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 .
Claim Status
Claims 5-7 were amended in the response filed 6/23/2026. Claims 1-11 are pending and rejected.
Priority
The Application was filed on 9/19/2023 and claims the benefit of:
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See filing receipt dated 1/10/2024. Though the previous OA indicated that certified copies of paper required by 37 CFR 1.55 were received by the office, upon review, this is not correct. The Applicant has only filed an interim copy of the foreign priority document CN202110197792.6 and there does not appear to be a certified copy of PCT/CN2021/130661.
Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged. Applicant has not complied with one or more conditions for receiving the benefit of an earlier filing date under 35 U.S.C. 120 as follows: no certified copy has been filed. See MPEP 1895.01: “A certified copy of the international application (and an English translation of the international application) may be required by the examiner to perfect the claim for benefit under 35 U.S.C. 120 and 365(c) if the international application did not originate in the United States and such is necessary, for example, where an intervening reference is found and applied in a rejection of one or more claims.”
Acknowledgement is made of applicant's claim for foreign priority based on an application filed in China on 2/22/2021. It is noted, however, that applicant has not filed a certified copy of the CN202110197792.6 application as required by 37 CFR 1.55.
Withdrawn Claim Objections and Rejections
The amendments to the specification, drawings, and claims filed on 6/23/2026 are acceptable. Therefore, the objections of record on p. 2-3 of the OA dated 4/1/2026 are withdrawn. The claim amendments were also persuasive to overcome the 35 USC 112(b) rejection on p. 3-4 of the OA dated 4/1/2026. Therefore, this rejection is also withdrawn.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action. See p. 4-14 of the OA dated 4/1/2026 regarding the rejection of record. It is also noted that reference EP 3012243A1 was mistakenly referred to as “Luo” in the rejection statement and “Liu” in the rejection. The rejection statement was modified to clarify that the EP 3012243A1 reference is “Liu”.
Claim(s) 1-11 is/are rejected under 35 U.S.C. 103 as being unpatentable over Liu (EP 3012243A1, published on 4/27/2016, of record) in view of Tang (“Nitrocyclohexane hydrogenation over Ni-based catalyst modified with metal promoter” China Excellent Doctoral and Master’s Thesis Full Text Database (Master’s) Engineering Science and Technology I, 2018, No. 2. P. B016-57, of record as NPL #3 in the IDS filed on 8/15/2023, and including a partial translation thereof), Flack (US 3157702, published on 11/17/1964, of record), and Luo (CN11153831, published on 5/15/2020, of record in the IDS filed on 8/15/2023, including a machine generated translation).
Applicant claims: A method for producing adipic acid and cyclohexanone oxime from cyclohexane, comprising:
(1) subjecting cyclohexane and NOx to catalytic or non-catalytic oxidation-nitration reaction to produce a first reaction mixture containing adipic acid, nitrocyclohexane and by-product A; and separating adipic acid and nitrocyclohexane from the first reaction mixture; wherein the NOx is a mixture of molecular oxygen and one or more of N2O, NO, NO2 N2O3, N2O4 and N2O5, and x represents a ratio of the number of O atoms to the number of N atoms in the NOx; and the by-product A is 1-nitro-1-cyclohexene, cyclohexyl nitrate, glutaric acid, succinic acid, cyclohexanone, cyclohexanol or a combination thereof;
(2) subjecting the nitrocyclohexane obtained in the step (1) to catalytic hydrogenation with hydrogen to produce cyclohexanone oxime and cyclohexylamine; and separating cyclohexanone oxime from cyclohexylamine;
(3) subjecting the cyclohexylamine obtained in the step (2) to partial oxidation with molecular oxygen under the action of a catalyst to obtain a second reaction mixture containing cyclohexanone oxime and by-product B, wherein cyclohexylamine is absent or present in the second reaction mixture; and the by-product B is water, hexamethyleneimine, cyclohexanone, nitrocyclohexane, N-cyclohexyl hexamethyleneimine, dicyclohexylamine or a combination thereof; and
(4-1) without separation, or after separating part or all of water from the second reaction mixture, subjecting the second reaction mixture to simultaneous hydrogenation and amination in the presence of H2 and NH3 under the action of a catalyst, or sequentially to hydrogenation with H2 and amination with NH3 under the action of a catalyst, followed by separation to obtain cyclohexanone oxime; or
(4-2) without separation, or after removing part or all of water from the second reaction mixture by distillation, under the action of a catalyst, subjecting the second reaction mixture to hydrogenation with H2 followed by separation to obtain cyclohexanone oxime.
