DETAILED ACTION
Claims 1, and 4-9 are currently pending in the instant application.
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 .
Response to Amendment
Applicant's amendments and arguments filed 12/22/2025 have been fully considered and entered into the application. Applicant has overcome
The 35 U.S.C. 112(b) rejection of claims 1-9 in view of Applicant’s amendments to the claims.
Regarding the 35 U.S.C. 103(a) rejection, Applicant’s arguments have been considered but they are not persuasive. Applicant argues that since SHAW uses an alcohol having a boiling point lower than that of the aliphatic/cycloaliphatic solvent and the alcohol is removed along with the aromatic solvent and unreacted acrylonitrile leaving remaining aliphatic/cycloaliphatic solvent used as the catalyst extraction solvent, one would have motivated one to select an alcohol found in the teaching of FELDMAN having a lower boiling point than the hydrocarbon solvent. Additionally, Applicant argues that FELDMAN and SHAW both teach isopropanol as a preferred alcohol and isopropanol has been shown in the instant Specification to be incapable of achieving phase separation with the acrylonitrile dimer.
In response to Applicant’s arguments, it appears that Applicant has drawn out different teachings from SHAW (i.e. one would have motivated one to select an alcohol found in the teaching of FELDMAN having a lower boiling point than the hydrocarbon solvent) than the teachings Examiner has applied from SHAW in the 103 rejection. The Examiner has used the teachings of SHAW to show that it is known that upon removal of the unconverted acrylonitrile through distillation, the product (acrylonitrile dimer) and catalyst may be separated by leaving said mixture to separate into two phases, one phase which comprises the catalyst and the other phase comprises the dinitrile (the desired product) - see col. 1, lines 27-32 and lines 50-56. Thus, SHAW teaches an alternative method of separating the product and catalyst by leaving said mixture to separate into two phases.
Examiner applies these teachings of SHAW to the teaching of FELDMAN as discussed in the following 103 rejection.
In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971).
Regarding Applicant’s argument that FELDMAN and SHAW both teach isopropanol as a preferred alcohol, MPEP 2123, Section II, states that “Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments. In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971). Thus, since FELDMAN teaches alcohols such as cyclohexanol (see col. 3, line 4), the rejections have been maintained.
Maintained 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.
Claims 1 and 4-9 are rejected under 35 U.S.C. 103 as being unpatentable over FELDMAN (see US Pat. No. 3,732,281, issued 05/08/1973, cited in IDS filed 12/06/2022) in view of SHAW (see US Pat. No. 4,958,042, issued 09/18/1990, cited in IDS filed 12/06/2022).
FELDMAN teaches preparation of dimers of acrylonitrile compounds in presence of tertiary phosphines and alcohol as a co-catalyst and states alcohols have an optimum range of from 3 to 10 carbon atoms (see col. 2, lines 63-67) and names alcohols including cyclohexanol (see col. 3, line 4). FELDMAN teaches the dimerization reaction may be conducted in hydrocarbon solvents, and names benzene or xylene (see col. 3, lines 36-37) stating that in hydrocarbon solution, the addition of small amounts of alcohol appears to be beneficial. FELDMAN teaches that the solvent and unreacted acrylonitrile are removed by distillation as the temperature is maintained below about 100 ºC (see col. 3, lines 63-65) and the remaining solvent may be removed by distillation. The solution containing the dimer is then washed with water and reminder of solvent distilled off (see col. 3, lines 70-73). FELDMAN teaches the catalyst can be recycled (see col. 3, line 73). The boiling point of benzene is 80.1 ºC, xylene is 137-140 ºC and cyclohexanol is 161 ºC. Thus, FELDMAN teaches the limitations of claims 1 and 4-5 as the alcohol has a higher boiling point than the hydrocarbon-based solvent and removal of solvent and unreacted acrylonitrile occurs through distillation. FELDMAN teaches the concentration of alcohol may range from about 1 to about 20 %, which reads on the limitations of claim 7.
FELDMAN teaches separation of phosphonium salt from crude dimer by extraction with dilute acid (see col. 3, lines 67-68) rather than allowing the resulting reaction mixture to stand for phase separation as disclosed by instant claim 1. Specifically, FELDMAN exemplifies the removal of the unreacted acrylonitrile and solvent through distillation while the remaining crude product of acrylonitrile dimer and phosphonium salt is distilled out in benzene solvent and then extracted with dilute aqueous sulfuric acid (see Example 3).
SHAW teaches dimerization of acrylonitrile in a liquid phase comprising a phosphinite catalyst with a proton donating solvent and an aromatic hydrocarbon solvent (see abstract). SHAW exemplifies the use of isopropyl bi-p-tolyl phosphinite catalyst (see Example 1, col. 4, line 19). Further SHAW teaches that when the unconverted acrylonitrile and aromatic solvent are evaporated or distilled form the reaction product – the mixture separates into 2 phases, one of which comprises a major proportion of catalyst and the other comprises major proportion of the dinitrile (see claim 1, col. 5). SHAW teaches that the phase comprising a major proportion of the catalyst may be recycled to the reaction as may the distilled aromatic solvent and inert proton donating solvent and acrylonitrile (see col. 4, lines 5-9), which corresponds to the limitations of claim 9.
Thus it would have been prima facie obvious to one of ordinary skill in the art to utilize the teachings of SHAW in the art of FELDMAN as an alternative method of purification of the final product. While FELDMAN teaches separation of phosphonium salt from crude dimer by extraction with dilute acid (see col. 3, lines 67-68) rather than allowing the resulting reaction mixture to stand for phase separation, SHAW teaches that following distillation of unconverted acrylonitrile and aromatic solvent, the remaining mixture is left and separates into 2 phases, one comprising the catalyst and the other the dinitrile product. By utilizing the teachings of SHAW to the art of FELDMAN, one would save the step of adding dilute acid into the mixture of FELDMAN, thereby simplifying the purification process.
Regarding the limitations of claims 6, FELDMAN teaches hydrocarbon solvents such as benzene or xylene. However, since benzene and xylene are both aromatic hydrocarbon solvents, this would render toluene obvious since benzene, toluene and xylene are structurally similar and toluene differs from both benzene and xylene by the presence of a methyl group. As stated in re Wood, 199 USPQ 137, hydrogen and methyl are deemed obvious variants, and substitution of a methyl for the hydrogen (i.e. substitution of CH3 for H). Regarding claim 8, SHAW teaches the phosphorus-based catalyst as a phosphinite, and exemplifies isopropyl bis-p-tolyl phosphinite catalyst (see Example 1). Thus, it would be obvious to substitute the catalyst of SHAW into the teachings of FELDMAN as both are taught to catalyze dimerization of acrylonitrile in liquid solution.
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 KAREN CHENG whose telephone number is (703)756-4699. The examiner can normally be reached M-F, 9AM-6PM PST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Adam Milligan can be reached at 571-270-7674. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/KAREN CHENG/Primary Examiner, Art Unit 1623
/ADAM C MILLIGAN/Supervisory Patent Examiner, Art Unit 1623