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 .
DETAILED ACTION
This Office action is responsive to Applicant's Response to Election/Restriction. filed February 20, 2026. As filed, claims 1-14 are pending.
Priority
This application, filed 01/09/2024 is a Continuation of 17273342 , filed 03/04/2021 ,now U.S. Patent # 11904301
17273342 is a National Stage entry of PCT/US19/49889 , International Filing Date: 09/06/2019
PCT/US19/49889 Claims Priority from Provisional Application 62728392 , filed 09/07/2018.
Information Disclosure Statement Applicants' information disclosure statements (IDS) have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herewith.
Election/Restrictions
Applicant's election without traverse of Group II, claims 5-9, drawn to the process to prepare 2,3,3,3-tetrafluoropropene (1234yf) as recited in the claims in the reply filed on 02/20/2026 is acknowledged.
Claim 1-4, 10-14 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Claims 5-9 will be examined on the merits herein.
Claim Interpretation
Claim 5 recitation “wherein the chlorine-containing antimony catalyst is prepared by
treating a spent antimony fluorohalide catalyst comprising:
(i) SbFnXs-n, wherein n is an integer of 1 to 5, and Xis a halogen other than
fluorine,
(ii) SbFmX'3-m, wherein mis an integer of 1 to 3, and X' is a halogen other than
fluorine, or
(iii) mixtures of (i) and (ii),
with a regenerating agent selected from 2-chloro-3,3,3-trifluoropropene (1233xf),
1, 1, 1,3-tetrachloropropane (250fb ), 2-chloro-l, 1, 1,2-tetrafluoropropane (HCFC-
244bb ), and combinations of two or more of 1233xf, 250fb, and 244bb, under conditions effective to produce the chlorine-containing antimony catalyst from the spent antimony fluorohalide catalyst” is interpreted as product-by-process limitations which are considered to the extent that they limit the structure of the “chlorine-containing antimony catalyst”. Should the Applicant wish to have the limitations treated as actively required process steps then the Applicant should amend the claims so that the step of forming the chlorine-containing antimony catalyst is including in “further comprising” language. See MPEP 2111.04 and MPEP 2113.
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 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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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 5-9 are rejected under 35 U.S.C. 103 as being unpatentable over US 2010/0331583, Dec. 30, 2010 by Johnson et al. (“the ‘583 publication”; cited by Applicants in IDS) and further in view of GB772484A, 1968, by Oelderik (“the ‘484 publication”; cited by Applicants in IDS).
Instant claims are drawn to process to prepare 2,3,3,3-tetrafluoropropene (1234yf) comprising the steps:
a) providing a starting composition comprising at least one compound having the
structure of Formula I:
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wherein each X" is independently selected from F, Cl, Br, and I, provided that at
least one of X" is not F;
b) contacting said starting composition with HF under conditions effective to
produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene
(1233xf);
c) contacting said first intermediate composition comprising 1233xf with HF and a
chlorine-containing antimony catalyst under conditions effective to produce a second
intermediate composition comprising 244bb; and
d) dehydrochlorinating at least a portion of said 244bb to produce a reaction product
comprising 1234yf,
wherein the chlorine-containing antimony catalyst is prepared by
treating a spent antimony fluorohalide catalyst comprising:
(i) SbFnXs-n, wherein n is an integer of 1 to 5, and Xis a halogen other than
fluorine,
(ii) SbFmX'3-m, wherein mis an integer of 1 to 3, and X' is a halogen other than
fluorine, or
(iii) mixtures of (i) and (ii),
with a regenerating agent selected from 2-chloro-3,3,3-trifluoropropene (1233xf),
1, 1, 1,3-tetrachloropropane (250fb ), 2-chloro-l, 1, 1,2-tetrafluoropropane (HCFC-
244bb ), and combinations of two or more of 1233xf, 250fb, and 244bb, under conditions effective to produce the chlorine-containing antimony catalyst from the spent antimony fluorohalide catalyst.
