Prosecution Insights
Last updated: August 18, 2026
Application No. 17/789,456

METHOD FOR PREPARING 1,4-CYCLOHEXANEDIMETHANOL

Non-Final OA §102§103§112
Filed
Jun 27, 2022
Priority
Dec 27, 2019 — RE 10-2019-0176139 +2 more
Examiner
KELLY-O'NEILL, YOLANDA LYNNETTE
Art Unit
1692
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Hanwha Corporation
OA Round
5 (Non-Final)
31%
Grant Probability
At Risk
5-6
OA Rounds
0m
Est. Remaining
64%
With Interview

Examiner Intelligence

Grants only 31% of cases
31%
Career Allowance Rate
11 granted / 35 resolved
-28.6% vs TC avg
Strong +32% interview lift
Without
With
+32.1%
Interview Lift
resolved cases with interview
Typical timeline
3y 7m
Avg Prosecution
39 currently pending
Career history
97
Total Applications
across all art units

Statute-Specific Performance

§101
1.1%
-38.9% vs TC avg
§103
48.2%
+8.2% vs TC avg
§102
10.0%
-30.0% vs TC avg
§112
21.2%
-18.8% vs TC avg
Black line = Tech Center average estimate • Based on career data from 35 resolved cases

Office Action

§102 §103 §112
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 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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 18 June 2026 has been entered. Status of the Claims Claims 1 and 6-8 are pending. Claim 1 is currently mended. Claim 10 is currently cancelled. Claims 2-5 and 9 were previously cancelled. Response to Amendments Applicant’s amendments filed on 18 June 2026 are acknowledged. Claim Rejections - 35 USC § 112 Applicant’s amendment to claim 1 and cancellation of claim 10 are sufficient to overcome the rejection of claims 1, 6-8, 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. Claim 1 has been amended to delete the relative term “type”. The rejection is withdrawn. Claim Rejections - 35 USC § 102 Applicant’s cancellation of claim 10 is sufficient to overcome the rejection of claim 10 under 35 U.S.C. 102(a)(1) as being anticipated by Hembre et al. (US20150183699, published 02 July 2015, hereinafter Hembre). The rejection is withdrawn. Claim Rejections - 35 USC § 103 Applicant’s amendments to claim 1 adding specifics regarding the structure and function of the gas-induced stirrer not taught by Hembre is sufficient to overcome the rejections of: Claims 1, 6, and 7 under 35 U.S.C. 103 as being unpatentable over Hembre et al. (US20150183699, published 02 July 2015, hereinafter Hembre) in view of Yoshiyuki et al. (JP2014177422, published 25 September 2014, see machine translation, hereinafter Yoshiyuki), and in further view of Crezee et al. (“Three-phase hydrogenation of D-glucose over a carbon supported ruthenium catalyst—mass transfer and kinetics”, published 2003, Applied Catalysis A: General, Vol. 251, Pgs. 1-17, hereinafter Crezee); and, Claims 1, 6, 7, and 8 under 35 U.S.C. 103 as being unpatentable over Hembre et al. (US20150183699, published 02 July 2015, hereinafter Hembre) in view of Yoshiyuki et al. (JP2014177422, published 25 September 2014, see machine translation, hereinafter Yoshiyuki), and in further view of Crezee et al. (“Three-phase hydrogenation of D-glucose over a carbon supported ruthenium catalyst—mass transfer and kinetics”, published 2003, Applied Catalysis A: General, Vol. 251, Pgs. 1-17, hereinafter Crezee), as applied to claims 1, 6, and 7 in the 35 USC 103 rejection above, in further view of Nieves-Remacha et al. (“Gas−Liquid Flow and Mass Transfer in an Advanced-Flow Reactor”, 30 May 2013, Industrial & Engineering Chemistry Research, Vol. 52, Pgs. 8996-9010, hereinafter Nieves-Remacha). The above rejections are withdrawn. Due to the amendment to claim 1, additional new and previous ground(s) of rejection is/are provided below. Response to Arguments Applicant’s arguments filed on 18 June 2026 have been fully considered but they are either moot or not persuasive. Applicant’s argue that Hembre, Yoshiyuki, Crezee, and Nieves-Remacha do not disclose the limitations as recited in newly amended claim 1. These arguments have been considered but are either moot or not persuasive for the reasons set forth in the new and previous grounds of rejection below and the response to arguments below. Applicant’s arguments throughout the remarks filed on 18 June 2026 with respect to Crezee have been considered but are moot because the new ground of rejection does not rely on Crezee applied in the prior rejection of record for any teaching or matter specifically challenged in the argument. In response to applicant’s argument on pages 13-15 of the remarks filed on 18 June 2026 that “Applicants believe the combination of the specific CHDA concentration and the specific gas-induced stirrer of claim 1 provides remarkable and unexpected results that eliminate the need for an additional isomerization step”. 