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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination (RCE) under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 07 August 2026 has been entered.
Status of the Claims
Claims 1-4, 6-10, 12-15 and 17-25 are pending.
Claims 24 and 25 are new.
Claims 1 and 4 are amended.
Claims 5, 11, and 16 were previously canceled.
Response to Amendments
Applicant’s amendments filed 07 August 2026 are acknowledged.
Claim Rejections - 35 USC § 103
Applicant’s amendments to claims 1 and 4 lowering the dehydration column acetaldehyde content to 140 ppm or lower and the crotonaldehyde content to 100 ppm or lower is taught by Tsuji and are not sufficient to overcome the rejection of:
Claims 1-4, 6-10, 12-15, and 17-21 and claim 23 under 35 U.S.C. 103 as being unpatentable over US 2003/0018224 A1 to Tsuji et al. (published 23 January 2003, hereinafter Tsuji) in view of WO 2018/183628 A1 Khandurina et al. (published 04 October 2018, hereinafter Khandurina), in further view of Iqbal et al. (“Appropriate selections of distillation column control variable to improve integrating material recycle response”, published online 03 August 2018, Journal of King Saud University – Engineering Sciences, Vol. 31, Pgs. 106-113, hereinafter Iqbal).
The above rejection is maintained; however, due to the addition of new claim 25, the above rejection is modified.
Applicant’s amendments to claims 1 and 4 lowering the dehydration column acetaldehyde content to 140 ppm or lower and the crotonaldehyde content to 100 ppm or lower is taught by Tsuji and are not sufficient to overcome the rejection of:
Claim 22 under 35 U.S.C. 103 as being unpatentable over US 2003/0018224 A1 to Tsuji et al. (published 23 January 2003, hereinafter Tsuji) in view of WO 2018/183628 A1 Khandurina et al. (published 04 October 2018, hereinafter Khandurina), in further view of Iqbal et al. (“Appropriate selections of distillation column control variable to improve integrating material recycle response”, published online 03 August 2018, Journal of King Saud University – Engineering Sciences, Vol. 31, Pgs. 106-113, hereinafter Iqbal), as applied to claims 1-4, 6-10, 12-15, and 17-21 and claim 23 in the 35 USC 103 rejection above, as evidenced by Daicel Corporation, (“1,3-Butylene Glycol (Cosmetic Grade)”, published October 2018, 1 Pg., hereinafter Daicel). The rejection is maintained.
Double Patenting
Applicant’s amendments to claims 1 and 4 lowering the dehydration column acetaldehyde content to 140 ppm or lower and the crotonaldehyde content to 100 ppm or lower is taught by Shimizu ‘991, and are not sufficient to overcome the rejections of:
Claims 1, 3, and 6-9 on the ground of nonstatutory double patenting as being unpatentable over claims 1-6, 8, 9, and 11-16 of copending Application No. 17/788,991 to Shimizu et al. (hereinafter Shimizu ‘991) (reference application); and,
Claim 22 on the ground of nonstatutory double patenting as being unpatentable over claim 1 and 17 of copending Application No. 17/788,991 to Shimizu et al. (hereinafter Shimizu ‘991), as applied to claims 1, 3, and 6-9 in the nonstatutory double patenting rejection above, in further view of US 2003/0018224 A1 to Tsuji et al. (published 23 January 2003, hereinafter Tsuji), as evidenced by Daicel Corporation, (“1,3-Butylene Glycol (Cosmetic Grade)”, published October 2018, 1 Pg., hereinafter Daicel), and WO 2018/183628 A1 Khandurina et al. (published 04 October 2018, hereinafter Khandurina).
Due to the issue and the grant of copending Application No. 17/788,991 to Shimizu ‘991, the rejection is withdrawn and a new ground(s) of rejection is/are provided below on the ground of Patent No. US 12,472,134 to Shimizu et al. (patented 18 November 2025, hereinafter Shimizu ‘134).
Applicant’s amendments to claims 1 and 4 lowering the dehydration column acetaldehyde content to 140 ppm or lower and the crotonaldehyde content to 100 ppm or lower is taught by Shimizu ‘113, and are not sufficient to overcome the rejections of:
Claims 1-4, 6-10, 12-15, 17-21 and 23 on the ground of nonstatutory double patenting as being unpatentable over claim over claims 1, 2, 5-11, 13, and 21-23 of copending Application 17/789,113 to Shimizu et al. (hereinafter Shimizu ‘113) in view of Iqbal et al. (“Appropriate selections of distillation column control variable to improve integrating material recycle response”, published online 03 August 2018, Journal of King Saud University – Engineering Sciences, Vol. 31, Pgs. 106-113, hereinafter Iqbal). The above rejection is maintained; however, due to the addition of new claims 24 and 25, the above rejection is modified; and,
Claim 22 on the ground of nonstatutory double patenting as being unpatentable over claim over claims 1 and 7 of copending Application 17/789,113 to Shimizu et al. (hereinafter Shimizu ‘113) in view of Iqbal et al. (“Appropriate selections of distillation column control variable to improve integrating material recycle response”, published online 03 August 2018, Journal of King Saud University – Engineering Sciences, Vol. 31, Pgs. 106-113, hereinafter Iqbal), as applied to claims 1-4, 6-10, 12-15, 17-21 and 23 in the nonstatutory double patenting rejection above, in further view of US 2003/0018224 A1 to Tsuji et al. (published 23 January 2003, hereinafter Tsuji), as evidenced by Daicel Corporation, (“1,3-Butylene Glycol (Cosmetic Grade)”, published October 2018, 1 Pg., hereinafter Daicel), and WO 2018/183628 A1 Khandurina et al. (published 04 October 2018, hereinafter Khandurina). The above rejection is maintained in modified form.
Response to Arguments
Applicant’s arguments filed 07 August 2026 have been fully considered but they are not persuasive.
Applicant’s argue that Tsuji, Khandurina, Iqbal, and Daicel do not disclose the limitations as recited in amended claim 1 and amended claim 4. These arguments have been considered but are not persuasive for the reasons set forth in the new grounds of rejection below and the response to arguments below.
In response to Applicant’s arguments on pages 6-8 of the remarks filed on 07 August 2026 regarding the unexpected results associated with the criticality regarding an acetaldehyde content (AD) of 140 ppm or lower and a crotonaldehyde content (CR) of 100 ppm or lower in “achieving 1,3-butylene glycol having superior initial boiling point, potassium permanganate test value (PMT), dry point, and 1,3-butylene glycol recovery rate” and in “achieving high-quality 1,3-butylene glycol having a high initial boiling point, a low dry point, an excellent PMT, and a low content of aldehyde impurities while maintaining a high recovery rate”.
“Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the “objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support.” In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980)”, see MPEP 716.02(d). In addition, “[t]o establish unexpected results over a claimed range, applicants should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range”, In re Hill, 284 F.2d 955, 128 USPQ 197 (CCPA 1960), see MPEP 716.02(d).
Instant application claims 1 and 4 state in the dehydration column, “the liquid feed containing 1,3-butylene glycol and water with an acetaldehyde content of [[200]] 140 ppm or lower and a crotonaldehyde content of [[130]] 100 ppm or lower”. Applicant’s argue, as stated above, this range leads to a criticality providing “1,3-butylene glycol having superior initial boiling point, potassium permanganate test value (PMT), dry point, and 1,3-butylene glycol recovery rate” and “high-quality 1,3-butylene glycol having a high initial boiling point, a low dry point, an excellent PMT, and a low content of aldehyde impurities while maintaining a high recovery rate”; however, Applicants have not provided a proper comparison to the closest prior art and have not established test points inside over the entirety of the claimed range of the acetaldehyde content and the crotonaldehyde content in order to support the argument of the criticality of the range leading to surprising and unexpected results, see MPEP 716.02(e).
The instant specification is relied upon for any comparison tests/examples. Applicants have provided a comparison between Example 18 as compared to Example 26 indicating criticality and unexpected results obtained within the as instantly claimed dehydration column acetaldehyde content (AD) of 140 ppm or lower and crotonaldehyde content (CR) of 100 ppm or lower. As indicated by the Applicant, Example 26 with an AD of 3 and a CR of 1 provides differing results as compared to Example 18 with an AD of 145 and a CR of 110, see instant application Tables 1-3.
In this case, Example 26 is the only example with an AD content and a CR content of both below 70 ppm. Examples applying the same dehydration column and product column reflux ratios of 1 are Examples 14-21, all with an AD content of 145 ppm and a CR content of 110 ppm. The AD and CR contents of Examples 14-21 are all outside the claimed range and vastly higher than the AD and CR contents of Example 26. Examples within the claimed range of an AD content of 140 ppm or lower and a CR content of 100 ppm or lower applying reflux ratios differing from Example 26 are Examples 1-3, 22, and 27, all with an AD content of 130 ppm and a CR content of 89 ppm, and Example 24 has an AD content of 85 ppm and a CR content of 71 ppm. The closest AD and CR contents as Example 26 is Example 24 with an AD content of 85 ppm and a CR content of 71 ppm; however, the reflux ratios of Example 24 differ from the reflux ratios of Example 26 and Example 18. Therefore, the instant specification does not provide support for unexpected results or the criticality of a range within the entire claimed range of between 4 ppm and 140 ppm for AD content and between 2 ppm and 100 ppm CR content applying the same dehydration column and product column reflux ratios.
