JPS585908B2 - パ−フルオロアリルフルオロサルフエ−トの製法 - Google Patents

パ−フルオロアリルフルオロサルフエ−トの製法

Info

Publication number: JPS585908B2
Authority: JP; Japan
Prior art keywords: double line; fluorosulfate; sultone; perfluoroallyl fluorosulfate; perfluoroallyl
Prior art date: 1978-08-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP9952579A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5527185A (en

Inventor

カール・ジヨージ・クレスパン

デビツト・チヤールズ・イングランド

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-08-08

Filing date

1979-08-06

Publication date

1983-02-02

1979-08-06 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1980-02-27 Publication of JPS5527185A publication Critical patent/JPS5527185A/ja

1983-02-02 Publication of JPS585908B2 publication Critical patent/JPS585908B2/ja

Status Expired legal-status Critical Current

Links

LIZZWVXXYAALGG-UHFFFAOYSA-N 1,1,2,3,3-pentafluoro-3-fluorosulfonyloxyprop-1-ene Chemical compound FC(F)=C(F)C(F)(F)OS(F)(=O)=O LIZZWVXXYAALGG-UHFFFAOYSA-N 0.000 title claims description 32
238000000034 method Methods 0.000 title claims description 5
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 58
239000000203 mixture Substances 0.000 claims description 11
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 10
HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 7
JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 6
229910015900 BF3 Inorganic materials 0.000 claims description 5
150000001639 boron compounds Chemical class 0.000 claims description 5
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 5
229910052810 boron oxide Inorganic materials 0.000 claims description 2
150000008053 sultones Chemical class 0.000 description 20
238000009835 boiling Methods 0.000 description 19
239000003054 catalyst Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
-1 cyclic sulfonate sulfate anhydride Chemical class 0.000 description 10
238000004458 analytical method Methods 0.000 description 8
239000007788 liquid Substances 0.000 description 7
BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 6
XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical class FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 6
239000011521 glass Substances 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
229920001577 copolymer Polymers 0.000 description 5
QARLOMBMXGVKNV-UHFFFAOYSA-N 1,2,2-trifluoroethenesulfonyl fluoride Chemical compound FC(F)=C(F)S(F)(=O)=O QARLOMBMXGVKNV-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
238000007334 copolymerization reaction Methods 0.000 description 4
238000000372 flame atomic fluorescence spectroscopy Methods 0.000 description 4
UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
230000008707 rearrangement Effects 0.000 description 3
WIRDPVWSIWULKR-UHFFFAOYSA-N 1,1,1-trifluoro-2-fluorosulfonyloxyethane Chemical compound FC(F)(F)COS(F)(=O)=O WIRDPVWSIWULKR-UHFFFAOYSA-N 0.000 description 2
NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
238000004293 19F NMR spectroscopy Methods 0.000 description 1
NHJFHUKLZMQIHN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl 2,2,3,3,3-pentafluoropropaneperoxoate Chemical compound FC(F)(F)C(F)(F)C(=O)OOC(=O)C(F)(F)C(F)(F)F NHJFHUKLZMQIHN-UHFFFAOYSA-N 0.000 description 1
229910015446 B(OCH3)3 Inorganic materials 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
LTROKCHOAFSNBG-UHFFFAOYSA-N [B].ClOOOCl Chemical compound [B].ClOOOCl LTROKCHOAFSNBG-UHFFFAOYSA-N 0.000 description 1
OOQNXUPSKIQMSX-UHFFFAOYSA-N [B].FOOOF Chemical compound [B].FOOOF OOQNXUPSKIQMSX-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
238000005266 casting Methods 0.000 description 1
239000003518 caustics Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000007872 degassing Methods 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
229960001826 dimethylphthalate Drugs 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910001092 metal group alloy Inorganic materials 0.000 description 1
VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
235000019392 nitrosyl chloride Nutrition 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000012070 reactive reagent Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000013519 translation Methods 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/18—Monomers containing fluorine
- C08F14/185—Monomers containing fluorine not covered by the groups C08F14/20 - C08F14/28
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/12—Fluorides
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
- B01J31/0212—Alkoxylates
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
- B01J31/10—Ion-exchange resins sulfonated
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
- B01J39/04—Processes using organic exchangers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/26—Halogenosulfates, i.e. monoesters of halogenosulfuric acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/18—Monomers containing fluorine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP9952579A 1978-08-08 1979-08-06 パ−フルオロアリルフルオロサルフエ−トの製法 Expired JPS585908B2 (ja)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US93190478A	1978-08-08	1978-08-08

