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 1-7 are pending.
Claims 6 and 7 are new.
Response to Amendments
Applicant’s amendments filed 09 September 2025 are acknowledged.
Response to Arguments
Applicant’s arguments filed 09 September 2025 have been fully considered but they are not persuasive.
Applicant argues that Susumu and Luxin, as evidenced by ASTM® do not disclose the limitations as recited in the claims. These arguments have been considered but are not persuasive for the reasons set forth in the response to arguments below.
In response to applicant’s arguments on pages 6-8 of the remarks filed on 09 September 2025 that the references fail to show certain features of the invention, it is noted that the features upon which applicant relies (i.e., “to produce 1,4-cyclohexanedione” and “yield of 1,4-cyclohexanedione”) are not recited in the rejected claim(s). Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims, see In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s arguments on pages 6-8 of the remarks filed on 09 September 2025 that “[n]one of Susumu, Luxin, and ASTM teaches or suggests using the specific transition metal salt claimed as a catalyst in the hydrolysis of DMSS to produce 1,4-cyclohexanedione”, “Susumu is silent with respect to the use of a transition metal salt as the catalysts”, and since the hydrolysis reactant and products in Susumu and Luxin are different “a skilled artisan after referring to Luxin would not have been motivated to utilize the specific transition metal salt (e.g. CuSO4), which is useful for the hydrolysis of saccharides, to hydrolyze DMSS to produce 1,4-cyclohexanedione”, 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).
In this case, Susumu is applied to teach a method of hydrolysis of dimethyl succinyl succinate (DMSS)
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, a cyclic carbon oxygen compound, by reacting in a reactor with stirring a succinyl succinic acid diester, such as dimethyl succinyl succinate, with water and an acid catalyst, such as hydrochloric acid, sulfuric acid, and paratoluenesulfonic acid, see Susumu, Pgs. 1-2 and Pg. 2, Example 1, and Luxin is applied to teach a mixture of hydrolysis acid catalysts including sulfuric acid and/or hydrochloric acid and/or CuSO4 and/or Fe2(SO4)3, see Luxin, Paras. [0034]-[0035];[0057], in the hydrolysis of five-carbon saccharides
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and six-carbon saccharides
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, cyclic carbon oxygen compounds, see Luxin, Abstract. Since Susumu teaches the use of an acid catalysts, such as hydrochloric acid and sulfuric acid, in the hydrolysis of a cyclic carbon oxygen compound, see Susumu, Abstract, Pg. 2, Lns. 72-73, and Luxin teaches hydrolysis acid catalysts selected from sulfuric acid and/or hydrochloric acid and/or CuSO4 and/or Fe2(SO4)3, in the hydrolysis of a cyclic carbon oxygen compound, see Luxin, Abstract, Paras. [0034]-[0035];[0057], the combined teachings of the references would have suggested to those of ordinary skill in the art, before the effective filing date of the claimed invention, that the hydrolysis acid catalysts of Susumu may be selected from sulfuric acid and/or hydrochloric acid and/or CuSO4 and/or Fe2(SO4)3, as taught by Luxin. For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s arguments on pages 6-8 of the remarks filed on 09 September 2025 that “the reaction of Susumu needs to be carried out at a temperature higher than 120 ◦C” and “that a skilled artisan after referring to Susumu would not have learned how to select a suitable catalyst to decrease the reaction temperature”. Susumu teaches lower temperatures increase the reaction time; but, does not “criticize, discredit, or otherwise discourage” the use of a lower temperature, see Susumu, Pg. 2, Lns. 60-62 and MPEP 2145 X.D.1. On the contrary, Susumu teaches if the temperature is too high “the solvent decomposes or the reaction is so fast that carbon dioxide gas is rapidly produced, causing operational problems”, see Susumu, Pg. 2, Lns. 60-62. Since Susumu does not teach away from lowering the reaction temperature, it would have been obvious to those of ordinary skill in the art, before the effective filing date of the claimed invention, to modify the Susumu reaction time when the hydrolysis is performed at the temperature of 80-110 ◦C as taught by Luxin, Para. [0025]. For the reasons indicated above, applicant’s above argument is not persuasive.