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). 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 claim 1 states “wherein the 1,4-cyclohexane dicarboxylic acid(CHDA) comprising cis isomers and trans isomers is included in the amount of 10 to 23 wt%, based on a total weight of the 1,4-cyclohexane dicarboxylic acid and water, wherein the 1,4-cyclohexane dicarboxylic acid comprises 60 wt% or more of trans isomers” and “wherein the gas-induced stirrer comprises a gas inlet, a gas passage, an impeller, and plural jet orifices, and wherein the hydrogen gas inhaled in the gas inlet is passed to a lower part of the reactor through the gas passage, and the hydrogen gas passed to the lower part of the reactor is sprayed and fed into the reaction solution through the plural jet orifices of the stirrer”. Applicant’s argue, as stated above, the concentration of the total CHDA and the total CHDA trans isomers in combination with the use of the gas-induced stirrer “provides remarkable and unexpected results that eliminate the need for an additional isomerization step”; however, Applicant’s have not provided a proper comparison to the closest prior art and have not established test points inside and outside the claimed range of the concentration of the total CHDA, the concentration of the total CHDA trans isomers, and the use of the gas-induced stirrer in order to support the argument of surprising and unexpected results, see MPEP 716.02(e). The instant specification is relied upon for any comparison tests/examples. The Examples vary the concentration of the total CHDA trans isomers only between 56-75 wt%, i.e. narrowly below and within the claimed range, the Examples vary the total concentration of CHDA only within and below the claimed range, and all of the Example reactions are performed within a gas-induced stirrer reactor, see instant specification, Pgs. 20-23; Table 1. None of the examples provide comparison results in a reactor without a gas-induced stirrer. Therefore, the instant specification does not provide a comparison to the closest prior art, detailing tests above the total concentration of CHDA and tests in a reactor without a gas-induced stirrer suitably below, within, and above the claimed CHDA concentration ranges in order to support the argument of surprising and unexpected results relating to the concentration of the total CHDA and the total CHDA trans isomers in combination with the use of the gas-induced stirrer, see MPEP 716.02(e). For the reasons indicated above, applicant’s above arguments are not persuasive. In response to applicant’s argument on pages 14-15 of the remarks filed on 18 June 2026 against the Hembre, Yoshiyuki, and Nieves-Remacha references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986) and MPEP 2145 IV. The test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981) and MPEP 2145. “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). In this case, as stated in the previous office action dated 18 March 2026 (hereinafter POA): Hembre is applied to teach a hydrogenation “method of producing at least one hydroxymethylcyclohexane, such as 1,4-cyclohexanedimethanol (CHDM), see Paras. [0002];[0008]-[0010], by supplying at least one cyclohexanecarboxylic acid, such as 1,4-cyclohexanedicarboxylic acid (CHDA), with hydrogen and an acid hydrogenation catalyst in a second reaction zone under second reaction conditions, such as continuous stirring, effective to hydrogenate the acid groups on at least some of the at least one cyclohexanecarboxylic acid to produce a second composition containing at least one hydroxymethylcyclohexane compound and the at least one solvent, see Paras. [0002];[0008]-[0010];[0052];[0095]-[0097], Table 12”, see also Pgs. 9-10 of the POA; Yoshiyuki is applied to teach “the hydrogenation of mostly trans 1,4-cyclohexane dicarboxylic acid, 1,4-CHDA, in the presence of a ruthenium and tin catalyst in an aqueous liquid phase to produce 1,4-cyclohexanedimethanol, 1,4-CHDM, with a trans content of 1 to 99 wt %, more preferably 5 to 80 wt %, and even more preferably 30 to 75 wt %, where the hydrogenation and isomerization reaction proceed simultaneously, see Paras. [0001];[0006];[0012];[0016];[0023];[0025];[0033]-[0034]”, see also Pg. 11 of the POA; and, Nieves-Remacha is applied to teach “bubble generating systems of gas-liquid contacting reactors, such as bubble columns with interfacial areas of 50−600 m2/m3, see Abstract”, see also Pg. 16 of the POA. 