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
The preliminary amendment filed on 01/06/2026 has been entered. Claims 1 and 7 have been amended. Thus claims 1-13 are currently pending.
Election/Restrictions
Applicant's election with traverse of Group I, claims 1-10 in the reply filed on 01/06/2026 is acknowledged. The traversal is on the ground(s) that claims 12-13 that were grouped with Group II in the restriction/election requirement are drawn to process and should have been part of Group I. This is found persuasive and thus Group I, claims 1-10 and 12-13 are under current examination.
Claim 11 is withdrawn from further consideration by the examiner pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking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 is objected to because of the following informalities: add “a” before “catalytic fluorination” (ln. 2) to correct the idiomatic error.
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 1-10 and 12-13 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 “elevated” in claim 1 is a relative term which renders the claim indefinite. The term “elevated” is not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. The temperature and pressure of catalyst activation step have been rendered indefinite by the use of the term “elevated”.
Claims 2-10 and 12-13 are also indefinite for their dependency on claim 1.
For purpose of applying art, any temperature and pressure used in the catalyst activation step will be interpreted as reading on the claimed “elevated temperature and pressure”.
Regarding claims 4 and 12-13, the limitation “a ratio of vinyl chloride to hydrogen fluoride” renders the claims vague and indefinite as it is unclear whether the ratio is a weight ratio or a molar ratio. For purpose of applying art, the ratio is interpreted in view of the specification, i.e. molar ratio of vinyl chloride to hydrogen fluoride (pg. 4).
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 1-4, 8-9 and 12-13 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Patent application publication number US2005/0222472A1 (US’472; cited in IDS 10/17/2023).
Regarding claims 1-2, US’472 teaches in Examples 1-2 a process for the production of 1,1-difluoroethane (HFC-152a) by a catalytic fluorination, in vapor phase, of a composition comprising vinyl chloride with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising activated carbon to an activation treatment comprising treating the catalyst with hydrogen fluoride at a temperature of 100° C. and atmospheric pressure ([0025]-[0026]), and then contacting the vinyl chloride with the hydrogen fluoride, at temperature of 100° C. ([0026]) and of 180° C. ([0027]), in the presence of the treated catalyst.
Regarding claim 3, Examples 1-2 of US’472 conduct the reaction at atmospheric pressure which is equivalent to about 1.01 bar.
Regarding claims 4 and 12-13, a mole ratio of HF to HCC-30 of between about 7:1-8:1 has been used in US’472 ([0026]).
Regarding claims 8-9, US’472 teaches separation by distillation and recycling of unreacted reactants, which encompasses HF, from which the desired hydrofluorocarbon product (i.e. 1,1-difluoroethane) has been separated, back to the reaction zone of the reaction vessel ([0022]-[0023]).
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 1-7 and 12-13 are rejected under 35 U.S.C. 103 as being unpatentable over Patent number CN1931431A (CN’431, cited in IDS 06/26/2023 and machine translation attached herewith) in view of Patent application publication number US2003/0022785A1 (US’785).
Claims 1-7 and 12-13 are rejected under 35 U.S.C. 103 as being unpatentable over Patent number CN1931431A (CN’431, cited in IDS 06/26/2023 and machine translation attached herewith) in view of Patent number RU2322291C1 (RU’291; original and machine translation attached herewith).
Regarding claims 1-2, CN’431 teaches in the examples ([0028]-[0055] of the translation) a process for the production of 1,1-difluoroethane (HFC-152a) by a catalytic fluorination, in vapor phase, of a composition comprising vinyl chloride with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising chromium or chromium and aluminum to an activation treatment comprising treating the catalyst with hydrogen fluoride ([0031]), and then contacting the vinyl chloride with the hydrogen fluoride, at temperature of 150-200° C. ([0031]), in the presence of the treated catalyst.
Regarding claim 4 and 12-13, a mole ratio of HF:vinyl chloride = 2-4:1 has been used in CN’431 ([0031]). With respect to claim 13, the claimed mole ratio of from 1:5 to 1:30, or from 1:10 to 1:25 is merely close that of CN’431. In view of MPEP § 2144.05, absent any showing of unexpected results or criticality, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.
Regarding claim 5, that chromium catalyst is chromium oxide ([0017]), which is equivalent to chromia.