As stated above, Susumu teaches the use of an acid catalysts in the hydrolysis, such as hydrochloric acid and sulfuric acid, see Susumu, Pg. 2, Lns. 72-73, and Luxin teaches hydrolysis acid catalysts selected from sulfuric acid and/or hydrochloric acid and/or CuSO4 and/or Fe2(SO4)3, see Luxin, Paras. [0034]-[0035];[0057], the combined teachings of the references would have suggested to those of ordinary skill in the art, before the effective filing date of the claimed invention, that the hydrolysis acid catalysts of Susumu may be selected from sulfuric acid and/or hydrochloric acid and/or CuSO4 and/or Fe2(SO4)3, as taught by Luxin. For the reasons indicated above, applicant’s above argument is not persuasive.
In response to applicant's arguments in the remarks filed on 09 September 2025 against the 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).
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-5 are rejected under 35 U.S.C. 103 as being unpatentable over Susumu et al. (JPS6357544, published 12 March 1988, see machine translation, hereinafter Susumu) in view of Luxin et al. (CN111111601, published 08 May 2020, see machine translation, hereinafter Luxin), as evidenced by ASTM® International (“Designation: E202-12 Standard Test Methods for Analysis of Ethylene Glycols and Propylene Glycols”, 22 August 2012, Pgs. 1-13).
Susumu teaches the claims 1-4 limitations of a method of hydrolysis of dimethyl succinyl succinate (DMSS) to 1,4-cyclohexanedione, by reacting in a reactor with stirring a succinyl succinic acid diester, such as dimethyl succinyl succinate, with water, where the water charged into the reactor is 2 to 50 moles, preferably 3 to 10 moles, per mole of the above ester, polyethylene glycol, and an acid catalyst, such as hydrochloric acid, sulfuric acid, and paratoluenesulfonic acid, at a temperature of 120 to 200 ◦C, preferably 140 to 170 ◦C, see Pgs. 1-2 and Pg. 2, Example 1; polyethylene glycol, such as diethylene glycol and triethylene glycol have water contents of 0.0498 % mass for TEG and 0.0649 % mass for DEG, as evidenced by ASTM®, Pgs. 3-4, Table 4, meeting:
1) adding DMSS and water to a reactor, and stirring; 2) adding a phase transfer catalyst to the reactor, and heating; and 3) adding an acid and to the reactor for hydrolysis of DMSS; wherein the acid is sulfuric acid, hydrochloric acid in claim 1;
Wherein in 1), an addition amount of the water is 5-20 times that of DMSS by weight in claim 2;
Wherein in 2), the phase transfer catalyst is polyethylene glycol in claim 3; and,
Wherein an addition amount of the phase transfer catalyst accounts for 0.01-0.1 wt. % that of the water in claim 4.
Susumu does not teach the claim 1 limitations of the specific order of the claimed steps of adding ingredients and adding a transition metal salt, a H+ ion concentration of a mixture in the reactor is 0.2-12 mol/L; the transition metal salt is a nitrate, sulfate, or chloride of copper, nickel, zinc or manganese, or a combination thereof, and a metal ion concentration of the mixture in the reactor is 0.01-0.1 mol/L.
Susumu does not teach the claim 5 limitations of wherein the mixture in the reactor is heated to 60- 1000C, and then the acid and the transition metal salt are added to the reactor.
Luxin relates to hydrolysis of hydrocarbons, see Abstract. The hydrolysis chamber/first reaction chamber is preheated to a temperature of 80-110 ◦C, then a hydrocarbon slurry including wastewater is added to the vessel, see Paras. [0047]-[0049];[0051], after the mixed solution of the raw material liquid is in the preheated first reaction chamber, the catalyst and the organic solvent are injected into the first reaction chamber, see Paras. [0049];[0058], the catalyst is an acid catalysts, such as sulfuric acid and/or hydrochloric acid, with a H+ ion concentration of 0.01-0.5 mol/L and the catalyst is a transition metal sulfate, such as CuSO4 and/or Fe2(SO4)3, with a metal ion concentration of 0.01-0.5 mol/L, see Paras. [0034]-[0035];[0057], meeting:
Adding a transition metal salt, a H+ ion concentration of a mixture in the reactor is 0.2-12 mol/L; the transition metal salt is a sulfate, and a metal ion concentration of the mixture in the reactor is 0.01-0.1 mol/L in claim 1; and,
Wherein the mixture in the reactor is heated to 60- 1000C, and then the acid and the transition metal salt are added to the reactor in claim 5.
