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 15-34 filed on 06/22/2023 are currently pending.
Election/Restrictions
Applicant’s election without traverse of claims 15-32 in the reply filed on 03/05/2026 is acknowledged.
Claims 33-34 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.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
Claims 27-28 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
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 15-17, 19 and 29-32 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Patent application publication number US2012/0271069A1 (US’069; cited in IDS 06/22/2023).
Regarding claims 15-17 and 31, US’069 teaches in Examples 2-3 gas phase isomerization of cis-1233zd (1-chloro-3,3,3-trifluoropropene) in the presence of 243fa (1,1,1-trifluoro-3,3-dichloropropane) to trans-1233zd. The starting compound cis-1233zd is a specie of the claimed formula (1), wherein n is 0 and X is H.
Regarding claim 19 and 31, the isomerization process in Example 3 is combined with the dehydrochlorination of 243fa, and thus HCl byproduct produced as a result of the dehydrochlorination process is necessarily present in the isomerization process.
Regarding claim 29, Example 2 teaches that the contacting is conducted in the presence of activated carbon (Co/AC in Table 2).
Regarding claim 30, the reactions in Examples 2-3 are conducted at a temperature of 150, 200 and 225 °C.
Regarding claim 32, Example 2 uses 88.0% cis-1233zd and 11.0% 243fa. The amount is not specified whether it is weight percent or mole percent. However, if the amount of each is based on mol%, the molar ratio of 243fa to cis-1233zd is 0.125:1. Furthermore, if the amount of each is based on weight percent, the molar ration of 243fa to cis-1233zd is 0.066:0.67 or 0.098:1 (each moles calculated wt/mol.wt, wherein the mol. wt. for 243fa and cis-1233zd are 166.96g/mol and 130.5g/mol, respectively).
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.
Claims 20-21, 23-24 and 26 are rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2012/0271069A1 (US’069; cited in IDS 06/22/2023) in view of Patent application publication number US2014/0288336A1 (US’336; cited in IDS 06/22/2023).
The teachings of US’069 have been set forth above.
Regarding claims 20-21 and 23-24, while US’069 teaches a gas phase isomerization of the cis-1-chloro-3,3,3-trifluoropropene to the trans isomer in the presence of 243fa (1,1,1-trifluoro-3,3-dichloropropane), the reference fails to teach isomerization of the trans-1-chloro-3,3,3-trifluoropropene to the cis isomer.
Regarding claim 26, US’069 further teaches in Examples 2-3 the reaction is conducted in the presence of a catalyst. The reference however fails to teach that the contacting is performed in the presence of a filler.
The above deficiencies are cured by US’336.
Regarding claims 20-21 and 23-24, US’336 teaches isomerization of (E)-1-chloro-3,3,3,-trifluoropropene to (Z)-1-chloro-3,3,3,-trifluoropropene. The reference uses the same catalysts ([0020]) as taught by US’069. Thus, replacing the cis-1-chloro-3,3,3-trifluoropropene starting material of US’069 with (E)-1-chloro-3,3,3,-trifluoropropene of US’336, and conducting the isomerization reaction in the presence of 243fa (1,1,1-trifluoro-3,3-dichloropropane), a skilled artisan has a reasonable expectation of success in obtaining nothing more than the (Z) isomer product.
Regarding claim 26, US’336 further teaches that the reactor vessel includes a packing material that is packed in the reaction vessel ([0018]). The reference teaches that the large surface area of the packing material facilitate the conversion reaction between the (E) and (Z) isomers ([0018]). Accordingly, the skilled artisan would have been motivated in using the packing material of US’336 in the process of US’069 with a reasonable expectation of success in facilitating the isomerization process.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a method for producing a geometric isomer (isomer 2) represented by the following formula (1) by geometrically isomerizing a corresponding geometric isomer (isomer 1) represented by the following formula (1), the method comprising: contacting the geometric isomer (isomer 1) represented by the following formula (1) with a compound (A) which is at least one of a dichlorotrifluoropropane and hydrogen chloride in a gas phase, wherein when n is 0, X is a hydrogen atom and the dichlorotrifluoropropane is 1,1-dichloro-3,3,3-trifluoropropane, and wherein the geometric isomer (isomer 1) represented by the formula (1) is a trans isomer, and the produced geometric isomer (isomer 2) is a cis isomer and wherein the contacting is performed in the presence of at least one of a catalyst and a filler in view of the teachings of US’069 and US’336.
Claims 15, 18-19, 22 and 31-32 are rejected under 35 U.S.C. 103 as being unpatentable over International publication WO2018047972A1 (WO’972; cited in IDS 06/22/2023 and machine translation is attached) in view of International publication WO2019189024A1 (WO’024; original and machine translation are attached).