Comparing Examples 18, 24, and 26, Example 24 has reflux ratios within the claimed ranges, that differ from Examples 18 and 26 and the closest AD and CR contents within the claimed ranges as compared to Example 26. Example 24 obtains a lower % BG of 99.0 than the 99.8 of Example 18 and the 99.9 or higher of Example 26, a lower boiling point of 206.7 than the 207.4 of Example 18 and the 207.6 of Example 26, a higher dry point of 208.9 than the 208.6 of Example 18 and the 208.5 of Example 26, a higher PMT value of 50 than the 40 of Example 18 and a lower PMT value than the 65 of Example 26, lower aldehyde impurities than Example 18 and higher aldehyde impurities than Example 26, and the same BG recovery of 99.9 or higher as Example 18 and Example 26. Therefore, the AD and CR contents within the claimed range is not the only factor determining the criticality to achieving 1,3-butylene glycol “having a low dry point, an excellent PMT,” and “a high recovery rate”.
The instant specification does not provide a comparison to the closest prior art and tests within the entire claimed range of between 4 ppm and 140 ppm for AD content and between 2 ppm and 100 ppm CR content applying the same dehydration column and product column reflux ratios in order to support the argument of unexpected results or the criticality of the range for the AD and CR contents, see MPEP 716.02(e). On the contrary, the instant specification appears to detail the AD and CR contents within the claimed range is not the only factor determining the criticality to achieving the above detailed results.
In addition, the fact that the inventor has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious, see Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985) and MPEP 716.02(d). It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, that a feed with a lower aldehyde content fed into a dehydration column designed to remove aldehydes would result in a product with a lower aldehyde content.
For the reasons indicated above, Applicant’s above arguments are not persuasive.
Double Patenting
Applicant’s argument on pages 7-8 of the remarks filed on 07 August 2026 that the rejections “are provisional in nature and will address the obviousness-type double patenting rejection upon indication that the claims are otherwise allowable” has been considered but is not persuasive for the reasons set forth in the double patenting rejections detailed in the previous office action dated 07 May 2026 and in the modified and new grounds of rejection below.
Maintained, Modified, and New Rejections Based on the RCE and the Amendments to the Claims in the reply filed on 07 August 2026
For clarity between the new and modified rejections, the below specific new and modified rejections are in italics.
Claim Interpretation
Many of the instant application claims state ranges as “is lower”, “lower than”, “or lower”, “or higher”, etc. Many of the instant claims do no recite a specific low limit or a specific high limit; thus, the claim limitations imply a low limit of zero and a high limit of infinity.
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 1-4, 6-10, 12-15, 17-21, and 23 stand rejected in modified form and claim 25 is rejected under 35 U.S.C. 103 as being unpatentable over US 2003/0018224 A1 to Tsuji et al. (published 23 January 2003, hereinafter Tsuji) in view of WO 2018/183628 A1 Khandurina et al. (published 04 October 2018, hereinafter Khandurina), in further view of Iqbal et al. (“Appropriate selections of distillation column control variable to improve integrating material recycle response”, published online 03 August 2018, Journal of King Saud University – Engineering Sciences, Vol. 31, Pgs. 106-113, hereinafter Iqbal).
Tsuji teaches the claims 1, 2, 4, 6-10, 12-15, 17-21, and 25 limitations of a method of producing and purifying 1,3-butylene glycol from a crude reaction liquid containing 1,3-butylene glycol, see Paras. [0037]-[0046];[0246]-[0248], Fig. 1. The 1,3-butylene glycol is produced from acetaldol and hydrogen by hydrogenation catalytic reduction of acetaldols, see Paras. [0067];[0246]. After hydrogenation the crude liquid is neutralized with sodium hydroxide, then low boiling point substances, such as the alcohols ethanol and butanol, are removed, then a feed containing preferably 10 ppm by weight or less of the aldehyde groups remaining in a hydrogenation crude mixture, water, and 1,3-butylene glycol is subjected to dehydration in tower 1-1, i.e., less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances of the crude mixture prior to dehydration, see Paras. [0065];[0093]-[0095];[0097];[0246]. The resultant crude 1,3-butylene glycol/solution to be fed* is fed into dehydration tower 1-1 at a middle location to remove generated water and subject impurities to azeotropic distillation with water for removal of low-boiling-point substances and water from the top of the column and a crude 1,3-butylene glycol containing water in an amount of 0.5% by weight or less was obtained from the bottom of the distillation tower, see Paras. [0072];[0096]-[0097];[0102]-[0105];[0246], Fig. 1, meeting:
The crude reaction liquid, most of the dehydration step, and within the aldehyde ppm range in instant application claim 1 and in instant application claim 4, and in instant application claim 25;
The crude reaction liquid in instant application claim 6 and in instant application claim 17;
The dealcoholization step in instant application claim 9 and in instant application claim 20;
From dehydration tower 1-1 the crude 1,3-butylene glycol containing water in an amount of 0.5% by weight or less bottom is fed to into a salt-removal tower 1-2, where salts, high-boiling-point substances, and a portion of 1,3-butylene glycol, total 5 parts on the basis of 100 parts of the fed solution, are discharged, as a residue, from the bottom of the salt-removal tower and from the top of the salt-removal tower, 1,3-butylene glycol, low-boiling-point substances, and a portion of high-boiling-point substances, total 95 parts, are distilled, see Para. [0246], Fig. 1, meeting the desalting step in instant application claim 8 and in instant application claim 19;
The 1,3-butylene glycol, low-boiling-point substances, and high-boiling-point substances distilled from the salt-removal tower 1-2 are fed into a middle plate of a continuous high boiling point distillation tower 1-3 including 20 plates at a reflux ratio of 1.5 for further purification of the 1,3-butylene glycol by removing high-boiling-point substances, and the high-boiling-point substances and a portion of 1,3-butylene glycol, total 20 parts, are discharged from the bottom of the distillation tower and 1,3-butylene glycol and low-boiling-point substances, total 80 parts, are distilled off from the top of the distillation tower, see Paras. [0246];[0258], Fig. 1, meeting:
The high boiling substance removal step and within the reflux ratio range in instant application claim 1, in instant application claim 2, and in instant application claim 4;
The crude reaction liquid in instant application claim 12;
The desalting step in instant application claim 14;
The dealcoholization step in instant application claim 15;
A 10% by weight sodium hydroxide aqueous solution was added to the fed solution from the continuous distillation tower 1-3 such that the concentration of sodium hydroxide in the solution was 0.2% by weight, then the feed is sent to an alkali-removal tower 1-5, where alkali, high-boiling-point substances, and a portion of 1,3-butylene glycol, total 10 parts on the basis of 100 parts of the fed solution, are discharged from the bottom of the alkali-removal tower and 1,3-butylene glycol and low-boiling-point substances, total 90 parts, are distilled from the top of the alkali-removal tower, and then fed into the subsequent final product distillation tower 1-6, see Paras. [0246]-[0247], Fig. 1, meeting:
The alkaline treatment in instant application claim 7, in instant application claim 13, and instant application claim 18;
1,3-butylene glycol and low-boiling-point substances from the top of alkali-removal tower 1-5 is fed at a middle position into the final product distillation tower 1-6 having a theoretical plate number of about 10-20, where low-boiling-point substances and a portion of 1,3-butylene glycol, total 10% by weight on the basis of 100 parts of the fed solution, are obtained as a distillate from the top of the final product distillation tower 1-6 operated at a reflux ratio of 0.5-2.0 and from the bottom of the distillation tower, 1,3-butylene glycol is obtained as a product, see Paras. [0080];[0246]-[0247], Fig. 1. Since the starting crude mixture has preferably 10 ppm by weight or less of the aldehyde groups, the resultant liquid feed to the product distillation tower 1-6 will inherently have less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde, see Paras. [0093];[00132]-[0140], Tables 2-1, 2-2, Fig. 1 and MPEP 2112, meeting:
The product distillation step and within the reflux ratio range in instant application claim 1; and,
Within the range of reflux ratios in instant application claim 21.
Tsuji also teaches distillation steps that remove water at a reflux ratio of 3 and 5, see Paras. [0307]-[0309], and distillation columns with theoretical plates, perforated plates, and actual plates, see Paras. [0079]-[0080];[0137];[0234];[0258].
