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 .
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 07/21/2026 has been entered.
Response to Arguments
Applicant's arguments filed 06/24/2026 have been fully considered but they are not persuasive. Applicant argues that SHAW teaches removal of alcohol by distillation and preferable hydroxylic solvents are used. However as discussed before, 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. Thus, Applicant’s argument that the alcohol of SHAW is not retained to serve as extraction solvent is not relevant to the rejection.
Applicant argues that neither FELDMAN or SHAW provides any teaching, suggestion or motivation to provide a partition coefficient, and that the KROH/AND of the phosphorus-based catalyst is 1.0 or more is not taught in either FELDMAN or SHAW. However, since the partition coefficient is based upon the affinity of the phosphorus-based catalyst in either alcohol or adiponitrile, and FELDMAN teaches the same phosphorus-based catalyst, and cyclohexanol as the alcohol, the inclusion of the partition coefficient, which is a property of the phosphorus-based catalyst would not render the claims patentable. MPEP 2112, Section I states that SOMETHING WHICH IS OLD DOES NOT BECOME PATENTABLE UPON THE DISCOVERY OF A NEW PROPERTY - "[T]he discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer." Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). Thus the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977). Further MPEP 2112, Section II states that “There is no requirement that a person of ordinary skill in the art would have recognized the inherent disclosure at the relevant time, but only that the subject matter is in fact inherent in the prior art reference. Schering Corp. v. Geneva Pharm. Inc., 339 F.3d 1373, 1377, 67 USPQ2d 1664, 1668 (Fed. Cir. 2003) (rejecting the contention that inherent anticipation requires recognition by a person of ordinary skill in the art before the critical date and allowing expert testimony with respect to post-critical date clinical trials to show inherency); see also Toro Co. v. Deere & Co., 355 F.3d 1313, 1320, 69 USPQ2d 1584, 1590 (Fed. Cir. 2004) ("[T]he fact that a characteristic is a necessary feature or result of a prior-art embodiment (that is itself sufficiently described and enabled) is enough for inherent anticipation, even if that fact was unknown at the time of the prior invention."); Abbott Labs v. Geneva Pharms., Inc., 182 F.3d 1315, 1319, 51 USPQ2d 1307, 1310 (Fed. Cir. 1999).”
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 claim 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.
Further regarding the new limitation,
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, although the prior art is silent regarding this limitation, such a limitation will naturally flow from the method made obvious by the prior art (see above rejection), since the same phosphorus-based catalyst is used reaction process. In other words, products of identical or similar composition cannot exert mutually exclusive properties when administered under the same or similar circumstances. MPEP 2112, Section I states that SOMETHING WHICH IS OLD DOES NOT BECOME PATENTABLE UPON THE DISCOVERY OF A NEW PROPERTY - "[T]he discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer." Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999).
By practicing the method made obvious by the prior art: "A preparation method of an acrylonitrile dimer, the method comprising: a reaction process of preparing an acrylonitrile dimer by reacting a reaction mixture comprising: a hydrocarbon-based solvent, an alcohol selected from cyclohexanol, ethylene glycol or a combination thereof, acrylonitrile and phosphorus-based catalyst", one will also be meeting the limitations of "wherein an alcohol-adiponitrile partition coefficient of the phosphorus-based catalyst" even though the prior art was silent as to these parameters. In the instant case, the KROH/ADN of the phosphorus-based catalyst would be considered an inherent property of the catalyst. The discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art's functioning, does not render the old composition patentably new to the discoverer. See Atlas Powder Co. v. Ireco Inc., 190 F.3d 1342, 1347-49 (Fed. Cir. 1999); accord Toro Co. v. Deere & Co., 355 F.3d 1313, 1320-21 (Fed. Cir. 2004).
Conclusion
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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/KAREN CHENG/Primary Examiner, Art Unit 1623
/ANAND U DESAI/Supervisory Patent Examiner, Art Unit 1655
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