing date of the claimed invention for knowledge generally available within the butanol distillation purification art regarding the reflux ratio and process step recycle lines, see MPEP 2143 B & G and 2141, for the benefit of efficiently removing and refining impurities mixed in a butanediol feed in order to obtain a butanediol of high purity and good color tone, see Utsunomiya, Abstract, Paras. [0150]-[0153];[0157]; and, MPEP 2143 I. B-D.
An “obvious to try” rationale may support a conclusion that a claim would have been obvious where one skilled in the art is choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success, see MPEP 2145 X.B.
Since both Tsuji and Utsunomiya teach modification of reflux ratios in the purification of butanol from a hydrogenation reaction product crude mixture, the prior art contains “detailed enabling methodology, a suggestion to modify the prior art to produce the claimed invention, and evidence suggesting the modification would be successful”, see MPEP 2145 X.B.; therefore, it would have been obvious for one of ordinary skill in the art at the time the invention was made to try the differing reflux ratios of Utsunomiya in the distillation product column of Tsuji to specifically separate 1,3-butylene glycol from the hydrogenation reaction product crude mixture.
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant's argument on pages 5-6 of the remarks filed on 26 January 2026 that Utsunomiya is drawn to separating product 1,4-butanediol and not product 1,3-butanediol, “in Utsunomiya, 1,3-butylene glycol is treated as a “low-boiling component””, “[i]n the present application, 1,4-butylene glycol would be considered a “high boiling point substance” because it has a higher boiling point than 1,3-butylene glycol”, and in Utsunomiya “[n]one of (i)-(iii) provide purified 1,3-butylene glycol as set forth in claim 1, and thus does not provide one of ordinary skill in the art the requisite motivation to make the combination.” The test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981) and MPEP 2145.
As stated above, Utsunomiya is not applied to teach purified 1,3-butylene glycol, Utsunomiya is applied to teach the reflux ratio and recycle process steps in the purification of butanol from a hydrogenation reaction product crude mixture; therefore, a person of ordinary skill in the art has good reason to modify Tsuji by relying upon Utsunomiya before the effective filing date of the claimed invention for knowledge generally available within the butanol distillation purification art regarding the reflux ratio and process step recycle lines. For all of the reasons provided above, applicant’s above arguments are not persuasive.
The rejection of claims 1-5, 7-14 and 21 under 35 U.S.C. 103 as being unpatentable over Tsuji et al. (US20030018224, hereinafter Tsuji) in view of Utsunomiya et al. (US20150087038, hereinafter Utsunomiya) is maintained.
The rejections of:
Claims 1-5, 7-14, and 21 on the ground of nonstatutory double patenting as being unpatentable over claims 14-18 of copending Application No. 17/789,067 to Shimizu et al. (hereinafter Shimizu ‘067) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji);
Claims 1-5, 7-13, and 21 on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 and 9-16 of copending Application No. 17/788,991 to Shimizu et al. (hereinafter Shimizu ‘991) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji);
Claim 14 on the ground of nonstatutory double patenting as being unpatentable over claim 1 of copending Application No. 17/788,991 to Shimizu et al. (hereinafter Shimizu ‘991) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji) and Utsunomiya et al. (US20150087038, hereinafter Utsunomiya);
Claims 1-5, 7-10, and 21 on the ground of nonstatutory double patenting as being unpatentable over claims 1, 4, 6-9, and 12-20 of copending Application No. 17/789,093 to Shimizu et al. (hereinafter Shimizu ‘093) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji);
Claims 11-14 on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 4 of copending Application No. 17/789,093 to Shimizu et al. (hereinafter Shimizu ‘093) in view of US 20030018224 A1 to Tsuji et al. (hereinafter Tsuji) and Utsunomiya et al. (US20150087038, hereinafter Utsunomiya);
Claims 1-5, 7-11 and 21 on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 4-11 of copending Application No. 17/789,113 to Shimizu et al. (hereinafter Shimizu ‘113) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji);
Claims 12-14 on the ground of nonstatutory double patenting as being unpatentable over claims 1, 4, and 8 of copending Application No. No. 17/789,113 to Shimizu et al. (hereinafter Shimizu ‘113) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji) and Utsunomiya et al. (US20150087038, hereinafter Utsunomiya);
Claims 1-5, 7-11, 13, 14, and 21 on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 and 9-14 of copending Application No. 17/788,803 to Shimizu (hereinafter Shimizu ‘803) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji); and,
Claim 12 on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 2 of copending Application No. No. 17/788,803 to Shimizu (hereinafter Shimizu ‘803) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji) and Utsunomiya et al. (US20150087038, hereinafter Utsunomiya), are all maintained.
Due solely to the amendment to the claims adding new claim 22, modified and new ground(s) of rejection is/are provided below.
Maintained, Modified, and New Rejections based on the Amendments filed 26 January 2026
Claim Objections
Claim 1 is newly objected to because of the following informalities:
“After each claim number, the status identifier of the claim must be presented in a parenthetical expression, and the text of each claim under examination as well as all withdrawn claims (each with markings if any, to show current changes) must be presented”, see MPEP 714 II.C.
As stated above, claim 1 appears to include an improper amendment. Lines 9-10 of instant claim 1 state “a liquid feed obtained through the dehydration step and §is fed to the product column”. The addition of the “§” is new and the claim deletes “the high boiling substance removal step” after “and” and before “is” as recited in the previous version of the claims dated 25 August 2025. Therefore, claim 1 is newly amended and includes the improper identifier of “(presently presented)” instead of (currently amended).
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claims 1-5, 7-14, 21, and 22 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Claim 1 is newly rejected under 35 U.S.C. 112(b) as being incomplete for omitting essential elements, such omission amounting to a gap between the elements, see MPEP § 2172.01. As stated above, claim 1 appears to include an improper amendment. Lines 9-10 of instant claim 1 state “a liquid feed obtained through the dehydration step and §is fed to the product column”. The recitation of “and §is fed” appears to lack the elements as recited in the previous version of the claims dated 25 August 2025. The previous version of claim 1 states “a liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to the product column”. The current recitation of claim 1, lines 9-10 is missing “the high boiling substance removal step” after “and” and before “is”. Since instant claim 1 states it is “(previously presented)” and contains no mark ups removing and/or adding limitations, the instant claim 1 recitation of “§is” appears to be a mistake. Instant claim 1, lines 9-10 is interpreted to state “a liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to the product column”.
Claims 2-5, 7-14, 21, and 22 depend from base claim 1 and are included in this rejection as they do not correct the informalities identified in base claim 1.
For clarity between the maintained, modified, and new rejections, the specific modified and new rejections below are in italics.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-5, 7-14 and 21 stand rejected under 35 U.S.C. 103 as being unpatentable over Tsuji et al. (US20030018224, hereinafter Tsuji) in view of Utsunomiya et al. (US20150087038, hereinafter Utsunomiya).
Tsuji teaches the claims 1-5, 7-10, 12-14, and 21 limitations of a method for manufacturing 1,3-butylene glycol, see Abstract; Paras. [0052]-[0081];[0242]-[0248]; Table 1-1; Fig. 1, which is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid obtained by hydrogen reduction of an acetaldol, i.e., solution to be fed*, containing 1,3-butylene glycol, see Fig. 1, Paras. [0068];[0246], the method comprising: a dehydration step in dehydration tower 1-1 which removes water from the crude reaction liquid containing 1,3-butylene glycol by distillation, see Fig. 1, Para. [0246], meeting:
The dehydration step in instant application claim 1;
The reaction liquid in instant application claim 2 and in instant application claim 12;
A high boiling substance removal step of removing a high boiling point component by distillation in distillation tower 1-3, see Fig. 1; Para. [0247], meeting the high boiling point substance removal step in instant application claim 1;
A final product distillation tower 1-6 for obtaining purified 1,3-butylene glycol, see Fig. 1; Para. [0247], where in the product distillation step, a product column 1-6 is used, a liquid feed from 1-1 thru 1-5 enters as depicted in the middle of the column 1-6 at a feed plate and is distilled under a condition of reflux that is the same as the low boiling point distillation with a reflux ratio of 2-5, see Fig. 1, Paras. [0079]-[0080];[0136]-[0137];[0234], Table 2-2, meeting most of the product distillation step in instant application claim 1;
A liquid concentrated with acetaldehyde and crotonaldehyde is distilled off from a position above the feed plate of the product column in the product tower with 10-20 plates, where the feed is in the middle of tower 1-6, low-boiling-point substances, such as acetaldehyde and crotonaldehyde, are obtained as a distillate on the top, see Paras. [0065];[0080];[0247]; Fig. 1, and 1,3-butylene glycol is extracted from a position below the feed plate of the product column, see Paras. [0080];[0247]; Fig. 1. The concentration of low-boiling-point compounds having an unsaturated bond, such as acetaldehyde and crotonaldehyde contained in the solution fed into the tower is 5% or less which results in a liquid feed having a 1,3-butylene glycol concentration of 95% or higher, see Paras. [0080];[0247], i.e., “higher” implies an upper limit of infinity and within the range of 97% or higher, and by the time tower 1-6 is reached with the feed there is less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances, see Paras. [0065];[0080];[0153];[0247], Fig. 1, meeting:
The arrangement of the product distillation column in instant application claim 1;
Within the glycol, acetaldehyde, and crotonaldehyde concentration in instant application claim 1, in instant application claim 7, in instant application claim 8 and instant application claim 21;
Within the range of theoretical plates in instant application claim 10;
The 1,3-butylene glycol containing process stream is treated with a base in alkali reactor 1-4 & removal tower 1-5, see Para. [0247], Fig. 1, meeting the alkaline treatment step in instant application claim 3;
The 1,3-butylene glycol containing process stream is treated to remove salt in salt remover tower 1-2, see Paras. [0067];[0246], Fig. 1, meeting the salt removal step in instant application claim 4;
The 1,3-butylene glycol containing process stream is treated to dealcoholize low boiling point substances, see Paras. [0067];[0246], meeting the dealcoholization step in instant application claim 5;
1,3-butylene glycol, total 10% by weight on the basis of 100 parts of the fed solution, was obtained as a distillate and/or 10 parts 1,3-butylene glycol fed into 1-6 product column, 10%/parts 1,3-butylene glycol taken from the top of 1-6 and/or recycled back into 1-6, 90%/parts 1,3-butylene glycol removed from the bottom of tower 1-6 and/or recycled back to tower 10-6, see Fig. 1, Para. [0247], as calculated by the examiner the distillation rate is 0 to 10% of the initial feed, meeting and within the range in instant application claim 9;
A least a portion of the distillate from the product column is recycled and returned to the product column, see Fig. 1; Para. [0247]; and,
An amount of the distillate from the product column being recycled is lower than 10 wt.% with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column, where 10 parts 1,3-butylene glycol plus 90 parts low-boiling-point substances fed into product column 1-6, 10 %/parts 1,3-butylene glycol taken from the top of 1-6 recycled back into 1-6 and 90 %/parts 1,3-butylene glycol removed from the bottom of tower 1-6, see Fig. 1, Para. [0247], meeting and within the ranges in instant application claim 13 and in instant application claim 14.