Regarding the limitations of instant application claim 4, since the starting crude mixture has preferably 10 ppm by weight or less of the aldehyde groups, the resultant liquid feed to the high boiling point removal column distillation tower 1-3 will inherently have less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde, see Paras. [0093];[00132]-[0140];[0246]-[0248], Tables 2-1, 2-2, Fig. 1 and MPEP 2112, meeting within the acetaldehyde and crotonaldehyde content ppm in instant application claim 4.
Tsuji teaches the above citations in a variety of embodiments.
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 by applying “routine optimization” and “predictable results” to mix and match differing procedures, towers, reflux ratios, and steps of the five inventions detailing the production of high purity 1,3-butylene glycol, with a reasonable expectation of success. One of ordinary skill in the art would have been motivated to make these modifications 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], MPEP 2144.05 IIB, and MPEP 2144.04 VI.C.
Tsuji does not specifically teach:
The instant application claims 1 and 4 limitations of a dehydration column having feed plates and a reflux ratio of 0.3 or higher and lower than 50; and,
The limitations of instant application claims 3 and 10.
Khandurina relating to the distillation purification of 1,3-butanediol compositions, see Abstract; Paras. [0028]-[0029];[00165]-[00168]. The purification includes a dewatering step with a distillation column having plates and at a reflux ratio of 1-10 or more, see Paras. [00165];[00176]-[0178];[00274]-[00275], Table 2, meeting a dehydration column having feed plates and within the reflux ratio range in instant application claim 1 and instant application claim 4; and,
The liquid feed into the FS 300 product column 570” has a concentration of 1,3-butylene glycol of 99.60 GC area% and a content of water is 0.1711 wt.%, see Paras. [00252];[00284];[00313];[00322], Fig. 15C, Table 14, meeting and within the ranges of the limitations in instant application claim 3 and in instant application claim 10.
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 use the plated dehydration tower and the reflux ratios to obtain the desired liquid feeds and product purity as taught by Khandurina with a reasonable predictability of success for the purpose of purifying a mixed stream containing 1,3-butanediol, 1,3-BG, by utilizing one or more distillation columns to remove materials that have a higher or lower boiling point than 1,3-BG by generating streams of materials with boiling points higher or lower than 1,3-BG in order to obtain highly pure cosmetic grade, food grade, and/or pharmaceutical grade 1,3-BG, see Khandurina, Paras. [0073]-[0076];[00165]-[00169].
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 both Tsuji and Khandurina teach distillation purification of 1,3-butanediol compositions, a person of ordinary skill in the art has good reason to purify 1,3-butanediol by pursuing the known options within their technical grasp, such as adjusting the reflux ratio and plates in the distillation columns, for the benefit of efficiently purifying a mixed stream containing 1,3-BG by utilizing one or more distillation columns to remove materials that have a higher or lower boiling point than 1,3-BG by generating streams of materials with boiling points higher or lower than 1,3-BG in order to obtain highly pure cosmetic grade, food grade, and/or pharmaceutical grade 1,3-BG, see Khandurina, Paras. [0073]-[0076];[00165]-[00169], MPEP 2141, and MPEP 2144.05 I.
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.
Further, In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929) states “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree,” such as adjusting the reflux ratio, “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”.
Regarding the limitations of instant application claim 1, Tsuji teaches as depicted in Fig. 1, at the top of tower 1-6 a stream is passed through condenser 1-6-2 and is recycled back to tower 1-6, see Fig. 1; Paras. [0046];[0247].
Regarding the limitations of instant application claim 1, Khandurina teaches “vapor is returned to the first, second, or third distillation column, or combinations thereof”, see Para. [00244].
Tsuji and Khandurina do not specifically teach the instant application claim 1 limitations of the distillate recycle to a differing step wt.% amount.
Iqbal is in the known prior art field of distillation of hydrocarbons with recycle loop distillation columns while ensuring “a safe and stable column operation” by controlling “the purities/or impurities in distillate and bottoms product streams” in order to optimize the recovery of the product, see Abstract; Figs. 1, 6, 8; Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis.
Regarding the limitations of instant application claim 1, Iqbal teaches distillates from column 1 and column 2 are recycled to previous columns, see Fig. 1; Pg. 108, Col. 1, where for example column 2 is charged with 58 kmol/h and the distillate sent back to column 1 is 8 kmol/h, see Fig. 1, as calculated by the examiner (8/58) x 100 = 13.8 wt. % of the charge amount is sent to column 1, meeting the recycle and within the recycle amount range in instant application claim 1.
Tsuji and Khandurina do not teach the instant application claims 4 and 23 limitations of the bottom rate wt.%.
Regarding the limitations of instant application claim 4, Iqbal teaches column 1 is charged with 275.76 kmol/h and the bottom rate is 50.05 kmol/h, see Fig. 1; Pg. 108, Col. 1, as calculated by the examiner, (50.05/275.76) x 100 = 18.1 wt. %, meeting within the bottom rate range in instant application claim 4.
Regarding the limitations of instant application claim 23, Iqbal teaches column 1 is charged with 275.76 kmol/h and the bottom rate is 50.05 kmol/h, see Fig. 1; Pg. 108, Col. 1, as calculated by the examiner, (50.05/275.76) x 100 = 18.1 wt. %, and column 1 is charged with 269.52 kmol/h and the bottom rate is 46.73 kmol/h, see Fig. 8, as calculated by the examiner, (46.73/269.51) x 100 = 17.3 wt. %, where the flow rate of the column bottoms B1 and B2 within the distillation system is varied as a manipulative variable in order to control the recovery of the product, see Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis.
Since “a prima facie case of obviousness exists” where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” and where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05, one of ordinary skill in the art, before the effective filing date of the claimed invention, would be able to predictably determine the flow rate of the column bottom to be under 15 wt.% in order to achieve the desired product recovery based upon the charge rate into the column and other variable column parameters, see Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis, obviously meeting within the bottom rate range in instant application claim 23.
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 distillation column recycle configuration of Tsuji, as taught by Khandurina and Iqbal, and to have modified, controlled, and quantified the distillation column bottom rates of Tsuji as taught by Iqbal with a reasonable predictability of success for the purpose of efficiently purifying a hydrocarbon by distillation with high purity and a high recovery rate, see Iqbal, Abstract; Figs. 1, 6, 8; Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis; Khandurina, Paras. [0073]-[0076];[00165]-[00169].
The 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. One of ordinary skill in the art would have been capable of modifying the distillation column recycle and bottom rate of Tsuji by applying the known techniques of distillation recycle configurations and bottom rates as taught by Khandurina and Iqbal with a reasonable predictability of success for the purpose of efficiently purifying a hydrocarbon by distillation with high purity and a high recovery rate, see Iqbal, Abstract; Figs. 1, 6, 8; Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis; Khandurina, Paras. [0073]-[0076];[00165]-[00169]; and, MPEP 2143 I. B-D.
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, Khandurina, and Iqbal all teach purifying a hydrocarbon by distillation, a person of ordinary skill in the art has good reason to modify Tsuji by relying upon Khandurina and Iqbal before the effective filing date of the claimed invention for knowledge generally available within the distillation hydrocarbon purification art regarding recycle lines and bottom rates, see MPEP 2143 B & G and 2141, for the benefit of efficiently purifying a hydrocarbon by distillation with high purity and a high recovery rate, see Iqbal, Abstract; Figs. 1, 6, 8; Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis; Khandurina, Paras. [0073]-[0076];[00165]-[00169]; and, MPEP 2141 and 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 Tsuji, Khandurina, and Iqbal all teach purifying a hydrocarbon by distillation, 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 recycle lines and bottom rates teachings of Khandurina and Iqbal in the distillation purification of 1,3-BG of Tsuji.
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.
“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 recycle line concentrations, bottom rates, and concentrations of the impurities throughout the process, “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 recycle line concentrations, bottom rates, and concentrations of the impurities throughout the process, “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.
Furthermore, “[t]he discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning,” such as the column bottom rates, “does not render the old composition patentably new to the discoverer” and “the claiming of a new use, new function or unknown property”, such as the column bottom rates, “which is inherently present in the prior art does not necessarily make the claim patentable”, see MPEP 2112 I.
Claim 22 stands rejected under 35 U.S.C. 103 as being unpatentable over US 2003/0018224 A1 to Tsuji et al. (published 23 January 2003, hereinafter Tsuji) in view of WO 2018/183628 A1 Khandurina et al. (published 04 October 2018, hereinafter Khandurina), in further view of Iqbal et al. (“Appropriate selections of distillation column control variable to improve integrating material recycle response”, published online 03 August 2018, Journal of King Saud University – Engineering Sciences, Vol. 31, Pgs. 106-113, hereinafter Iqbal), as applied to claims 1-4, 6-10, 12-15, 17-21, 23, and 25 in the 35 USC 103 rejection above, as evidenced by Daicel Corporation, (“1,3-Butylene Glycol (Cosmetic Grade)”, published October 2018, 1 Pg., hereinafter Daicel).
