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 .
Status of the Claims
Claims 1, 2, and 4-17 are pending.
Claims 1, 4, 6, 9-12, and 17 are amended.
Claims 3, 18, and 19 are cancelled.
Response to Amendments
Applicant’s amendments filed 11 November 2025 are acknowledged.
Claim Rejections - 35 USC § 112
Applicant’s amendment to claim 1 and cancellation of claims are sufficient to overcome the rejections of claims 1-19 under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Claims 1, 4, 6, 9, 11, 12, and 17 have been amended to correct the antecedent basis issues. The rejections are withdrawn.
Applicant’s amendment to claim 1 is sufficient to overcome the rejections of claims 6 and 7 under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. The amendment to claim 1 corrects the antecedent basis issues in claims 6 and 7. The rejections are withdrawn.
Applicant’s amendments to claims 9 and 10 are sufficient to overcome the rejections of claims 9 and 10 under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Claims 9 and 10 have been amended to correct the antecedent basis issues. The rejections are withdrawn.
Claim Rejections - 35 USC § 103
Applicant’s amendment to claim 1 incorporating the limitations of claims 18 and 19 into claim 1 which are not taught by Fischer in view of Binder and the cancellation of claim 3 are sufficient to overcome the rejection of claims 1-17 under 35 U.S.C. 103 as being unpatentable over Fischer et al. (US20190202764, cited by applicants 11 December 2023, hereinafter Fischer), as evidenced by Kalagias (US20080275277), in view of Binder et al. (US20080103340, hereinafter Binder). Due to the amendment to claim 1 incorporating the limitations of claims 18 and 19 into claim 1 which are not taught by Fischer in view of Binder and the cancellation of claim 3 the rejection is withdrawn and a new ground(s) of rejection is/are provided below.
Applicant’s cancellation of claims 18 and 19 is sufficient to overcome the rejection of claims 18 and 19 under 35 U.S.C. 103 as being unpatentable over Fischer et al. (US20190202764, cited by applicants 11 December 2023, hereinafter Fischer), as evidenced by Kalagias (US20080275277), in view of Binder et al. (US20080103340, hereinafter Binder), as applied to claims 1-17 in the 35 USC 103 rejection above, in further view of Campbell et al. (“Thermoset materials characterization by thermal desorption or pyrolysis based gas chromatography-mass spectrometry methods”, 21 November 2019, Polymer Degradation and Stability, Vol. 174, Pgs. 1-18, hereinafter Campbell). The rejection is withdrawn.
Double Patenting
Applicant’s amendments to claims 9 and 10 regarding the distillation process sequence not taught by the claims of Kalagias and the cancellation of claims are sufficient to overcome the rejections of:
Claims 1-19 on the ground of nonstatutory double patenting as being unpatentable over claims 1-4, 7-9, 12, 13, and 18 of copending Application No. 18293462 to Kajanto in view of Fischer et al. (US20190202764, cited by applicants 11 December 2023, hereinafter Fischer), as evidenced by Kalagias (US20080275277).
Due to the amendments of claims 9 and 10 regarding the distillation process sequence not taught by the claims of Kalagias and the cancellation of claims, the nonstatutory double patenting rejections are withdrawn and a new ground(s) of rejection is/are provided below.
Response to Arguments
Applicant’s arguments filed 06 November 2025 have been fully considered but they are not persuasive.
Applicant’s argue that Fischer, Kalagias, Binder, and Campbell do not disclose the limitations as recited in amended claim 1. 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 6-7 of the remarks filed on 06 November 2025, that “Fischer discloses removing said impurities from the first distillation column with the top stream together with mono-propylene glycol (MPG, Table 5) and, further, removing said impurities from the second distillation column with the top stream (Table 6)” and “Fischer does not disclose, teach, or suggest that the organic impurity, which is to be separated from the mono-propylene glycol, should be removed in a bottom stream, as recited in independent claim 1”. Patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123.
To clarify, as stated on page 7 in the previous office action dated 12 August 2025 (hereinafter POA), Fischer teaches the “feed stream comprising MPG”, i.e. a C3 diol, “is first distilled in column 105 to remove a bottoms stream comprising high boiling by-products from a top stream”, where high boiling by-products bottom stream 106 contains heavies, such as other poly-alcohols, especially other C3-C6 sugar alcohols, see Fig. 1; Claims 1 and 3; Paras. [0024];[0043];[0049];[0065];[0068]; Table 5. Therefore, Fischer teaches separating organic impurities from MPG as a bottom stream from the first distillation column. For the reasons indicated above, applicant’s above argument is not persuasive.
In response to applicant’s arguments on pages 6-7 of the remarks filed on 06 November 2025, that the instant claims are drawn to a step where “the organic impurity that forms an azeotrope with the mono-propylene glycol is removed in the bottom stream from the first distillation column”. It is noted that the organic impurity as an azeotrope is not instantly claimed.