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 Hembre, Yoshiyuki, Nieves-Remacha all teach gas-liquid flow mass transfer reactions, such as hydrogenation reactions, a person of ordinary skill in the art has good reason to modify Hembre by relying upon Yoshiyuki and Nieves-Remacha before the effective filing date of the claimed invention for knowledge generally available within the gas-liquid flow mass transfer reactions art regarding hydrogenation reactions and reactors, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing a high melting point polyester or polyesteramide as a derivative of 1,4-CHDM by producing high trans content 1,4-CHDM from a high trans content 1,4-CHDA, while using the optimal hydrogenation catalyst to promote the isomerization of cyclohexanedimethanol from the cis isomer to the trans isomer and suppress the isomerization of the trans isomer to the cis isomer, see Yoshiyuki, Paras. [0005]-[0006];[0025];[0028]; while also, optimizing the reaction speed, efficiency, and conversion by optimizing the mass transfer rate between the liquid and gas phases while minimizing power consumption, see Nieves-Remacha, Pg. 9007, Col. 1-Pg. 9008, Col. 2, Table 2; and, MPEP 2141 and 2143 I. B-D. For the reasons indicated above, applicant’s above arguments are not persuasive. New and Previous Rejections Based on Amendments to the Claims and the RCE filed on 18 June 2026 For clarity between the new and previous rejections, the specific new rejections below are in italics. In the Spirit of Compact Prosecution Throughout prosecution the examiner has attempted to identify all objections and clarity issues amongst the claims, applicant is advised that some objections and clarity issues may still remain. Going forward, the examiner respectfully requests applicant to perform a detailed review of the claims regarding clarity, grammar, antecedent basis, word spacing, and spelling issues. New and Previous 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, 6, and 7 are newly rejected under 35 U.S.C. 103 as being unpatentable over Hembre et al. (US20150183699, published 02 July 2015, hereinafter Hembre) in view of Yoshiyuki et al. (JP2014177422, published 25 September 2014, see machine translation, hereinafter Yoshiyuki), and in further view of Fung et al. (US20120226069, published 06 September 2012, hereinafter Fung). Hembre teaches the claim 1 limitations of a method of producing at least one hydroxymethylcyclohexane, such as 1,4-cyclohexanedimethanol (CHDM), see Paras. [0002];[0008]-[0010], by supplying at least one cyclohexanecarboxylic acid, such as 1,4-cyclohexanedicarboxylic acid (CHDA), with hydrogen and an acid hydrogenation catalyst in a second reaction zone under second reaction conditions, such as continuous stirring, effective to hydrogenate the acid groups on at least some of the at least one cyclohexanecarboxylic acid to produce a second composition containing at least one hydroxymethylcyclohexane compound and the at least one solvent, see Paras. [0002];[0008]-[0010];[0052];[0095]-[0097], Table 12, where the cyclohexanecarboxylic diacid (CHDA) feed has a cis/trans ratio, see Para. [0040], the hydroxymethylcyclohexane (CHDM) produced from the cyclohexanecarboxylic diacid (CHDA) feed has a cis/trans ratio of from about 0.20 to about 5.00, see Paras. [0040];[0053]-[0054], as calculated by the examiner a ratio of about 0.20 equals 1 cis:5 trans or about 20% cis to about 80% trans and a ratio of about 5.00 equals 5 cis:1 trans or about 80% cis to about 20% trans, the solvent is water, see Para. [0027];[0095]-[0097], Table 12, and the acid hydrogenation catalyst contains a ruthenium compound, see Paras. [0017];[0043], meeting: The supplying a reaction solution with cis and trans isomers, conducting the hydrogenation reaction under conditions of stirring, and preparing 1,4-cyclohexanedimethanol (CHDM) within the range of trans isomers in instant application claim 1; and, The hydrogen gas is supplied to the hydrogen reactor at a pressure of 1,500-2,500 psig or 103-172 bar and the reaction is conducted at a temperature of from about 100 to about 250° C, see Paras. [0008]-[0010];[0019];[0051];[0061], meeting: Supplying hydrogen, within the range of hydrogen gas pressure, and within the range of hydrogenation reactor temperature in instant application claim 1. Hembre does not teach: The instant application claim 1 limitations of wherein the 1,4-cyclohexane dicarboxylic acid (CHDA) comprising cis isomers and trans isomers is included in the amount of 10 to 23 wt%, based on a total weight of the 1,4-cyclohexane dicarboxylic acid and water and wherein the 1,4-cyclohexane dicarboxylic acid comprises 60 wt% or more of trans isomers; and, The limitations of instant application claims 6 and 7. Yoshiyuki relates to the hydrogenation of mostly trans 1,4-cyclohexane dicarboxylic acid, 1,4-CHDA, in the presence of a ruthenium and