Regarding the limitations of instant application claim 22, Tsuji currently assigned to Daicel Corporation teaches the purified 1,3-butylene glycol, see Paras. [0037]-[0046];[0246]-[0248], Fig. 1, with an initial boiling point of 206 ◦C or higher and a dry point of lower than 209 ◦C, as evidenced by Daicel, 1,3-butylene glycol with a boiling point of 207.5 ◦C, an initial boiling point of a minimum of 203 ◦C, and a dry point of a maximum of 209 ◦C, see Daicel, Pg. 1, i.e., the initial boiling point is inherently between 203 ◦C and 207.5 ◦C, see MPEP 2112, meeting within the boiling point and dry point range in instant application claim 22.
Further, as detailed above, Tsuji in view of Khandurina and Iqbal teach the purified 1,3-butylene glycol and the method of purifying the purified 1,3-butylene glycol. Therefore, with regard to the instant application claim 22 functional limitations of “wherein the purified 1,3-butylene glycol has an initial boiling point of 206 ◦C or higher and a dry point of lower than 209 ◦C”, Tsuji in view of Khandurina and Iqbal teach an identical or a substantially identical purified 1,3-butylene glycol purified by an identical or a substantially identical method as instantly claimed. As a result, a prima facie case of either anticipation or obviousness has been established, where ““[p]roducts of identical chemical composition can not have mutually exclusive properties”, see In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990), and a chemical composition and its properties are inseparable, see MPEP 2112. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present.
Since Tsuji in view of Khandurina and Iqbal teach an identical or a substantially identical purified 1,3-butylene glycol purified by an identical or a substantially identical method as instantly claimed, the purified 1,3-butylene glycol will inherently possess the functional properties of an initial boiling point of 206 ◦C or higher and a dry point of lower than 209 ◦C. In addition, ““the discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer.” Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). Thus the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977)”, see MPEP 2112 I, meeting inherently within the boiling point and dry point range in instant application claim 22.
Tsuji does not teach:
The instant application claim 22 limitation of wherein the method has a 1,3-butylene glycol recovery rate of 99% or higher.
Regarding the limitations of instant application claim 22, Khandurina teaches “[t]he distillation can be carried out with a distillation system provided herein to produce a purified bioderived 1,3-BG product. The purified bioderived 1,3-BG product can be or include greater than 90%, 92%, 94%, 96%, 97%, 98%, 99%, 99.5%,99.7% or 99.9% bioderived 1,3-BG (1,3- BDO) on a weight/weight basis” and “[t]he recovery of bioderived 1,3-BG in the purified bioderived 1,3-BG (1,3-BDO) product can be calculated as a percentage of the amount of bioderived 1,3-BG (1,3-BDO) in the purified bioderived 1,3-BG product divided by the amount of bioderived 1,3-BG or target compound in the crude bioderived 1,3-BG mixture that was purified”, see Para. [00165], where “the 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”, see Para. [0083], as calculated by the examiner, the precent recovery of 1,3-BG may be (90% purified 1,3-BG/90% crude 1,3-BG) = 100% recovery of 1,3-BG, meeting within the range of recovery in instant application claim 22.
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 recovery rate of Tsuji to use the distillation parameters and recovery rate as taught by Khandurina with a reasonable predictability of success for the purpose of efficiently purifying 1,3-BG with high purity and a high recovery rate by using recycle loops and the optimal distillation parameters, see Khandurina, Paras. [0073]-[0076];[00165]-[00169];[00244].
The 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. One of ordinary skill in the art would have been capable of modifying the distillation column recycle and recovery rate of Tsuji by applying the known techniques of distillation recycle configurations as taught by Khandurina with a reasonable predictability of success for the purpose of efficiently purifying 1,3-BG with high purity and a high recovery rate by using recycle loops and the optimal distillation parameters, see Khandurina, Paras. [0073]-[0076];[00165]-[00169];[00244]; and, MPEP 2143 I. B-D.
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 Khandurina both teach purifying 1,3-BG by distillation, a person of ordinary skill in the art has good reason to modify Tsuji by relying upon Khandurina before the effective filing date of the claimed invention for knowledge generally available within the distillation 1,3-BG purification art regarding recycle lines, see MPEP 2143 B & G and 2141, for the benefit of efficiently purifying 1,3-BG with high purity and a high recovery rate by using recycle loops and the optimal distillation parameters, see Khandurina, Paras. [0073]-[0076];[00165]-[00169];[00244]; and, MPEP 2141 and 2143 I. B-D.
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.
“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 recycle line concentrations to improve recovery rates, “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 recycle line concentrations to improve recovery rates, “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.
Claim 24 is rejected under 35 U.S.C. 103 as being unpatentable over US 2003/0018224 A1 to Tsuji et al. (published 23 January 2003, hereinafter Tsuji) in view of WO 2018/183628 A1 Khandurina et al. (published 04 October 2018, hereinafter Khandurina), in further view of Iqbal et al. (“Appropriate selections of distillation column control variable to improve integrating material recycle response”, published online 03 August 2018, Journal of King Saud University – Engineering Sciences, Vol. 31, Pgs. 106-113, hereinafter Iqbal), as applied to claims 1-4, 6-10, 12-15, 17-21, 23, and 25 in the 35 USC 103 rejection above, in further view of US 2018/0273459 to Shimizu (published 27 September 2018, hereinafter Shimizu ‘459).
Regarding the limitations of instant application claim 24, Tsuji teaches after hydrogenation the crude liquid is neutralized with sodium hydroxide, then low boiling point substances, such as the alcohols ethanol and butanol, are removed, then a feed containing preferably 10 ppm by weight or less of the aldehyde groups remaining in a hydrogenation crude mixture, water, and 1,3-butylene glycol is subjected to dehydration in tower 1-1, i.e., less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the low-boiling-point substances of the crude mixture prior to dehydration, see Paras. [0065]-[0066];[0093]-[0095];[0097];[0246], where due to the low amounts of acetaldehyde and crotonaldehyde the 1,3-butylene glycol product exhibits a “potassium permanganate color-fading time of at least 15 minutes, preferably at least 25 minutes, more preferably at least 35 minutes” and low odor, see Paras. [0065]-[0071];[0131]-[0137], Tables 2-1 and 2-2, meeting:
The feed to the dehydration tower comprises 1,3-butylene glycol and water with acetaldehyde and crotonaldehyde in instant application claim 24.
Regarding the limitations of instant application claim 24, Khandurina teaches the feed into the dehydration column is a “crude bioderived 1,3-BG mixture” having “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”, and/or “bioderived 1,3-BG that has been partially purified using one or more processes”, “such as a bioderived 1,3-BG (1,3-BDO) product stream from a dewatering column”, see Paras. [0083]-[0086];[00174]-[00178];[00200];[00273], where the impurities in the crude bioderived 1,3-BG are “detectable levels of a compound such as acetaldehyde, … diacetyl, 2-butenal (crotonaldehyde)” and the purified bioderived 1,3-BG has “a level of less than 1 ppm” of “acetaldehyde, … diacetyl, 2-butenal (crotonaldehyde)” and low odor, see Paras. [00143];[00152]-[00154], Table 1, meeting:
The feed to the dehydration tower comprises 1,3-butylene glycol and water with acetaldehyde and crotonaldehyde in instant application claim 24.
Tsuji does not specifically teach:
Within the instant application claim 24 range of extremely low levels of acetaldehyde and crotonaldehyde contents.
Shimizu ‘459 is in the known prior art field of methods “capable of industrially and efficiently producing” a product “having a good potassium permanganate test value without a large cost” by removing crotonaldehyde and acetaldehyde from the process, see Abstract; Paras. [0003]-[0005];[0009]-[0010], and is applied to teach the same.
Regarding the limitations of instant application claim 24, Shimizu ‘459 teaches the starting crude reaction mixture contains water, a lower limit of 1 ppm by mass of acetaldehyde, and a lover limit of 0 ppm by mass of crotonaldehyde, see Paras. [0065]-[0070]; Claims 1, 9-11, where the reaction mixture is present in reaction vessel 1 then sent via line 16 to evaporator 2 which separates water as a vapor in line 17 and as a residue in line 18 and line 17 is eventually forwarded to “dehydration column” 5 and through further residual “acetaldehyde removal column” 9 and residual “crotonaldehyde removal column” 10, see Paras. [0059];[0073];[0076]-[0080];[0088];[0104]; Fig. 1, in order to improve “the potassium permanganate test value” of the product, see Paras. [0010];[0040];[0086]-[0089], meeting:
The feed to the dehydration tower comprises the product compound and water with acetaldehyde and crotonaldehyde within the low ppm ranges in instant application claim 24.