Publications (2)

Publication Number	Publication Date
JPS5527185A JPS5527185A (en)	1980-02-27
JPS585908B2 true JPS585908B2 (ja)	1983-02-02

Family

ID=25461506

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
JP9952579A Expired JPS585908B2 (ja)	1978-08-08	1979-08-06	パ−フルオロアリルフルオロサルフエ−トの製法
JP44682A Granted JPS57141411A (en)	1978-08-08	1982-01-06	Manufacture of homogeneous polymer or copolymer of perfluoroarylfluorosulfate

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
JP44682A Granted JPS57141411A (en)	1978-08-08	1982-01-06	Manufacture of homogeneous polymer or copolymer of perfluoroarylfluorosulfate

Country Status (2)

Country	Link
JP (2)	JPS585908B2 (fr)
BE (1)	BE878131A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2009298700A (ja) *	2006-10-04	2009-12-24	Asahi Glass Co Ltd	フルオロスルホニル基を有する化合物の製造方法

1979
- 1979-08-06 JP JP9952579A patent/JPS585908B2/ja not_active Expired
- 1979-08-07 BE BE0/196641A patent/BE878131A/fr not_active IP Right Cessation
1982
- 1982-01-06 JP JP44682A patent/JPS57141411A/ja active Granted

Also Published As

Publication number	Publication date
BE878131A (fr)	1980-02-07
JPS6238362B2 (fr)	1987-08-18
JPS57141411A (en)	1982-09-01
JPS5527185A (en)	1980-02-27

Publication	Publication Date	Title
US4349650A (en)	1982-09-14	Polyfluoroallyloxy compounds, their preparation and copolymers therefrom
US4275225A (en)	1981-06-23	Polyfluoroallyloxy compounds, their preparation and copolymers therefrom
US3242218A (en)	1966-03-22	Process for preparing fluorocarbon polyethers
DE2817366C2 (fr)	1989-01-26
US4273729A (en)	1981-06-16	Polyfluoroallyloxy compounds, their preparation and copolymers therefrom
Cram et al.	1961	Electrophilic Substitution at Saturated Carbon. XIII. Solvent Control of Rate of Acid-Base Reactions that Involve the Carbon-Hydrogen Bond1, 2
US2671799A (en)	1954-03-09	Perhalocarbon compounds and method of preparing them
JPS58103385A (ja)	1983-06-20	パーフルオロジオキソール及びその製造方法
US2992276A (en)	1961-07-11	Process for preparing polyfluoro alkyl compounds
JPH0234935B2 (fr)	1990-08-07
RU2252210C2 (ru)	2005-05-20	Способ получения vic-дихлорфторангидрида
US2543530A (en)	1951-02-27	Treatment of polymeric chlorotrifluoroethylene
US3821297A (en)	1974-06-28	Purification of perfluorosulfonyl fluoride perfluorovinyl ethers by thermal decomposition of unstable isomers
Dostrovsky et al.	1946	44. Mechanism of substitution at a saturated carbon atom. Part XXVI. The rôle of steric hindrance.(Section A) introductory remarks, and a kinetic study of the reactions of methyl, ethyl, n-propyl, iso butyl, and neo pentyl bromides with sodium ethoxide in dry ethyl alcohol
Hauptschein et al.	1957	Thermal Syntheses of Telomers of Fluorinated Olefins. I. Perfluoropropene1
JPS585908B2 (ja)	1983-02-02	パ−フルオロアリルフルオロサルフエ−トの製法
US3129248A (en)	1964-04-14	Preparation of fluorocyclobutanones
US4206138A (en)	1980-06-03	Perfluoroallyl fluorosulfate and its sultone and polymers
US4235804A (en)	1980-11-25	Preparation of perfluoroallyl fluorosulfate
US3311599A (en)	1967-03-28	Selected n, n-bis (perfluoroalkyl) aminoethylenes and polymers thereof
Krespan	1972	Synthesis and pyrolysis of fluorosulfates
US2806865A (en)	1957-09-17	New fluorine-containing compounds and method of preparation thereof
US4287128A (en)	1981-09-01	Process for preparing epoxides
US4709060A (en)	1987-11-24	Substituted trifluorooxetanes
US2773089A (en)	1956-12-04	Fluorinated olefinic nitriles