Regarding claim 6, some of the exemplified catalysts in CN’431 comprise Cr and Zn ([0013], [0015], [0040], [0046]).
Regarding claim 7, the catalysts used in the examples are Cr:Co, Cr:Mg, Cr:C, Cr∶Co∶Fe, Cr∶Co∶Al, Cr∶Zn∶Al, Cr∶Mg∶Al, Cr∶Mg∶Fe, Cr∶Zn∶Fe, Cr∶Al, Cr∶Mn∶Fe, Cr∶Mn∶Al, Cr∶Fe, and Cr∶Ni∶Fe.
Regarding claim 1, while CN’431 teaches activation of the fluorination catalyst, it fails to teach or suggest the activation step at elevated pressure.
Regarding claim 3, CN’431 further teaches that the reaction pressure does not affect the types of reaction products ([0024]) but fails to teach that the reaction pressure if between 1 barg and 20 barg.
The deficiencies however are cured by US’785 or RU’291.
US’785
Regarding claim 1, US’785 teaches activation of chromium based fluorination catalysts ([0020]) with HF as an activating agent ([0025] and [0044]) via a low pressure exposing step and a high pressure exposing step, wherein the pressure in this initial exposing step is preferably at least about 25 psig less than the pressure in the second exposing step, and the second exposing step is carried out at a pressure of from about 15 psig to about 200 psig ([0035]-[0036]).
Regarding claim 3, US’785 teaches that the operating pressure of the catalyst, i.e. the fluorination reaction, is from about 50 psig (~3.44 barg) to about 200 psig (~13.8 barg) ([0042]).
RU’291
Regarding claim 1, RU’291 teaches activation of chromium based fluorination catalyst with HF at pressure of 1-0.02 MPa (0.2-10 barg) ([0026]-[0029]).
Regarding claim 3, the reference teaches the fluorination process of halogenated hydrocarbons is carried out with hydrogen fluoride at a pressure of 0.1-0.5 MPa (1-5 barg) ([0030]).
Accordingly, a skilled artisan would have been motivated to use the catalyst activation pressure and fluorination reaction pressure of US’785 or RU’291 in the fluorination process of CN’431, with a reasonable expectation of success in obtaining 1,1-difluoroethane from vinyl chloride.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a process for the production of 1,1-difluoroethane (HFC-152a) by catalytic fluorination, in vapor phase, of a composition comprising vinyl chloride with hydrogen fluoride (HF), the method comprising subjecting a catalyst to an activation treatment comprising treating the catalyst with hydrogen fluoride at an elevated temperature and pressure to achieve a desired catalytic performance, and then contacting the vinyl chloride with the hydrogen fluoride, at temperatures between 100 and 5000C, in the presence of the treated catalyst, which comprises comprising one or more of chromia, alumina, or carbon in view of the teachings of CN’431 and US’785 OR in view of the teachings of CN’431 and RU’291.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-7 and 12-13 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 5-7, 12-16, 26-28 and 31 of copending Application No. 19/251,054 in view of Patent number CN1931431A (CN’431, cited in IDS 06/26/2023 and machine translation attached herewith).
Copending claims 12 and 26-28 and instant claim are drawn to a process for the production of fluorinated hydrocarbon by catalytic fluorination, in vapor phase, of a halogenated hydrocarbon/(hydro)haloalkene with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising chromia to an activation treatment comprising treating the catalyst with hydrogen fluoride at a temperature of from 500° C. to about 700° C, and then contacting the halogenated hydrocarbon/(hydro)haloalkene with the hydrogen fluoride, in the presence of the treated catalyst.
Copending claim 12 fails to recite that the activation step is conducted at elevated pressure, however, copending claim 13 recites that the activation step is conducted at a pressure of from 0.1 bara to 20 bara. Thus, a skilled artisan would arrive at instant claim 1’s elevated pressure of the activation step by combining copending claims 12 and 13.
Furthermore, copending claim 26-28 and 31 fails to recite that the halogenated hydrocarbon/(hydro)haloalkene is vinyl chloride and that the fluorinated hydrocarbon is 1,1-difluoroethane as in instant claim 1 and the ratio of vinyl chloride to hydrogen fluoride as instant claims 4 and 12-13. The deficiencies are however cured by CN’431.