tin catalyst in an aqueous liquid phase to produce 1,4-cyclohexanedimethanol, 1,4-CHDM, with a trans content of 1 to 99 wt %, more preferably 5 to 80 wt %, and even more preferably 30 to 75 wt %, where the hydrogenation and isomerization reaction proceed simultaneously, see Paras. [0001];[0006];[0012];[0016];[0023];[0025];[0033]-[0034]. Yoshiyuki teaches the content of the trans isomer in the cycloalkanedicarboxylic acid, 1,4-CHDA, raw material is preferably 1 to 99 wt %, more preferably 5 to 80 wt %, the remaining weight percent is cis isomer, and when water is used as a solvent, it is preferably used so that the concentration of the raw material compounds before the reaction is 5 to 50% by weight, more preferably 10 to 40% by weight, see Paras. [0004];[0015];[0017], meeting and within the range limitations of trans isomer and cis isomer 1,4-CHDA and within the range of weight % 1,4-CHDA content in the raw material in instant application claim 1; and, The hydrogenation catalyst includes ruthenium and tin, see Para. [0018], meeting the catalysts material limitations in instant application claim 6 and in instant application claim 7. 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 hydrogenation of Hembre to use the reactant concentrations and the specific catalysts as taught by Yoshiyuki with a reasonable predictability of success for the purpose of producing a high melting point polyester or polyesteramide as a derivative of 1,4-CHDM by producing high trans content 1,4-CHDM from a high trans content 1,4-CHDA, while using the optimal hydrogenation catalyst to promote the isomerization of cyclohexanedimethanol from the cis isomer to the trans isomer and suppress the isomerization of the trans isomer to the cis isomer, see Yoshiyuki, Paras. [0005]-[0006];[0025];[0028]. 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 Hembre and Yoshiyuki teach producing 1,4-CHDM by the ruthenium catalyzed hydrogenation of 1,4-CHDA, a person of ordinary skill in the art has good reason to produce high trans content 1,4-CHDM by pursuing the known options within their technical grasp for the benefit of producing a high melting point polyester or polyesteramide as a derivative of 1,4-CHDM by producing high trans content 1,4-CHDM from a high trans content 1,4-CHDA, while using the optimal hydrogenation catalyst to promote the isomerization of cyclohexanedimethanol from the cis isomer to the trans isomer and suppress the isomerization of the trans isomer to the cis isomer, see Yoshiyuki, Paras. [0005]-[0006];[0025];[0028] and MPEP 2141. In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as reactant concentrations, temperatures, pressures, and cis/trans ratios, “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. Selection of a known material, such as a ruthenium and tin catalyst and an aqueous solvent system, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07. Regarding currently amended instant application claim 1, Hembre teaches hydrogenation to produce hydroxymethylcyclohexane, such as 1,4-cyclohexanedicarboxylic acid (CHDM), is performed in a stirred autoclave on a carbon supported ruthenium catalysts, see Paras. [0002];[0061]-[0062];[0068]-[0070];[0095]-[0098]. Hembre does not teach the currently amended instant application claim 1 limitation of a gas-induced type stirrer and wherein the gas-induced stirrer comprises a gas inlet, a gas passage, an impeller, and plural jet orifices, and wherein the hydrogen gas inhaled in the gas inlet is passed to a lower part of the reactor through the gas passage, and the hydrogen gas passed to the lower part of the reactor is sprayed and fed into the reaction solution through the plural jet orifices of the stirrer. Fung is in the known prior art field of methods “for preparing esters of cyclohexane polycarboxylic acids from esters of benzene polycarboxylic acids” “by using a reaction tank having a gas-introducing mixer capable of extracting and exhausting air and stirring to hydrogenate an ester of a benzene polycarboxylic acids into an ester of a cyclohexane polycarboxylic acid in the presence of a hydrogenation catalyst” “selected from a ruthenium catalyst, a palladium catalyst, a platinum catalyst and a rhodium catalyst”, see Abstract; Paras. [0011]-[0022]. Regarding currently amended instant application claim 1, Fung teaches the hydrogenation is performed by “e) starting the gas-introducing mixer to make a hollow rotatory shaft of the gas-introducing mixer and vanes attached to a terminal of the rotatory shaft rotate at a predetermined speed to let the hydrogen gas be drawn into the hollow rotatory shaft through air-extracting holes formed on the hollow rotatory shaft above a liquid surface of the