Liu teaches a method for the co-production of adipic acid and nitrocyclohexane. The method comprises contacting cyclohexane with nitrogen oxides (NOx), acting as both an oxidant and nitrating agent, to produce adipic acid and nitrocyclohexane. See abstract and claims. Thus, Liu corresponds to instant step (1). Regarding the composition of NOx, Liu teaches that 1 <x <3, and recites at least NO2, N2O4, N2O3, N2O5, and mixtures thereof. See [0021]. Liu teaches that the side reactions may also occur during the oxidation/nitration step, including alcohols (cyclohexanol), ketones (cyclohexanone), acids, esters, and the like and even deep oxidation products CO and CO2. See [0015] and [0054]. Example 8 on p. 10, lines 24-38 teaches that the oxidation by-products further include cyclohexyl nitrate, succinic acid, and glutaric acid. Liu teaches that the adipic acid and nitrocyclohexanone are separated from each other and the reaction mixture in a separation unit (S1) in Fig. 1, wherein line 5, comprising the nitrocyclohexanone and light products can be further separated in (S2) and line 8, comprising the adipic acid and heavy products can be further separated in (S3). See Figure 1 and [0054].
Liu further teaches that the total selectivity of the combination of adipic acid and nitrocyclohexane can include >95% and all of the examples have a selectivity of at least 93%. These values fall within the range of claim 2. See [0057] and examples, including Table bridging p. 9-10. Liu further teaches that the selectivity of the adipic acids in the range of 60-90% and that the ratio is adjustable. See [0051]. The Table bridging p. 9-10 recites selectivities of adipic acid to nitrocyclohexane, but these appear to be based on mass and not moles. The ratio selectivities (wt%) of adipic acid: nitrocyclohexane range from 72.7 : 25.3 to 82.7: 12.7. Therefore, though the ratio is adjustable, the main product in the examples is adipic acid. An estimate of the moles of each is calculated below by assuming a total weight of 100 g.
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72.7 g adipic acid x [ 1 mole/146.1 g] = 0.5 moles adipic acid
82.7 g adipic acid x [1 mole/146.1 g] = 0.6 moles adipic acid
25.3 g nitrocyclohexane x [1 mole/129.1 g] = 0.2 moles nitrocyclohexane
12.7 g nitrocyclohexane x [1 mole/129.1 g] = 0.1 moles nitrocyclohexane
Therefore, the estimated molar ratio of adipic acid : nitrocyclohexane ranges from 0.6-0.5 mol adipic acid : 0.1 – 0.2 mol nitrocyclohexane, or 0.6/0.1 (6 : 1) to 0.5/0.2 (2.5:1). This range falls within that of claim 2. Also see MPEP 2144.05.
Liu further teaches that the oxidation-nitration step can be performed in the presence of a solid catalyst and an inducer. See [0048-0049]. The catalyst and inducer can be any of the options listed in claims 6 and 7. Also see Table bridging p. 9-10. Liu teaches that adipic acid (hexanedioic acid) and nitrocyclohexane are important industrial materials and/or intermediates in a number of processes. See [0002-0003]. Liu teaches that the nitrocyclohexanone can be hydrogenated to produce cyclohexanone oxime. See [0003].
Liu does not explicitly teach instant steps (2) to (4-2).