Regarding claim 1, CN’431 teaches in the examples ([0028]-[0055] of the translation) a process for the production of 1,1-difluoroethane (HFC-152a) by a catalytic fluorination, in vapor phase, of a composition comprising vinyl chloride with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising chromium or chromium and aluminum to an activation treatment comprising treating the catalyst with hydrogen fluoride ([0031]), and then contacting the vinyl chloride with the hydrogen fluoride, at temperature of 150-200° C. ([0031]), in the presence of the treated catalyst.
Regarding claims 4 and 12-13, a mole ratio of HF:vinyl chloride = 2-4:1 has been used in CN’431 ([0031]). With respect to claim 13, the claimed mole ratio of from 1:5 to 1:30, or from 1:10 to 1:25 is merely close that of CN’431. In view of MPEP § 2144.05, absent any showing of unexpected results or criticality, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.
The reference further teaches that 1,1-difluoroethane is a widely used fluorinated organic compound that can be used as a refrigerant, a spray agent, and a raw material for the production of fluoroplastics, in particular with its ozone depletion potential (ODP) is 0 and its global warming potential (GWP) is 0.02, making it an increasingly popular alternative to CFCs. As such, one of ordinary skilled in art would have been motivated to use the teachings of CN’431 in the copending claims with a reasonable expectation of success in arriving at the instantly claimed invention.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct the claimed process for the production of 1,1-difluoroethane (HFC-152a) in view of the combination of the copending claims and the teachings of CN’431.
This is a provisional nonstatutory double patenting rejection.
Claims 1-7 and 12-13 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 6-8, 10, 15, 17-18 and 24 of U.S. Patent No. 12357968B2 (‘968) in view of Patent number CN1931431A (CN’431, cited in IDS 06/26/2023 and machine translation attached herewith).
Claims 1, 10 and 24 of ‘968 and instant claim are drawn to a process for the production of fluorinated hydrocarbon by catalytic fluorination, in vapor phase, of a halogenated hydrocarbon with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising chromia to an activation treatment comprising treating the catalyst with hydrogen fluoride at a temperature of from 100° C. to about 500° C, and then contacting the halogenated hydrocarbon with the hydrogen fluoride, in the presence of the treated catalyst.
Claim 24 of ‘968 fails to recite that the activation step is conducted at elevated pressure, however, claims 6 and 15 recite that the activation step is conducted at a pressure of from 0.1 bara to 20 bara, or from 3 bara to 10 bara. Thus, a skilled artisan would arrive at instant claim 1’s elevated pressure of the activation step by combining claims 1, 6 and 15 of ‘968.
Furthermore, claims 1 and 24 of ‘968 fails to recite that the halogenated hydrocarbon is vinyl chloride and that the fluorinated hydrocarbon is 1,1-difluoroethane as in instant claim 1 and the ratio of vinyl chloride to hydrogen fluoride as instant claims 4 and 12-13. The deficiencies are however cured by CN’431.
Regarding claim 1, CN’431 teaches in the examples ([0028]-[0055] of the translation) a process for the production of 1,1-difluoroethane (HFC-152a) by a catalytic fluorination, in vapor phase, of a composition comprising vinyl chloride with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising chromium or chromium and aluminum to an activation treatment comprising treating the catalyst with hydrogen fluoride ([0031]), and then contacting the vinyl chloride with the hydrogen fluoride, at temperature of 150-200° C. ([0031]), in the presence of the treated catalyst.
Regarding claims 4 and 12-13, a mole ratio of HF:vinyl chloride = 2-4:1 has been used in CN’431 ([0031]). With respect to claim 13, the claimed mole ratio of from 1:5 to 1:30, or from 1:10 to 1:25 is merely close that of CN’431. In view of MPEP § 2144.05, absent any showing of unexpected results or criticality, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.
The reference further teaches that 1,1-difluoroethane is a widely used fluorinated organic compound that can be used as a refrigerant, a spray agent, and a raw material for the production of fluoroplastics, in particular with its ozone depletion potential (ODP) is 0 and its global warming potential (GWP) is 0.02, making it an increasingly popular alternative to CFCs. As such, one of ordinary skilled in art would have been motivated to use the teachings of CN’431 in the claims of ‘968 and would have a reasonable expectation of success in arriving at the instantly claimed invention.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct the claimed process for the production of 1,1-difluoroethane (HFC-152a) in view of the combination of claims of ‘968 and the teachings of CN’431.
