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
The amendment filed on 01/07/2026 has been entered. Claim 1 has been amended and claim 11 has been canceled. Thus claims 1-10 are currently pending and are under examination.
Withdrawn Rejection
The 112(b) rejection of record has been withdrawn in view of the amendment of claim 11.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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 1-10 are rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2019/0062244A1 (US’244) in view of Patent number CN106866373A (CN’373).
Regarding claims 1-3, US’244 teaches a process for the separation of a diol from a product stream, said process comprising the steps of: (i) separating the product stream comprising three or more C2 to C7 diols, C3 to C6 sugar alcohols, and C4 to C6 polyhydric alcohols with at least 3 hydroxyl groups in the molecule, and a catalyst, by a first distillation column to produce a first stream comprising the three or more C2 to C6 diols; (ii) separating the first stream comprising the three or more C2 to C7 diols by a second distillation column using an extractant into a) a second stream comprising a first diol and b) a third stream comprising two or more diols ([0014], [0016]-[0017], [0025], Figs. 1-2, Tables 5-6).
Regarding claims 5-6, US’244 teaches that the extractant is selected from the group of C3 to C6 sugar alcohols and mixtures thereof, wherein sugar alcohols have the general formula HOCH2(CHOH)nCH2OH and include glycerol, erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galacticol and iditol ([0034]).
Regarding claim 7, the distillation in the second distillation column of US’244 is carried out at a temperature in the range of from 50 to 250° C and a pressure of at least 1 kPa ([0037]).
Regarding claim 8, the extractant is added in an amount such that the weight ratio of the feed comprising extractant to the mixture comprising the two or more C2 to C7 diols is at least 0.05:1, more preferably at least 0.1:1, even more preferably at least 0.25:1, based on the overall weight of the feed/mixture ([0036]).
Regarding claim 9, wherein the separating of the first stream of step (ii) comprises distilling the first stream to produce the second stream and the third stream at a temperature and pressure as follows (Table 5):
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Regarding claim 10, US’244 is silent that the third stream comprises an azeotrope of MEG and 1,2-BDO or an azeotrope of MPG and 2,3 BDO, however, there is a prima facie case of anticipation or obviousness for the third stream of US’244 to comprise an azeotrope of MEG and 1,2-BDO or an azeotrope of MPG and 2,3 BDO since the reference teaches the same process as claimed to obtain the third stream. See MPEP § 2112.01.
Regarding claims 1, 7 and 11, US’244 further teaches that the product stream is obtained by the saccharide hydrogenolysis, and that in addition to C2 to C7 diols, the reaction product streams comprise oxygenates and hydrocarbons ([0025). However, US’244 fails to teach the presence of unsaturated hydrocarbons and/or one or more compounds with a carbonyl group in the second stream, and (iii) hydrogenating the second stream comprising a first diol and unsaturated hydrocarbons and/or one or more compounds with a carbonyl group to provide a purified diol stream, wherein the hydrogenating of step (iii) comprises a hydrogenation reaction carried out at a temperature within a range of about 20° C to about 300° C and a pressure within a range of about 0.5 bara to about 250 bara in the presence of a hydrogenation catalyst.
The deficiency is however cured by CN’373.
Regarding claims 1 and 7, CN’373 teaches a method for refining ethylene glycol obtained by catalytic hydrogenation degradation of biomass, wherein the biomass is one or more of cellulose, hemicellulose, glucose, xylose, xylooligosaccharides, fructose, fructooligosaccharides, starch, arabinose, erythrose, chitosan, chitooligosaccharides, glycerol, sorbitol, mannitol and xylitol ([0017]). The reference teaches that impurities are introduced during the catalytic conversion and distillation processes, especially trace substances such as carboxylic acids, aldehydes, and ketones with unsaturated chemical functional groups, making it difficult for the ultraviolet transmittance of ethylene glycol products to meet polymerization grade requirements ([0006]). Thus, CN’373 teaches catalytically hydrogenating a small amount of impurity compounds containing unsaturated chemical bonds in crude ethylene glycol during the distillation under the action of a metal catalyst to reduce them to saturated compounds without UV absorption, thereby improving the UV transmittance of the ethylene glycol product to reach polymerization grade ([0019]).
CN’373 teaches that the catalytic hydrogenation is conducted at vacuum distillation ([0019]), in which the top condenser temperature is 20°C, the distillation section temperature is controlled at 110-130°C, the reaction section temperature is 120-140°C, the stripping section temperature is 130-160°C, the bottom reboiler temperature is 145°C, and the top pressure is 5 kPa ([0029] and [0035]). In other embodiment, the reaction the top pressure is 1-20 kPa ([0014]) (0.01-0.2 bar. In view of MPEP § 2144.05, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close absent any showing of unexpected results or criticality.
Hence, since US’244 teaches that the reaction product streams comprises oxygenates and hydrocarbons, and CN’373 teaches that these impurities make it difficult for the ultraviolet transmittance of ethylene glycol products to meet polymerization grade requirements, a skilled artisan would have been motivated in using the methods of CN’373 by hydrogenating the impurities recognized by both references with a reasonable expectation of success in improving the UV transmittance of the ethylene glycol product to reach polymerization grade.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a process for the separation of a diol from a product stream, said process comprising the steps of: (i) separating the product stream comprising three or more C2 to C6 diols, C3 to C6 sugar alcohols, and C4 to C6 polyhydric alcohols with at least 3 hydroxyl groups in the molecule, and a catalyst, to produce a first stream comprising the three or more C2 to C6 diols; (ii) separating the first stream comprising the three or more C2 to C6 diols into (a) a second stream comprising a first diol and unsaturated hydrocarbons and/or one or more compounds with a carbonyl group, and b) a third stream comprising two or more diols; (iii) hydrogenating the second stream comprising a first diol and unsaturated hydrocarbons and/or one or more compounds with a carbonyl group to provide a purified diol stream, wherein the hydrogenating of step (iii) comprises a hydrogenation reaction carried out at a temperature within a range of about 20° C to about 300° C and a pressure within a range of about 0.5 bara to about 250 bara in the presence of a hydrogenation catalyst in view of the combination of US’244 and CN’373.
Response to Arguments
Applicant argues that claim 1 recites hydrogenation step at a pressure of about 0.5 bar to about 250 bar, whereas CN’373 teaches a pressure of 20 kPa maximum and that a skilled artisan would not have been motivated to increase the pressure to arrive at the instantly claimed hydrogenation pressure.
The arguments are not persuasive. The instantly claimed pressure and the pressure of CN’373 are merely close and in view of MPEP § 2144.05, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close absent any showing of unexpected results or criticality.
In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) (Claimed process which was performed at a temperature between 40°C and 80°C and an acid concentration between 25% and 70% was held to be prima facie obvious over a reference process which differed from the claims only in that the reference process was performed at a temperature of 100°C and an acid concentration of 10%).
In this instance, there is no record in the instant invention of unexpected results when conducting the hydrogenation pressure at the claimed pressure, and thus claim 1 as amended remains obvious over US’244 in view of CN’373 in the absence of evidence indicating that such hydrogenation pressure is critical.
Conclusion
Claims 1-10 are rejected and no claims are allowed.
THIS ACTION IS MADE FINAL. 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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/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692