PROCESSES FOR PRODUCING NITRILES AND PHOSPHORUS-CONTAINING CATALYSTS FOR USE IN SUCH PROCESSES

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 . Priority The instant application claims priority as follows: PNG media_image1.png 32 358 media_image1.png Greyscale and of PNG media_image2.png 20 258 media_image2.png Greyscale . 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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 08/20/2026 has been entered. Receipt of claim amendments filed on 06/11/2026 is acknowledged. Claims 23-27 and 29-34, and 36-42 are now pending. All rejections and objections not reiterated herein have been withdrawn in view of the claim amendments. The examiner has considered the allowability of withdrawn Group II, claims 40-41. Claims 40 and 41 are allowable. The restriction requirement between Group I and II is hereby withdrawn. However, claim 42, directed to Group III remains withdrawn from consideration because it does not require all the limitations of an allowable claim. In view of the above noted withdrawal of the restriction requirement, applicant is advised that if any claim presented in a divisional application is anticipated by, or includes all the limitations of, a claim that is allowable in the present application, such claim may be subject to provisional statutory and/or nonstatutory double patenting rejections over the claims of the instant application. Once a restriction requirement is withdrawn, the provisions of 35 U.S.C. 121 are no longer applicable. See In re Ziegler, 443 F.2d 1211, 1215, 170 USPQ 129, 131-32 (CCPA 1971). See also MPEP § 804.01. Claims 42 remains withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to nonelected inventions, there being no allowable generic or linking claim. Applicant timely traversed the restriction requirement in the reply filed on 01/08/2026. Claims 23-27, 29-34 and 36-41 are the subject of this Office Action. 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. Claims 23-27, 29-30, 34, 36 and 39 are rejected under 35 U.S.C. 103 as being unpatentable over Foo (US 5,821,378) and Tam et al. (US 5,723,641), in view of Paciello (Angew. Chem. Int. Ed. 1999, 38, No. 13/14; p. 1920-1923) and Brammer (US 8,741,173) or Steyer (Dalton Trans., 2005, 1301-1309), and references therein, as evidenced by Hamden and Santoro. Teachings of Foo Foo disclosed an improved process for the hydrocyanation of diolefinic compounds (and subsequent isomerization of the resulting 2-alkyl-3-monoalkenenitriles to 3 and/or 4-monoalkene linear nitriles) comprising reacting an acyclic aliphatic diolefinic compound with a source of HCN in the presence of a catalyst precursor comprising zero-valent nickel and at least one multidentate phosphite ligand selected from Formulas I -XV, wherein ligands of formula II are calix[4]arene bisphosphites of the following formula: PNG media_image3.png 326 340 media_image3.png Greyscale PNG media_image4.png 88 326 media_image4.png Greyscale , and wherein ligands of formula VII are phosphites of the following formula PNG media_image5.png 236 338 media_image5.png Greyscale wherein “R2 is isopropyl” (at least claim 11), and wherein the diolefinic compounds of the claims are selected from 1,3-butadiene, 1,3-pentadiene and others. See at least claims 1, 15, 6, 16 and 20. Foo also taught that: PNG media_image6.png 62 360 media_image6.png Greyscale PNG media_image7.png 90 262 media_image7.png Greyscale PNG media_image8.png 130 287 media_image8.png Greyscale . See at least column 15. Foo recognized that some multidentate phosphite ligands useful in the present invention for the hydrocyanation of diolefins have been used for the hydrocyanation of monoolefins. Teachings of Tam Tam et al. taught the hydrocyanation reaction of monoolefins with HCN catalyzed by calix[4]arene phosphite ligands of formula II: PNG media_image9.png 292 254 media_image9.png Greyscale in which R6 and R7 are t-butyl, in a complex with zero-valence nickel. See Example 60 and claim 9. The process provides hydrocyanation of the following monoolefins (col. 8): PNG media_image10.png 266 366 media_image10.png Greyscale See Examples 58-61. Example 61 used ligand G in the reaction: PNG media_image11.png 198 306 media_image11.png Greyscale PNG media_image12.png 206 354 media_image12.png Greyscale Tam disclosed that some of the ligands used therein for the hydrocyanation reaction of olefins have been disclosed to be useful for the hydroformylation reaction of olefins in catalyst complexes with rhodium (column 1, lines 63-67). Teachings of Paciello Paciello teaches the same ligand encompassed by Tam for the hydroformylation of olefins, and structural variants 2, 3 and 4. Paciello varied the substituents on the aryl groups of the phosphite units to tune the ligand, and therefore the catalyst’s regioselectivity. The different aryl substituents were investigated for structure-activity optimization. Paciello taught that bis-ortho methyl (3) and bis-ortho-isopropyl (2) calix[4]arene bisphosphites produced a significant improvement in activity in a hydroformylation reaction with half the reaction time as compared to the tert-butyl substituted calix[4]arene bisphosphate (1), while calix[4]arene bisphosphate (1) had the highest regioselectivity, and unsubstituted ligand (4) had the poorest regioselectivity. PNG media_image13.png 226 356 media_image13.png Greyscale PNG media_image14.png 238 354 media_image14.png Greyscale Paciello also recognized that their catalysts produce olefin isomerization. See the third paragraph at page 1922 and the section named “Hydroformylation