Claims 1-7 and 12-13 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-17 of U.S. Patent No. 10974227B2 (‘227) in view of Patent number CN1931431A (CN’431, cited in IDS 06/26/2023 and machine translation attached herewith) and Patent application publication number US2003/0022785A1 (US’785).
Claims 1 and 17 of ‘227 and instant claim are drawn to a process for the production of fluorinated hydrocarbon by catalytic fluorination, in vapor phase, of a halogenated hydrocarbon with hydrogen fluoride (HF), the method comprising, contacting the halogenated hydrocarbon with the hydrogen fluoride, in the presence of chromium-containing catalyst.
Claims 1 and 17 of ‘227 fails to recite the instant claim’s:
- subjecting the catalyst to an activation treatment comprising treating the catalyst with hydrogen fluoride at an elevated temperature and pressure to obtain treated catalyst, and
- that the halogenated hydrocarbon is vinyl chloride and that the fluorinated hydrocarbon is 1,1-difluoroethane.
However, the deficiencies are cured by claim 6 of ‘227, CN’431 and US’785.
Regarding claim 1, ‘227 recites in claim 6 that the catalyst is subjected to a fluorination step.
Regarding claim 1, CN’431 teaches in the examples ([0028]-[0055] of the translation) a process for the production of 1,1-difluoroethane (HFC-152a) by a catalytic fluorination, in vapor phase, of a composition comprising vinyl chloride with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising chromium or chromium and aluminum to an activation treatment comprising treating the catalyst with hydrogen fluoride ([0031]), and then contacting the vinyl chloride with the hydrogen fluoride, at temperature of 150-200° C. ([0031]), in the presence of the treated catalyst.
Regarding claims 4 and 12-13, a mole ratio of HF:vinyl chloride = 2-4:1 has been used in CN’431 ([0031]). With respect to claim 13, the claimed mole ratio of from 1:5 to 1:30, or from 1:10 to 1:25 is merely close that of CN’431. In view of MPEP § 2144.05, absent any showing of unexpected results or criticality, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.
The reference further teaches that 1,1-difluoroethane is a widely used fluorinated organic compound that can be used as a refrigerant, a spray agent, and a raw material for the production of fluoroplastics, in particular with its ozone depletion potential (ODP) is 0 and its global warming potential (GWP) is 0.02, making it an increasingly popular alternative to CFCs.
Regarding claim 1, US’785 teaches activation of chromium based fluorination catalysts ([0020]) with HF as an activating agent ([0025] and [0044]) via a low pressure exposing step and a high pressure exposing step, wherein the pressure in this initial exposing step is preferably at least about 25 psig less than the pressure in the second exposing step, and the second exposing step is carried out at a pressure of from about 15 psig to about 200 psig ([0035]-[0036]).
As such, one of ordinary skilled in art would have been motivated to use the teachings of CN’431 and US’785 in the claims of ‘227 and would have a reasonable expectation of success in arriving at the instantly claimed invention.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct the claimed process for the production of 1,1-difluoroethane (HFC-152a) in view of the combination of claims of ‘227 and the teachings of CN’431 and US’785.
Claims 1-7 and 12-13 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-11 of U.S. Patent No. 9862659B2
(‘659) in view of Patent number CN1931431A (CN’431, cited in IDS 06/26/2023 and machine translation attached herewith) and Patent application publication number US2003/0065985A1 (US’785).
Claims 1 and 11 of ‘659 and instant claim are drawn to a process for the production of fluorinated hydrocarbon by catalytic fluorination, in vapor phase, of a halogenated hydrocarbon with hydrogen fluoride (HF), the method comprising, contacting the halogenated hydrocarbon with the hydrogen fluoride, in the presence of chromium-containing catalyst.
Claims 1 and 11 of ‘659 fails to recite the instant claim’s:
- subjecting the catalyst to an activation treatment comprising treating the catalyst with hydrogen fluoride at an elevated temperature and pressure to obtain treated catalyst, and
- that the halogenated hydrocarbon is vinyl chloride and that the fluorinated hydrocarbon is 1,1-difluoroethane.
However, the deficiencies are cured by claim 6 of ‘659, CN’431 and US’785.
Regarding claim 1, ‘659 recites in claim 6 that the catalyst is subjected to a fluorination step.
