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:
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and of
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.
Receipt of claim amendments filed on 05/07/2026 is acknowledged. Claims 23-27 and 29-42 are now pending.
The claims have been amended to remove subject matter directed to the process wherein in the catalyst, the phosphorous atom of each aryl phosphite group is bonded to two adjacent benzene rings of the calixarene backbone through oxygen atoms of hydroxyl groups of the calixarene and each of the phosphorous atoms has an OR2 substituent, wherein R2 is a phenyl ring substituted with 1-5 primary alkyl groups and all other carbon atoms are unsubstituted. The amendments have overcome the 103 rejection and indefinite rejections presented in the Office Action of 02/09/2026.
Claims 40-42 remain withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to nonelected inventions, there being no allowable generic or linking claim.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 and 29-39 are the subject of this Final 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), 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:
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, and wherein ligands of formula VII are phosphites the following formula
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, 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:
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.
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:
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, in a complex with zero-valence nickel. The process provides hydrocyanation of the following monoolefins (col. 8):
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See Examples 58-61. Example 61 used ligand G in the reaction:
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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 described in Tam for the hydroformylation of olefins, and structural variants 2, 3 and 4. Paciello taught that the calix[4]arene bisphosphites with bis-ortho methyl (3) or bis-ortho-isopropyl (2), produce 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) described in Tam.
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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 calix[4]arene bisphosphite ligands of formula
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as catalysts useful for the hydroformylation of olefins.
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 rhodium. 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
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, wherein R1-R4 are t-butyl, Y1-Y2 are alkyl and Ar1-Ar4 are each 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. A skilled artisan would have been motivated to make such a substitution in order to search for improvements on the hydrocyanation reaction of the references, just like Paciello tested various calix[4]arene aryl bisphosphite ligands searching for improvement on the hydroformylation reaction. The artisan would have reasonably expected such substitution to work because calix[4]arene aryl bisphosphite ligands are used in hydrocyanation of olefins.
In the alternative, Foo taught the same hydrocyanation reaction with phosphite ligands of formula
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and also with phosphite ligands containing the calix[4]arene core of formula
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. The ordinary skilled artisan would have been motivated to make the ligand of formula
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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 unsubstituted or substituted, and therefore, the substituted aryl phosphite calix[4]arene of claims 23-27, 29, 34 and 39 would have been obvious.
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.
Claim 32 is 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.
Claim 32 is ambiguous because it recites a definition for R3 however, the claim is directed to the group -NHR4. In addition, there is no definition for R4 in claim 32.
Note to Applicants
Not every piece of prior art found in the search has been applied against the instant claims. See MPEP 904.03.
Conclusion
Claims 31, 33, 35 and 37-38 are objected to for depending of rejected claims.
Claims 23-27, 29-30, 32, 34, 36 and 39 are rejected.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 VALERIE RODRIGUEZ-GARCIA whose telephone number is (571)270-5865. The examiner can normally be reached Monday-Friday 9:30am-5:30pm.
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/VALERIE RODRIGUEZ-GARCIA/Primary Examiner, Art Unit 1621
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