In addition, Fischer teaches the “separation of these diols by fractional distillation is complicated due to the similarity in boiling points”, “close-boiling, azeotrope-forming glycol pair is MPG and 2,3-pentanediol”, “close boiling and/or azeotropic mixtures may also be formed between other diols present”, see Para. [0007], and the separation of close boiling-point azeotropes is performed by using “one or more sugar alcohols” “as extractant for the selective extractive distillation of the first diol”, where “the strong interaction between the sugar alcohols and the first diol breaks any azeotrope and affects the volatility of the diols present, allowing them to be separated” and a “simple distillation of the first diol”, such as MPG, “as overhead product from the extractant in a third distillation column results in a high purity first diol stream”, see Para. [0063]; Fig. 1. In addition, see Table 5, where portions of MPG and close boiling azeotropes, such as 2,3 PDO, are present in the bottom stream of the first distillation, where mostly MPG is in the top stream of the first distillation. As stated above, Fischer teaches sugar alcohols are removed from the bottom of the first distillation column, sugar alcohols form azeotropes with the first diol, such as MPG, and diol azeotropes are removed from the bottom of the first distillation column; therefore, Fischer teaches azeotropes are also removed from the bottom stream of the first distillation column. For the reasons indicated above, applicant’s above argument is not persuasive.
In response to applicant’s arguments on pages 6-7 of the remarks filed on 06 November 2025, that “Fischer does not disclose, teach, or suggest the use of a pressure of 0.3-1.0 bar in the first distillation column”. Patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123.
To clarify, as stated on page 7 of the POA, Fischer teaches in the first distillation column “the distillation is at a pressure of 1.2 bar” with a “top pressure of 0.2 bar” and a “bottom pressure of 0.13 bar”, see Table 5; Paras. [0048];[0051], which will inherently lead to a pressure within the first distillation tower between 0.13 bar to 1.2 bar, see MPEP 2112. Fischer further teaches “[d]egradation of the products at high temperatures makes the use of higher than atmospheric pressure for distillation undesirable”, see Para. [0008]. As stated on page 11 of the POA, “[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, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means,” such as distillation pressures, “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.
In addition, 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 pressure of the distillation columns in order to maintain the components of the composition in liquid form, to control the boiling points of the components of the composition, and to control the distillation pressure to below atmospheric pressure, see Fischer, Paras. [0008];[0039];[0048];[0051];[0056].
For the reasons indicated above, applicant’s above argument is not persuasive.
In response to applicant’s arguments on pages 8-9 of the remarks filed on 06 November 2025, that the instant claims are drawn to a step of especially “ensuring a sufficient pressure difference between the first distillation process and the second distillation process to ensure the separation of high purity mono-propylene glycol. One technical feature distinguishing the methods of the pending claims from Fischer is the difference in the distillation conditions and especially in the relevant pressure difference between the first and the second distillation process” and “Fischer also does not disclose, teach, or suggest the use of the pressure of 0.3-1.0 bar in the first distillation column.” Patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123.
In this case, as stated above Fischer teaches a pressure within the first distillation tower between 0.13 bar to 1.2 bar. As stated on page 8 in the POA, Fischer teaches a second distillation column 109 having a pressure of at least 1 kPa to at most 400 kPa or 0.01 bar to 4 bar, see Para. [0051];[0068]-[0070]. Therefore, Fischer teaches within the range of the second column pressure and a pressure difference in the columns, where the first column at 0.13 bar or 0.2 bar may have an eight to ten fold higher pressure than the second column. For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s arguments on pages 8-9 of the remarks filed on 06 November 2025, that “the methods recited in the pending claims thus have the technical utility of providing an efficient process for breaking the azeotrope formed between the organic impurity and mono-propylene glycol for recovering mono-propylene glycol in high purity without requiring any additional extractant”. Patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123.
As stated above, Fischer teaches the separation of close boiling-point azeotropes is performed by using “one or more sugar alcohols” “as extractant for the selective extractive distillation of the first diol”, where “the strong interaction between the sugar alcohols and the first diol breaks any azeotrope and affects the volatility of the diols present, allowing them to be separated” and a “simple distillation of the first diol as overhead product from the extractant in a third distillation column results in a high purity first diol stream”, see Para. [0063]; Fig. 1. Fischer also teaches “as the extractant, this stream may also comprise certain heavies, such as other poly-alcohols, especially other sugar alcohols, from a recycle stream in the process. One example of a suitable recycle stream is the bottoms stream comprising high boiling by-products provided in step (ii) of the instant process. Such high boiling by-products will include C3-C6 sugar alcohols. Preferably, at least a portion of said bottoms stream may be used as at least a portion of the extractant”, see Para. [0049]. Therefore, Fischer teaches the process does not require additional extractant because the bottom stream from the first distillation 106 containing heavies, such as other poly-alcohols, especially other C3-C6 sugar alcohols, is recycled as the extractant, see Paras. [0043];[0049];[0068]. For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s arguments on page 9 of the remarks filed on 06 November 2025, that “neither Kalagias nor Binder - either alone or in combination with each other or with Fischer - provides any motivation, teaching, or suggestion to achieve the method recited in independent claim 1”. The examiner recognizes that obviousness may be established by combining or modifying the teachings of the prior art to produce the claimed invention where there is some teaching, suggestion, or motivation to do so found either in the references themselves or in the knowledge generally available to one of ordinary skill in the art, see In re Fine, 837 F.2d 1071, 5 USPQ2d 1596 (Fed. Cir. 1988), In re Jones, 958 F.2d 347, 21 USPQ2d 1941 (Fed. Cir. 1992), KSR International Co. v. Teleflex, Inc., 550 U.S. 398, 82 USPQ2d 1385 (2007), and MPEP 2143.