Regarding claim 1, CN’431 teaches in the examples ([0028]-[0055] of the translation) a process for the production of 1,1-difluoroethane (HFC-152a) by a catalytic fluorination, in vapor phase, of a composition comprising vinyl chloride with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising chromium or chromium and aluminum to an activation treatment comprising treating the catalyst with hydrogen fluoride ([0031]), and then contacting the vinyl chloride with the hydrogen fluoride, at temperature of 150-200° C. ([0031]), in the presence of the treated catalyst.
Regarding claims 4 and 12-13, a mole ratio of HF:vinyl chloride = 2-4:1 has been used in CN’431 ([0031]). With respect to claim 13, the claimed mole ratio of from 1:5 to 1:30, or from 1:10 to 1:25 is merely close that of CN’431. In view of MPEP § 2144.05, absent any showing of unexpected results or criticality, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.
The reference further teaches that 1,1-difluoroethane is a widely used fluorinated organic compound that can be used as a refrigerant, a spray agent, and a raw material for the production of fluoroplastics, in particular with its ozone depletion potential (ODP) is 0 and its global warming potential (GWP) is 0.02, making it an increasingly popular alternative to CFCs.
Regarding claim 1, US’785 teaches activation of chromium based fluorination catalysts ([0020]) with HF as an activating agent ([0025] and [0044]) via a low pressure exposing step and a high pressure exposing step, wherein the pressure in this initial exposing step is preferably at least about 25 psig less than the pressure in the second exposing step, and the second exposing step is carried out at a pressure of from about 15 psig to about 200 psig ([0035]-[0036]).
As such, one of ordinary skilled in art would have been motivated to use the teachings of CN’431 and US’785 in the claims of ‘659 and would have a reasonable expectation of success in arriving at the instantly claimed invention.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct the claimed process for the production of 1,1-difluoroethane (HFC-152a) in view of the combination of claims of ‘659 and the teachings of CN’431 and US’785.
Claims 1-7 and 12-13 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-9 of U.S. Patent No. 10906853B2
(‘853) in view of Patent number CN1931431A (CN’431, cited in IDS 06/26/2023 and machine translation attached herewith) and Patent application publication number US2003/0065985A1 (US’785).
Claims 1 and 9 of ‘853 and instant claim are drawn to a process for the production of fluorinated hydrocarbon by catalytic fluorination, in vapor phase, of a halogenated hydrocarbon with hydrogen fluoride (HF), the method comprising, contacting the halogenated hydrocarbon with the hydrogen fluoride, in the presence of chromium-containing catalyst.
Claims 1 and 9 of ‘853 fails to recite the instant claim’s:
- subjecting the catalyst to an activation treatment comprising treating the catalyst with hydrogen fluoride at an elevated temperature and pressure to obtain treated catalyst, and
- that the halogenated hydrocarbon is vinyl chloride and that the fluorinated hydrocarbon is 1,1-difluoroethane.
However, the deficiencies are cured by claim 6 of ‘853, CN’431 and US’785.
Regarding claim 1, ‘853 recites in claim 6 that the catalyst is subjected to a fluorination step.
Regarding claim 1, CN’431 teaches in the examples ([0028]-[0055] of the translation) a process for the production of 1,1-difluoroethane (HFC-152a) by a catalytic fluorination, in vapor phase, of a composition comprising vinyl chloride with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising chromium or chromium and aluminum to an activation treatment comprising treating the catalyst with hydrogen fluoride ([0031]), and then contacting the vinyl chloride with the hydrogen fluoride, at temperature of 150-200° C. ([0031]), in the presence of the treated catalyst.
Regarding claims 4 and 12-13, a mole ratio of HF:vinyl chloride = 2-4:1 has been used in CN’431 ([0031]). With respect to claim 13, the claimed mole ratio of from 1:5 to 1:30, or from 1:10 to 1:25 is merely close that of CN’431. In view of MPEP § 2144.05, absent any showing of unexpected results or criticality, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.
The reference further teaches that 1,1-difluoroethane is a widely used fluorinated organic compound that can be used as a refrigerant, a spray agent, and a raw material for the production of fluoroplastics, in particular with its ozone depletion potential (ODP) is 0 and its global warming potential (GWP) is 0.02, making it an increasingly popular alternative to CFCs.