Tsuji does not specifically teach:
The claim 1 limitations of a liquid feed having a 1,3-butylene glycol concentration of 97% or higher and a product column reflux ratio of 6 to 500; and,
The recycle limitations in instant application claims 11-14.
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified Tsuji by applying “routine optimization” to continue distillation in tower 1-5 until a 1,3-butylene glycol concentration of 97% or higher is obtained prior to feeding the 1,3-butylene glycol and low boiling-point substances to tower 1-6, as suggested in Tsuji, Para. [0080] & the recirculation of the product depicted in multiple towers of Fig. 1, with a reasonable expectation of success. One of ordinary skill in the art would have been motivated to make this modification because Tsuji provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to pursue the known options within their technical grasp for the benefit of efficiently creating an environmentally friendly process for the manufacture of 1,3-butylene glycol with high purity, substantially zero odor, and sufficiently long potassium permanganate color-fading time, see Tsuji, Para. [0081] and MPEP 2144.05 IIB.
Tsuji teaches the first invention is drawn to 1,3-butylene glycol having a high PMT value, preferably “at least 35 minutes”, where the concentration of the aldehyde groups remaining in the 1,3-butylene glycol process stream after hydrogenation is “preferably 10 ppm by weight or less” because the presence of the aldehyde groups lead to the discoloration of 1,3-butylene glycol, see Tsuji, Paras. [0025];[0071];[0153]. To obtain good color the cut percentage of low-boiling-point-substances and/or high-boiling-point substances correlates to the separation plate number of the distillation tower and the reflux ratio, for example, increased reflux ratio leads to a reduced cut percentage with a 1,3-butylene glycol with an aldehyde content of less than 10 ppm having a discoloration time of 16 hours or more, see Tsuji, Paras. [0131]-[0137], Tables 2-1 and 2-2.
Tsuji teaches higher reflux ratios increase cost; but, does not “criticize, discredit, or otherwise discourage” the use of higher reflux ratios, see Tsuji, Paras. [0137];[0231] and MPEP 2145 X.D.1. On the contrary, Tsuji teaches if the reflux ratio is low, the amount of the removed low-boiling-point components is small, see Tsuji, Para. [0298].
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since Tsuji does not teach away from a higher reflux ratio and an increased reflux ratio leads to a reduction in cut percentage which produces a 1,3-butylene glycol with an aldehyde content of less than 10 ppm that has a discoloration time of 16 hours or more, a person of ordinary skill in the art has good reason to modify Tsuji to raise the reflux ratio of the product stream in a distillation column from 2-5 to 6-500 by pursuing the known options within their technical grasp for the benefit of producing 1,3-butylene glycol with good color retention and no odor issues, see Tsuji, Paras. [0081];[0131]-[0137];[0234], Tables 2-1 and 2-2 and MPEP 2141.
Utsunomiya relating to providing high quality butanediol aka butylene glycol with good color tone by efficiently removing and refining impurities mixed in a stream obtained from producing a biomass-derived butanediol on an industrial scale, where the butanediol is produced from hydrogenated biomass-derived compounds, see Abstract, Paras. [0001]-[0006];[0050]. The impurities are removed by various distillations, then hydrogenation, and then a final distillation step (d) at a reflux ratio of 0.01 to 100 to obtain refined butanediol with a purity of 99.5 mass % or more, see Paras. [0016]-[0022];[0148]-[0157];[0203], Fig. 1, meeting and within the range of the reflux ratio in instant application claim 1; and,
As depicted in Fig. 1, a portion of the top distillate of product column (d) is recycled back to (f) where the butanediol is brought into contact with a base which is before the hydrogenation reactor (c), see Fig. 1, Paras. [0016]-[0022], meeting:
The recycle in instant application claim 11, in instant application claim 12, in instant application claim 13, and in instant application claim 14.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified Tsuji to rearrange the purification method by including additional recycle lines, see MPEP 2144.04 VI., to distill the butanediol mixed feed until a concentration of butanediol of greater than 97% is obtained, to include the recycle line, and to use the product column reflux ratio range as taught by Utsunomiya with a reasonable predictability of success for the purpose of efficiently removing and refining impurities mixed in a butanediol feed in order to obtain a butanediol of high purity and good color tone, see Utsunomiya, Abstract, Paras. [0150]-[0153];[0157].
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since Utsunomiya teaches a butanediol with good color tone is obtained after product distillation at a reflux ratio of 0.01 to 100, a person of ordinary skill in the art has good reason to purify a butanediol product stream at a reflux ratio of from 6 to 100 by pursuing the known options within their technical grasp for the benefit of efficiently removing and refining impurities mixed in a butanediol feed in order to obtain a butanediol of high purity and good color tone, see Utsunomiya, Abstract, Paras. [0150]-[0153];[0157] and MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as reflux ratio, “or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means,” such as recycle lines, “is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions.” In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929), see MPEP 2144.05.
“The normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as the product concentration or purity, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
Claim 1 is newly rejected and claim 22 is rejected under 35 U.S.C. 103 as being unpatentable over Khandurina et al. (WO2018183628, published 04 October 2018, hereinafter Khandurina).
As stated on page 63 of the first non-final office action dated 06 December 2024, “WO 2018/183628 A1 to Khandurina et al. teach 1,3-butanediol compositions where the purity of the 1,3-butanediol is tested via GC and the 1,3-butanediol contaminants are not detectable or minimally detectable (Paras. [00134];[00152];[00154];[00280]-[00282]; [00286]; Table 3).”
Khandurina is in the known prior art field of “a process of purifying bioderived 1,3-BG”, where “1,3-BG (which also can be referred to as BG, 1,3-butanediol, 1,3-BDO, 13-BDO, 1,3- butylene glycol, or butylene glycol)”, see Paras. [0004];[0028]-[0044].
Regarding the limitations of instant application claim 1, Khandurina teaches a crude “1,3-BG mixture or partially purified bioderived 1,3-BG 500 is fed to the dewatering column 510, where light materials 512 (materials with boiling points lower than 1,3-BG, such as water) are removed from the top of the first column 510”, see Paras. [00250]-[00251];[00273]-[00275];Figs. 15A-15B, where the dewatering column is a distillation column, see Paras. [00175]-[00178];[00225];[00273]-[00275], meeting the dehydration step in instant application claim 1;
Then a “1,3-BG-containing product stream 514 exits the bottom of the first column and is fed to a first distillation column 520. Heavy materials 524 (materials with boiling points higher than 1,3-BG) are removed from the bottom of the first distillation column 520, and a bioderived 1,3 BG-containing product stream 522 exits from the top of the first distillation column 520”, see Paras. [00250]-[00251];[00273]-[00275]; Figs. 15A-15B, meeting the high boiling point substance removal step in instant application claim 1;
The “1,3-BG-containing product stream 522 is fed to a second distillation column 530. Distillation column 530 removes light materials 532 from the top of the column 530 and a third bioderived 1,3-BG-containing product stream 534 from the bottom of column 530”, see Paras. [00250]-[00251];[00273]-[00275]; Figs. 15A-15B, where the feed 522 to column 530 is depicted in the middle of the column and bottom stream 534 is below the feed, see Figs. 15A-15B, the distillation columns include plates, see Para. [00165], and “the reflux ratio in the dewatering column, or the first, second or third distillation column in a process or system provided herein is … 6:1 or more, 7:1 or more, 8:1 or more, 9:1 or more, or 10:1 or more”, see Para. [00177], meeting a product distillation column, the liquid feed, the feed plate, within the reflux ratio range, and the 1,3-BG-containing product bottom stream below the feed stream in instant application claim 1;
The light materials 532 are removed from the top of the column 530 above the middle feed 522, see Paras. [00250]-[00251]; Figs. 15A-15B; Table 7, where the top of the distillation column has a condenser in order to obtain a liquid from the top, see Paras. [00166];[00243];[00273], and “the term “lights” refers to compounds in a 1,3-BG sample (e.g., a bio- BG or petro-BG sample) that elute at earlier retention times than 1,3-BG, e.g., in a GC-MS chromatogram or an LC-MS chromatogram”, see Para. [0090]. Instant specification Para. [0074] states “[w]hen the relative retention time of the peak of 1,3-butylene glycol is 1.0 in the GC-MS analysis conditions, a relative retention time of a peak of acetaldehyde is from 0.3 to 0.5, and a relative retention time of a peak of crotonaldehyde is from 0.3 to 0.5”; therefore, acetaldehyde and crotonaldehyde are removed from the top of distillation column 530 as a condensed liquid, meeting the liquid concentrate acetaldehyde and crotonaldehyde distilled off from a position above the feed in instant application claim 1;
“[T]he term “crude bioderived 1,3-BG mixture” means a mixture of bioderived 1,3-BG (1,3-BDO) that is or includes about 50% to 90% bioderived 1,3-BG and 50% to 1%) water with one or more other impurities that are derived from a fermentation process”, see Para. [0083], where “base was added to a crude bio-BG preparation obtained after heavies distillation in a lab-scale (2L) batch distillation system as described, e.g., in Example 1”, then the product distillation is performed, where the feed of the various “Cut” samples numbers 1-8 has a 1,3-BG concentration/purity of 99.1-99.9, see Paras. [00326]-[00329], Tables 15 & 16, meeting within the liquid feed 1,3-BG concentration range in instant application claim 1; and,
The 1,3-BG has levels of acetaldehyde and crotonaldehyde of less than 200 ppm, see Paras. [00152]-[00154], where a 99.9% purity cut of 1,3-BG can only contain up to 1000 ppm of impurities, see Paras. [00326]-[00329], Tables 15 & 16, meeting within the range of acetaldehyde and crotonaldehyde in instant application claim 1.