reaction liquid, and then exhausted out from air-exhausting holes formed on the hollow rotatory shaft at a location immersed in the reaction liquid, for having the hydrogen gas evenly distributed over the reaction liquid as the vanes stirring the reaction liquid”, see Para. [0016], where “gas-introducing mixer 50 structurally comprises a hollow rotatory shaft 51 and vanes 52 attached to a terminal of the hollow rotatory shaft 51. The hollow rotatory shaft 51 is internally formed as a gas channel 53, for delivering hydrogen gas. The hollow rotatory shaft 51 at its upper part has several air-extracting holes 54 communicated with the gas channel 53. In use, the air-extracting holes 54 are located above a liquid surface 31 of the reaction liquid 30, so that the hydrogen gas can be drawn into the gas channel 53. The hollow rotatory shaft 51 at its lower part further has several air-exhausting holes 55 also communicated with the gas channel 53, for allowing the hydrogen gas drawn into the gas channel 53 to be exhausted out from the air-exhausting holes 54”, see Para. [0029]; Fig. 2, and “a pressure of the hydrogen gas at 5-60 kg/cm2, or preferably 20-40 kg/cm2”, see Para. [0035], i.e., the hydrogen gas leaves holes 55 under a jet pressure induced by the pressure of the reactor and the drawing of the hydrogen gas by the rotating shaft and vanes, meeting the gas-induced stirrer construction, inhalation of hydrogen gas that is passed to a lower part of the reactor, and the spraying of the hydrogen gas from the lower part of the reactor into the reactor solution in instant application claim 1. 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 stirrer of Hembre to use the hollow rotary shaft drawn hydrogen gas stirrer as taught by Fung with a reasonable predictability of success for the purpose of efficiently controlling the hydrogen gas–liquid mass transfer coefficients in order to enhance “the activity of the hydrogenation catalyst”, speed up hydrogenation, lower the pressure and temperature of the hydrogenation reaction, lower the “costs in fabrication, operation and maintenance of the hydrogenation tank” “while improving the yield of a resultant” hydrogenation product, see Fung, Paras. [0009]-[0010];[0019]-[0022];[0027]. 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 stirrer of Hembre by applying the known technique of the hollow rotary shaft drawn hydrogen gas stirrer as taught by Fung with a reasonable predictability of success for the purpose of efficiently controlling the hydrogen gas–liquid mass transfer coefficients in order to enhance “the activity of the hydrogenation catalyst”, speed up hydrogenation, lower the pressure and temperature of the hydrogenation reaction, lower the “costs in fabrication, operation and maintenance of the hydrogenation tank” “while improving the yield of a resultant” hydrogenation product, see Fung, Paras. [0009]-[0010];[0019]-[0022];[0027]; 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 Hembre and Fung both teach catalytic hydrogenation reactions with stirring in the catalytic hydrogenation industry, a person of ordinary skill in the art has good reason to modify the stirrer of Hembre by relying upon the hollow rotary shaft drawn hydrogen gas stirrer of Fung before the effective filing date of the claimed invention for knowledge generally available within the stirrers for catalytic hydrogenation reactors art, see MPEP 2143 B & G and 2141, for the benefit of efficiently controlling the hydrogen gas–liquid mass transfer coefficients in order to enhance “the activity of the hydrogenation catalyst”, speed up hydrogenation, lower the pressure and temperature of the hydrogenation reaction, lower the “costs in fabrication, operation and maintenance of the hydrogenation tank” “while improving the yield of a resultant” hydrogenation product, see Fung, Paras. [0009]-[0010];[0019]-[0022];[0027]; and MPEP 2141. As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied, 426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design incentives and other market forces can prompt variations of it, either in the same field or a different one. If a person of ordinary skill can implement a predictable variation, §103 likely bars its patentability. For the same reason, if a technique has been used to improve one device, and a person of ordinary skill in the art would recognize that it would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”, see MPEP 2141. Claim 8 is newly rejected under 35 U.S.C. 103 as being unpatentable over Hembre et al. (US20150183699, published 02 July 2015, hereinafter Hembre) in view of Yoshiyuki et al. (JP2014177422, published 25 September 2014, see machine translation, hereinafter