Regarding claim 1, US’785 teaches activation of chromium based fluorination catalysts ([0020]) with HF as an activating agent ([0025] and [0044]) via a low pressure exposing step and a high pressure exposing step, wherein the pressure in this initial exposing step is preferably at least about 25 psig less than the pressure in the second exposing step, and the second exposing step is carried out at a pressure of from about 15 psig to about 200 psig ([0035]-[0036]).
As such, one of ordinary skilled in art would have been motivated to use the teachings of CN’431 and US’785 in the claims of ‘853 and would have a reasonable expectation of success in arriving at the instantly claimed invention.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct the claimed process for the production of 1,1-difluoroethane (HFC-152a) in view of the combination of claims of ‘853 and the teachings of CN’431 and US’785.
Claims 1-7 and 12-13 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-15 of U.S. Patent No. 12024478B2
(‘478) in view of Patent number CN1931431A (CN’431, cited in IDS 06/26/2023 and machine translation attached herewith) and Patent application publication number US2003/0065985A1 (US’785).
Claims 1 and 11 of ‘478 and instant claim are drawn to a process for the production of fluorinated hydrocarbon by catalytic fluorination, in vapor phase, of a halogenated hydrocarbon with hydrogen fluoride (HF), the method comprising, contacting the halogenated hydrocarbon with the hydrogen fluoride, in the presence of chromium-containing catalyst.
Claims 1 and 11 of ‘478 fails to recite the instant claim’s:
- subjecting the catalyst to an activation treatment comprising treating the catalyst with hydrogen fluoride at an elevated temperature and pressure to obtain treated catalyst, and
- that the halogenated hydrocarbon is vinyl chloride and that the fluorinated hydrocarbon is 1,1-difluoroethane.
However, the deficiencies are cured by claim 8 of ‘478, CN’431 and US’785.
Regarding claim 1, ‘478 recites in claim 8 that the catalyst is subjected to a fluorination step.
Regarding claim 1, CN’431 teaches in the examples ([0028]-[0055] of the translation) a process for the production of 1,1-difluoroethane (HFC-152a) by a catalytic fluorination, in vapor phase, of a composition comprising vinyl chloride with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising chromium or chromium and aluminum to an activation treatment comprising treating the catalyst with hydrogen fluoride ([0031]), and then contacting the vinyl chloride with the hydrogen fluoride, at temperature of 150-200° C. ([0031]), in the presence of the treated catalyst.
The reference further teaches that 1,1-difluoroethane is a widely used fluorinated organic compound that can be used as a refrigerant, a spray agent, and a raw material for the production of fluoroplastics, in particular with its ozone depletion potential (ODP) is 0 and its global warming potential (GWP) is 0.02, making it an increasingly popular alternative to CFCs.
Regarding claim 1, US’785 teaches activation of chromium based fluorination catalysts ([0020]) with HF as an activating agent ([0025] and [0044]) via a low pressure exposing step and a high pressure exposing step, wherein the pressure in this initial exposing step is preferably at least about 25 psig less than the pressure in the second exposing step, and the second exposing step is carried out at a pressure of from about 15 psig to about 200 psig ([0035]-[0036]).
As such, one of ordinary skilled in art would have been motivated to use the teachings of CN’431 and US’785 in the claims of ‘478 and would have a reasonable expectation of success in arriving at the instantly claimed invention.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct the claimed process for the production of 1,1-difluoroethane (HFC-152a) in view of the combination of claims of ‘478 and the teachings of CN’431 and US’785.
Claims 1-7 and 12-13 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-9 of U.S. Patent No. 9771309B2
(‘309) in view of Patent number CN1931431A (CN’431, cited in IDS 06/26/2023 and machine translation attached herewith).
Claims 1 and 7-8 of ‘309 and instant claim are drawn to a process for the production of fluorinated hydrocarbon by catalytic fluorination, in vapor phase, of a halogenated hydrocarbon with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising chromia to an activation treatment comprising treating the catalyst with hydrogen fluoride at a temperature of from 100° C. to about 500° C and at atmospheric or superatmospheric pressure, and then contacting the halogenated hydrocarbon with the hydrogen fluoride, in the presence of the treated catalyst.
Claims 1 and 7-8 of ‘309 fail to recite that the halogenated hydrocarbon is vinyl chloride and that the fluorinated hydrocarbon is 1,1-difluoroethane as in instant claim 1 and the ratio of vinyl chloride to hydrogen fluoride as instant claims 4 and 12-13. The deficiencies are however cured by CN’431.