Regarding the limitations of instant application claim 22, Khandurina teaches “FIG. 15B adds an alkali reactor 560' to the system of FIG. 15A”, where after dewatering in 510', “[a] bioderived 1,3-BG-containing product stream 514' exits the bottom of the first column and is fed to a first distillation column 520' . Heavy materials 524' (materials with boiling points higher than 1,3-BG) are removed from the bottom of the first distillation column 520', and a bioderived 1,3 BG-containing product stream 522' exits from the top of the first distillation column 520'” then the “bioderived 1,3-BG-containing product stream 522' is fed to the alkali reactor 560', which sends the stream 562' to the second distillation column 530'”, see Paras. [00250]-[00251]; Figs. 15A-15B, where “the process includes adding a base to a bioderived 1,3-BG-containing product stream before or after any one of” the distillation steps and the base is “an alkali metal compound, such as sodium hydroxide, potassium hydroxide, sodium (bi)carbonate, ammonium hydroxide, or a combination thereof”, see Paras. [0028];[00179]-[00183], meeting the alkaline reaction step and the specific sodium carbonate or sodium bicarbonate in instant application claim 22.
Khandurina does not teach the limitations of the above instant application claims in one single express embodiment or Example.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified Khandurina to choose the embodiment represented by Fig. 15B with a sodium (bi)carbonate base, see MPEP 2144.07, a distillation column with plates, see MPEP 2144.04 VI., to test for and limit the amount of impurities in the process streams, see MPEP 2112 and 2144.05, and to adjust the reflux ratio to 6 or more, see MPEP 2144.05, with a reasonable predictability of success for the purpose of efficiently producing 1,3-BG having a chemical purity of 99% or higher with an overall level of heavies of 0.8% or less, an overall level of lights of 0.2% or less, and an improved odor “for use in the cosmetic and food industries”, see Khandurina, Paras. [0022];[0028];[0072]-[0077].
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying Khandurina to select the optimal embodiments of alkaline treatment, process stream concentrations, and reflux ratios as taught by Khandurina with a reasonable predictability of success for the purpose of efficiently producing 1,3-BG having a chemical purity of 99% or higher with an overall level of heavies of 0.8% or less, an overall level of lights of 0.2% or less, and an improved odor “for use in the cosmetic and food industries”, see Khandurina, Paras. [0022];[0028];[0072]-[0077]; and MPEP 2143 I. B-D.
Furthermore, an “obvious to try” rationale may support a conclusion that a claim would have been obvious where one skilled in the art is choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success, see MPEP 2145 X.B. Since Khandurina teaches alkaline treatments, process stream concentrations, and reflux ratios, the prior art contains “detailed enabling methodology, a suggestion to modify the prior art to produce the claimed invention, and evidence suggesting the modification would be successful”, see MPEP 2145 X.B.; therefore, it would have been obvious for one of ordinary skill in the art at the time the invention was made to try the differing embodiments of alkaline treatments, process stream concentrations, and reflux ratios in order to purify 1,3-BG.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”, see MPEP 2141.
Selection of a known material, such as an alkali metal compound, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
“The normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as the concentration of the product and impurities in the process streams, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as the reflux ratio and the concentration of the product and impurities in the process streams, “or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions. In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-5, 7-14, and 21 stand provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 14-18 of copending Application No. 17/789,067 to Shimizu et al. (hereinafter Shimizu ‘067) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 1, the claims of Shimizu ‘067 recite a method for manufacturing 1,3-butylene glycol, which is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid containing 1,3- butylene glycol (Claims 14 & 16), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3- butylene glycol by distillation (Claims 14 & 16); a high boiling substance removal step of removing a high boiling point component by distillation (Claims 14 & 16); and a product distillation step of obtaining purified 1,3-butylene glycol (Claim 14), wherein in the product distillation step, a product column is used at a reflux ratio of 0.3 or greater (Claim 14, i.e., “greater” implies an upper limit of infinity and within the range of 6 to 500), a liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to the product column and distilled in the product column under a condition of a reflux ratio (Claim 14), and the liquid feed has a 1,3-butylene glycol concentration of 97% or higher, an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower (Claims 14 & 16).
The claims of Shimizu ‘067 lack fed to the product column at a feed plate, a liquid concentrated with acetaldehyde and crotonaldehyde is distilled off from a position above the feed plate of the product column, and 1,3-butylene glycol is extracted from a position below the feed plate of the product column.
Tsuji teaches fed to the product column at a feed plate (Fig. 1, final product distillation tower 1-6, where feed from 1-1 and 1-3 enters as depicted in the middle of the column; Para. [0079], “The final product distillation tower may be a perforated plate tower”), a liquid concentrated with acetaldehyde and crotonaldehyde is distilled off from a position above the feed plate of the product column (Paras. [0065];[0080];[0247]; Figure, product tower with 10-20 plates, feed is in the middle of tower 1-6, low-boiling-point substances, such as acetaldehyde and crotonaldehyde, obtained as a distillate, i.e., a liquid, from the top of the final product distillation tower 1-6), and 11,3-butylene glycol is extracted from a position below the feed plate of the product column (Paras. [0080];[0247]; Figure).
Regarding claims 2-5, 11, and 12, claims 12-15, 17, and 18 of Shimizu ‘067 recite the same limitations as claims 2-5, 11, and 12.
Regarding claim 7, the claims of Shimizu ‘067 lack wherein the liquid feed into the product column has an acetaldehyde content of 205 ppm or lower.
Tsuji teaches wherein the liquid feed into the product column has an acetaldehyde content of 205 ppm or lower (Paras. [0065];[0247], low-boiling-point compounds having an unsaturated bond, such as acetaldehyde, butyraldehyde, crotonaldehyde, acetone, or methyl vinyl ketone; Para. [0080], concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less; Para. [0153], less than 10 ppm by weight aldehyde groups remaining in the hydrogenation crude mixture; Figure, i.e., by the time tower 1-6 is reached with the feed there may be less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances).
Regarding claim 8, the claims of Shimizu ‘067 lack wherein the liquid feed into the product column has a crotonaldehyde content of 110 ppm or lower.
Tsuji teaches wherein the liquid feed into the product column has a crotonaldehyde content of 110 ppm or lower (Paras. [0065];[0247], low-boiling-point compounds having an unsaturated bond, such as acetaldehyde, butyraldehyde, crotonaldehyde, acetone, or methyl vinyl ketone; Para. [0080], concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less; Para. [0153], less than 10 ppm by weight aldehyde groups remaining in the hydrogenation crude mixture; Figure, i.e., by the time tower 1-6 is reached with the feed there may be less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances).
Regarding claim 9, the claims of Shimizu ‘067 lack wherein the product column has a distillation rate of lower than 20 wt.%
Tsuji teaches wherein the product column has a distillation rate of lower than 20 wt.% (Figure; Para. [0247], 1,3-butylene glycol (total 10% by weight on the basis of 100 parts of the fed solution) were obtained as a distillate and/or 10 parts 1,3-butylene glycol fed into 1-6 product column, 10 %/parts 1,3-butylene glycol taken from the top of 1-6 and/or recycled back into 1-6, 90 %/parts 1,3-butylene glycol removed from the bottom of tower 1-6 and/or recycled back to tower 10-6, i.e., the distillation rate may be 0 to 10% of the initial feed).
Regarding claim 10, the claims of Shimizu ‘067 lack wherein the product column has the number of theoretical plates of from 1 to 100.
Tsuji teaches wherein the product column has a number of theoretical plates of from 1 to 100 (Para. [0080], the theoretical plate number of the tower is about 10-20).
Regarding claim 13, the claims of Shimizu ‘067 lack wherein an amount of the distillate from the product column being recycled to a step prior to the product distillation step is lower than 30 wt.% with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column.
Tsuji teaches wherein an amount of the distillate from the product column being recycled is lower than 30 wt.% with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column (Figure; Para. [0247], 10 parts 1,3-butylene glycol plus 90 parts low-boiling-point substances fed into product column 1-6, 10 %/parts 1,3-butylene glycol taken from the top of 1-6 recycled back into 1-6 and 90 %/parts 1,3-butylene glycol removed from the bottom of tower 1-6).
Shimizu ‘084 teaches at least a portion of the distillate from the product column is recycled to the hydrogen reduction of an acetaldol or a step upstream of the hydrogen reduction (Fig. 1, column 8 to line 81 to 83 to 90 to reactor 1; Paras. [0079];[0105]).
Regarding claim 14, the claims of Shimizu ‘067 lack wherein an amount of the distillate from the product column being recycled to a step prior to the product distillation step is 0.01 wt.% or higher with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column.
Tsuji teaches wherein an amount of the distillate from the product column being recycled is 0.01 wt.% or higher with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column (Figure; Para. [0247], 10 parts 1,3-butylene glycol plus 90 parts low-boiling-point substances fed into product column 1-6, 10 %/parts 1,3-butylene glycol taken from the top of 1-6 recycled back into 1-6 and 90 %/parts 1,3-butylene glycol removed from the bottom of tower 1-6).
Shimizu ‘084 teaches at least a portion of the distillate from the product column is recycled to the hydrogen reduction of an acetaldol or a step upstream of the hydrogen reduction (Fig. 1, column 8 to line 81 to 83 to 90 to reactor 1; Paras. [0079];[0105]).
For claims 13 and 14, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the claims of Shimizu ‘067 to include the method, as taught by Tsuji and Shimizu ‘084, in order to obtain an odorless 1,3-butylene glycol with a higher yield and the desired purity.
Regarding claim 21, the claims of Shimizu ‘067 lack wherein the liquid feed into the product column has a crotonaldehyde content of 100 ppm or lower
Tsuji teaches wherein the liquid feed into the product column has a crotonaldehyde content of 100 ppm or lower (Paras. [0065];[0247], low-boiling-point compounds having an unsaturated bond, such as acetaldehyde, butyraldehyde, crotonaldehyde, acetone, or methyl vinyl ketone; Para. [0080], concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less; Para. [0153], less than 10 ppm by weight aldehyde groups remaining in the hydrogenation crude mixture; Figure, i.e., by the time tower 1-6 is reached with the feed there may be less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances).
In reference to the above claims, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the claims of Shimizu ‘067 to include the method and recovered product, as taught by Tsuji, in order to obtain an odorless 1,3-butylene glycol with a higher yield and the desired purity.
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the claims of Shimizu ‘067 to claim the method of Tsuji by applying "routine optimization" to continue distillation in tower 1-5 until a 1,3-butylene glycol concentration of 97% or higher was obtained prior to feeding the 1,3-butylene glycol and low boiling-point substances to tower 1-6, as suggested in Tsuji, Para. [0080] & the recirculation of the product depicted in multiple towers of the Figure, with a reasonable expectation of success. One of ordinary skill in the art would have been motivated to make this modification because Tsuji provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to pursue the known options within their technical grasp for the benefit of efficiently creating an environmentally friendly process for the manufacture of 1,3-butylene glycol with high purity, substantially zero odor, and sufficiently long potassium permanganate color-fading time (Tsuji, Para. [0081]). See MPEP 2144.05 IIB.