“A reference is analogous art to the claimed invention if: (1) the reference is from the same field of endeavor as the claimed invention (even if it addresses a different problem); or (2) the reference is reasonably pertinent to the problem faced by the inventor (even if it is not in the same field of endeavor as the claimed invention).”, see MPEP 2141.01(a).
As stated on page 7 of the POA, Kalagias is only applied to teach the boiling point of MPG and 2,3-butandiol.
Binder is in the known prior art field of the purification and separation of propylene glycol from a bioderived polyol feedstock, see Paras. [0011];[0031]-[0035]. Binder is applied to teach the concentration of propylene glycol in the mixed feedstock.
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 both Fischer and Binder teach distillate purification of diols from bio-based feedstocks, a person of ordinary skill in the art has good reason to modify Fischer by relying upon Binder before the effective filing date of the claimed invention for knowledge generally available within the bio-based feedstock distillation separation art regarding the concentration of the feed stock, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing bio-derived propylene glycol through use of purifying a hydrogenolysis product stream in order to obtain a suitable replacement for petroleum derived propylene glycol, see Binder, Paras. [0007]-[0009];[0035] and MPEP 2141.
Double Patenting
Applicant’s arguments on page 10 of the remarks filed on 06 November 2025 that it is premature to address the provisional nonstatutory double patenting rejection have been considered but are not persuasive because a request to hold a rejection in abeyance is not a proper response to a rejection. Rather, a request to hold a matter in abeyance may only be made in response to an objection or requirements as to form, see MPEP 37 CFR 1.111(b) and 714.02.
New 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.
Claims 1, 2, and 4-17 are newly rejected under 35 U.S.C. 103 as being unpatentable over Fischer et al. (US20190202764, published 04 July 2019, hereinafter Fischer), as evidenced by Kalagias (US20080275277, published 06 November 2008), in view of Binder et al. (US20080103340, published 01 May 2008, hereinafter Binder) and Campbell et al. (“Thermoset materials characterization by thermal desorption or
pyrolysis based gas chromatography-mass spectrometry methods”, published 21 November 2019, Polymer Degradation and Stability, Vol. 174, Pgs. 1-18, hereinafter Campbell).
New Rejections Based on Amendments to the Claims in the reply filed on 06 November 2025
As detailed in the previous office action dated 12 August 2025
Fischer teaches the instant application claims 1, 2, 4-8, and 11-17 limitations of recovering desired diol products, such as monopropylene glycol, MPG aka propylene glycol or 1,2-propanediol, from a product stream comprising monoethylene glycol, MEG, monopropylene glycol, MPG, 1,2-butanediol, 1,2-BDO, and glycerol, see Paras. [0007];[0038]. The product stream is derived from a cellulose, sugar, or saccharide hydrolysis process or other bio-based processes, see Paras. [0003];[0007];[0013], meeting the bio-derived diols and an organic impurity in instant claim 1;
In an experimental mixture to mimic an actual product stream, the Example 2 feed stream mixture comprises 3.6 wt.% monoethylene glycol, MEG, 71.8 wt.% monopropylene glycol, MPG, 13.5 wt.% 1,2-butanediol, 1,2-BDO, 0.9 wt.% 2,3-butanediol, 2,3-BDO, [i.e., BDOs are butylene glycols], pentanediols, hexanediols, heptanediols and byproducts, see Paras. [0007];[0013];[0082]-[0086], and Table 5, meeting:
Within the MPG feed content stream range in instant claim 1 and in instant claim 12;
The specific MEG, MPG, BDO, and impurity contents of the stream and within the MEG, MPG, BDO, and impurity range in instant claim 11;
The feed stream comprising MPG is first distilled in column 105 to remove a bottoms stream comprising high boiling by-products from a top stream comprising a mixture comprising the two or more C2 to C7 diols with close boiling points, such as MPG, 2,3-butanediol, 2,3-pentanediol, and light glycols, i.e., all existing as a top stream inherently have a boiling point the same as or lower than MPG, where the distillation is at a pressure of 1.2 bar and a temperature of 130.0° C, top pressure of 0.2 bar and a temperature of 141.1° C, and a bottom pressure of 0.13 bar and a temperature of 160.8° C, see Paras. [0014]-[0015];[0043]-[0045];[0083]-[0084], Table 5, Fig. 1, and MPEP 2112, as evidenced by Kalagias, Pg. 2, Table 1, MPG or propylene glycol has a boiling point of 187° C and 2,3-butanediol has a boiling point of 182° C, meeting:
The step (ia) separation and within the step (ia) separation ranges in instant claim 1;
The top stream content in instant claim 6;
Within the temperature range in instant claim 13;
The top stream comprising MPG is fed to a second distillation column 109, where MPG and impurity glycerol are separated as a bottom stream, i.e., as higher boiling point materials, from the top stream of 2,3-BDO and 2,3-petanediol, i.e., lower boiling point materials, at a temperature in the range of from 50 to 250° C and a pressure at least 1 kPa to at most 400 kPa or 0.01 bar to 4 bar, see Paras. [0016];[0018]-[0019];[0051]-[0054];[0084], Table 6, and Fig. 1, as evidenced by Kalagias, Pg. 2, Table 1, glycerol or glycerin has a boiling point of 290° C, meeting:
The step(ib) separation and within the step (ib) ranges in instant claim 1;
The distillation sequence order in instant claim 2 and in instant claim 5;
The top and bottom stream contents in instant claim 4;
The second distillation feed in instant claim 7;
Within the temperature range in instant claim 15;
Within the pressure range in instant claim 16;
The bottom feed from the second distillation column 109 comprising MPG and the impurity glycerol is fed to a third distillation column 111, where high purity 99.96 wt.% MPG is recovered as a top stream, see Paras. [0020];[0054];[0056]-[0057];[0085], Table 7, and Fig. 1. The third distillation in Fischer is the same as instant application step (ia) first distillation carried out at a temperature of 110 ◦C to 200 ◦C and pressure of 0.13 to 1.2 bar, see Table 7, where MPG is separated and obtained as a top product and the impurity glycerol is obtain as a bottom, see Table 7; therefore, the second distillation in column 109 is performed before an instant application step (ia) first distillation in column 111, meeting:
The recovery (ii) step in instant claim 1;
The distillation sequence in instant claim 8; and,
Within the recovery range in instant claim 17.
Fischer teaches three distillation columns, where the distillations may be carried out at a pressure of from about 0.1 kPa to at most 400 kPa or 0.01 bar to 4 bar which may be varied by a person skilled in the art to achieve suitable conditions, recycle of a distillation bottom stream containing MPG and the glycerol impurity to a differing distillation column, and purification and further processing of a recycle stream containing MPG, see Paras. [0049];[0051]-[0053];[0060];[0062], and Fig. 1, meeting within the distillation pressure range in instant claim 14.
Regarding instant amended application claim 1, Fischer teaches in the first distillation column “the distillation is at a pressure of 1.2 bar” with a “top pressure of 0.2 bar” and a “bottom pressure of 0.13 bar”, see Table 5; Paras. [0048];[0051], which will inherently lead to a pressure within the first distillation tower between 0.13 bar to 1.2 bar, see MPEP 2112, and “[d]egradation of the products at high temperatures makes the use of higher than atmospheric pressure for distillation undesirable”, see Para. [0008], meeting within the pressure range of the first distillation tower in instant application claim 1; and,
Fischer teaches the “feed stream comprising MPG”, i.e. a C3 diol, “is first distilled in column 105 to remove a bottoms stream comprising high boiling by-products from a top stream” and a top stream 107 comprising mixtures of C2 to C7 diols, including MPG, where high boiling by-products bottom stream 106 contains heavies, such as other poly-alcohols, especially other C3-C6 sugar alcohols, see Fig. 1; Claims 1 and 3; Paras. [0024];[0043];[0049];[0065];[0068]; Table 5, meeting the top and bottom stream contents from the first distillation column in instant application claim 1.
Regarding the instant amended application claim 1, the scope of the method claim is not limited by claim language that suggests or makes optional but does not require steps to be performed, or by claim language that does not limit a claim to a particular structure, see MPEP 2111.04. In this case, the “wherein” clauses drawn to the organic impurity characterization does not appear to not give “meaning and purpose to the manipulative steps”, see MPEP 2111.04.
Regarding instant amended application claims 9 and 10, Fischer teaches the columns are arranged in an “orthogonal separation”, where heavies are removed from in a column followed by extractive distillation in another column, see Paras. [0065];[0070].