Since “a prima facie case of obviousness exists” where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” and where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05, one of ordinary skill in the art, before the effective filing date of the claimed invention, would be able to modify the less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the dehydration column of Tsuji in order to predictably determine the low levels of acetaldehyde and crotonaldehyde in the dehydration column, as taught by Shimizu ‘459, in order to efficiently produce a product “having a good potassium permanganate test value without a large cost”, see Shimizu ‘459, Abstract; Paras. [0003]-[0005];[0009]-[0010];[0040];[0086]-[0089].
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 less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the dehydration column of Tsuji to use acetaldehyde and crotonaldehyde concentrations as taught by Shimizu ‘459 with a reasonable predictability of success for the purpose of efficiently producing a product “having a good potassium permanganate test value without a large cost”, see Shimizu ‘459, Abstract; Paras. [0003]-[0005];[0009]-[0010];[0040];[0086]-[0089].
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 less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde in the dehydration column of Tsuji by applying the known technique of the extremely low acetaldehyde and crotonaldehyde concentrations as taught by Shimizu ‘459 with a reasonable predictability of success for the purpose of efficiently producing a product “having a good potassium permanganate test value without a large cost”, see Shimizu ‘459, Abstract; Paras. [0003]-[0005];[0009]-[0010];[0040];[0086]-[0089]; and MPEP 2143 I. B-D.
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 Shimizu ‘459 both are directed to the problem to be solved of limiting aldehydes in the purification process in order to produce a product with a good potassium permanganate test value, see MPEP 2141.01(a), a person of ordinary skill in the art has good reason to modify Tsuji by relying upon Shimizu ‘459 before the effective filing date of the claimed invention for knowledge generally available within the product distillation purification in order to obtain a product with a good potassium permanganate test value art, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing a product “having a good potassium permanganate test value without a large cost”, see Shimizu ‘459, Abstract; Paras. [0003]-[0005];[0009]-[0010];[0040];[0086]-[0089]; and, MPEP 2141 and 2143 I. B-D.
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, “[t]he 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 aldehydes throughout the process, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), 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, 3, and 6-9 are newly rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6, 8, 9, and 11-16 of U.S. Patent No. 12472134 to Shimizu et al. (patented 18 November 2025, hereinafter Shimizu ‘134).
Although the claims at issue are not identical, they are not patentably distinct from each other.
Regarding claim 1, the claims of Shimizu ‘134 recite a method for manufacturing 1,3-butylene glycol (Claim 1), from a crude reaction liquid containing 1,3-butylene glycol (Claims 1 & 2), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3-butylene glycol by distillation; a high boiling substance removal step of removing a high boiling point component by distillation (Claims 1 & 2); and a product distillation step of obtaining purified 1,3-butylene glycol (Claim 1), wherein in the dehydration step, a dehydration column is used, a liquid feed is fed to the dehydration column at a feed plate and distilled in the dehydration column (Claims 1 & 8), and a liquid concentrated with a low boiling point component containing water is distilled off from at a position above the feed plate of the dehydration column (Claims 1 & 8), the liquid feed containing 1,3-butylene glycol and water with an acetaldehyde content of 140 ppm or lower and a crotonaldehyde content of 100 ppm or lower (Claims 1 & 6), in the product distillation step, a product column is used, a 1,3-butylene glycol liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to a feed plate of the product column and distilled in the product column under a condition of a reflux ratio of higher than 0.1 and 1000 or lower (Claims 1 & 13), a liquid concentrated with a low boiling point component is distilled off from a position above the feed plate of 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), the 1,3-butylene glycol liquid feed having an acetaldehyde content of 40 ppm or lower and a crotonaldehyde content of 30 ppm or lower (Claims 1 & 11), the dehydration column has a reflux ratio of 0.3 or higher and lower than 50 (Claim 1), at least a portion of a distillate from the product column is recycled to a step prior to the product distillation step (Claims 14-16), and the amount of the distillate recycled is 0.01 wt.% or higher and lower than 30 wt.% with respect to the charged amount into the product column (Claims 12 & 14-16).
Regarding claim 3, the claims of Shimizu ‘134 recite wherein the liquid feed into the product column has a concentration of 1,3-butylene glycol of 90 GC area% or higher, and a content of water is 3 wt.% or lower (Claim 9).
Regarding claim 6, the claims of Shimizu ‘134 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).
Regarding claim 7, the claims of Shimizu ‘134 recite further comprising an alkaline treatment step of treating a process stream containing 1,3-butylene glycol with a base (Clam 3).
Regarding claim 8, the claims of Shimizu ‘134 recite further comprising a desalting step of removing a salt in a process stream containing 1,3-butylene glycol (Claim 4).
Regarding claim 9, the claims of Shimizu ‘134 recite further comprising a dealcoholization step of removing a low boiling substance containing alcohols in a process stream containing 1,3- butylene glycol (Claim 5).
Regarding claim 24, the claim of Shimizu ‘134 recite wherein the liquid feed contains 1,3-butylene glycol and water with an acetaldehyde content of 3 ppm or lower and a crotonaldehyde content of 1 ppm or lower (Claims 1 & 6).
Claims 2, 10, 12-15, and 21 are newly rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 and 9 of U.S. Patent No. 12472134 to Shimizu et al. (patented 18 November 2025, hereinafter Shimizu ‘134), as applied in the nonstatutory double patenting rejection of claims 1, 3, and 6-9 above, in view of US 2003/0018224 A1 to Tsuji et al. (published 23 January 20023, hereinafter Tsuji).
Regarding claim 2, the claims of Shimizu ‘134 lack wherein in the high boiling substance removal step, a high boiling substance removal column is used, a liquid feed containing 1,3-butylene glycol obtained through the dehydration step is fed into a feed plate of the high boiling substance removal column and distilled in the high boiling substance removal column under a condition of a reflux ratio of 0.02 or higher, higher-purity 1,3-butylene glycol is distilled off from a position above the feed plate, and a liquid concentrated with the high boiling point component is extracted from a position below the feed plate of the high boiling substance removal column.
Regarding claim 21, the claims of Shimizu ‘134 lack the reflux ratio of the high boiling substance removal step.
Regarding the limitations of claims 2 and 21, Tsuji teaches the 1,3-butylene glycol, low-boiling-point substances, and high-boiling-point substances distilled from the salt-removal tower 1-2 are fed into a middle plate of a continuous high boiling point distillation tower 1-3 including 20 plates at a reflux ratio of 1.5 for further purification of the 1,3-butylene glycol by removing high-boiling-point substances, and the high-boiling-point substances and a portion of 1,3-butylene glycol, total 20 parts, are discharged from the bottom of the distillation tower and 1,3-butylene glycol and low-boiling-point substances, total 80 parts, are distilled off from the top of the distillation tower, see Paras. [0246];[0258], Fig. 1, meeting:
The high boiling substance removal step and within the reflux ratio range in instant application claim 2 and in instant application claim 21.
Regarding claim 10, the claims of Shimizu ‘134 recite wherein the liquid feed into the product column has a concentration of 1,3-butylene glycol of 90 GC area% or higher, and a content of water is 3 wt.% or lower (Claim 9).
Regarding claim 12, the claims of Shimizu ‘134 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).
Regarding claim 13, the claims of Shimizu ‘134 recite further comprising an alkaline treatment step of treating a process stream containing 1,3-butylene glycol with a base (Clam 3).
Regarding claim 14, the claims of Shimizu ‘134 recite further comprising a desalting step of removing a salt in a process stream containing 1,3-butylene glycol (Claim 4).
Regarding claim 15, the claims of Shimizu ‘134 recite further comprising a dealcoholization step of removing a low boiling substance containing alcohols in a process stream containing 1,3- butylene glycol (Claim 5).
Regarding claim 21, the claim of Shimizu ‘134 recite the reflux ratio in the product distillation step is 0.5 or higher and 1000 or lower (Claims 1 & 6).
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 ‘134 to use the high boiling point tower process and the reflux ratios as taught by Tsuji to obtain the desired liquid feeds and product purity with a reasonable predictability of success for the purpose of purifying a mixed stream containing 1,3-butanediol, 1,3-BG, by utilizing one or more distillation columns to remove materials that have a higher or lower boiling point than 1,3-BG by generating streams of materials with boiling points higher or lower than 1,3-BG in order to obtain highly pure cosmetic grade and/or pharmaceutical grade 1,3-BG exhibiting high purity and a “sufficiently long potassium permanganate color-fading time”, see Tsuji, Abstract; Paras. [0081];[0318]-[0323].
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 both the claims of Shimizu ‘134 and Tsuji teach distillation purification of 1,3-butanediol compositions, a person of ordinary skill in the art has good reason to purify 1,3-butanediol by pursuing the known options within their technical grasp, such as adjusting the reflux ratio and plates in the distillation columns, for the benefit of efficiently purifying a mixed stream containing 1,3-BG by utilizing one or more distillation columns to remove materials that have a higher or lower boiling point than 1,3-BG by generating streams of materials with boiling points higher or lower than 1,3-BG in order to obtain highly pure cosmetic grade and/or pharmaceutical grade 1,3-BG exhibiting high purity and a “sufficiently long potassium permanganate color-fading time”, see Tsuji, Abstract; Paras. [0081];[0318]-[0323], MPEP 2141, and MPEP 2144.05 I.