Yoshiyuki), and in further view of Fung et al. (US20120226069, published 06 September 2012, hereinafter Fung), as applied to claims 1, 6, and 7 in the 35 USC 103 rejection above, in further view of Nieves-Remacha et al. (“Gas−Liquid Flow and Mass Transfer in an Advanced-Flow Reactor”, 30 May 2013, Industrial & Engineering Chemistry Research, Vol. 52, Pgs. 8996-9010, hereinafter Nieves-Remacha). Hembre teaches feeding hydrogen into the reactor at a pressure of 1500 psig under an agitation of 1000 rpm and maintaining this pressurized feed and agitation for 10 hours, see Paras. [0061];[0070], meeting the stirring and hydrogen gas in instant application claim 8. Hembre does not teach the instant application claim 8 limitations of wherein the stirring is conducted such that a surface area per unit volume of hydrogen gas bubbles becomes 15 m2/m3 or more. Nieves-Remacha relating to bubble generating systems of gas-liquid contacting reactors, such as bubble columns with interfacial areas of 50−600 m2/m3, see Abstract, teaches in stirred reactors the bubble size distribution depends on the agitation speed, the design and type of impeller, and the physical properties of the fluids, see Pg. 8999, Col. 1, First Full Para., where stirred tank reactors have interfacial areas of 100−2000 m2/m3, see Pg. 9007, Col. 1 and Pg. 9008, Table 2, meeting the stirring to obtain a surface area per unit volume of gas bubbles of 15 m2/m3 or more in instant application claim 8. 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 reactor stirring of Hembre with the stirred reactor bubble generation teachings of Nieves-Remacha with a reasonable predictability of success for the purpose of optimizing the reaction speed, efficiency, and conversion by optimizing the mass transfer rate between the liquid and gas phases while minimizing power consumption, see Nieves-Remacha, Pg. 9007, Col. 1-Pg. 9008, Col. 2 and Table 2. By applying “routine optimization” and “predictable results” to select the optimal agitation for gas bubble liquid contact reactions, one of ordinary skill in the art would have been motivated to make these modifications because Nieves-Remacha provides a finite number of identified, predictable solutions. A person of ordinary skill in the art has good reason to efficiently conduct a gas-liquid reaction by pursuing the known options within their technical grasp for the benefit of optimizing the reaction speed, efficiency, and conversion by optimizing the mass transfer rate between the liquid and gas phases while minimizing power consumption, see Nieves-Remacha, Pg. 9007, Col. 1-Pg. 9008, Col. 2, Table 2, and MPEP 2141. As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied, 426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design incentives and other market forces can prompt variations of it, either in the same field or a different one. If a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability. For the same reason, if a technique has been used to improve one device, and a person of ordinary skill in the art would recognize that it would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”, see MPEP 2141. In addition, “[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 stirring rate as it relates to surface area per unit volume of hydrogen gas bubbles, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05. Conclusion No claims are allowed. Any inquiry concerning this communication or earlier communications from the examiner should be directed to Y. Lynnette Kelly-O'Neill whose telephone number is (571) 270-3456. The examiner can normally be reached Tuesday-Friday, 8:30 a.m. - 6:30 p.m., EST, with Flex Time. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Yen-Ye Goon can be reached at (571) 270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /YO/Examiner, Art Unit 1692 /FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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Prosecution Timeline

Show 7 earlier events
Sep 18, 2025
Request for Continued Examination
Sep 22, 2025
Response after Non-Final Action
Oct 01, 2025
Non-Final Rejection mailed — §102, §103, §112
Jan 02, 2026
Response Filed
Mar 18, 2026
Final Rejection mailed — §102, §103, §112
Jun 18, 2026
Request for Continued Examination
Jun 22, 2026
Response after Non-Final Action
Jul 23, 2026
Non-Final Rejection mailed — §102, §103, §112 (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

5-6
Expected OA Rounds
31%
Grant Probability
64%
With Interview (+32.1%)
3y 7m (~0m remaining)
Median Time to Grant
High
PTA Risk
Based on 35 resolved cases by this examiner. Grant probability derived from career allowance rate.

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