Fischer teaches column 111, where extractant heavies/organic impurities are removed from the bottom of the column in line 113, and diols, such as C2 to C7 diols, i.e., MPG is a C3 diol, are removed from the top of the column in line 112, see Paras. [0024];[0060];[0067]-[0070]; Fig. 1; Table 7. Column 111 is operated at a temperature in the range of from 50 to 250° C and a pressure of at least 1 kPa to at most 400 kPa aka 0.01 bar to 4 bar, see Paras. [0051];[0056]; Table 7. Therefore, column 111 also meets the instantly claimed first distillation process.
Line 113 bottom containing heavies from column 111 is recycled back to column 109, where diols with a boiling point lower than the target diol, such as 1,2-BDO, and some target diol, such as MPG, are removed from the top of the column in line 114, and the target diol, such as MPG, and heavies are removed from the bottom of the column in line 110, see Paras. [0024];[0060];[0067]-[0070]; Fig. 1; Table 6. Column 109 is operated at a temperature in the range of from 50 to 250° C and a pressure of at least 1 kPa to at most 400 kPa aka 0.01 bar to 4 bar, see Paras. [0051];[0056]; Table 6. Line 110 containing MPG and heavies/organic impurities from column 109 is sent to column 111, see Fig. 1; Para. [0068].
Therefore, column 109 meets:
The instantly claimed first distillation process where MPG is removed from the top of the column and heavies/organic impurities are removed from the bottom of the column;
The instantly claimed second distillation process where diols with a boiling point lower than MPG are removed from the top of the column and MPG and heavies/organic impurities are removed from the bottom of the column; and,
As stated above, line 110 containing MPG and heavies/organic impurities from column 109 is sent to column 111, i.e., a first distillation process, see Fig. 1; Para. [0068], meeting:
The first distillation process column 111 is carried out after the second distillation process column 109 in instant application claim 9 and in instant application claim 10;
The composition of the second bottom stream in instant application claim 9; and,
The feeding the second bottom stream to the first distillation in instant application claim 10.
Regarding instant application claim 14, as stated above, Fischer teaches in the first distillation column “the distillation is at a pressure of 1.2 bar” with a “top pressure of 0.2 bar” and a “bottom pressure of 0.13 bar”, see Table 5; Paras. [0048];[0051], which will inherently lead to a pressure within the first distillation tower between 0.13 bar to 1.2 bar, see MPEP 2112, and “[d]egradation of the products at high temperatures makes the use of higher than atmospheric pressure for distillation undesirable”, see Para. [0008], meeting within the pressure range of the first distillation tower in instant application claim 14.
Fischer does not specifically teach:
The instant application claim 1 limitations of the product stream comprising bio-derived diols comprises mono-propylene glycol in an amount of at least 50 weight-% of the total weight of the mixture, the specific order of method steps, and,
wherein the organic impurity is characterized by a retention time of 6.5 - 6.7 minutes when determined by gas-chromatography-flame ionization detector (GC-FID) and by a tallest peak value at 59 m/z when determined by a gas-chromatography-mass-spectrometer (GC-MS).
Fischer teaches an example mixture of diols to mimic the process of the separation from an actual bioderived product stream comprising a mixture of glycols, see Paras. [0082]-[0086], Table 5. Fischer also teaches diol concentrations of the actual product stream after solvent removal of 1 wt.% to 95 wt.%, see Paras. [0034]-[0037];[0043].
Binder is in the known prior art field of the purification and separation of propylene glycol from a bioderived polyol feedstock, see Paras. [0011];[0031]-[0035], and is applied to teach the same.
Regarding instant application claim 1, Binder teaches bioderived propylene glycol from the hydrogenolysis product of a bioderived polyol feedstock selected from the group consisting of glucose, glycerol, a polyglycerol, a plant fiber hydrolyzate, a fermentation product from a plant fiber hydrolyzate, and mixtures of any thereof, where the hydrogenolysis product comprises a mixture of propylene glycol, ethylene glycol, and one or more of glycerol, lactic acid, glyceric acid, and butanediols, see Para. [0011]. The hydrogenolysis product mixture is purified to separate the propylene glycol by distillation, see Para. [0035], and the hydrogenolysis product mixture prior to purification contains 0.1% to 99.9% by weight of propylene glycol, see Paras. [0031];[0035], meeting and within the range of the bio-derived starting feedstock in instant application claim 1.
Campbell is in the known prior art field of applying GC-MS techniques for the separation, quantification, and identification of compounds, see Abstract, and is applied to teach the same.
Regarding instant amended application claim 1, Campbell teaches GC-MS techniques for the separation, quantification, and identification of compounds, where compounds are identified based on their specific pyrolysis degradation products, such as compound Dy-D/917 by thermal extraction desorption (TED) GC-MS retention time peaks of 6-7 minutes, see Pg. 2, Col. 1, 1.; Pg. 5, Col. 1, 2.5.-Pg. 6, Figs. 7, 14, and 26, and GC-MS characterizations of compounds with the tallest peak vale at 59 m/z at retention times between 6-7 minutes, see Pgs. 8-10, Figs. 11, and 12C, meeting the organic impurity characterization ranges in instant application claim 1.