Claims 1-5, 7-13, and 21 stand provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 and 9-16 of copending Application No. 17/788,991 to Shimizu et al. (hereinafter Shimizu ‘991) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 1, the claims of Shimizu ‘991 recite a method for manufacturing 1,3-butylene glycol, which is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid containing 1,3- butylene glycol (Claim 1), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3- butylene glycol by distillation (Claim 1); a high boiling substance removal step of removing a high boiling point component by distillation (Claim 1); and a product distillation step of obtaining purified 1,3-butylene glycol (Claim 1), wherein in the product distillation step, a product column is used at a reflux ratio of higher than 0.1 (Claim 1, i.e., “higher” implies an upper limit of infinity and within the range of 6 to 500), a liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to the product column at a feed plate and distilled in the product column under a condition of a reflux ratio (Claims 1, 9, and 10), a liquid is distilled off from a position above the feed plate of the product column (Claim 1), and 1,3-butylene glycol is extracted from a position below the feed plate of the product column (Claim 1), and the liquid feed has a 1,3-butylene glycol concentration, an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower (Claim 1).
The claims of Shimizu ‘991 lack a liquid concentrated with acetaldehyde and crotonaldehyde is distilled off from a position above the feed plate of the product column, and a liquid feed having a 1,3-butylene glycol concentration of 97% or higher.
Tsuji teaches a 1,3-butylene glycol concentration of 95% or higher (Para. [0247]; Para. [0080], the concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less, i.e., the feed to the product tower of 1,3-butylene glycol and low-boiling-point substances contains 95% or higher 1,3-butylene glycol) and a liquid concentrated with acetaldehyde and crotonaldehyde is distilled off from a position above the feed plate of the product column (Figure, final product distillation tower 1-6, where feed from 1-1 and 1-3 enters as depicted in the middle of the column; Para. [0079], “The final product distillation tower may be a perforated plate tower”).
Regarding claims 2-5 and 7-13, claims 1-6 and 11-16 of Shimizu ‘991 recite the same limitations as claims 2-5 and 7-13.
Regarding claim 21, the claims of Shimizu ‘991 lack wherein the liquid feed into the product column has a crotonaldehyde content of 100 ppm or lower
Tsuji teaches wherein the liquid feed into the product column has a crotonaldehyde content of 100 ppm or lower (Paras. [0065];[0247], low-boiling-point compounds having an unsaturated bond, such as acetaldehyde, butyraldehyde, crotonaldehyde, acetone, or methyl vinyl ketone; Para. [0080], concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less; Para. [0153], less than 10 ppm by weight aldehyde groups remaining in the hydrogenation crude mixture; Figure, i.e., by the time tower 1-6 is reached with the feed there may be less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the claims of Shimizu ‘991 to claim the method of Tsuji by applying "routine optimization" to continue distillation in tower 1-5 until a 1,3-butylene glycol concentration of 97% or higher was obtained prior to feeding the 1,3-butylene glycol and low boiling-point substances to tower 1-6, as suggested in Tsuji, Para. [0080] & the recirculation of the product depicted in multiple towers of the Figure, with a reasonable expectation of success. One of ordinary skill in the art would have been motivated to make this modification because Tsuji provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to pursue the known options within their technical grasp for the benefit of efficiently creating an environmentally friendly process for the manufacture of 1,3-butylene glycol with high purity, substantially zero odor, and sufficiently long potassium permanganate color-fading time (Tsuji, Para. [0081]). See MPEP 2144.05 IIB.
Claim 14 stands provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 of copending Application No. 17/788,991 to Shimizu et al. (hereinafter Shimizu ‘991) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji) and Utsunomiya et al. (US20150087038, hereinafter Utsunomiya).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 14, the claims of Shimizu ‘991 lack wherein an amount of the distillate from the product column being recycled to a step prior to the product distillation step is 0.01 wt.% or higher with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column.
Tsuji teaches wherein an amount of the distillate from the product column being recycled is 0.01 wt.% or higher with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column (Figure; Para. [0247], 10 parts 1,3-butylene glycol plus 90 parts low-boiling-point substances fed into product column 1-6, 10 %/parts 1,3-butylene glycol taken from the top of 1-6 recycled back into 1-6 and 90 %/parts 1,3-butylene glycol removed from the bottom of tower 1-6).
Utsunomiya teaches as depicted in Fig. 1, a portion of the top distillate of product column (d) is recycled back to (f) where the butanediol is brought into contact with a base which is before the hydrogenation reactor (c), see Fig. 1, Paras. [0016]-[0022].
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the claims of Shimizu ‘991 to include the methods, as taught by Tsuji and Utsunomiya, in order to obtain an odorless 1,3-butylene glycol with a higher yield and the desired purity.
Claims 1-5, 7-10, and 21 stand provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 4, 6-9, and 12-20 of copending Application No. 17/789,093 to Shimizu et al. (hereinafter Shimizu ‘093) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 1, the claims of Shimizu ‘093 recite a method for manufacturing 1,3-butylene glycol, which is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid containing 1,3- butylene glycol (Claims 1 and 4), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3- butylene glycol by distillation (Claims 1 and 4); a high boiling substance removal step of removing a high boiling point component by distillation (Claims 1 and 4); and a product distillation step of obtaining purified 1,3-butylene glycol (Claim 1), wherein in the product distillation step, a product column is used at a reflux ratio of 0.1 to 1000, a liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to the product column at a feed plate (Claim 1) and distilled in the product column under a condition of a reflux ratio (Claim 1), a liquid concentrated is distilled off from a position above the feed plate of the product column (Claim 1), and 1,3-butylene glycol is extracted from a position below the feed plate of the product column (Claim 1), and, an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower (Claim 1).
The claims of Shimizu ‘093 lack a liquid feed having a 1,3-butylene glycol concentration of 97% or higher and a liquid concentrated with acetaldehyde and crotonaldehyde.
Tsuji teaches a 1,3-butylene glycol concentration of 95% or higher (Para. [0247]; Para. [0080], the concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less, i.e., the feed to the product tower of 1,3-butylene glycol and low-boiling-point substances contains 95% or higher 1,3-butylene glycol) and a liquid concentrated with acetaldehyde and crotonaldehyde is distilled off from a position above the feed plate of the product column (Paras. [0065];[0080];[0247]; Figure, product tower with 10-20 plates, feed is in the middle of tower 1-6, low-boiling-point substances, such as acetaldehyde and crotonaldehyde, obtained as a distillate, i.e., a liquid, from the top of the final product distillation tower 1-6).
Tsuji also teaches the limitations not recited in claim 4 of Shimizu ‘093 (see 35 USC 103 rejection above).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the claims of Shimizu ‘093 to claim the method of Tsuji by applying "routine optimization" to continue distillation in tower 1-5 until a 1,3-butylene glycol concentration of 97% or higher was obtained prior to feeding the 1,3-butylene glycol and low boiling-point substances to tower 1-6, as suggested in Tsuji, Para. [0080] & the recirculation of the product depicted in multiple towers of the Figure, with a reasonable expectation of success. One of ordinary skill in the art would have been motivated to make this modification because Tsuji provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to pursue the known options within their technical grasp for the benefit of efficiently creating an environmentally friendly process for the manufacture of 1,3-butylene glycol with high purity, substantially zero odor, and sufficiently long potassium permanganate color-fading time (Tsuji, Para. [0081]). See MPEP 2144.05 IIB.
Regarding claims 2-5, claims 6-9 and 12-20 of Shimizu ‘093 recite the same limitations as claims 2-5.
Regarding claim 7, the claims of Shimizu ‘093 lack wherein the liquid feed into the product column has an acetaldehyde content of 205 ppm or lower.
Tsuji teaches wherein the liquid feed into the product column has an acetaldehyde content of 205 ppm or lower (Paras. [0065];[0247], low-boiling-point compounds having an unsaturated bond, such as acetaldehyde, butyraldehyde, crotonaldehyde, acetone, or methyl vinyl ketone; Para. [0080], concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less; Para. [0153], less than 10 ppm by weight aldehyde groups remaining in the hydrogenation crude mixture; Figure, i.e., by the time tower 1-6 is reached with the feed there may be less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances).
Regarding claim 8, the claims of Shimizu ‘093 lack wherein the liquid feed into the product column has a crotonaldehyde content of 110 ppm or lower.
Tsuji teaches wherein the liquid feed into the product column has a crotonaldehyde content of 110 ppm or lower (Paras. [0065];[0247], low-boiling-point compounds having an unsaturated bond, such as acetaldehyde, butyraldehyde, crotonaldehyde, acetone, or methyl vinyl ketone; Para. [0080], concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less; Para. [0153], less than 10 ppm by weight aldehyde groups remaining in the hydrogenation crude mixture; Figure, i.e., by the time tower 1-6 is reached with the feed there may be less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances).
Regarding claim 9, the claims of Shimizu ‘093 lack wherein the product column has a distillation rate of lower than 20 wt.%
Tsuji teaches wherein the product column has a distillation rate of lower than 20 wt.% (Figure; Para. [0247], 1,3-butylene glycol (total 10% by weight on the basis of 100 parts of the fed solution) were obtained as a distillate and/or 10 parts 1,3-butylene glycol fed into 1-6 product column, 10 %/parts 1,3-butylene glycol taken from the top of 1-6 and/or recycled back into 1-6, 90 %/parts 1,3-butylene glycol removed from the bottom of tower 1-6 and/or recycled back to tower 10-6, i.e., the distillation rate may be 0 to 10% of the initial feed).
Regarding claim 10, the claims of Shimizu ‘093 lack wherein the product column has the number of theoretical plates of from 1 to 100.
Tsuji teaches wherein the product column has a number of theoretical plates of from 1 to 100 (Para. [0080], the theoretical plate number of the tower is about 10-20).
Regarding claim 21, the claims of Shimizu ‘093 lack wherein the liquid feed into the product column has a crotonaldehyde content of 100 ppm or lower
Tsuji teaches wherein the liquid feed into the product column has a crotonaldehyde content of 100 ppm or lower (Paras. [0065];[0247], low-boiling-point compounds having an unsaturated bond, such as acetaldehyde, butyraldehyde, crotonaldehyde, acetone, or methyl vinyl ketone; Para. [0080], concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less; Para. [0153], less than 10 ppm by weight aldehyde groups remaining in the hydrogenation crude mixture; Figure, i.e., by the time tower 1-6 is reached with the feed there may be less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances).
In reference to the above claims, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the claims of Shimizu ‘093 to include the method and recovered product, as taught by Tsuji, in order to obtain an odorless 1,3-butylene glycol with a higher yield and the desired purity.