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.
Claims 4, 17-20, 23, and 25 are newly rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 and 8 of U.S. Patent No. 12472134 to Shimizu et al. (patented 18 November 2025, hereinafter Shimizu ‘134) in view of US 2003/0018224 A1 to Tsuji et al. (published 23 January 20023, hereinafter Tsuji).
Regarding claim 4, the claims of Shimizu ‘134 recite a method for manufacturing 1,3-butylene glycol (Claim 1), from a crude reaction liquid containing 1,3-butylene glycol (Claims 1 & 2), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3-butylene glycol by distillation; a high boiling substance removal step of removing a high boiling point component by distillation (Claims 1 & 2); wherein in the dehydration step, a dehydration column is used, a liquid feed is fed to the dehydration column at a feed plate and distilled in the dehydration column (Claims 1 & 8), and a liquid concentrated with a low boiling point component containing water is distilled off from at a position above the feed plate of the dehydration column (Claims 1 & 8), the liquid feed containing 1,3-butylene glycol and water with an acetaldehyde content of 140 ppm or lower and a crotonaldehyde content of 100 ppm or lower (Claims 1 & 6), the dehydration column has a reflux ratio of 0.3 or higher and lower than 50 (Claim 1).
Regarding claim 4, the claims of Shimizu ‘134 lack in the high boiling substance removal step, a high boiling substance removal column is used, a liquid feed containing 1,3-butylene glycol obtained through the dehydration step is fed into a feed plate of the high boiling substance removal column and distilled in the high boiling substance removal column under a condition of a reflux ratio of higher than 0.02 and 100 or lower, higher- purity 1,3-butylene glycol is distilled off from a position above the feed plate, and a liquid concentrated with the high boiling point component is extracted from a position below the feed plate of the high boiling substance removal column, the 1,3-butylene glycol liquid feed having an acetaldehyde content of 50 ppm or lower and a crotonaldehyde content of 40 ppm or lower, and a bottom rate of the high boiling substance removal column is lower than 30 wt.%.
Regarding instant application claim 23, the claims of Shimizu ‘134 lack the bott9om rate %.
The high boiling point substance removal teachings of Tsuji are detailed above.
Regarding the limitations of instant application claim 4, Tsuji further teaches since the starting crude mixture has preferably 10 ppm by weight or less of the aldehyde groups, the resultant liquid feed to the high boiling point removal column distillation tower 1-3 will inherently have less than 10 ppm by weight of a mixture of both acetaldehyde and crotonaldehyde, see Paras. [0093];[00132]-[0140];[0246]-[0248], Tables 2-1, 2-2, Fig. 1 and MPEP 2112, meeting within the acetaldehyde and crotonaldehyde content ppm in instant application claim 4.
Regarding the limitations of instant application claim 4, Iqbal teaches column 1 is charged with 275.76 kmol/h and the bottom rate is 50.05 kmol/h, see Fig. 1; Pg. 108, Col. 1, as calculated by the examiner, (50.05/275.76) x 100 = 18.1 wt. %, meeting within the bottom rate range in instant application claim 4.
Regarding the limitations of instant application claim 23, Iqbal teaches column 1 is charged with 275.76 kmol/h and the bottom rate is 50.05 kmol/h, see Fig. 1; Pg. 108, Col. 1, as calculated by the examiner, (50.05/275.76) x 100 = 18.1 wt. %, and column 1 is charged with 269.52 kmol/h and the bottom rate is 46.73 kmol/h, see Fig. 8, as calculated by the examiner, (46.73/269.51) x 100 = 17.3 wt. %, where the flow rate of the column bottoms B1 and B2 within the distillation system is varied as a manipulative variable in order to control the recovery of the product, see Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis.
Since “a prima facie case of obviousness exists” where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” and where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05, one of ordinary skill in the art, before the effective filing date of the claimed invention, would be able to predictably determine the flow rate of the column bottom to be under 15 wt.% in order to achieve the desired product recovery based upon the charge rate into the column and other variable column parameters, see Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis, obviously meeting within the bottom rate range in instant application claim 23.
Regarding claim 17, the claims of Shimizu ‘134 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).
Regarding claim 18, the claims of Shimizu ‘134 recite further comprising an alkaline treatment step of treating a process stream containing 1,3-butylene glycol with a base (Clam 3).
Regarding claim 19, the claims of Shimizu ‘134 recite further comprising a desalting step of removing a salt in a process stream containing 1,3-butylene glycol (Claim 4).
Regarding claim 20, the claims of Shimizu ‘134 recite further comprising a dealcoholization step of removing a low boiling substance containing alcohols in a process stream containing 1,3- butylene glycol (Claim 5).
Regarding claim 25, the claims of Shimizu ‘134 recite wherein the liquid feed contains 1,3-butylene glycol and water with an acetaldehyde content of 130 ppm or lower and a crotonaldehyde content of 90 ppm or lower (Claims 1 & 6).
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 ‘134 to use the high boiling point tower process and the reflux ratios as taught by Tsuji to obtain the desired liquid feeds and product purity with a reasonable predictability of success for the purpose of purifying a mixed stream containing 1,3-butanediol, 1,3-BG, by utilizing one or more distillation columns to remove materials that have a higher or lower boiling point than 1,3-BG by generating streams of materials with boiling points higher or lower than 1,3-BG in order to obtain highly pure cosmetic grade and/or pharmaceutical grade 1,3-BG exhibiting high purity and a “sufficiently long potassium permanganate color-fading time”, see Tsuji, Abstract; Paras. [0081];[0318]-[0323].
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 both the claims of Shimizu ‘134 and Tsuji teach distillation purification of 1,3-butanediol compositions, a person of ordinary skill in the art has good reason to purify 1,3-butanediol by pursuing the known options within their technical grasp, such as adjusting the reflux ratio and plates in the distillation columns, for the benefit of efficiently purifying a mixed stream containing 1,3-BG by utilizing one or more distillation columns to remove materials that have a higher or lower boiling point than 1,3-BG by generating streams of materials with boiling points higher or lower than 1,3-BG in order to obtain highly pure cosmetic grade and/or pharmaceutical grade 1,3-BG exhibiting high purity and a “sufficiently long potassium permanganate color-fading time”, see Tsuji, Abstract; Paras. [0081];[0318]-[0323], MPEP 2141, and MPEP 2144.05 I.
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 distillation column recycle configuration of the claims of Shimizu ‘134, as taught by Iqbal, and to have modified, controlled, and quantified the distillation column bottom rates of the claims of Shimizu ‘134 as taught by Iqbal with a reasonable predictability of success for the purpose of efficiently purifying a hydrocarbon by distillation with high purity and a high recovery rate, see Iqbal, Abstract; Figs. 1, 6, 8; Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis.
The 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. One of ordinary skill in the art would have been capable of modifying the distillation column recycle and bottom rate of the claims of Shimizu ‘134 by applying the known techniques of distillation recycle configurations and bottom rates as taught by Iqbal with a reasonable predictability of success for the purpose of efficiently purifying a hydrocarbon by distillation with high purity and a high recovery rate, see Iqbal, Abstract; Figs. 1, 6, 8; Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis; and, MPEP 2143 I. B-D.
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.
Claim 22 is newly rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 17 of U.S. Patent No. 12472134 to Shimizu et al. (patented 18 November 2025, hereinafter Shimizu ‘134), as applied in the nonstatutory double patenting rejection of claims 1, 3, and 6-9 above, in view of US 2003/0018224 A1 to Tsuji et al. (published 23 January 20023, hereinafter Tsuji), as evidenced by Daicel Corporation, (“1,3-Butylene Glycol (Cosmetic Grade)”, published October 2018, 1 Pg., hereinafter Daicel), and WO 2018/183628 A1 Khandurina et al. (published 04 October 2018, hereinafter Khandurina).
Regarding the limitations of instant application claim 22, the claims of Shimizu ‘134 recite the purified 1,3-butylene glycol has an initial boiling point of 206 ◦C or higher (Claim 17).
The claims of Shimizu ‘134 do not recite the instant application claim 22 limitations of a dry point of lower than 209 ◦C and wherein the method has a 1,3-butylene glycol recovery rate of 99% or higher.
Regarding the limitations of instant application claim 22, Tsuji currently assigned to Daicel Corporation teaches the purified 1,3-butylene glycol, see Paras. [0037]-[0046];[0246]-[0248], Fig. 1, with an initial boiling point of 206 ◦C or higher and a dry point of lower than 209 ◦C, as evidenced by Daicel, 1,3-butylene glycol with a boiling point of 207.5 ◦C, an initial boiling point of a minimum of 203 ◦C, and a dry point of a maximum of 209 ◦C, see Daicel, Pg. 1, i.e., the initial boiling point is inherently between 203 ◦C and 207.5 ◦C, see MPEP 2112, meeting within the boiling point and dry point range in instant application claim 22.