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 Fischer to rearrange the purification method by including additional recycle lines and top/bottom streams to differing purification columns, see MPEP 2144.04 VI., to adjust the distillation pressures, see MPEP 2144.05 II., to use a bioderived starting feed comprising up to 99.9% by weight propylene glycol as taught by Binder and to specifically identify the impurity removed as taught by Campbell with a reasonable predictability of success for the purpose of efficiently producing bio-derived propylene glycol through use of purifying a hydrogenolysis product stream in order to obtain a suitable replacement for petroleum derived propylene glycol, see Binder, Paras. [0007]-[0009];[0035]; while, specifically identifying the impurity removed from the bio-derived formulation, see Campbell, Abstract.
By applying “routine optimization” and “predictable results” to select the optimal starting feed concentrations, one of ordinary skill in the art would have been motivated to make these modifications because Binder provides a finite number of identified, predictable solutions. A person of ordinary skill in the art has good reason to purify a glycol by purification of a product stream, such as a hydrogenolysis product stream, by pursuing the known options within their technical grasp for the benefit of efficiently producing bio-derived propylene glycol through purification of a hydrogenolysis product stream in order to obtain a suitable replacement for petroleum derived propylene glycol, see Binder, Paras. [0007]-[0009];[0035], and MPEP 2141.
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 both Fischer and Binder teach distillate purification of diols from bio-based feedstocks, a person of ordinary skill in the art has good reason to modify Fischer by relying upon Binder before the effective filing date of the claimed invention for knowledge generally available within the bio-based feedstock distillation separation art regarding the concentration of the feed stock, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing bio-derived propylene glycol through use of purifying a hydrogenolysis product stream in order to obtain a suitable replacement for petroleum derived propylene glycol, see Binder, Paras. [0007]-[0009];[0035] and MPEP 2141.
“The discovery of a previously unappreciated property of a prior art composition,” such as the identity of the impurity removed from the bio-derived formulation, “or of a scientific explanation for the prior art’s functioning, 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 identity of the impurity removed from the bio-derived formulation, “which is inherently present in the prior art does not necessarily make the claim patentable”, see MPEP 2112 I.
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, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means,” such as distillation pressures and reactant concentrations, “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.
Maintained 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.
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Claims 1, 2, and 4-17 stand provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-4, 7-9, 12, 13, and 18 of copending Application No. 18293462 to Kajanto in view of Fischer et al. (US20190202764, published 04 July 2019, hereinafter Fischer), as evidenced by Kalagias (US20080275277, published 06 November 2008).
This is a provisional nonstatutory double patenting rejection.
The claims of Kajanto recite the instant application claims 1, 2, 5, 7, 11-13, and 17-19 limitations of a method for recovering mono-propylene glycol from a mixture comprising bio-derived diols and an organic impurity, wherein the mixture comprises mono-propylene glycol in an amount of at least 45 weight-% of the total weight of the mixture, see claims 1 and 2, meeting the preamble and within the MPG range in instant application claim 1 and instant application claim 12;
Wherein the mixture comprises mono-ethylene glycol, mono-propylene glycol, butylene glycol, and an organic impurity in an amount of at least 80 weight-%, see claim 3, meeting instant application claim 11;
The method comprises: (ia) separating the organic impurity from mono-propylene glycol in a first distillation process, wherein the first distillation process is carried out at a temperature within the range of 75-230 0C and a pressure, see claims 1, 12, and 13, with removing the organic impurity in a first bottom stream from the first distillation process and removing mono-propylene glycol in a first top stream from the first distillation process, see claim 7, meeting most of step (ia) in instant application claim 1 and within the range in instant application claim 13;
(ib) mono-propylene glycol from the first distillation top stream is fed into a second distillation process, see claim 18;
(ii) recovering mono-propylene glycol, see claim 1, wherein the method comprises recovering mono-propylene glycol at a concentration of at least 75 weight-%, see claim 4, meeting:
The second distillation and step (ii) in instant application claim 1;
The distillation sequence in instant application claim 2, in instant application claim 5, in instant application claim 7, and,
The within the recovery % range in instant application claim 17; and,
The organic impurity has a retention time of 6.5 - 6.7 minutes when determined by gas-chromatography-flame ionization detector (GC-FID), see claim 8, and the organic impurity is characterized by the tallest peak value at 59 m/z when determined by gas-chromatography-mass-spectrometer (GC-MS), see claim 9, meeting and within the ranges in instant application claim 1.
The claims of Kajanto do not recite:
The instant application claim 1 limitations of the first distillation at a pressure within the range of 0.3 - 1.0 bar; (ib) separating diols that have a boiling point lower than the boiling point of mono-propylene glycol, wherein the second distillation process is carried out at a temperature within the range of 90 - 150 0C and a pressure within the range of 0.05 - 0.2 bar; and,
The limitations of instant application claims 4, 6, 8-10, and 14-16.