Claims 11-14 stand provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 4 of copending Application No. 17/789,093 to Shimizu et al. (hereinafter Shimizu ‘093) in view of US 20030018224 A1 to Tsuji et al. (hereinafter Tsuji) and Utsunomiya et al. (US20150087038, hereinafter Utsunomiya).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 11, the claims of Shimizu ‘093 lack wherein at least a portion of a distillate from the product column is recycled to a step prior to the product distillation step.
Tsuji teaches wherein the crude reaction liquid containing 1,3-butylene glycol is a crude reaction liquid obtained by hydrogen reduction of an acetaldol (Paras. [0067];[0246]) and at least a portion of the distillate from the product column is recycled (Figure; Para. [0247], 10 parts 1,3-butylene glycol plus 90 parts low-boiling-point substances fed into product column 1-6, 10 %/parts 1,3-butylene glycol taken from the top of 1-6 recycled back into 1-6 and 90 %/parts 1,3-butylene glycol removed from the bottom of tower 1-6)
Utsunomiya teaches as depicted in Fig. 1, a portion of the top distillate of product column (d) is recycled back to (f) where the butanediol is brought into contact with a base which is before the hydrogenation reactor (c), see Fig. 1, Paras. [0016]-[0022].
Regarding claim 12, the claims of Shimizu ‘093 lack wherein the crude reaction liquid containing 1,3-butylene glycol is a crude reaction liquid obtained by hydrogen reduction of an acetaldol, and at least a portion of the distillate from the product column is recycled to the hydrogen reduction of an acetaldol or a step upstream of the hydrogen reduction.
Tsuji teaches wherein the crude reaction liquid containing 1,3-butylene glycol is a crude reaction liquid obtained by hydrogen reduction of an acetaldol (Paras. [0067];[0246]) and at least a portion of the distillate from the product column is recycled (Figure; Para. [0247]).
Utsunomiya teaches as depicted in Fig. 1, a portion of the top distillate of product column (d) is recycled back to (f) where the butanediol is brought into contact with a base which is before the hydrogenation reactor (c), see Fig. 1, Paras. [0016]-[0022].
Regarding claim 13, the claims of Shimizu ‘093 lack wherein an amount of the distillate from the product column being recycled to a step prior to the product distillation step is lower than 30 wt.% with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column.
Tsuji teaches wherein an amount of the distillate from the product column being recycled is lower than 30 wt.% with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column (Figure; Para. [0247], 10 parts 1,3-butylene glycol plus 90 parts low-boiling-point substances fed into product column 1-6, 10 %/parts 1,3-butylene glycol taken from the top of 1-6 recycled back into 1-6 and 90 %/parts 1,3-butylene glycol removed from the bottom of tower 1-6).
Utsunomiya teaches as depicted in Fig. 1, a portion of the top distillate of product column (d) is recycled back to (f) where the butanediol is brought into contact with a base which is before the hydrogenation reactor (c), see Fig. 1, Paras. [0016]-[0022].
Regarding claim 14, the claims of Shimizu ‘093 lack wherein an amount of the distillate from the product column being recycled to a step prior to the product distillation step is 0.01 wt.% or higher with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column.
Tsuji teaches wherein an amount of the distillate from the product column being recycled is 0.01 wt.% or higher with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column (Figure; Para. [0247], 10 parts 1,3-butylene glycol plus 90 parts low-boiling-point substances fed into product column 1-6, 10 %/parts 1,3-butylene glycol taken from the top of 1-6 recycled back into 1-6 and 90 %/parts 1,3-butylene glycol removed from the bottom of tower 1-6).
Utsunomiya teaches as depicted in Fig. 1, a portion of the top distillate of product column (d) is recycled back to (f) where the butanediol is brought into contact with a base which is before the hydrogenation reactor (c), see Fig. 1, Paras. [0016]-[0022].
In reference to the above claims, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the claims of Shimizu ‘093 to include the method, as taught by Tsuji and Utsunomiya, in order to obtain an odorless 1,3-butylene glycol with a higher yield and the desired purity.
Claims 1-5, 7-11 and 21 stand provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 4-11 of copending Application No. 17/789,113 to Shimizu et al. (hereinafter Shimizu ‘113) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 1, the claims of Shimizu ‘113 recite a method for manufacturing 1,3-butylene glycol (Claims 1 and 7), which is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid containing 1,3- butylene glycol (Claims 1 and 3), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3- butylene glycol by distillation (Claims 1 and 7); a high boiling substance removal step of removing a high boiling point component by distillation (Claims 1 and 7); and a product distillation step of obtaining purified 1,3-butylene glycol (Claim 1), wherein in the product distillation step, a product column is used (Claim 1), a liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to the product column at a feed plate and distilled in the product column under a condition of a reflux ratio higher than 0.1 (Claim 1, “higher” implies an upper limit of infinity and within the range of 6 to 500), a liquid concentrated is distilled off from a position above the feed plate of the product column (Claim 1), and 1,3-butylene glycol is extracted from a position below the feed plate of the product column (Claim 1), and an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower (Claim 1).
The claims of Shimizu ‘113 lack a liquid concentrated with acetaldehyde and crotonaldehyde is distilled off, a liquid feed having a 1,3-butylene glycol concentration of 97% or higher.
The teaching of Tsuji are detailed above.
Tsuji also teaches the limitations not recited in claim 7 of Shimizu ‘113 (see 103 rejection above).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the claims of Shimizu ‘113 to claim the method of Tsuji by applying "routine optimization" to continue distillation in tower 1-5 until a 1,3-butylene glycol concentration of 97% or higher was obtained prior to feeding the 1,3-butylene glycol and low boiling-point substances to tower 1-6, as suggested in Tsuji, Para. [0080] & the recirculation of the product depicted in multiple towers of the Figure, with a reasonable expectation of success. One of ordinary skill in the art would have been motivated to make this modification because Tsuji provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to pursue the known options within their technical grasp for the benefit of efficiently creating an environmentally friendly process for the manufacture of 1,3-butylene glycol with high purity, substantially zero odor, and sufficiently long potassium permanganate color-fading time (Tsuji, Para. [0081]). See MPEP 2144.05 IIB.
Regarding claims 2-5, 7, 8, 10, and 11, claims 1 and 4-11 of Shimizu ‘113 recite the same limitations as claims 2-5, 7, 8, 10, and 11.
Regarding claim 9, the claims of Shimizu ‘113 lack wherein the product column has a distillation rate of lower than 20 wt.%
Tsuji teaches wherein the product column has a distillation rate of lower than 20 wt.% (Figure; Para. [0247], 1,3-butylene glycol (total 10% by weight on the basis of 100 parts of the fed solution) were obtained as a distillate and/or 10 parts 1,3-butylene glycol fed into 1-6 product column, 10 %/parts 1,3-butylene glycol taken from the top of 1-6 and/or recycled back into 1-6, 90 %/parts 1,3-butylene glycol removed from the bottom of tower 1-6 and/or recycled back to tower 10-6, i.e., the distillation rate may be 0 to 10% of the initial feed).
Regarding claim 21, the claims of Shimizu ‘113 lack wherein the liquid feed into the product column has a crotonaldehyde content of 100 ppm or lower
Tsuji teaches wherein the liquid feed into the product column has a crotonaldehyde content of 100 ppm or lower (Paras. [0065];[0247], low-boiling-point compounds having an unsaturated bond, such as acetaldehyde, butyraldehyde, crotonaldehyde, acetone, or methyl vinyl ketone; Para. [0080], concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less; Para. [0153], less than 10 ppm by weight aldehyde groups remaining in the hydrogenation crude mixture; Figure, i.e., by the time tower 1-6 is reached with the feed there may be less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances).
In reference to the above claims, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the claims of Shimizu ‘113 to include the method and recovered product, as taught by Tsuji, in order to obtain an odorless 1,3-butylene glycol with a higher yield and the desired purity.
Claims 12-14 stand provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 4, and 8 of copending Application No. No. 17/789,113 to Shimizu et al. (hereinafter Shimizu ‘113) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji) and Utsunomiya et al. (US20150087038, hereinafter Utsunomiya).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 12, the claims of Shimizu ‘113 recite wherein the crude reaction liquid containing 1,3-butylene glycol is a crude reaction liquid obtained by hydrogen reduction of an acetaldol (Claim 8).
The claims of Shimizu ‘113 lack at least a portion of the distillate from the product column is recycled to the hydrogen reduction of an acetaldol or a step upstream of the hydrogen reduction.
Tsuji teaches wherein the crude reaction liquid containing 1,3-butylene glycol is a crude reaction liquid obtained by hydrogen reduction of an acetaldol (Paras. [0067];[0246]) and at least a portion of the distillate from the product column is recycled (Figure; Para. [0247]).
Utsunomiya teaches as depicted in Fig. 1, a portion of the top distillate of product column (d) is recycled back to (f) where the butanediol is brought into contact with a base which is before the hydrogenation reactor (c), see Fig. 1, Paras. [0016]-[0022].
Regarding claim 13, the claims of Shimizu ‘113 lack wherein an amount of the distillate from the product column being recycled to a step prior to the product distillation step is lower than 30 wt.% with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column.
Tsuji teaches wherein an amount of the distillate from the product column being recycled is lower than 30 wt.% with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column (Figure; Para. [0247], 10 parts 1,3-butylene glycol plus 90 parts low-boiling-point substances fed into product column 1-6, 10 %/parts 1,3-butylene glycol taken from the top of 1-6 recycled back into 1-6 and 90 %/parts 1,3-butylene glycol removed from the bottom of tower 1-6).
Utsunomiya teaches as depicted in Fig. 1, a portion of the top distillate of product column (d) is recycled back to (f) where the butanediol is brought into contact with a base which is before the hydrogenation reactor (c), see Fig. 1, Paras. [0016]-[0022].
Regarding claim 14, the claims of Shimizu ‘113 lack wherein an amount of the distillate from the product column being recycled to a step prior to the product distillation step is 0.01 wt.% or higher with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column.
Tsuji teaches wherein an amount of the distillate from the product column being recycled is 0.01 wt.% or higher with respect to a charged amount into the product column within a range not higher than a distilled amount in the product column (Figure; Para. [0247], 10 parts 1,3-butylene glycol plus 90 parts low-boiling-point substances fed into product column 1-6, 10 %/parts 1,3-butylene glycol taken from the top of 1-6 recycled back into 1-6 and 90 %/parts 1,3-butylene glycol removed from the bottom of tower 1-6).
Utsunomiya teaches as depicted in Fig. 1, a portion of the top distillate of product column (d) is recycled back to (f) where the butanediol is brought into contact with a base which is before the hydrogenation reactor (c), see Fig. 1, Paras. [0016]-[0022].
