DETAILED ACTION
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 .
Status of claims
Pending claims 1-14 have been examined on the merits.
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 1-14 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.
Claims 1 recites “each of the aryl phosphite groups is chemically bonded via an oxygen atom to different one of the C1 to C4 alkyl substituents on the backbone.” The claim does not distinctly identify whether the C1-C4 alkyl substituents are located on bicyclo-octatriene core, either one or both arene groups attached to the bicyclo-octatriene core, or any combination of those locations. This uncertainty creates ambiguity, which renders the claim indefinite.
Claim Rejections – 35 USC § 102
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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-4 are rejected under 35 U.S.C. 102(a)(l) as being anticipated by Smith et al. Organometallics, vol. 30, no. 13, July 2011, pp. 3643–51 (IDS, 01/31/2025).
Smith (page S-16; page 3648, Table 5) teaches the following compound which meets each and every chemical structure variable as listed in the instant claims, wherein iptycene backbone comprises three arene groups attached to the bicyclo-octatriene core of the backbone, aryl containing phosphite units, phosphite groups connected via O atoms, alkyl substituted aryl groups are
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296
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.
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1064
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Therefore, claims 1-4 are anticipated.
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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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 non-obviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 5-14 are rejected under 35 U.S.C. 103 as being unpatentable over Smith et. al. Organometallics, vol. 30, no. 13, July 2011, pp. 3643–51 (IDS, 01/31/2025), and as applied to claims 1-4 above, Kreutzer et al., US 5,512,696 (IDS, 01/31/2025), Foo et al., US 5,821,378 (IDS, 01/31/2025). Supporting Information is included at the end of Smith’s document.
Regarding claims 5-7, for clarity of record, the Examiner refers to the structures disclosed in Smith’s supporting information as the “compound of Formula 6A” and “compound of Formula 7A. Formula 6A and Formula 7A show that the R1-R3 substituent positions are correspondingly located on the same aryl phosphite unit, while the R4-R6 positions, although differently numbered, occupy corresponding position on the other aryl phosphite unit (Smith, page S-16). Furthermore, Smith (page S-16) also discloses R1-R2 = methyl and tert-butyl, and R3= hydrogen and methyl as alternatives at these corresponding positions. Therefore, a person of ordinary skill in the art (POSITA) would have been motivated to apply these disclosed substituent alternatives to Formula 7A, including selecting R1=R2=methyl; R3=hydrogen; R4=R5=methyl; R6=hydrogen, to arrive at the claimed ligand. A POSA would have had reasons to select from among the disclosed substituents and use them as sites for analog design. Moreover, routine optimization of variants would have generated a more divers chemical library and potentially yielded a more efficient ligand, to arrive at the claimed compound.
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Regarding claims 8-14, Smith (page 3643; page 3645, Scheme 1 and Table 1) teaches a catalyst complex comprising multidentate phosphite and a transition metal, rhodium. Smith, however, does not explicitly teach nickel or hydrogen cyanide, as an example.
Kreutzer (abstract; col. 2, line 7-16; col. 6, line 14-40) teaches
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Kreutzer (col. 32, claim 4) teaches the ethylenically unsaturated compound is 3-pentenenitrile or 4-pentenenitrile. Kreutzer (col. 1, line 15-21) also teaches butadiene [1,3-butadiene] can be used in hydrocyanation process to form penetenenitrile (PN).
However, the combined teachings of Smith and Kreutzer do not explicitly teach process of isomerization.
Foo (col. 53, claim 1; col 14, line 55-58; col. 15, line 55-67 bridged col. 16, line 1-6) discloses an improved liquid-phase process for :1) hydrocyanating acyclic aliphatic diolefin, including 1,3-butadiene, with HCN, in the presence of zero-valent nickel and at least one multidentate phosphite ligand; 2) and subsequently isomerizing the resulting products, nonconjugated 2-alkyl-3-monoalkenenitriles, including 2-Methyl-3-butenenitrile (2M3BN), to linear 3 and/or 4-monoalkene linear nitriles. Foo (col. 17, Example 1) discloses in Example 1, butadiene hydrocyanation, and in Example 6 demonstrates 2M3BN isomerization. Therefore, a POSITA would have been motivated to combine the teachings of Smith, Kreutzer and Foo by using the triptycene complex as the multidentate phosphite ligand, to further improve the hydrocyanation/isomerization process such as butadiene hydrocyanation followed isomerization of 2M3BN to produce linear pentenenitrile. In fact, Foo (col. 1, line 34-36) discloses that pentenenitrile can be used to make adiponitrile, a critical component for manufacturing nylon. Therefore, a POSITA would have recognized a more efficient phosphite ligand could improve catalyst activity, selectivity, stability, and conversion of branched nitriles intermediates into commercially valuable pentenitriles products.
Conclusion
No claims are allowed
Any inquiry concerning this communication or earlier communications from the examiner should be directed to PIERRE PAUL ELENISTE whose telephone number is (571)270-0589. The examiner can normally be reached Monday - Friday 8:00 am - 5:00 pm (EST).
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/P.P.E./Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622