Fischer teaches recovering desired diol products, such as monopropylene glycol, MPG aka propylene glycol or 1,2-propanediol, from a product stream comprising monoethylene glycol, MEG, monopropylene glycol, MPG, 1,2-butanediol, 1,2-BDO, and glycerol, see Paras. [0007];[0038]. The product stream is derived from a saccharide hydrolysis process or other bio-based processes, see Para. [0013], meeting the bio-derived diols and an organic impurity in instant application claim 1;
The feed stream comprising MPG is first distilled in column 105 to remove a bottoms stream comprising high boiling by-products from a top stream comprising a mixture comprising the two or more C2 to C7 diols with close boiling points, such as MPG, 2,3-butanediol, 2,3-pentanediol, and light glycols, i.e., all existing as a top stream inherently have a boiling point the same as or lower than MPG, where the distillation is at a pressure of 1.2 bar and a temperature of 130.0° C, top pressure of 0.2 bar and a temperature of 141.1° C, and a bottom pressure of 0.13 bar and a temperature of 160.8° C, see Paras. [0014]-[0015];[0043]-[0045];[0083]-[0084], Table 5, Fig. 1, and MPEP 2112, as evidenced by Kalagias, Pg. 2, Table 1, MPG or propylene glycol has a boiling point of 187° C and 2,3-butanediol has a boiling point of 182° C, meeting:
The step (ia) separation and within the step (ia) separation ranges in instant application claim 1;
The top stream content in instant application claim 6;
The top stream comprising MPG is fed to a second distillation column 109, where MPG and impurity glycerol are separated as a bottom stream, i.e., as higher boiling point materials, from the top stream of 2,3-BDO and 2,3-petanediol, i.e., lower boiling point materials, at a temperature in the range of from 50 to 250° C and a pressure at least 1 kPa to at most 400 kPa or 0.01 bar to 4 bar, see Paras. [0016];[0018]-[0019];[0051]-[0054];[0084], Table 6, and Fig. 1, as evidenced by Kalagias, Pg. 2, Table 1, glycerol or glycerin has a boiling point of 290° C, meeting:
The step(ib) separation and within the step (ib) ranges in instant application claim 1;
The top and bottom stream contents in instant application claim 4;
Within the temperature range in instant application claim 15;
Within the pressure range in instant application claim 16;
The bottom feed from the second distillation column 109 comprising MPG and the impurity glycerol is fed to a third distillation column 111, where high purity 99.96 wt.% MPG is recovered as a top stream, see Paras. [0020];[0054];[0056]-[0057];[0085], Table 7, and Fig. 1. The third distillation in Fischer is the same as instant application step (ia) first distillation carried out at a temperature of 110 ◦C to 200 ◦C and pressure of 0.13 to 1.2 bar, see Table 7, where MPG is separated and obtained as a top product and the impurity glycerol is obtain as a bottom, see Table 7; therefore, the second distillation in column 109 is performed before an instant application step (ia) first distillation in column 111, meeting:
The distillation sequence in instant application claim 8;
The second bottom stream contents in instant application claim 9; and,
The further distillation within the step (ai) parameters in instant application claim 10.
Fischer teaches three distillation columns, where the distillations may be carried out at a pressure of from about 0.1 kPa to at most 400 kPa or 0.01 bar to 4 bar which may be varied by a person skilled in the art to achieve suitable conditions, recycle of a distillation bottom stream containing MPG and the glycerol impurity to a differing distillation column, and purification and further processing of a recycle stream containing MPG, see Paras. [0049];[0051]-[0053];[0060];[0062], and Fig. 1, meeting:
The recycle of the second bottom stream to a distillation column in instant application claim 10; and,
Within the distillation pressure range in instant application claim 14.
Further regarding instant amended application claim 1, Fischer teaches in the first distillation column “the distillation is at a pressure of 1.2 bar” with a “top pressure of 0.2 bar” and a “bottom pressure of 0.13 bar”, see Table 5; Paras. [0048];[0051], which will inherently lead to a pressure within the first distillation tower between 0.13 bar to 1.2 bar, see MPEP 2112, and “[d]egradation of the products at high temperatures makes the use of higher than atmospheric pressure for distillation undesirable”, see Para. [0008], meeting within the pressure range of the first distillation tower in instant application claim 1; and,
Fischer teaches the “feed stream comprising MPG”, i.e. a C3 diol, “is first distilled in column 105 to remove a bottoms stream comprising high boiling by-products from a top stream” and a top stream 107 comprising mixtures of C2 to C7 diols, including MPG, where high boiling by-products bottom stream 106 contains heavies, such as other poly-alcohols, especially other C3-C6 sugar alcohols, see Fig. 1; Claims 1 and 3; Paras. [0024];[0043];[0049];[0065];[0068]; Table 5, meeting the top and bottom stream contents from the first distillation column in instant application claim 1.