In reference to the above claims, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the claims of Shimizu ‘113 to include the method, as taught by Tsuji and Utsunomiya, in order to obtain an odorless 1,3-butylene glycol with a higher yield and the desired purity.
Claims 1-5, 7-11, 13, 14, and 21 stand provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 and 9-14 of copending Application No. 17/788,803 to Shimizu (hereinafter Shimizu ‘803) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 1, the claims of Shimizu ‘803 recite method for manufacturing 1,3-butylene glycol, which is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid containing 1,3- butylene glycol (Claim 1), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3- butylene glycol by distillation (Claim 1); a high boiling substance removal step of removing a high boiling point component by distillation (Claim 1); and a product distillation step of obtaining purified 1,3-butylene glycol (Claim 1), wherein in the product distillation step, a product column is used, a liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to the product column at a feed plate and distilled in the product column under a condition of a reflux ratio is 0.4 or greater (Claim 1, i.e., “greater” implies an upper limit of infinity and within the range of 6 to 500), a liquid concentrated is distilled off from a position above the feed plate of the product column (Claim 1), and 1,3-butylene glycol is extracted from a position below the feed plate of the product column (Claim 1), and the liquid feed has a 1,3-butylene glycol concentration of 97% or higher, an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower.
The claims of Shimizu ‘803 lack a reflux ratio of 3 or higher, a 1,3-butylene glycol concentration of 97% or higher; an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower; a liquid concentrated with acetaldehyde and crotonaldehyde is distilled off from above a feed plate, and feed plates.
Tsuji teaches a 1,3-butylene glycol concentration of 95% or higher (Para. [0247]; Para. [0080], the concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less, i.e., the feed to the product tower of 1,3-butylene glycol and low-boiling-point substances contains 95% or higher 1,3-butylene glycol), an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower (Paras. [0065];[0247], low-boiling-point compounds having an unsaturated bond, such as acetaldehyde, butyraldehyde, crotonaldehyde, acetone, or methyl vinyl ketone; Para. [0080], concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less; Para. [0153], less than 10 ppm by weight aldehyde groups remaining in the hydrogenation crude mixture; Figure, i.e., by the time tower 1-6 is reached with the feed there may be less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances), and a liquid concentrated with acetaldehyde and crotonaldehyde is distilled off from above a feed plate (Paras. [0065];[0080];[0247]; Figure, product tower with 10-20 plates, feed is in the middle of tower 1-6, low-boiling-point substances, such as acetaldehyde and crotonaldehyde, obtained as a distillate, i.e., a liquid, from the top of the final product distillation tower 1-6), and 1,3-butylene glycol is extracted from below the feed plate (Paras. [0080];[0247]; Figure).
It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the claims of Shimizu ‘803 to claim the method of Tsuji by applying "routine optimization" to continue distillation in tower 1-5 until a 1,3-butylene glycol concentration of 97% or higher was obtained prior to feeding the 1,3-butylene glycol and low boiling-point substances to tower 1-6, as suggested in Tsuji, Para. [0080] & the recirculation of the product depicted in multiple towers of the Figure, with a reasonable expectation of success. One of ordinary skill in the art would have been motivated to make this modification because Tsuji provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to pursue the known options within their technical grasp for the benefit of efficiently creating an environmentally friendly process for the manufacture of 1,3-butylene glycol with high purity, substantially zero odor, and sufficiently long potassium permanganate color-fading time (Tsuji, Para. [0081]). See MPEP 2144.05 IIB.
Regarding claims 2-5, 9-11, 13, and 14, claims 2-6 and 10-14 of Shimizu ‘803 recite the same limitations as claims 2-5, 9-11, 13, and 14.
Regarding claim 7, the claims of Shimizu ‘803 lack wherein the liquid feed into the product column has an acetaldehyde content of 205 ppm or lower.
Tsuji teaches wherein the liquid feed into the product column has an acetaldehyde content of 205 ppm or lower (Paras. [0065];[0247], low-boiling-point compounds having an unsaturated bond, such as acetaldehyde, butyraldehyde, crotonaldehyde, acetone, or methyl vinyl ketone; Para. [0080], concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less; Para. [0153], less than 10 ppm by weight aldehyde groups remaining in the hydrogenation crude mixture; Figure, i.e., by the time tower 1-6 is reached with the feed there may be less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances).
Regarding claim 8, the claims of Shimizu ‘803 lack wherein the liquid feed into the product column has a crotonaldehyde content of 110 ppm or lower.
Tsuji teaches wherein the liquid feed into the product column has a crotonaldehyde content of 110 ppm or lower (Paras. [0065];[0247], low-boiling-point compounds having an unsaturated bond, such as acetaldehyde, butyraldehyde, crotonaldehyde, acetone, or methyl vinyl ketone; Para. [0080], concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less; Para. [0153], less than 10 ppm by weight aldehyde groups remaining in the hydrogenation crude mixture; Figure, i.e., by the time tower 1-6 is reached with the feed there may be less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances).
Regarding claim 21, the claims of Shimizu ‘803 lack wherein the liquid feed into the product column has a crotonaldehyde content of 100 ppm or lower
Tsuji teaches wherein the liquid feed into the product column has a crotonaldehyde content of 100 ppm or lower (Paras. [0065];[0247], low-boiling-point compounds having an unsaturated bond, such as acetaldehyde, butyraldehyde, crotonaldehyde, acetone, or methyl vinyl ketone; Para. [0080], concentration of low-boiling-point substances contained in the solution fed into the tower is 5% or less; Para. [0153], less than 10 ppm by weight aldehyde groups remaining in the hydrogenation crude mixture; Figure, i.e., by the time tower 1-6 is reached with the feed there may be less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances).
In reference to the above claims, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the claims of Shimizu ‘803 to include the method and recovered product, as taught by Tsuji, in order to obtain an odorless 1,3-butylene glycol with a higher yield and the desired purity.
Claim 12 stands provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 2 of copending Application No. No. 17/788,803 to Shimizu (hereinafter Shimizu ‘803) in view of US 2003/0018224 A1 to Tsuji et al. (hereinafter Tsuji) and Utsunomiya et al. (US20150087038, hereinafter Utsunomiya).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 12, the claims of Shimizu ‘803 recite wherein the crude reaction liquid containing 1,3-butylene glycol is a crude reaction liquid obtained by hydrogen reduction of an acetaldol (Claim 2).
The claims of Shimizu ‘803 lack at least a portion of the distillate from the product column is recycled to the hydrogen reduction of an acetaldol or a step upstream of the hydrogen reduction.
Tsuji teaches wherein the crude reaction liquid containing 1,3-butylene glycol is a crude reaction liquid obtained by hydrogen reduction of an acetaldol (Paras. [0067];[0246]) and at least a portion of the distillate from the product column is recycled (Figure; Para. [0247]).
Utsunomiya teaches as depicted in Fig. 1, a portion of the top distillate of product column (d) is recycled back to (f) where the butanediol is brought into contact with a base which is before the hydrogenation reactor (c), see Fig. 1, Paras. [0016]-[0022].
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the claims of Shimizu ‘803 to include the method, as taught by Tsuji and Utsunomiya, in order to obtain an odorless 1,3-butylene glycol with a higher yield and the desired purity.
Claim 1 is newly rejected and claim 22 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 14 and 16 of copending Application No. 17/789,067 to Shimizu et al. (hereinafter Shimizu ‘067) in view of Khandurina et al. (WO2018183628, published 04 October 2018, hereinafter Khandurina).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 1, the claims of Shimizu ‘067 recite a method for manufacturing 1,3-butylene glycol, which is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid containing 1,3- butylene glycol (Claims 14 & 16), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3- butylene glycol by distillation (Claims 14 & 16); a high boiling substance removal step of removing a high boiling point component by distillation (Claims 14 & 16); and a product distillation step of obtaining purified 1,3-butylene glycol (Claim 14), wherein in the product distillation step, a product column is used at a reflux ratio of 0.3 or greater (Claim 14, i.e., “greater” implies an upper limit of infinity and within the range of 6 to 500), a liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to the product column and distilled in the product column under a condition of a reflux ratio (Claim 14), and the liquid feed has a 1,3-butylene glycol concentration of 97% or higher, an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower (Claims 14 & 16).
The claims of Shimizu ‘067 lack fed to the product column at a feed plate, a liquid concentrated with acetaldehyde and crotonaldehyde is distilled off from a position above the feed plate of the product column, and 1,3-butylene glycol is extracted from a position below the feed plate of the product column; and, the limitations of instant application claim 22.
Regarding the limitations of instant application claim 1, Khandurina teaches the “1,3-BG-containing product stream 522 is fed to a second distillation column 530. Distillation column 530 removes light materials 532 from the top of the column 530 and a third bioderived 1,3-BG-containing product stream 534 from the bottom of column 530”, see Paras. [00250]-[00251];[00273]-[00275]; Figs. 15A-15B, where the feed 522 to column 530 is depicted in the middle of the column and bottom stream 534 is below the feed, see Figs. 15A-15B, the distillation columns include plates, see Para. [00165], and “the reflux ratio in the dewatering column, or the first, second or third distillation column in a process or system provided herein is … 6:1 or more, 7:1 or more, 8:1 or more, 9:1 or more, or 10:1 or more”, see Para. [00177], meeting a product distillation column, the liquid feed, the feed plate, within the reflux ratio range, and the 1,3-BG-containing product bottom stream below the feed stream in instant application claim 1; and,
The light materials 532 are removed from the top of the column 530 above the middle feed 522, see Paras. [00250]-[00251]; Figs. 15A-15B; Table 7, where the top of the distillation column has a condenser in order to obtain a liquid from the top, see Paras. [00166];[00243];[00273], and “the term “lights” refers to compounds in a 1,3-BG sample (e.g., a bio- BG or petro-BG sample) that elute at earlier retention times than 1,3-BG, e.g., in a GC-MS chromatogram or an LC-MS chromatogram”, see Para. [0090]. Instant specification Para. [0074] states “[w]hen the relative retention time of the peak of 1,3-butylene glycol is 1.0 in the GC-MS analysis conditions, a relative retention time of a peak of acetaldehyde is from 0.3 to 0.5, and a relative retention time of a peak of crotonaldehyde is from 0.3 to 0.5”; therefore, acetaldehyde and crotonaldehyde are removed from the top of distillation column 530 as a condensed liquid, meeting the liquid concentrate acetaldehyde and crotonaldehyde distilled off from a position above the feed in instant application claim 1.