Tang teaches a nitrocyclohexane hydrogenation over Ni-based catalyst modified with metal promoter which corresponds to instant step (2). See English abstract on p. II to III. Tang teaches that optimized conditions comprise the hydrogenation of nitrocyclohexane with hydrogen gas in the presence of a 1.5%Cu-20%Ni/AC catalyst, wherein AC is activated carbon, at a reaction temperature of 60°C, a reaction pressure at 0.3 MPa, and a reaction time at 7 h to produce cyclohexanone oxime in a selectivity of 77.73% and with a nitrocyclohexane conversion of 99.55%. The process is described with respect to Figure 4-14 on p. 53-54 of the dissertation, which shows the effect of reaction time on the hydrogenation:
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See partial translation of p. 53-54 (lines 1-99), which includes summary section 4.4. Tang provides selectivities in weight percentages. See partial translation of p. 17-18 (lines 100-172). Figure 4-14 on p. 54 shows a selectivity of cyclohexanone oxime is between 70-80% by mass and the selectivity of cyclohexyl amine is around 20%.
Therefore, the selectivity is about 75% : 20% (cyclohexanone oxime: cyclohexyl amine). The molar ratio of the cyclohexanone oxime to cyclohexylamine is estimated as follows (the same process described above with respect to Liu):
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Assuming a total mass of 100 g:
75 g cyclohexanone oxime x [1 mole / 113.16 g/mol] = 0.66 mol cyclohexanone oxime
20 g cyclohexyl amine x [1 mole / 99.17 g/mol] = 0.2 mol cyclohexyl amine
So the molar ratio can roughly be estimated to be 0.66 : 0.2, or 3.3:1 (oxime : amine), which falls within the range of claim 3. Also see MPEP 2144.05. It is also noted that the catalyst of Tang (1.5%Cu-20%Ni/AC catalyst) is almost identical to the catalyst used in example 7 of the specification as filed (1 %Cu-20%Ni/AC catalyst), with a slightly higher Cu loading. This further supports the conclusion that the process of Tang will produce substantially the same results as those in instant example 7. Further the catalyst comprises Ni, a group VIII transition metal, and Cu, a promoter from Group IB to VIIIB (claims 8-9 wrt step 2).
The partial translation of Tang does not appear to explicitly teach separating cyclohexanone oxime from cyclohexylamine as required by instant step (2).
Flack is directed toward an analogous reaction to that of Tang, wherein nitrocyclohexane is hydrogenated to cyclohexanone oxime. See col. 1, lines 1-35 and example 1 in col. 2-3. In example 1, the catalyst is 5wt% Pd on acetylene black (activated carbon) containing 1 wt% of magnesium as a promotor. Like Tang, the process of Flack also produces a mixture comprising cyclohexanone oxime and cyclohexylamine. Flack teaches that the cyclohexanone oxime can be predictably separated from the cyclohexylamine by acid/base extraction to obtain both in high quality. See examples 1-4 and claims.
Neither of Tang or Flack appear to teach instant steps (3) and (4-1) or (4-2).
Luo is directed to an analogous process for preparing cyclohexanone oxime to that of Liu, Tang, and Flack. Luo teaches a method comprising: “(1) oxidizing cyclohexane and molecular oxygen under the action of a solid catalyst, carrying out one-step reaction to generate KA oil, and performing separation to obtain the KA oil; (2) directly aminating the KA oil with ammonia and hydrogen under the action of a solid catalyst to generate cyclohexylamine and a small amount of byproduct-A, and performing separation to obtain cyclohexylamine; (3) carrying out partial oxidation on cyclohexylamine and molecular oxygen under the action of a solid catalyst to obtain an oxidation product mainly composed of cyclohexanone-oxime, a small amount of byproduct-B and cyclohexylamine which may not be completely converted; and (4) aminating the oxidation product, namely, directly carrying out amination reaction on the oxidation product obtained in the step (3), ammonia and hydrogen under the action of a solid catalyst without separation, converting the byproduct-B into cyclohexylamine, and performing separation to obtain cyclohexanone-oxime”. See abstract. Step (3) of Luo corresponds to instant step (3) step (4) of Luo corresponds to instant step (4-1).