Further regarding the instant amended application claim 1, the scope of the method claim is not limited by claim language that suggests or makes optional but does not require steps to be performed, or by claim language that does not limit a claim to a particular structure, see MPEP 2111.04. In this case, the “wherein” clauses drawn to the organic impurity characterization does not appear to not give “meaning and purpose to the manipulative steps”, see MPEP 2111.04.
Further regarding instant amended application claims 9 and 10, Fischer teaches the columns are arranged in an “orthogonal separation”, where heavies are removed from in a column followed by extractive distillation in another column, see Paras. [0065];[0070].
Fischer teaches column 111, where extractant heavies/organic impurities are removed from the bottom of the column in line 113, and diols, such as C2 to C7 diols, i.e., MPG is a C3 diol, are removed from the top of the column in line 112, see Paras. [0024];[0060];[0067]-[0070]; Fig. 1; Table 7. Column 111 is operated at a temperature in the range of from 50 to 250° C and a pressure of at least 1 kPa to at most 400 kPa aka 0.01 bar to 4 bar, see Paras. [0051];[0056]; Table 7. Therefore, column 111 also meets the instantly claimed first distillation process.
Line 113 bottom containing heavies from column 111 is recycled back to column 109, where diols with a boiling point lower than the target diol, such as 1,2-BDO, and some target diol, such as MPG, are removed from the top of the column in line 114, and the target diol, such as MPG, and heavies are removed from the bottom of the column in line 110, see Paras. [0024];[0060];[0067]-[0070]; Fig. 1; Table 6. Column 109 is operated at a temperature in the range of from 50 to 250° C and a pressure of at least 1 kPa to at most 400 kPa aka 0.01 bar to 4 bar, see Paras. [0051];[0056]; Table 6. Line 110 containing MPG and heavies/organic impurities from column 109 is sent to column 111, see Fig. 1; Para. [0068].
Therefore, column 109 meets:
The instantly claimed first distillation process where MPG is removed from the top of the column and heavies/organic impurities are removed from the bottom of the column;
The instantly claimed second distillation process where diols with a boiling point lower than MPG are removed from the top of the column and MPG and heavies/organic impurities are removed from the bottom of the column; and,
As stated above, line 110 containing MPG and heavies/organic impurities from column 109 is sent to column 111, i.e., a first distillation process, see Fig. 1; Para. [0068], meeting:
The first distillation process column 111 is carried out after the second distillation process column 109 in instant application claim 9 and in instant application claim 10;
The composition of the second bottom stream in instant application claim 9; and,
The feeding the second bottom stream to the first distillation in instant application claim 10.
Further regarding instant application claim 14, as stated above, Fischer teaches in the first distillation column “the distillation is at a pressure of 1.2 bar” with a “top pressure of 0.2 bar” and a “bottom pressure of 0.13 bar”, see Table 5; Paras. [0048];[0051], which will inherently lead to a pressure within the first distillation tower between 0.13 bar to 1.2 bar, see MPEP 2112, and “[d]egradation of the products at high temperatures makes the use of higher than atmospheric pressure for distillation undesirable”, see Para. [0008], meeting within the pressure range of the first distillation tower in instant application claim 14.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the claims of Kajanto to rearrange the purification method by including additional recycle lines and top/bottom stream purification columns, see MPEP 2144.04 VI., and to adjust the distillation pressures, see MPEP 2144.05 II., as taught by Fischer with a reasonable predictability of success for the purpose of efficiently producing bio-derived propylene glycol through use of purifying a hydrogenolysis product stream in order to obtain a suitable replacement for petroleum derived propylene glycol, see Fischer, Paras. [0002]-[0003];[0005];[0007];[0013].
By applying “routine optimization” and “predictable results” to select the optimal starting feed concentrations, one of ordinary skill in the art would have been motivated to make these modifications because Fischer provides a finite number of identified, predictable solutions. A person of ordinary skill in the art has good reason to purify a glycol by purification of a product stream, such as a hydrogenolysis product stream, by pursuing the known options within their technical grasp for the benefit of efficiently producing bio-derived propylene glycol through use of purifying a hydrogenolysis product stream in order to obtain a suitable replacement for petroleum derived propylene glycol, see Fischer, Paras. [0002]-[0003];[0005];[0007];[0013], and MPEP 2141.
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 both the claims of Kajanto and Fischer teach distillate purification of diols from bio-based feedstocks, a person of ordinary skill in the art has good reason to modify the claims of Kajanto by relying upon Fischer before the effective filing date of the claimed invention for knowledge generally available within the bio-based feedstock distillation separation art regarding the concentration of the feed stock, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing bio-derived propylene glycol through use of purifying a hydrogenolysis product stream in order to obtain a suitable replacement for petroleum derived propylene glycol, see Fischer, Paras. [0002]-[0003];[0005];[0007];[0013], and MPEP 2141.
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699