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 the Claims
Claims 1-5 and 8-13 filed on 10/27/2023 are currently pending.
Election/Restrictions
Applicant’s election of Group I, claims 1-5 and 8-11 in the reply filed on 06/09/2026 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Claims 12-13 are withdrawn by the examiner from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Claim Objections
Claim 1 objected to because of the following informalities: amend “an ether” in line 2 to “the ether” as there is an earlier recitation of “solvent containing an ether” set forth in claim 1.
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.
Claims 1, 3-5 and 8-11 are rejected under 35 U.S.C. 102(a)(1)/102(a)(2) as being anticipated by International publication WO2020/171011A1 (WO’011; cited in IDS 10/27/2023 and translation attached herein).
Regarding claims 1, 4-5 and 8-10, WO’011 exemplifies a method for producing a fluoroalkyne compound CF3C≡CCF3 by subjecting CF3CFHCFHCF3 to a dehydrofluorination reaction in the presence of dibutyl ether (Bu2O) and potassium tert-butoxide (t-BuOK) as a base, wherein the method satisfies (I) with -CF3 as the C1 fluoroalkyl group and (II) with Bu2O being a chain ether (Example 3 and Table 1).
Regarding claim 3, the number of ether bonds in Bu2O is 1.
Regarding claim 11, the dehydrofluorination reaction in Example 3 of WO’011 is conducted at a temperature of 60 °C.
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.
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.
Claim 2 is rejected under 35 U.S.C. 103 as being unpatentable over International publication WO2020/171011A1 (WO’011; cited in IDS 10/27/2023 and translation attached herein) in view of Sigma-Aldrich (“Dibutyl ether, anhydrous, 99.3%” Deposit and available date 2009-05-13, pages 1-2).
Regarding claim 2, WO’011 further teaches that different solvents such as water and non-aqueous solvents can be used in the dehydrofluorination reaction, but that non-aqueous solvents are preferred, with dibutyl ether being most preferred ([0026]). The reference however fails to teach the water concentration of the solvent containing the ether is 0.001 to 500 mass ppm based on the total amount of the solvent containing an ether taken as 100 mass%.
Sigma-Aldrich cures the deficiency by teaching the commercial availability of anhydrous dibutyl ether, 99.3%, before the effective filing date of the instant invention, wherein water is present at an amount of ≤ 0.005% (≤ 50 ppm) (page 2). Thus, using the anhydrous dibutyl ether of Sigma-Aldrich as the non-aqueous solvent of WO’011, a skilled artisan would have a reasonable expectation of success in conducting nothing more than the predictable dehydrofluorination reaction and in obtaining fluoroalkyne product from the fluoroalkane starting material.
It would thus have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant to conduct a method for producing a fluoroalkyne compound represented by formula (1), R1C≡CR2, wherein R1 and R2 are the same or different and each is a fluorine atom or a fluoroalkyl group, the method comprising subjecting a fluoroalkane compound represented by formula (2), R1CHX1CFX2R2, wherein R1 and R2 are as defined above; and X1 is a fluorine atom and X2 is a hydrogen atom, or X1 is a hydrogen atom and X2 is a fluorine atom, to a dehydrofluorination reaction in the presence of a solvent containing an ether, and a base comprising a hydroxide and/or alkoxide of an alkali metal and/or alkaline earth metal, the method satisfying at least one requirement selected from the group consisting of the following: (I) the fluoroalkyl group is a C1-C4 fluoroalkyl group, and (II) the ether is a chain ether in view of the combination of WO’011 and Sigma-Aldrich.
Conclusion
Claims 1-5 and 8-11 are rejected and no claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692
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