Regarding claims 15, 18 and 22, WO’972 teaches a gas phase isomerization of 1-chloro-2,3,3-trifluoropropene (E) (E-1233yd) to 1-chloro-2,3,3-trifluoropropene (Z) (Z-1233yd) and vice versa. The starting compound 1233yd is a specie of the claimed formula (1), wherein n is 1 and X is F.
Regarding claim 15, WO’972 fails to teach contacting the 1233yd isomer with a compound with a compound (A) which is at least one of dichlorotrifluoropropane and hydrogen chloride, wherein the dichlorotrifluoropropane is at least one of 1,1-dichloro-2,3,3-trifluoropropane and 1,2-dichloro-2,3,3-trifluoropropane. The deficiency is however cured by WO’024.
WO’024 teaches a method for producing Z-isomer of 1-chloro-2,3,3-trifluoropropene and the E-isomer of 1-chloro-2,3,3-trifluoropropene by dehydrochlorinating 1,2-dichloro-2,3,3-trifluoropropane in gas phase ([0006] and [0008]).
Both WO’972 and WO’024 use the same catalysts in the gas phase reactions (see underlined):
WO’972 ([0038]-[0039])
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275
634
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240
631
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WO’024 ([0051])
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241
811
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Thus, combining Z-isomer of 1-chloro-2,3,3-trifluoropropene or the E-isomer of 1-chloro-2,3,3-trifluoropropene of WO’972 with 1,2-dichloro-2,3,3-trifluoropropane of WO’024 and subjecting the compounds to the gas phase reaction in the presence of the above underlined catalysts, a skilled artisan has a reasonable expectation of success in obtaining nothing more than the Z-isomer of 1-chloro-2,3,3-trifluoropropene from the E-isomer of 1-chloro-2,3,3-trifluoropropene or vice versa.
In accordance to MPEP 2143, 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 and discussed circumstances in which a patent might be determined to be obvious. In this case, at least prong (A) Combining prior art elements according to known methods to yield predictable results applies.
Regarding claims 19 and 31, because of the combination of the isomerization process of WO’972 with the dehydrochlorination process of WO’024, it is obvious to the skilled artisan that HCl byproduct produced as a result of the dehydrochlorination process would present in the reaction process.
Regarding claim 32, in view of the above, it has been established that the combination of the Z-isomer of 1-chloro-2,3,3-trifluoropropene or the E-isomer of 1-chloro-2,3,3-trifluoropropene with 1,2-dichloro-2,3,3-trifluoropropane would have been obvious in producing the Z-isomer of 1-chloro-2,3,3-trifluoropropene from the E-isomer of 1-chloro-2,3,3-trifluoropropene or vice versa. As such, any amount of each starting materials, including the mole ratio of 1,2-dichloro-2,3,3-trifluoropropane (compound (A)) to Z or E-isomer of 1-chloro-2,3,3-trifluoropropene as instantly claimed would still yield the isomerized 1-chloro-2,3,3-trifluoropropene product.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a method for producing a geometric isomer (isomer 2) represented by the following formula (1) by geometrically isomerizing a corresponding geometric isomer (isomer 1) represented by the following formula (1), the method comprising: contacting the geometric isomer (isomer 1) represented by the following formula (1) with a compound (A) which is at least one of a dichlorotrifluoropropane and hydrogen chloride in a gas phase, wherein when n is 1, X is a fluorine atom, and the dichlorotrifluoropropane is at least one of 1,1-dichloro-2,3,3-trifluoropropane and 1,2-dichloro-2,3,3-trifluoropropane in view of the teachings of WO’972 and WO’024.
Allowable Subject Matter
The subject matter of claims 27-28 is free of prior art reference.
The closest prior art is Patent application publication number US2012/0271069A1 (US’069; cited in IDS 06/22/2023).
The teachings of US’069 have been set forth above. US’069 further teaches in Examples 2-3 the reaction is conducted in the presence of a catalyst. The reference however fails to teach that the contacting is performed in the presence of a filler and the filler is an activated carbon that does not support a metal. Thus, US’069 fails to anticipate claims 27-29.
Furthermore, Patent application publication number US2014/0288336A1 (US’336; cited in IDS 06/22/2023) has been set forth above as teaching isomerization of (E)-1-chloro-3,3,3,-trifluoropropene to (Z)-1-chloro-3,3,3,-trifluoropropene. The reference further teaches that the reactor vessel includes a packing material that is packed in the reaction vessel ([0018]), for example with a stainless steel packing, nickel packing, inconel packing, monel packing ([0019]). However, US’336 fails to teach or suggest the use activated carbon that does not support a metal. Thus, combining US’069 and US’336, a skilled artisan would not have a reasonable expectation of success in arriving at the process of claims 27-28, wherein the filler is an activated carbon that does not support a metal.
In view of the foregoing, claims 27-28 are not obvious over the combination of US’069 and US’336.
Conclusion
Claims 1-26 and 29-32 are rejected and no claims are allowed.
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/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692
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