Regarding the limitations of instant application claim 22, Khandurina teaches “FIG. 15B adds an alkali reactor 560' to the system of FIG. 15A”, where after dewatering in 510', “[a] bioderived 1,3-BG-containing product stream 514' exits the bottom of the first column and is fed to a first distillation column 520' . Heavy materials 524' (materials with boiling points higher than 1,3-BG) are removed from the bottom of the first distillation column 520', and a bioderived 1,3 BG-containing product stream 522' exits from the top of the first distillation column 520'” then the “bioderived 1,3-BG-containing product stream 522' is fed to the alkali reactor 560', which sends the stream 562' to the second distillation column 530'”, see Paras. [00250]-[00251]; Figs. 15A-15B, where “the process includes adding a base to a bioderived 1,3-BG-containing product stream before or after any one of” the distillation steps and the base is “an alkali metal compound, such as sodium hydroxide, potassium hydroxide, sodium (bi)carbonate, ammonium hydroxide, or a combination thereof”, see Paras. [0028];[00179]-[00183], meeting the alkaline reaction step and the specific sodium carbonate or sodium bicarbonate in instant application claim 22.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the claims of Shimizu ‘067 with the purification of 1,3-BG process parameters and apparatus as taught by Khandurina with a reasonable predictability of success for the purpose of efficiently producing 1,3-BG having a chemical purity of 99% or higher with an overall level of heavies of 0.8% or less, an overall level of lights of 0.2% or less, and an improved odor “for use in the cosmetic and food industries”, see Khandurina, Paras. [0022];[0028];[0072]-[0077].
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying the claims of Shimizu ‘067 to select the optimal embodiments of purification of 1,3-BG as taught by Khandurina with a reasonable predictability of success for the purpose of efficiently producing 1,3-BG having a chemical purity of 99% or higher with an overall level of heavies of 0.8% or less, an overall level of lights of 0.2% or less, and an improved odor “for use in the cosmetic and food industries”, see Khandurina, Paras. [0022];[0028];[0072]-[0077]; and MPEP 2143 I. B-D.
Claim 1 is newly rejected and claim 22 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 of copending Application No. 17/788,991 to Shimizu et al. (hereinafter Shimizu ‘991) in view of Khandurina et al. (WO2018183628, published 04 October 2018, hereinafter Khandurina).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 1, the claims of Shimizu ‘991 recite a method for manufacturing 1,3-butylene glycol, which is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid containing 1,3- butylene glycol (Claim 1), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3- butylene glycol by distillation (Claim 1); a high boiling substance removal step of removing a high boiling point component by distillation (Claim 1); and a product distillation step of obtaining purified 1,3-butylene glycol (Claim 1), wherein in the product distillation step, a product column is used at a reflux ratio of higher than 0.1 (Claim 1, i.e., “higher” implies an upper limit of infinity and within the range of 6 to 500), a liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to the product column at a feed plate and distilled in the product column under a condition of a reflux ratio (Claim 1), a liquid is distilled off from a position above the feed plate of the product column (Claim 1), and 1,3-butylene glycol is extracted from a position below the feed plate of the product column (Claim 1), and the liquid feed has a 1,3-butylene glycol concentration, an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower (Claim 1).
The claims of Shimizu ‘991 lack a liquid concentrated with acetaldehyde and crotonaldehyde is distilled off from a position above the feed plate of the product column, and a liquid feed having a 1,3-butylene glycol concentration of 97% or higher; and, the limitations of instant application claim 22.
Regarding the limitations of instant application claim 1, Khandurina teaches the light materials 532 are removed from the top of the column 530 above the middle feed 522, see Paras. [00250]-[00251]; Figs. 15A-15B; Table 7, where the top of the distillation column has a condenser in order to obtain a liquid from the top, see Paras. [00166];[00243];[00273], and “the term “lights” refers to compounds in a 1,3-BG sample (e.g., a bio- BG or petro-BG sample) that elute at earlier retention times than 1,3-BG, e.g., in a GC-MS chromatogram or an LC-MS chromatogram”, see Para. [0090]. Instant specification Para. [0074] states “[w]hen the relative retention time of the peak of 1,3-butylene glycol is 1.0 in the GC-MS analysis conditions, a relative retention time of a peak of acetaldehyde is from 0.3 to 0.5, and a relative retention time of a peak of crotonaldehyde is from 0.3 to 0.5”; therefore, acetaldehyde and crotonaldehyde are removed from the top of distillation column 530 as a condensed liquid, meeting the liquid concentrate acetaldehyde and crotonaldehyde distilled off from a position above the feed in instant application claim 1; and,
“[T]he term “crude bioderived 1,3-BG mixture” means a mixture of bioderived 1,3-BG (1,3-BDO) that is or includes about 50% to 90% bioderived 1,3-BG and 50% to 1%) water with one or more other impurities that are derived from a fermentation process”, see Para. [0083], where “base was added to a crude bio-BG preparation obtained after heavies distillation in a lab-scale (2L) batch distillation system as described, e.g., in Example 1”, then the product distillation is performed, where the feed of the various “Cut” samples numbers 1-8 has a 1,3-BG concentration/purity of 99.1-99.9, see Paras. [00326]-[00329], Tables 15 & 16, meeting within the liquid feed 1,3-BG concentration range in instant application claim 1.
Regarding the limitations of instant application claim 22, Khandurina teaches “FIG. 15B adds an alkali reactor 560' to the system of FIG. 15A”, where after dewatering in 510', “[a] bioderived 1,3-BG-containing product stream 514' exits the bottom of the first column and is fed to a first distillation column 520' . Heavy materials 524' (materials with boiling points higher than 1,3-BG) are removed from the bottom of the first distillation column 520', and a bioderived 1,3 BG-containing product stream 522' exits from the top of the first distillation column 520'” then the “bioderived 1,3-BG-containing product stream 522' is fed to the alkali reactor 560', which sends the stream 562' to the second distillation column 530'”, see Paras. [00250]-[00251]; Figs. 15A-15B, where “the process includes adding a base to a bioderived 1,3-BG-containing product stream before or after any one of” the distillation steps and the base is “an alkali metal compound, such as sodium hydroxide, potassium hydroxide, sodium (bi)carbonate, ammonium hydroxide, or a combination thereof”, see Paras. [0028];[00179]-[00183], meeting the alkaline reaction step and the specific sodium carbonate or sodium bicarbonate in instant application claim 22.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the claims of Shimizu ‘991 with the purification of 1,3-BG process parameters and apparatus as taught by Khandurina with a reasonable predictability of success for the purpose of efficiently producing 1,3-BG having a chemical purity of 99% or higher with an overall level of heavies of 0.8% or less, an overall level of lights of 0.2% or less, and an improved odor “for use in the cosmetic and food industries”, see Khandurina, Paras. [0022];[0028];[0072]-[0077].
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying the claims of Shimizu ‘991 to select the optimal embodiments of purification of 1,3-BG as taught by Khandurina with a reasonable predictability of success for the purpose of efficiently producing 1,3-BG having a chemical purity of 99% or higher with an overall level of heavies of 0.8% or less, an overall level of lights of 0.2% or less, and an improved odor “for use in the cosmetic and food industries”, see Khandurina, Paras. [0022];[0028];[0072]-[0077]; and MPEP 2143 I. B-D.
Claim 1 is newly rejected and claim 22 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 4 of copending Application No. 17/789,093 to Shimizu et al. (hereinafter Shimizu ‘093) in view of Khandurina et al. (WO2018183628, published 04 October 2018, hereinafter Khandurina).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 1, the claims of Shimizu ‘093 recite a method for manufacturing 1,3-butylene glycol, which is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid containing 1,3- butylene glycol (Claims 1 and 4), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3- butylene glycol by distillation (Claims 1 and 4); a high boiling substance removal step of removing a high boiling point component by distillation (Claims 1 and 4); and a product distillation step of obtaining purified 1,3-butylene glycol (Claim 1), wherein in the product distillation step, a product column is used at a reflux ratio of 0.1 to 1000, a liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to the product column at a feed plate (Claim 1) and distilled in the product column under a condition of a reflux ratio (Claim 1), a liquid concentrated is distilled off from a position above the feed plate of the product column (Claim 1), and 1,3-butylene glycol is extracted from a position below the feed plate of the product column (Claim 1), and, an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower (Claim 1).
The claims of Shimizu ‘093 lack a liquid feed having a 1,3-butylene glycol concentration of 97% or higher and a liquid concentrated with acetaldehyde and crotonaldehyde; and, the limitations of instant application claim 22.
Regarding the limitations of instant application claim 1, Khandurina teaches the light materials 532 are removed from the top of the column 530 above the middle feed 522, see Paras. [00250]-[00251]; Figs. 15A-15B; Table 7, where the top of the distillation column has a condenser in order to obtain a liquid from the top, see Paras. [00166];[00243];[00273], and “the term “lights” refers to compounds in a 1,3-BG sample (e.g., a bio- BG or petro-BG sample) that elute at earlier retention times than 1,3-BG, e.g., in a GC-MS chromatogram or an LC-MS chromatogram”, see Para. [0090]. Instant specification Para. [0074] states “[w]hen the relative retention time of the peak of 1,3-butylene glycol is 1.0 in the GC-MS analysis conditions, a relative retention time of a peak of acetaldehyde is from 0.3 to 0.5, and a relative retention time of a peak of crotonaldehyde is from 0.3 to 0.5”; therefore, acetaldehyde and crotonaldehyde are removed from the top of distillation column 530 as a condensed liquid, meeting the liquid concentrate acetaldehyde and crotonaldehyde distilled off from a position above the feed in instant application claim 1; and,
“[T]he term “crude bioderived 1,3-BG mixture” means a mixture of bioderived 1,3-BG (1,3-BDO) that is or includes about 50% to 90% bioderived 1,3-BG and 50% to 1%) water with one or more other impurities that are derived from a fermentation process”, see Para. [0083], where “base was added to a crude bio-BG preparation obtained after heavies distillation in a lab-scale (2L) batch distillation system as described, e.g., in Example 1”, then the product distillation is performed, where the feed of the various “Cut” samples numbers 1-8 has a 1,3-BG concentration/purity of 99.1-99.9, see Paras. [00326]-[00329], Tables 15 & 16, meeting within the liquid feed 1,3-BG concentration range in instant application claim 1.