experiments”. Teachings of Brammer Brammer taught how to prepare calix[4]arene bisphosphite ligands of formula (IV) PNG media_image15.png 198 206 media_image15.png Greyscale and formula (V) PNG media_image16.png 286 506 media_image16.png Greyscale , and their use as catalysts in the hydroformylation of olefins. Teachings of Steyer Steyer taught how to prepare calix[4]arene bisphosphite ligands similar to Brammer’s of formula PNG media_image17.png 206 184 media_image17.png Greyscale . Steyer also disclosed highly active catalysts of formula PNG media_image18.png 158 458 media_image18.png Greyscale and PNG media_image19.png 188 330 media_image19.png Greyscale . Ascertainment of the difference between the prior art and the claims (MPEP §2141.02) The difference between the process of Foo or Tam and the claimed process is only the particular calix[4]arene phosphite ligands used in the reaction. Finding of prima facie obviousness--rational and motivation (MPEP §2142-2413) The level of skill is the level of the references cited in this action. Chelating aryl phosphite complexes were known to be excellent catalysts for both hydrocyanation and hydroformylation of olefins. The same ligands used for the hydroformylation reaction of olefins are known to be useful for the hydrocyanation of olefins in catalyst complexes with nickel. Evidence for this assertion can be found in at least Tam et al. and Foo, and the references cited therein, particularly the Baker references, and US 6,660,876. See also the calix[4]arene bisphosphite ligand in Paciello that was used in both hydrocyanation and hydroformylation reactions. Calix[4]arene bisphosphite ligands in catalyst complexes comprising zero-valence nickel were known in the art to catalyze the hydrocyanation reaction of olefins, per Foo and Tam et al. Additional calix[4]arene bisphosphite ligands were known in the art to be used in the related hydroformylation reaction. 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. See MPEP 2143. Examples of rationales that may support a conclusion of obviousness include: (A) Combining prior art elements according to known methods to yield predictable results; (B) Simple substitution of one known element for another to obtain predictable results; (C) Use of known technique to improve similar devices (methods, or products) in the same way; (D) Applying a known technique to a known device (method, or product) ready for improvement to yield predictable results; (E) "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success; (F) Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art; (G) Some teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention. Applying KSR example rationales (B) and (G), it would have been prima facie obvious to substitute the ligand catalyst in the hydrocyanation reactions of Foo or Tam with the aryl substituted ligand catalysts of Brammer of formula PNG media_image15.png 198 206 media_image15.png Greyscale , wherein R1-R4 are t-butyl, Y1-Y2 are alkyl and Ar1-Ar4 are each alkyl-substituted aryl radicals. These ligands have the same calix[4]arene aryl phosphite core, and are known to be useful in the same type of reactions. Adding an alkyl substituent on the phosphite aryl rings is a recognized way to modify the catalytic properties and regioselectivity of a phosphite ligand, as evidenced at least by Paciello. A skilled artisan would have been motivated to make such a substitution, as bis-ortho-methylphenyl and bis-ortho-isopropylphenyl, to search for similar improvements in the hydrocyanation reaction of the primary references with the same substituents that Paciello tested. The artisan would have reasonably expected such substitution to work because calix[4]arene aryl bisphosphite ligands with alkyl-substituted phenyl radicals are used in the hydrocyanation of olefins. Note that Foo and Tam disclosed ortho-isopropylphenyl and/or ortho-tert-butylphenyl phosphite ligands. In the alternative, Foo taught the same hydrocyanation reaction with phosphite ligands of formula PNG media_image5.png 236 338 media_image5.png Greyscale in which R2 is isopropyl (at least claim 11); and also with phosphite ligands containing the calix[4]arene core of formula PNG media_image3.png 326 340 media_image3.png Greyscale . The ordinary skilled artisan would have been motivated to make the ligand of formula PNG media_image5.png 236 338 media_image5.png Greyscale in which R2 is isopropyl of Foo also into a calix[4]arene, to obtain the benefits that using a calix[4]arene core/moiety provides in catalysis. Santoro (Coordination Chemistry Reviews 448 (2021) 214173) and Homden (Chem. Rev. 2008, 108, 5086-5130) show evidence of the superiority and ease of preparation of calixarenes compared to other systems. The aryl phosphite groups in formula VII are ortho-isopropyl phenyl phosphite groups, and therefore, the substituted aryl phosphite calix[4]arene of the rejected claims would have been obvious. Conclusion Claims 23-27, 29-30, 34, 36 and 39 are rejected. Claims 40 and 41 are allowable. Claims 31-33 and 37-38 are objected to for depending of rejected claims, but would be allowed if written in independent form. Any inquiry concerning this communication or earlier communications from the examiner should be directed to VALERIE RODRIGUEZ-GARCIA whose telephone number is (571)270-5865. The examiner can normally be reached Monday-Friday 9:30am-5:30pm. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton Brooks can be reached at 571-270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /VALERIE RODRIGUEZ-GARCIA/Primary Examiner, Art Unit 1621