Regarding claim 1, CN’431 teaches in the examples ([0028]-[0055] of the translation) a process for the production of 1,1-difluoroethane (HFC-152a) by a catalytic fluorination, in vapor phase, of a composition comprising vinyl chloride with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising chromium or chromium and aluminum to an activation treatment comprising treating the catalyst with hydrogen fluoride ([0031]), and then contacting the vinyl chloride with the hydrogen fluoride, at temperature of 150-200° C. ([0031]), in the presence of the treated catalyst.
Regarding claims 4 and 12-13, a mole ratio of HF:vinyl chloride = 2-4:1 has been used in CN’431 ([0031]). With respect to claim 13, the claimed mole ratio of from 1:5 to 1:30, or from 1:10 to 1:25 is merely close that of CN’431. In view of MPEP § 2144.05, absent any showing of unexpected results or criticality, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.
The reference further teaches that 1,1-difluoroethane is a widely used fluorinated organic compound that can be used as a refrigerant, a spray agent, and a raw material for the production of fluoroplastics, in particular with its ozone depletion potential (ODP) is 0 and its global warming potential (GWP) is 0.02, making it an increasingly popular alternative to CFCs. As such, one of ordinary skilled in art would have been motivated to use the teachings of CN’431 in the claims of ‘309 and would have a reasonable expectation of success in arriving at the instantly claimed invention.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct the claimed process for the production of 1,1-difluoroethane (HFC-152a) in view of the combination of claims of ‘309 and the teachings of CN’431.
Claims 1-7 and 12-13 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-9 of U.S. Patent No. 10189757B2
(‘757) in view of Patent number CN1931431A (CN’431, cited in IDS 06/26/2023 and machine translation attached herewith).
Claims 1 and 6-8 of ‘757 and instant claim are drawn to a process for the production of fluorinated hydrocarbon by catalytic fluorination, in vapor phase, of a halogenated hydrocarbon with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising chromia to an activation treatment comprising treating the catalyst with hydrogen fluoride at a temperature of from 100° C. to about 500° C and at atmospheric or superatmospheric pressure, and then contacting the halogenated hydrocarbon with the hydrogen fluoride, in the presence of the treated catalyst.
Claims 1 and 6-8 of ‘757 fail to recite that the halogenated hydrocarbon is vinyl chloride and that the fluorinated hydrocarbon is 1,1-difluoroethane as in instant claim 1 and the ratio of vinyl chloride to hydrogen fluoride as instant claims 4 and 12-13. The deficiencies are however cured by CN’431.
Regarding claim 1, CN’431 teaches in the examples ([0028]-[0055] of the translation) a process for the production of 1,1-difluoroethane (HFC-152a) by a catalytic fluorination, in vapor phase, of a composition comprising vinyl chloride with hydrogen fluoride (HF), the method comprising subjecting a catalyst comprising chromium or chromium and aluminum to an activation treatment comprising treating the catalyst with hydrogen fluoride ([0031]), and then contacting the vinyl chloride with the hydrogen fluoride, at temperature of 150-200° C. ([0031]), in the presence of the treated catalyst.
Regarding claims 4 and 12-13, a mole ratio of HF:vinyl chloride = 2-4:1 has been used in CN’431 ([0031]). With respect to claim 13, the claimed mole ratio of from 1:5 to 1:30, or from 1:10 to 1:25 is merely close that of CN’431. In view of MPEP § 2144.05, absent any showing of unexpected results or criticality, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.
The reference further teaches that 1,1-difluoroethane is a widely used fluorinated organic compound that can be used as a refrigerant, a spray agent, and a raw material for the production of fluoroplastics, in particular with its ozone depletion potential (ODP) is 0 and its global warming potential (GWP) is 0.02, making it an increasingly popular alternative to CFCs. As such, one of ordinary skilled in art would have been motivated to use the teachings of CN’431 in the claims of ‘757 and would have a reasonable expectation of success in arriving at the instantly claimed invention.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct the claimed process for the production of 1,1-difluoroethane (HFC-152a) in view of the combination of claims of ‘757 and the teachings of CN’431.
Conclusion
Claims 1-10 and 12-13 are rejected and no claims are allowed.
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/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692