Regarding step (3) of Luo, Luo teaches that cyclohexylamine is subjected to partial oxidation with molecular oxygen (O2) in the presence of a solid catalyst to obtain a reaction mixture comprising cyclohexanone oxime and by-product B, namely cyclohexanone, nitrocyclohexane, dicyclohexylamine, and cyclohexanone but also optionally comprising hexamethyleneimine and N-cyclohexylhexamethyleneimine. Water is also produced as a by-product. See equations in [0021] of the original patent and lines 349-434 of the translation. With respect to step (3) of claims 8-9, Luo teaches that the catalyst used in the partial oxidation is a surface hydroxyl-rich catalyst or its supported catalyst. See claims 7 and 9, lines 509-515, and example 3 in lines 625-640.
Regarding step (4) of Luo, Luo teaches directly feeding the reaction mixture of step (3) comprising cyclohexanone oxime and any by-products B (without separation), to a simultaneous hydrogenation, with H2, and amination, with NH3, in the presence of a catalyst to convert by-product B to cyclohexylamine (claim 5, (4-1)), which is easily separable from the cyclohexanone oxime by distillation (rectification by boiling point). Cyclohexanone oxime is inert to the hydrogenation and amination conditions such that it can be carried through the reaction without separation. See equations in [0023] of the original patent and lines 436-448 of the translation. Regarding claim 4, step (4) is not coupled with water separation. Regarding claims 10 and 11, the simultaneous hydrogenation and amination catalyst is a solid catalyst formed by compounding hydrotalcite or a hydrotalcite-like compound with a transition metal main active component and a transition metal auxiliary active component. The main active component comprises one or more group VIII transition metals and the auxiliary active component comprises one or more of Group IB-VIIB transition metals. See claim 8, lines 517-527 and example 4 in lines 642-656.
It would have been prima facie obvious to combine the teachings of Liu, Tang, Flack and Luo, all teaching the formation of cyclohexanone oxime and/or intermediates thereof, to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to modify the method of Liu, for co-producing adipic acid and nitrocyclohexane, to obtain cyclohexanone oxime from the catalytic hydrogenation of nitrocyclohexane (instant step 2) because Tang and Flack teach this is a well-known and predictable process to produce the industrially valuable cyclohexanone-oxime, which is also mentioned as an intended use of the nitrocyclohexane in Liu in [0003]. Therefore, combining two-well known processes to obtain an industrially valuable product is predictable and prima facie obvious.
A person of ordinary skill would have been further motivated to subject any cyclohexylamine obtained in the combined process of Liu, Tang, and Flack to partial oxidation according to instant step 3, because Luo teaches that more of the desired product, cyclohexanone oxime, is predictably produced from the oxidation process and increasing the yield of desired product, while decreasing side-products, is prima facie obvious. A person of ordinary skill would be further motivated to subject the oxidation product mixture to direct hydrogenation and amination because Luo teaches that the hydrogenation and amination conditions convert the by-products in the oxidation reaction mixture, which are not easily separable from cyclohexanone oxime, to cyclohexylamine, which is readily separable from cyclohexanone oxime by simple distillation. Further, Luo teaches in partial oxidation step 3 that cyclohexylamine is a productive starting material toward cyclohexanone amine. Therefore, in addition to simplifying the isolation process of the desired cyclohexanone amine, the hydrogenation-amination sequence additionally provides more starting material (cyclohexylamine) that can be transformed into the desired cyclohexanone oxime. Accordingly, both steps 3 and 4 of Luo teach increasing the yield of the desired product, while simplifying isolation of said product by reducing the number of side-products.
Therefore, combining instantly claimed steps 2-4, as taught by Tang, Flack, and Luo, with the process of instantly claimed step 1 of Liu will predictably lead to an optimized reaction sequence for obtaining cyclohexanone oxime, an industrially valuable product, with reduced side-products and facile isolation conditions to produce a more efficient and higher yielding predictable method for obtaining cyclohexanone oxime. Also see MPEP 2143(I)(A).
Response to Arguments on p. 7-8 of the response filed on 6/23/2026:
Applicant argues:
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The affidavit or declaration of attribution has been fully considered but is not persuasive to disqualify Luo-2 (Luo in the rejection) as a reference. There are several issues which are outlined below.
