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 .
Claims 23-42 are currently pending. Claims 23, 40 and 42 are independent.
Priority
The instant application claims priority as follows:
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and of
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.
Election/Restriction
Applicants’ election with traverse of Group I, claims 23-39,
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in the reply filed January 8, 2026 is acknowledged.
The traversal is on the grounds that if the search and examination of an entire application can be made without serious burden, the Examiner must examine it on the merits, even though it arguably may include claims to distinct or independent inventions. Applicant additionally states that it would not place an undue burden on the Examiner to search the subject matter of the claims of Groups I to III as a search to one group would likely yield results applicable to the other group.
Applicant’s arguments are found unpersuasive for the reasons of record and the following reasons. This application is a National Stage Application submitted under 35 USC 371, and as such unity of invention (not restriction practice pursuant to 37 CFR 1.141 - 1.146 ) is applicable. See MPEP 1893.03(d). The examiner previously stated that under PCT Rule 13.1 and 13.2 the claims herein lack unity of invention. Arguments that the search would not impose a serious burden on the Office, or that a search for one group may uncover results applicable to the other group, are not germane to the showing of Lack of Unity.
The requirement is deemed proper and therefore made FINAL.
Claims 40-42 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to nonelected inventions, there being no allowable generic or linking claim.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 23-39 are the subject of this Office Action.
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 23-30, 37 and 39 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.
The term “primary alkyl group” is unclear in the claims in view of the disclosure and claim 37. Alkyl carbons are classified as primary, secondary, tertiary and quaternary according to the number of carbons directly attached to the carbon in question. The carbon in question in this case is the carbon substituent attached to the phenyl ring represented by R2.
Thus, when the substituent on the phenyl ring is a methyl group, the methyl carbon would be classified as a primary alkyl for being attached to only one carbon of the phenyl ring. However, if the substituent would be an ethyl group, the ethyl carbon directly attached to the phenyl group would be classified as a secondary alkyl carbon for being attached on one side to a carbon of the phenyl group and on the other side to an end methyl group. The scope of “primary alkyl groups” here should not include ethyl, propyl, butyl, pentyl, etc., since these would all be secondary. Only the methyl group would be a primary alkyl group, and in accordance with this, the recitation of claim 37 of
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does not make sense.
If the case was that applicant assigns the classification as a primary alkyl to the alkyl in question without counting the attachment to the carbon of the phenyl group, the examiner would say that in that case a methyl group would not be encompassed by the “primary alkyl group” term, because without counting the phenyl group attachment a methyl group is not attached to another carbon.
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This rejection can be overcome by defining in the claims the specific alkyl groups that can substitute R2.
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 23-30, 34, 36-39 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 Steyer (Dalton Trans., 2005, 1301-1309), and references therein.
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 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 diphosphite ligands of the following 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 Steyer
Steyer taught additional calix[4]arene bisphosphite ligands of formula
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useful in providing high selectivity for lineal aldehydes when used in complexes as catalysts for 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 bisphosphite 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 authors of the references cited in this action. Chelating aryl bisphosphite complexes were known to be excellent catalysts for both hydrocyanation and hydroformylation of olefins. See at least the references cited in Tam et al. and Foo, 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 for example, the ligand catalyst of Paciello of formula 3
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, and the ligand catalysts of Steyer of formula
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These ligands have the same calix[4]arene aryl bisphosphite 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 and Steyer tested various calix[4]arene aryl bisphosphite ligands searching for improvement on the hydroformylation reaction. A skilled artisan would have reasonably expected that such a substitution would work because calix[4]arene aryl bisphosphite ligands are used in the hydrocyanation of olefins.
With respect to the specific embodiment recited in claims 28 and 38, Paciello showed better reactivity when ligand of formula 3
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was used in the hydroformylation reaction compared to the ligand of Tam et al. It would have been prima facie obvious to make and use the position isomer of claim 28 and 38 of the formula
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in which a methyl group is at position 4 instead of position 6 (as Paciello) because of the expectation of similar properties. The hydrocyanation of olefins using this ligand would have been obvious. The isomer is expected to be preparable by the same method and to have generally the same properties. Position isomers are a basic form of close “structural isomers.” MPEP 2144.09, second paragraph, states, “Compounds which are position isomers or homologs are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977).
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 and 35 are objected to for depending of rejected claims.
Claims 23-30, 34, 36-39 are rejected.
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.
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/VALERIE RODRIGUEZ-GARCIA/Primary Examiner, Art Unit 1621