Regarding the limitations of instant application claim 22, Khandurina teaches “FIG. 15B adds an alkali reactor 560' to the system of FIG. 15A”, where after dewatering in 510', “[a] bioderived 1,3-BG-containing product stream 514' exits the bottom of the first column and is fed to a first distillation column 520' . Heavy materials 524' (materials with boiling points higher than 1,3-BG) are removed from the bottom of the first distillation column 520', and a bioderived 1,3 BG-containing product stream 522' exits from the top of the first distillation column 520'” then the “bioderived 1,3-BG-containing product stream 522' is fed to the alkali reactor 560', which sends the stream 562' to the second distillation column 530'”, see Paras. [00250]-[00251]; Figs. 15A-15B, where “the process includes adding a base to a bioderived 1,3-BG-containing product stream before or after any one of” the distillation steps and the base is “an alkali metal compound, such as sodium hydroxide, potassium hydroxide, sodium (bi)carbonate, ammonium hydroxide, or a combination thereof”, see Paras. [0028];[00179]-[00183], meeting the alkaline reaction step and the specific sodium carbonate or sodium bicarbonate in instant application claim 22.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the claims of Shimizu ‘093 with the purification of 1,3-BG process parameters and apparatus as taught by Khandurina with a reasonable predictability of success for the purpose of efficiently producing 1,3-BG having a chemical purity of 99% or higher with an overall level of heavies of 0.8% or less, an overall level of lights of 0.2% or less, and an improved odor “for use in the cosmetic and food industries”, see Khandurina, Paras. [0022];[0028];[0072]-[0077].
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying the claims of Shimizu ‘093 to select the optimal embodiments of purification of 1,3-BG as taught by Khandurina with a reasonable predictability of success for the purpose of efficiently producing 1,3-BG having a chemical purity of 99% or higher with an overall level of heavies of 0.8% or less, an overall level of lights of 0.2% or less, and an improved odor “for use in the cosmetic and food industries”, see Khandurina, Paras. [0022];[0028];[0072]-[0077]; and MPEP 2143 I. B-D.
Claim 1 is newly rejected and claim 22 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 7 of copending Application No. 17/789,113 to Shimizu et al. (hereinafter Shimizu ‘113) in view of Khandurina et al. (WO2018183628, published 04 October 2018, hereinafter Khandurina).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 1, the claims of Shimizu ‘113 recite a method for manufacturing 1,3-butylene glycol (Claims 1 and 7), which is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid containing 1,3- butylene glycol (Claims 1 and 3), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3- butylene glycol by distillation (Claims 1 and 7); a high boiling substance removal step of removing a high boiling point component by distillation (Claims 1 and 7); and a product distillation step of obtaining purified 1,3-butylene glycol (Claim 1), wherein in the product distillation step, a product column is used (Claim 1), a liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to the product column at a feed plate and distilled in the product column under a condition of a reflux ratio higher than 0.1 (Claim 1, “higher” implies an upper limit of infinity and within the range of 6 to 500), a liquid concentrated is distilled off from a position above the feed plate of the product column (Claim 1), and 1,3-butylene glycol is extracted from a position below the feed plate of the product column (Claim 1), and an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower (Claim 1).
The claims of Shimizu ‘113 lack a liquid concentrated with acetaldehyde and crotonaldehyde is distilled off, a liquid feed having a 1,3-butylene glycol concentration of 97% or higher; and, the limitations of instant application claim 22.
The Khandurina teachings of the instant application claims 1 and 22 limitations are detailed above.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the claims of Shimizu ‘113 with the purification of 1,3-BG process parameters and apparatus as taught by Khandurina with a reasonable predictability of success for the purpose of efficiently producing 1,3-BG having a chemical purity of 99% or higher with an overall level of heavies of 0.8% or less, an overall level of lights of 0.2% or less, and an improved odor “for use in the cosmetic and food industries”, see Khandurina, Paras. [0022];[0028];[0072]-[0077].
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying the claims of Shimizu ‘113 to select the optimal embodiments of purification of 1,3-BG as taught by Khandurina with a reasonable predictability of success for the purpose of efficiently producing 1,3-BG having a chemical purity of 99% or higher with an overall level of heavies of 0.8% or less, an overall level of lights of 0.2% or less, and an improved odor “for use in the cosmetic and food industries”, see Khandurina, Paras. [0022];[0028];[0072]-[0077]; and MPEP 2143 I. B-D.
Claim 1 is newly rejected and claim 22 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 of copending Application No. 17/788,803 to Shimizu (hereinafter Shimizu ‘803) in view of Khandurina et al. (WO2018183628, published 04 October 2018, hereinafter Khandurina).
This is a provisional nonstatutory double patenting rejection.
Regarding claim 1, the claims of Shimizu ‘803 recite method for manufacturing 1,3-butylene glycol, which is a method for obtaining purified 1,3-butylene glycol from a crude reaction liquid containing 1,3- butylene glycol (Claim 1), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3- butylene glycol by distillation (Claim 1); a high boiling substance removal step of removing a high boiling point component by distillation (Claim 1); and a product distillation step of obtaining purified 1,3-butylene glycol (Claim 1), wherein in the product distillation step, a product column is used, a liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to the product column at a feed plate and distilled in the product column under a condition of a reflux ratio is 0.4 or greater (Claim 1, i.e., “greater” implies an upper limit of infinity and within the range of 6 to 500), a liquid concentrated is distilled off from a position above the feed plate of the product column (Claim 1), and 1,3-butylene glycol is extracted from a position below the feed plate of the product column (Claim 1), and the liquid feed has a 1,3-butylene glycol concentration of 97% or higher, an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower.
The claims of Shimizu ‘803 lack a reflux ratio of 6 or higher, a 1,3-butylene glycol concentration of 97% or higher; an acetaldehyde content of 500 ppm or lower, and a crotonaldehyde content of 200 ppm or lower; a liquid concentrated with acetaldehyde and crotonaldehyde is distilled off from above a feed plate, and feed plates; and, the limitations of instant application claim 22.
Regarding the limitations of instant application claim 1, Khandurina teaches the “1,3-BG-containing product stream 522 is fed to a second distillation column 530. Distillation column 530 removes light materials 532 from the top of the column 530 and a third bioderived 1,3-BG-containing product stream 534 from the bottom of column 530”, see Paras. [00250]-[00251];[00273]-[00275]; Figs. 15A-15B, where the feed 522 to column 530 is depicted in the middle of the column and bottom stream 534 is below the feed, see Figs. 15A-15B, the distillation columns include plates, see Para. [00165], and “the reflux ratio in the dewatering column, or the first, second or third distillation column in a process or system provided herein is … 6:1 or more, 7:1 or more, 8:1 or more, 9:1 or more, or 10:1 or more”, see Para. [00177], meeting a product distillation column, the liquid feed, the feed plate, within the reflux ratio range, and the 1,3-BG-containing product bottom stream below the feed stream in instant application claim 1;
The light materials 532 are removed from the top of the column 530 above the middle feed 522, see Paras. [00250]-[00251]; Figs. 15A-15B; Table 7, where the top of the distillation column has a condenser in order to obtain a liquid from the top, see Paras. [00166];[00243];[00273], and “the term “lights” refers to compounds in a 1,3-BG sample (e.g., a bio- BG or petro-BG sample) that elute at earlier retention times than 1,3-BG, e.g., in a GC-MS chromatogram or an LC-MS chromatogram”, see Para. [0090]. Instant specification Para. [0074] states “[w]hen the relative retention time of the peak of 1,3-butylene glycol is 1.0 in the GC-MS analysis conditions, a relative retention time of a peak of acetaldehyde is from 0.3 to 0.5, and a relative retention time of a peak of crotonaldehyde is from 0.3 to 0.5”; therefore, acetaldehyde and crotonaldehyde are removed from the top of distillation column 530 as a condensed liquid, meeting the liquid concentrate acetaldehyde and crotonaldehyde distilled off from a position above the feed in instant application claim 1;
“[T]he term “crude bioderived 1,3-BG mixture” means a mixture of bioderived 1,3-BG (1,3-BDO) that is or includes about 50% to 90% bioderived 1,3-BG and 50% to 1%) water with one or more other impurities that are derived from a fermentation process”, see Para. [0083], where “base was added to a crude bio-BG preparation obtained after heavies distillation in a lab-scale (2L) batch distillation system as described, e.g., in Example 1”, then the product distillation is performed, where the feed of the various “Cut” samples numbers 1-8 has a 1,3-BG concentration/purity of 99.1-99.9, see Paras. [00326]-[00329], Tables 15 & 16, meeting within the liquid feed 1,3-BG concentration range in instant application claim 1; and,
The 1,3-BG has levels of acetaldehyde and crotonaldehyde of less than 200 ppm, see Paras. [00152]-[00154], where a 99.9% purity cut of 1,3-BG can only contain up to 1000 ppm of impurities, see Paras. [00326]-[00329], Tables 15 & 16, meeting within the range of acetaldehyde and crotonaldehyde in instant application claim 1.
Regarding the limitations of instant application claim 22, Khandurina teaches “FIG. 15B adds an alkali reactor 560' to the system of FIG. 15A”, where after dewatering in 510', “[a] bioderived 1,3-BG-containing product stream 514' exits the bottom of the first column and is fed to a first distillation column 520' . Heavy materials 524' (materials with boiling points higher than 1,3-BG) are removed from the bottom of the first distillation column 520', and a bioderived 1,3 BG-containing product stream 522' exits from the top of the first distillation column 520'” then the “bioderived 1,3-BG-containing product stream 522' is fed to the alkali reactor 560', which sends the stream 562' to the second distillation column 530'”, see Paras. [00250]-[00251]; Figs. 15A-15B, where “the process includes adding a base to a bioderived 1,3-BG-containing product stream before or after any one of” the distillation steps and the base is “an alkali metal compound, such as sodium hydroxide, potassium hydroxide, sodium (bi)carbonate, ammonium hydroxide, or a combination thereof”, see Paras. [0028];[00179]-[00183], meeting the alkaline reaction step and the specific sodium carbonate or sodium bicarbonate in instant application claim 22.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the claims of Shimizu ‘803 with the purification of 1,3-BG process parameters and apparatus as taught by Khandurina with a reasonable predictability of success for the purpose of efficiently producing 1,3-BG having a chemical purity of 99% or higher with an overall level of heavies of 0.8% or less, an overall level of lights of 0.2% or less, and an improved odor “for use in the cosmetic and food industries”, see Khandurina, Paras. [0022];[0028];[0072]-[0077].
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying the claims of Shimizu ‘803 to select the optimal embodiments of purification of 1,3-BG as taught by Khandurina with a reasonable predictability of success for the purpose of efficiently producing 1,3-BG having a chemical purity of 99% or higher with an overall level of heavies of 0.8% or less, an overall level of lights of 0.2% or less, and an improved odor “for use in the cosmetic and food industries”, see Khandurina, Paras. [0022];[0028];[0072]-[0077]; and MPEP 2143 I. B-D.
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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