Non-Perfected Foreign and International Priority dates:
Firstly, there is a statutory bar against disqualifying Luo because the Applicant has not provided a certified copy and certified translation of foreign priority document CN202110197792.6, filed on 2/22/2021. As indicated in the priority section above, Applicant has only filed an interim copy of the original foreign priority application. Though the Applicant can file certified copy of the foreign application within the pendency of the application and before the patent is granted, a certified copy and certified translation are both required for the Applicant to perfect the foreign priority claim to a filing date of 2/22/2021. See MPEP 215.02.
Additionally, the instant application is a CON of PCT/CN2021/130661 (filed 11/15/2021), which is also not in English. Though, there does appear to be a proper certification of the PCT application filed on 9/19/2023 (that was filed as the original specification), there does not appear to be a certified copy of PCT/CN2021/130661 present in the application file. Therefore, the Applicant has not perfected priority for this application either. “A certified copy of the international application (and an English translation of the international application) may be required by the examiner to perfect the claim for benefit under 35 U.S.C. 120 and 365(c) if the international application did not originate in the United States and such is necessary, for example, where an intervening reference is found and applied in a rejection of one or more claims.” Also see MPEP 1895.01.
Therefore, as neither priority document has a perfected filing date, the effective filing date is the US filing date of 8/15/2023. Accordingly, Luo (published 5/15/2020) and prior art under 35 USC 102(a)(1), does not fall within the one-year grace period to be disqualified as a reference under a 35 USC 102(b) exception.
Deficiencies in the 37 CFR 1.130(a) Declaration
MPEP.07(a)(1) details the requirements for evaluation of Declarations or Affidavits under 37 CFR 1.130(a).
As discussed above, the criteria for (A) has not been met.
Criteria (B) then requires the following:
“(B) Whether the affidavit or declaration shows sufficient facts, in weight and character, to establish that
(1) the disclosure was made by the inventor or a joint inventor, or
(2) the subject matter disclosed was obtained directly or indirectly from the inventor or a joint inventor.
Some factors to consider are the following:[AltContent: rect]
(1) Where the authorship of the prior art disclosure includes the inventor or a joint inventor named in the application, an "unequivocal" statement from the inventor or a joint inventor that he/she (or some specific combination of named joint inventors) invented the subject matter of the disclosure, accompanied by a reasonable explanation of the presence of additional authors, may be acceptable in the absence of evidence to the contrary. See In re DeBaun, 687 F.2d 459, 463, 214 USPQ 933, 936 (CCPA 1982).
(2) A mere statement from the inventor or a joint inventor, without any accompanying reasonable explanation, may not be sufficient where there is evidence to the contrary, such as a contrary statement from another named author that was filed in another application on behalf of another party. See Ex parte Kroger, 219 USPQ 370 (Bd. App. 1982) (affirming rejection notwithstanding declarations by the alleged actual inventors as to their inventorship in view of a non-applicant author submitting a letter declaring the non-applicant author’s inventorship).”
In the affidavit/declaration filed on 6/23/2026, there does not appear to be an unequivocal statement by the joint inventors that they invented the subject matter of the disclosure. The document is only signed by 5 of the 6 instant inventors (leaving out Jian Jian). This raises questions as to named joint inventor Jian. Beyond that, the document has not stated that the inventors invented “the subject matter of” the disclosure. The document instead recites that the inventors invented “the invention described in” the instant application. Furthermore, there is no “reasonable explanation” for the presence of authors Fu and Wei on the Luo reference, which is also required. Therefore, the document filed on 6/23/2026 also fails to meet the requirements of criteria (B).
The final issue with the declaration is that it does not clearly state what it is. The title of the document states that it is an “affidavit or declaration of attribution or prior public disclosure under 37 CFR 1.130.” It was submitted as a 1.130(a) declaration according to the transmittal sheet, but the document itself talks about the “date of disclosure” (which concerns 102(b)(1)(B)) as well as the disclosure being made by the inventor/joint inventor or obtained directly/indirectly from an inventor/joint inventor (which are matters for 102(b)(1)(A)). The document needs to be clear about which exception it is attempting to invoke.
Therefore, the rejection of record is maintained as Luo is a prior art reference available under 35 USC 102(a)(1).
Conclusion
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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