Further, as detailed above, the claims of Shimizu ‘134 teach the purified 1,3-butylene glycol and the method of purifying the purified 1,3-butylene glycol. Therefore, with regard to the instant application claim 22 functional limitations of “wherein the purified 1,3-butylene glycol has an initial boiling point of 206 ◦C or higher and a dry point of lower than 209 ◦C”, the claims of Shimizu ‘134 teach an identical or a substantially identical purified 1,3-butylene glycol purified by an identical or a substantially identical method as instantly claimed. As a result, a prima facie case of either anticipation or obviousness has been established, where ““[p]roducts of identical chemical composition can not have mutually exclusive properties”, see In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990), and a chemical composition and its properties are inseparable, see MPEP 2112. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present.
Since the claims of Shimizu ‘134 teach an identical or a substantially identical purified 1,3-butylene glycol purified by an identical or a substantially identical method as instantly claimed, the purified 1,3-butylene glycol will inherently possess the functional properties of an initial boiling point of 206 ◦C or higher and a dry point of lower than 209 ◦C. In addition, ““the discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer.” Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). Thus the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977)”, see MPEP 2112 I, meeting inherently within the boiling point and dry point range in instant application claim 22.
Regarding the limitations of instant application claim 22, Khandurina teaches “[t]he distillation can be carried out with a distillation system provided herein to produce a purified bioderived 1,3-BG product. The purified bioderived 1,3-BG product can be or include greater than 90%, 92%, 94%, 96%, 97%, 98%, 99%, 99.5%,99.7% or 99.9% bioderived 1,3-BG (1,3- BDO) on a weight/weight basis” and “[t]he recovery of bioderived 1,3-BG in the purified bioderived 1,3-BG (1,3-BDO) product can be calculated as a percentage of the amount of bioderived 1,3-BG (1,3-BDO) in the purified bioderived 1,3-BG product divided by the amount of bioderived 1,3-BG or target compound in the crude bioderived 1,3-BG mixture that was purified”, see Para. [00165], where “the 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”, see Para. [0083], as calculated by the examiner, the precent recovery of 1,3-BG may be (90% purified 1,3-BG/90% crude 1,3-BG) = 100% recovery of 1,3-BG, meeting within the range of recovery in instant application claim 22.
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 boiling point, dry point, and recovery rate of the claims of Shimizu ‘134 by applying the recycle lines, distillation parameters, and recovery rate as taught by Tsuji and Khandurina with a reasonable predictability of success for the purpose of efficiently purifying 1,3-BG with high purity and a high recovery rate by using recycle loops and the optimal distillation parameters, see Khandurina, Paras. [0073]-[0076];[00165]-[00169];[00244].
The 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. One of ordinary skill in the art would have been capable of modifying the distillation column recycle and recovery rate of the claims of Shimizu ‘134 by applying the known techniques of distillation recycle and configurations as taught by Tsuji and Khandurina with a reasonable predictability of success for the purpose of efficiently purifying 1,3-BG with high purity and a high recovery rate by using recycle loops and the optimal distillation parameters, see Khandurina, Paras. [0073]-[0076];[00165]-[00169];[00244]; and, MPEP 2143 I. B-D.
Claims 1-4, 6-10, 12-15, 17-21 and 23 stand provisionally rejected in modified form and claims 24 and 25 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim over claims 1, 2, 5-11, 13, 21-23, and 25 of copending Application 17/789,113 to Shimizu et al. (hereinafter Shimizu ‘113) in view of Iqbal et al. (“Appropriate selections of distillation column control variable to improve integrating material recycle response”, published online 03 August 2018, Journal of King Saud University – Engineering Sciences, Vol. 31, Pgs. 106-113, hereinafter Iqbal).
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 & 7), from a crude reaction liquid containing 1,3- butylene glycol (Claims 1 & 7), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3- butylene glycol by distillation; a high boiling substance removal step of removing a high boiling point component by distillation (Claims 1, 7 & 8); and a product distillation step of obtaining purified 1,3-butylene glycol (Claims 1 & 8), wherein in the dehydration step, a dehydration column is used, a liquid feed is fed to the dehydration column at a feed plate and distilled in the dehydration column (Claims 1, 7 & 13), and a liquid concentrated with a low boiling point component containing water is distilled off from at a position above the feed plate of the dehydration column (Claims 1, 7 & 13), the liquid feed containing 1,3-butylene glycol and water with an acetaldehyde content of 140 ppm or lower and a crotonaldehyde content of 100 ppm or lower (Claims 1, 7, & 25), in the product distillation step, a product column is used, a 1,3-butylene glycol liquid feed obtained through the dehydration step and the high boiling substance removal step is fed to a feed plate of the product column and distilled in the product column under a condition of a reflux ratio of higher than 0.1 and 1000 or lower (Claims 1, 5 & 23), a liquid concentrated with a low boiling point component 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), the 1,3-butylene glycol liquid feed having an acetaldehyde content of 40 ppm or lower and a crotonaldehyde content of 30 ppm or lower (Claim 1), and the dehydration column has a reflux ratio of 0.3 or higher and lower than 50 (Claims 1, 7 & 21), at least a portion of a distillate from the product column is recycled to a step prior to the product distillation step (Claim 6).
Regarding claim 2, the claims of Shimizu ‘113 recite wherein in the high boiling substance removal step, a high boiling substance removal column is used in which a liquid feed containing 1,3-butylene glycol obtained through the dehydration step is fed into a feed plate of the high boiling substance removal column and distilled in the high boiling substance removal column under a condition of a reflux ratio of 0.02 or higher (Claims 1, 7, 13 & 22), higher-purity 1, 3-butylene glycol is distilled off from a position above the feed plate, and a liquid concentrated with the high boiling point component is extracted from below the feed plate of the high boiling substance removal column (Claims 1, 7 & 13).
Regarding claims 3 and 10, the claims of Shimizu ‘113 recite wherein the liquid feed into the product column has a concentration of 1,3-butylene glycol of 90 GC area% or higher, and a content of water is 3 wt.% or lower (Claim 2).
Regarding claim 4, the claims of Shimizu ‘113 recite a method for manufacturing 1,3-butylene glycol, from a crude reaction liquid containing 1,3-butylene glycol (Claims 1 & 7), the method comprising: a dehydration step of removing water from the crude reaction liquid containing 1,3- butylene glycol by distillation, and a high boiling substance removal step of removing a high boiling point component by distillation (Claims 1 & 7), wherein in the dehydration step, a dehydration column is used, a liquid feed is fed to the dehydration column at a feed plate and distilled in the dehydration column (Claims 1, 7 & 13), and a liquid concentrated with a low boiling point component containing water is distilled off from at a position above the feed plate of the dehydration column (Claims 1 & 7), the liquid feed containing 1,3-butylene glycol and water with an acetaldehyde content of 140 ppm or lower and a crotonaldehyde content of 100 ppm or lower (Claims 1 & 7), in the high boiling substance removal step, a high boiling substance removal column is used, a liquid feed containing 1,3-butylene glycol obtained through the dehydration step is fed into a feed plate of the high boiling substance removal column and distilled in the high boiling substance removal column under a condition of a reflux ratio of higher than 0.02 and 100 or lower, higher-purity 1,3-butylene glycol is distilled off from a position above the feed plate, and a liquid concentrated with the high boiling point component is extracted from a position below the feed plate of the high boiling substance removal column (Claims 1, 7, 13 & 22), the 1,3-butylene glycol liquid feed having an acetaldehyde content of 50 ppm or lower and a crotonaldehyde content of 40 ppm or lower (Claims 1 and 7, i.e., the liquid feed in to the high boiling point column from the dehydration column will inherently have an acetaldehyde content of 1000 ppm or lower and a crotonaldehyde content of 400 ppm or lower, see MPEP 2112), and the dehydration column has a reflux ratio of 0.3 or higher and lower than 50 (Claims 1, 7 & 21).
Regarding claims 6, 12, and 17, 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).
Regarding claims 7, 13, and 18, the claims of Shimizu ‘113 recite further comprising an alkaline treatment step of treating a process stream containing 1,3-butylene glycol with a base (Clam 9).
Regarding claims 8, 14, and 19, the claims of Shimizu ‘113 recite further comprising a desalting step of removing a salt in a process stream containing 1,3-butylene glycol (Claim 10).
Regarding claims 9, 15, and 20, the claims of Shimizu ‘113 recite further comprising a dealcoholization step of removing a low boiling substance containing alcohols in a process stream containing 1,3- butylene glycol (Claim 11).
Regarding claim 21, the claims of Shimizu ‘113 recite wherein the reflux ratio in the high boiling substance removal step is 0.05 or higher, and the reflux ratio in the product distillation step is 0.5 or higher and 1000 or lower (Claims 1, 7, 22 & 23, i.e. higher than 0.02 and 0.1 has an upper limit of infinity).