In reference to the above claims, In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) states “selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results” and In re Gibson, 39 F.2d 975, 5 USPQ 230 (CCPA 1930) states “[s]election of any order of mixing ingredients is prima facie obvious.”, see MPEP 2144.04 IV.C. Therefore, 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 sequence of adding ingredients of Susumu as desired with a reasonable predictability of success for the purpose of producing 1,4-cyclohexanedione with high yield.
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 hydrolysis of Susumu to include a transition metal catalysts at the optimal concentration, the acid catalysts at the optimal concentration, and to heat the reactor prior to the addition of the catalyst, as taught by Luxin, with a reasonable predictability of success for the purpose of hydrolysis of hydrocarbons under the optimal reaction conditions in order to improve the catalytic reaction rate, reduce the amount of by-products produced, and reduce the number of side reactions, see Luxin Paras. [0034]-[0035].
By applying “routine optimization” and “predictable results” to select the optimal
concentrations of catalysts, sequence of adding ingredients, and reaction temperatures, one of ordinary skill in the art would have been motivated to make these modifications because Luxin provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to efficiently hydrolyze hydrocarbons under the optimal reaction conditions in order to improve the catalytic reaction rate, reduce the amount of by-products produced, and reduce the number of side reactions, see Luxin Paras. [0034]-[0035] 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.
Selection of a known material, such as hydrolysis catalyst, 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.
In addition, “[t]he normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as the concentration of catalysts and the reaction temperature, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969). See MPEP 2144.05.
Claims 6 and 7 are rejected under 35 U.S.C. 103 as being unpatentable over Susumu et al. (JPS6357544, published 12 March 1988, see machine translation, hereinafter Susumu) in view of Luxin et al. (CN111111601, published 08 May 2020, see machine translation, hereinafter Luxin), as evidenced by ASTM® International (“Designation: E202-12 Standard Test Methods for Analysis of Ethylene Glycols and Propylene Glycols”, 22 August 2012, Pgs. 1-13), as applied to claims 1-5 in the 35 USC 103 rejection above, in further view of Scutt et al. (US20170183281, hereinafter Scutt).
Susumu does not teach the limitations of claims 6 and 7.
Susumu teaches a method of hydrolysis of dimethyl succinyl succinate (DMSS) to 1,4-cyclohexanedione by reacting in a reactor with stirring a succinyl succinic acid diester, such as dimethyl succinyl succinate, with water and an acid catalyst, such as hydrochloric acid, sulfuric acid, and paratoluenesulfonic acid, see Susumu, Pgs. 1-2 and Pg. 2, Example 1.
Scutt relating to the preparation of cyclohexanediones, see Para. [0001], by hydrolysis under known conditions, see Para. [0295] and reaction scheme, such as through use of an acid catalyst, see Para. [0243] and reaction scheme, where the cyclohexanedione is prepared in the presence of an acid catalyst which promotes rearrangement, such as mixtures of a Brönsted acid, for example sulfuric acid, hydrochloric acid, and a Lewis acid, for example zinc chloride, see Paras. [0246];[0251]-[0262];[0276]-[0277] and reaction schemes, meeting:
The specific metal salt 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 acid catalysts of Susumu to include a transition metal acid catalysts in the reaction, as taught by Scutt, with a reasonable predictability of success for the purpose of the hydrolysis of hydrocarbons under known reaction conditions in order to prepare cyclohexanedione or derivatives thereof with the desired physical properties, see Scutt, Paras. [0001];[0070];[0295].
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 Susumu and Scutt teach preparing cyclohexanedione or derivatives thereof through use of acid catalysts, a person of ordinary skill in the art has good reason to prepare cyclohexanedione or derivatives thereof by pursuing the known options within their technical grasp, such as using a Lewis acid transition metal, for the benefit of the hydrolysis of hydrocarbons under known reaction conditions in order to prepare cyclohexanedione or derivatives thereof with the desired physical properties, see Scutt, Paras. [0001];[0070];[0295] 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.
Selection of a known material, such as hydrolysis acid catalyst, 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.
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
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691