The ‘583 publication teaches a process for producing 2,3,3,3-tetrafluoropropene – which corresponds to the claimed product of the claimed method aka 1234yf- by production of its intermediate 2-chloro-1, 1, 1,2-tetrafluoropropane; wherein the 2-chloro-1, 1, 1,2-tetrafluoropropane is produced by reacting a feed material containing 2-chloro-3,3,3,-trifluoropropene and 2,3-dichloro-3 3-trifluoropropene which corresponds to the claimed Formula I in which X’ is Cl, F with hydrogen fluoride in the presence of a fluorination catalyst and without the need for continuous or intermittent catalyst regeneration. The ‘583 publication teaches that 2-chloro-3,3,3,-trifluoropropene is produced through the fluorination of 1,1,2,3,-tetrachloropropene (HCC-1230xa; instant claim 7) and/or 1,1,1,2,3-tetrachloropropane (HCC-240db), the reaction
does not normally proceed completely to forming 2-chloro-3 ,3 ,3, -trifluoropropene. 2,3-dichloro-3 ,3-trifluoropropene is produced as an intermediate – which correspond to steps a and b of claimed method [0008].The production of 2-chloro-1, 1, 1,2-tetrafluoropropane by reacting substantially pure 2-chloro-3 ,3 ,3, -trifluoropropene with hydrogen fluoride and a fluorination catalyst in the absence of an oxidizing agent. The 2-chloro-3,3,3,-trifluoropropene includes a composition of at least 99% 2-chloro-3,3,3-trifluoropropene, it may also include inorganic substrates, e.g. hydrogen fluoride, hydrogen chloride, etc., in any amount, which may be used as a reaction co-feed [0010]- which correspond to steps a and b of claimed method (instant claim 5).
Disclosed on [00176] of the cited reference is that process for producing 2,3,3,3-tetrafluoropropene by fluorinating 1,1,2,3,-tetrachloropropene and/or 1,1,1,2,3-
tetrachloropropane to produce an intermediate stream comprising 2-chloro-3,3,3-trifluoropropene and one or more impurities. 2-chloro-3,3,3-trifluoropropene is then separated from the intermediate stream to form a substantially pure
composition of 2-chloro-3,3,3-trifluoropropene on an organic basis, which is reacted with hydrogen fluoride and a fluorination catalyst in the absence of an oxidizing agent to produce 2-chloro-1,1,1,2-tetrafluoropropane. This product is then
dehydrohalogenated under conditions effective to produce 2,3,3,3-tetrafluoropropene; which correspond to step d of claimed method ([0050]-[0055];instant claim 5).
The ‘583 publication teaches example 1 on [0057] for production of 2-chloro-3,3,3-trifluoropropene using SbCl5 and SbCl3 as catalyst system which corresponds to
the claimed chlorine-containing antimony catalyst (instant claims 7-9).
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The method of the present application differs from the method described in the ‘583 publication in that prior art teaches dehydrochlorinating of the 244bb to
1234yf, mediated by SbCl3 and/or SbCl5 chlorine-containing antimony catalyst and it does not teach the catalyst system further comprising an antimony fluorohalide catalyst obtained by treatment with a regenerating agent.
However, the ‘583 publication teaches that the catalyst is dried, pre-treated and activated and that it might be advantageous to periodically regenerate the catalyst after prolonged use while in place in the reactor. Pre-treatment can be done by heating the catalyst to about 250° C. to about 430° C. in a stream of nitrogen or other inert gas. The catalyst may then be activated by treating it with a stream of HF diluted with a large excess of nitrogen gas in order to obtain high catalyst activity. Regeneration of the catalyst may be accomplished by any means known in the art [0027]. Therefore, the prior art relied upon, and knowledge generally available in the art before the effective filing date provide the suggestion that would have motivated the skilled artisan to regenerate the catalyst for the transhalogenation reaction.
Regarding the limitation of claim 5 “wherein the chlorine-containing antimony catalyst is prepared by …. , under conditions effective to produce the chlorine-containing antimony catalyst from the spent antimony fluorohalide catalyst” is interpreted as product-by-process limitations which are considered to the extent that they limit the structure of the “chlorine-containing antimony catalyst”.
Furthermore, it is noted that regeneration of antimony fluorohalide catalyst as alternative and more stable catalyst is known in the prior art as discussed in the ‘484 publication.
The ‘484 publication, describes that regenerated hexahalogeno antimonic
acid catalysts for transhalogenation reaction by the regeneration of spent hexahalogeno antimonic acid catalysts such as SbF3Cl; such as antimony trifluoride, antimony trifluorodichloride, antimony trifluorodibromide with halopropene enables chlorination of the fluoroantimony halide( page 4-6; see claims).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, to combine the teachings of the ‘583 publication concerning preparation of producing 2,3,3,3-tetrafluoropropene with the teachings of the ‘484 publication regarding regenerated of antimony fluorohalide as catalyst because the prior art teach specifically teach that catalyst system comprising antimony fluorohalide is stable and efficient for the reaction.
The rationale to support a conclusion that the claim would have been obvious is that 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. KSR, 550 U.S. at_, 82 USPQ2d at 1395.
Therefore, the claimed invention as a whole is prima facie obvious over the combined teachings of the prior art.
Conclusion
Claims 5-9 are rejected. Claims 1-4, 19-14 are withdrawn from consideration.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to:
Ana Muresan
(571) 270-7587 (phone)
(571)270-8587 (fax)
Ana.Muresan@uspto.gov
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692
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