Regarding claims 24 and 25, the claims of Shimizu ‘113 recite wherein the liquid feed contains 1,3-butylene glycol and water with an acetaldehyde content of 3 ppm or lower and a crotonaldehyde content of 1 ppm or lower and wherein the liquid feed contains 1,3-butylene glycol and water with an acetaldehyde content of 130 ppm or lower (Claims 1, 7, & 25).
The claims of Shimizu ‘113 do not recite:
The instant application claim 1 limitations of the amount of the distillate recycled is 0.01 wt.% or higher and lower than 30 wt.% with respect to the charged amount into the product column;
The instant application claim 4 limitations of a bottom rate of the high boiling substance removal column is lower than 30 wt.%; and,
The limitations of instant application claim 23.
Iqbal is in the known prior art field of distillation of hydrocarbons with recycle loop distillation columns while ensuring “a safe and stable column operation” by controlling “the purities/or impurities in distillate and bottoms product streams” in order to optimize the recovery of the product, see Abstract; Figs. 1, 6, 8; Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis.
Regarding the limitations of instant application claim 1, Iqbal teaches distillates from column 1 and column 2 are recycled to previous columns, see Fig. 1; Pg. 108, Col. 1, where for example column 2 is charged with 58 kmol/h and the distillate sent back to column 1 is 8 kmol/h, see Fig. 1, as calculated by the examiner (8/58) x 100 = 13.8 wt. % of the charge amount is sent to column 1, meeting the recycle and within the recycle amount range in instant application claim 1.
Regarding the limitations of instant application claim 4, Iqbal teaches column 1 is charged with 275.76 kmol/h and the bottom rate is 50.05 kmol/h, see Fig. 1; Pg. 108, Col. 1, as calculated by the examiner, (50.05/275.76) x 100 = 18.1 wt. %, meeting within the bottom rate range in instant application claim 4.
Regarding the limitations of instant application claim 23, Iqbal teaches column 1 is charged with 275.76 kmol/h and the bottom rate is 50.05 kmol/h, see Fig. 1; Pg. 108, Col. 1, as calculated by the examiner, (50.05/275.76) x 100 = 18.1 wt. %, and column 1 is charged with 269.52 kmol/h and the bottom rate is 46.73 kmol/h, see Fig. 8, as calculated by the examiner, (46.73/269.51) x 100 = 17.3 wt. %, where the flow rate of the column bottoms B1 and B2 within the distillation system is varied as a manipulative variable in order to control the recovery of the product, see Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis.
Since “a prima facie case of obviousness exists” where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” and where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05, one of ordinary skill in the art, before the effective filing date of the claimed invention, would be able to predictably determine the flow rate of the column bottom to be under 15 wt.% in order to achieve the desired product recovery based upon the charge rate into the column and other variable column parameters, see Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis, obviously meeting within the bottom rate range in instant application claim 23.
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 distillation column recycle configuration of the claims of Shimizu ‘113, as taught by Iqbal, and to have modified, controlled, and quantified the distillation column bottom rates of the claims of Shimizu ‘113 as taught by Iqbal with a reasonable predictability of success for the purpose of efficiently purifying a hydrocarbon by distillation with high purity and a high recovery rate, see Iqbal, Abstract; Figs. 1, 6, 8; Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis.
The 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. One of ordinary skill in the art would have been capable of modifying the distillation column recycle and bottom rate of the claims of Shimizu ‘113 by applying the known techniques of distillation recycle configurations and bottom rates as taught by Iqbal with a reasonable predictability of success for the purpose of efficiently purifying a hydrocarbon by distillation with high purity and a high recovery rate, see Iqbal, Abstract; Figs. 1, 6, 8; Table 1; Pg. 108, Col. 1-Pg. 110, 4. Discussion and analysis; and, MPEP 2143 I. B-D.
Claim 22 stands provisionally rejected in modified form on the ground of nonstatutory double patenting as being unpatentable over claim over claims 1, 7, and 25 of copending Application 17/789,113 to Shimizu et al. (hereinafter Shimizu ‘113) in view of Iqbal et al. (“Appropriate selections of distillation column control variable to improve integrating material recycle response”, published online 03 August 2018, Journal of King Saud University – Engineering Sciences, Vol. 31, Pgs. 106-113, hereinafter Iqbal), as applied to claims 1-4, 6-10, 12-15, 17-21, and 23-25 in the nonstatutory double patenting rejection above, in further view of US 2003/0018224 A1 to Tsuji et al. (published 23 January 2003, hereinafter Tsuji), as evidenced by Daicel Corporation, (“1,3-Butylene Glycol (Cosmetic Grade)”, published October 2018, 1 Pg., hereinafter Daicel), and WO 2018/183628 A1 Khandurina et al. (published 04 October 2018, hereinafter Khandurina).
This is a provisional nonstatutory double patenting rejection.
The claims of Shimizu ‘113 do not recite the limitations of instant application claim 22.
Regarding the limitations of instant application claim 22, Tsuji currently assigned to Daicel Corporation teaches the purified 1,3-butylene glycol, see Paras. [0037]-[0046];[0246]-[0248], Fig. 1, with an initial boiling point of 206 ◦C or higher and a dry point of lower than 209 ◦C, as evidenced by Daicel, 1,3-butylene glycol with a boiling point of 207.5 ◦C, an initial boiling point of a minimum of 203 ◦C, and a dry point of a maximum of 209 ◦C, see Daicel, Pg. 1, i.e., the initial boiling point is inherently between 203 ◦C and 207.5 ◦C, see MPEP 2112, meeting within the boiling point and dry point range in instant application claim 22.
Further, as detailed above, the claims of Shimizu ‘113 in view of Iqbal teach the purified 1,3-butylene glycol and the method of purifying the purified 1,3-butylene glycol. Therefore, with regard to the instant application claim 22 functional limitations of “wherein the purified 1,3-butylene glycol has an initial boiling point of 206 ◦C or higher and a dry point of lower than 209 ◦C”, the claims of Shimizu ‘113 in view of Iqbal teach an identical or a substantially identical purified 1,3-butylene glycol purified by an identical or a substantially identical method as instantly claimed. As a result, a prima facie case of either anticipation or obviousness has been established, where ““[p]roducts of identical chemical composition can not have mutually exclusive properties”, see In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990), and a chemical composition and its properties are inseparable, see MPEP 2112. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present.
Since the claims of Shimizu ‘113 in view of Iqbal teach an identical or a substantially identical purified 1,3-butylene glycol purified by an identical or a substantially identical method as instantly claimed, the purified 1,3-butylene glycol will inherently possess the functional properties of an initial boiling point of 206 ◦C or higher and a dry point of lower than 209 ◦C. In addition, ““the discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer.” Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). Thus the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977)”, see MPEP 2112 I, meeting inherently within the boiling point and dry point range in instant application claim 22.
Regarding the limitations of instant application claim 22, Khandurina teaches “[t]he distillation can be carried out with a distillation system provided herein to produce a purified bioderived 1,3-BG product. The purified bioderived 1,3-BG product can be or include greater than 90%, 92%, 94%, 96%, 97%, 98%, 99%, 99.5%,99.7% or 99.9% bioderived 1,3-BG (1,3- BDO) on a weight/weight basis” and “[t]he recovery of bioderived 1,3-BG in the purified bioderived 1,3-BG (1,3-BDO) product can be calculated as a percentage of the amount of bioderived 1,3-BG (1,3-BDO) in the purified bioderived 1,3-BG product divided by the amount of bioderived 1,3-BG or target compound in the crude bioderived 1,3-BG mixture that was purified”, see Para. [00165], where “the 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”, see Para. [0083], as calculated by the examiner, the precent recovery of 1,3-BG may be (90% purified 1,3-BG/90% crude 1,3-BG) = 100% recovery of 1,3-BG, meeting within the range of recovery in instant application claim 22.
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 boiling point, dry point, and recovery rate of the claims of Shimizu ‘113 by applying the recycle lines, distillation parameters, and recovery rate as taught by Tsuji and Khandurina with a reasonable predictability of success for the purpose of efficiently purifying 1,3-BG with high purity and a high recovery rate by using recycle loops and the optimal distillation parameters, see Khandurina, Paras. [0073]-[0076];[00165]-[00169];[00244].
The 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. One of ordinary skill in the art would have been capable of modifying the distillation column recycle and recovery rate of the claims of Shimizu ‘113 by applying the known techniques of distillation recycle and configurations as taught by Tsuji and Khandurina with a reasonable predictability of success for the purpose of efficiently purifying 1,3-BG with high purity and a high recovery rate by using recycle loops and the optimal distillation parameters, see Khandurina, Paras. [0073]-[0076];[00165]-[00169];[00244]; and, MPEP 2143 I. B-D.
Conclusion
No claims are allowed.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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