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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 06/09/2026 has been entered.
Status of the Claims
The amendment filed on 06/09/2026 has been entered. Claims 28-29 have been amended. Thus, claims 13, 15-16, 18-19 and 23-29 are currently pending; claims 16, 18-19, 23-24 and 26-27 have been withdrawn from further consideration; and thus claims 13, 15, 25 and 28-29 are under examination.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 13, 15, 25 and 28-29 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claims 13, 15-16, 18-19 and 23-24 contains the trademark/trade name Raney. Where a trademark or trade name is used in a claim as a limitation to identify or describe a particular material or product, the claim does not comply with the requirements of 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph. See Ex parte Simpson, 218 USPQ 1020 (Bd. App. 1982). The claim scope is uncertain since the trademark or trade name cannot be used properly to identify any particular material or product. A trademark or trade name is used to identify a source of goods, and not the goods themselves. Thus, a trademark or trade name does not identify or describe the goods associated with the trademark or trade name. In the present case, the trademark/trade name is used to identify/describe a hydrogenating catalyst and, accordingly, the identification/description is indefinite.
Claims 23-29 are also rendered indefinite for their dependency on claims 13, 16 and 23.
The examiner suggests replacing the trademark name “Raney nickel” with the synonymous term “spongy nickel”.
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 13 and 15 stand rejected and claims 25, and 28-29 are newly rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2011/0015429A1 (US’429; cited in PTO-892 06/05/2025) in view of Patent number US3,479,394 (US’394; cited in IDS 07/19/2022).
Regarding claim 13, US’429 teaches a method for preparing a mixture containing cyclohexanol and cyclohexanone, comprising a) oxidizing cyclohexane with molecular oxygen to give a reaction mixture comprising cyclohexyl hydroperoxide, cyclohexanol, cyclohexanone, 6-hydroxyperoxycaproic acid and unconverted cyclohexane ([0013]), b) hydrogenating cyclohexyl hydroperoxide in the presence of a catalyst (that includes nickel [0044]) to give cyclohexanol and cyclohexanone ([0043]-[0047]), wherein, prior to step b), the reaction mixture obtained in step a) is extracted with water to give an organic phase containing cyclohexyl hydroperoxide, cyclohexanol, cyclohexanone and unconverted cyclohexane and an aqueous phase containing 6-hydroxyperoxycaproic acid ([0013] and [0037]), and step b) is carried out in the organic phase ([0013] and [0037]).
Regarding claim 15, US’429 further teaches hydrogenating 6-hydroxyperoxycaproic acid in the aqueous phase to 6-hydroxycaproic acid ([0021]) in the presence of a catalyst such as Raney nickel ([0060]).
Regarding claim 25, US’429 teaches hydrogenation reaction to cyclohexanol and cyclohexanone can be continuous.
Regarding claims 28-29, US’429 teaches the hydrogenation reaction is conducted at a temperature of 80 to 100° C ([0044]). MPEP 2144.04 states “In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists” and “Similarly, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.” As such, the claimed temperature is rendered obvious over that of US’429.
Regarding claim 1, US’429 fails to teach that the nickel catalyst in the hydrogenation of cyclohexyl hydroperoxide containing unconverted cyclohexane to cyclohexanol and cyclohexanone is Raney nickel. The deficiency however is cured by US’394.
US’394 discusses that it is a known process to obtain cyclohexyl hydroperoxide in cyclohexane by air oxidation of cyclohexane, and reduce cyclohexyl hydroperoxide with hydrogen in the presence of catalysts such as Raney nickel to cyclohexanol and cyclohexanone (col. 2, lines 3-10). Thus, using Raney nickel of US’394 in place of the nickel catalyst of US’429, a skilled artisan would yield nothing more than the predictable cyclohexanol and cyclohexanone products.
In accordance with MPEP § 2143, the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. In this case, at least prong (B) simple substitution of one known element for another to obtain predictable results applies.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a method for preparing a mixture containing cyclohexanol and cyclohexanone, comprising the step of hydrogenating cyclohexyl hydroperoxide in cyclohexane in the presence of a Raney nickel catalyst to give cyclohexanol and cyclohexanone, comprising the steps of a) oxidizing cyclohexane with molecular oxygen to give a reaction mixture comprising cyclohexyl hydroperoxide, cyclohexanol, cyclohexanone, 6-hydroxyperoxycaproic acid and unconverted cyclohexane, b) hydrogenating cyclohexyl hydroperoxide in the presence of a Raney nickel catalyst to give cyclohexanol and cyclohexanone, wherein, prior to step b), the reaction mixture obtained in step a) is extracted with water to give an organic phase containing cyclohexyl hydroperoxide, cyclohexanol, cyclohexanone and unconverted cyclohexane and an aqueous phase containing 6-hydroxyperoxycaproic acid, and step b) is carried out in the organic phase in view of the combination of US’429 and US’394.
Response to Declaration under 37 CFR 1.132 and Arguments
The declaration under 37 CFR 1.132 filed 06/09/2026 is insufficient to overcome the rejection of claims 13 and 15 based upon 103 as set forth in the last Office action because: the experimental data of using the instantly claimed Raney nickel does not show unexpected results with the closest prior art.
The technical effect of using the claimed Raney nickel in the hydrogenation process is compared with the hydrogenation process that uses chromium catalyst, however the Applicant has not shown the unexpected effect over the closest prior art US’429. The reference teaches the use of nickel catalyst among other catalysts in the hydrogenation step to obtain cyclohexanol and cyclohexanone and the Applicant has failed to show the criticality of using the claimed Raney catalyst over the catalyst of US’429. Absent any showing of the criticality, the claimed invention remains obvious for reasons of record.
The Applicant further argues that step b) in the instant claim is carried out in the organic phase whereas US’429, the use of the nickel catalyst is in conjunction with the addition of water.
The examiner disagrees. US’429 teaches the workup step after cyclohexane oxidation step in which the oxidation mixture into an organic phase and an aqueous phase by the addition of water ([0037]), that the phases are separated [0038] and that the organic phase is converted to cyclohexanone and cyclohexanol by the hydrogenation process ([0040]). Hence, the hydrogenation step in US’429 is carried out in the organic phase as instantly claimed.
Applicant further argues
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and discusses the unexpected effect of using Raney nickel as presented in the declaration.
The examiner disagrees and reiterates as earlier that the experimental data only show the unexpected results of Raney nickel over chromium catalyst. However, there is no comparative data over the closest prior art’s catalyst, at least over the nickel catalyst as taught by US’429. In the absence of the criticality of Raney nickel over the catalyst of US’429, the instantly claimed method is not deemed unobvious over the combination of US’429 and US’394.
Conclusion
Claims 13, 15, 25 and 28-29 are rejected and no claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett 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.
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/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692
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