JPS5935379B2 - ヘキサフルオルプロピレンエポキシドとケトン又は酸フルオリドとの接触反応法 - Google Patents
ヘキサフルオルプロピレンエポキシドとケトン又は酸フルオリドとの接触反応法Info
- Publication number
- JPS5935379B2 JPS5935379B2 JP51034578A JP3457876A JPS5935379B2 JP S5935379 B2 JPS5935379 B2 JP S5935379B2 JP 51034578 A JP51034578 A JP 51034578A JP 3457876 A JP3457876 A JP 3457876A JP S5935379 B2 JPS5935379 B2 JP S5935379B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- formula
- group
- substituted
- sulfonyl
- Prior art date
- 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
Links
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 13
- 238000006243 chemical reaction Methods 0.000 title description 18
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 title description 14
- 239000002253 acid Substances 0.000 title description 10
- 150000002576 ketones Chemical class 0.000 title description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- -1 sulfonium halide Chemical class 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 6
- 229910052701 rubidium Inorganic materials 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 229910000077 silane Inorganic materials 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000012071 phase Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- CTIKAHQFRQTTAY-UHFFFAOYSA-N fluoro(trimethyl)silane Chemical compound C[Si](C)(C)F CTIKAHQFRQTTAY-UHFFFAOYSA-N 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 229910001512 metal fluoride Inorganic materials 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- YLCLKCNTDGWDMD-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)F YLCLKCNTDGWDMD-UHFFFAOYSA-N 0.000 description 1
- RUFSXELMOQBMOF-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,5-nonafluoropentanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RUFSXELMOQBMOF-UHFFFAOYSA-N 0.000 description 1
- YIHXQSQQJBEAKK-UHFFFAOYSA-N 2,2-difluoro-2-fluorosulfonylacetyl fluoride Chemical compound FC(=O)C(F)(F)S(F)(=O)=O YIHXQSQQJBEAKK-UHFFFAOYSA-N 0.000 description 1
- JEDHLIXWSMGAEZ-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,4,4,5,5,5-undecafluoropentoxy)propanoic acid Chemical compound OC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JEDHLIXWSMGAEZ-UHFFFAOYSA-N 0.000 description 1
- DCYHFNOZQINQHG-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,4,4,5,5,5-undecafluoropentoxy)propanoyl fluoride Chemical compound FC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F DCYHFNOZQINQHG-UHFFFAOYSA-N 0.000 description 1
- JJMSFRPBSYTEIN-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-fluorosulfonylethoxy)propanoyl fluoride Chemical compound FC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)S(F)(=O)=O JJMSFRPBSYTEIN-UHFFFAOYSA-N 0.000 description 1
- PDODMQGEIOOGPN-UHFFFAOYSA-N 3-ethoxypropanoyl fluoride Chemical compound O(CC)CCC(=O)F PDODMQGEIOOGPN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- BCZZCSPWPQMEQS-UHFFFAOYSA-N carbonic acid hydrofluoride Chemical compound C(O)(O)=O.F BCZZCSPWPQMEQS-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BHBIPLOIWQSVID-UHFFFAOYSA-N thiohypofluorous acid Chemical compound SF BHBIPLOIWQSVID-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/62—Preparation of carboxylic acid halides by reactions not involving the carboxylic acid halide group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56448375A | 1975-04-02 | 1975-04-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51127023A JPS51127023A (en) | 1976-11-05 |
| JPS5935379B2 true JPS5935379B2 (ja) | 1984-08-28 |
Family
ID=24254649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51034578A Expired JPS5935379B2 (ja) | 1975-04-02 | 1976-03-31 | ヘキサフルオルプロピレンエポキシドとケトン又は酸フルオリドとの接触反応法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4081466A (enExample) |
| JP (1) | JPS5935379B2 (enExample) |
| DE (1) | DE2614333C2 (enExample) |
| FR (1) | FR2306189A1 (enExample) |
| GB (1) | GB1529514A (enExample) |
| IT (1) | IT1058936B (enExample) |
| NL (1) | NL7603413A (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4131740A (en) * | 1977-04-20 | 1978-12-26 | E. I. Du Pont De Nemours And Company | Alkyl perfluoro-ω-fluoroformyl esters and their preparation |
| JPS58131935A (ja) * | 1982-12-29 | 1983-08-06 | Daikin Ind Ltd | 光学分割用試薬 |
| US4624853A (en) * | 1983-02-07 | 1986-11-25 | S. C. Johnson & Son, Inc. | Instant yogurt food product |
| US4749526A (en) * | 1986-09-12 | 1988-06-07 | Minnesota Mining And Manufacturing Co. | Process for preparing fluoraliphatic ether-containing carbonyl fluoride compositions |
| DE3631560A1 (de) * | 1986-09-17 | 1988-04-14 | Hoechst Ag | Halogenhaltige ether |
| DE3707367A1 (de) * | 1987-03-07 | 1988-09-15 | Hoechst Ag | Umsetzung von hexafluorpropenoxid mit fluorierten carbonsaeurefluoriden |
| US5210282A (en) * | 1987-10-30 | 1993-05-11 | Minnesota Mining And Manufacturing Company | Perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluorides and derivatives thereof |
| US4889656A (en) * | 1987-10-30 | 1989-12-26 | Minnesota Mining And Manufacturing Company | Perfluoro(cycloaliphatic methyleneoxyalkylene) carbonyl fluorides and derivatives thereof |
| US5414119A (en) * | 1993-03-02 | 1995-05-09 | Shin Etsu Chemical Co., Ltd. | Hexafluoropropylene oxide compounds and a method of making same |
| US5777179A (en) * | 1996-05-24 | 1998-07-07 | E. I. Du Pont De Nemours And Company | Co-production of perfluoromethyl perfluorovinyl ether and perfluoroethyl perfluorovinyl ether |
| RU2179548C2 (ru) * | 2000-05-16 | 2002-02-20 | Игумнов Сергей Михайлович | Способ получения перфторированных простых эфиров с концевыми функциональными группами |
| CN115368232A (zh) * | 2022-08-02 | 2022-11-22 | 浙江诺亚氟化工有限公司 | 一种全氟代酰氟的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3250808A (en) * | 1963-10-31 | 1966-05-10 | Du Pont | Fluorocarbon ethers derived from hexafluoropropylene epoxide |
| US3940402A (en) * | 1974-09-19 | 1976-02-24 | E. I. Dupont De Nemours And Company | Tris(substituted amino) sulfonium salts |
-
1976
- 1976-03-31 FR FR7609311A patent/FR2306189A1/fr active Granted
- 1976-03-31 GB GB12987/76A patent/GB1529514A/en not_active Expired
- 1976-03-31 JP JP51034578A patent/JPS5935379B2/ja not_active Expired
- 1976-04-01 NL NL7603413A patent/NL7603413A/xx not_active Application Discontinuation
- 1976-04-01 IT IT21859/76A patent/IT1058936B/it active
- 1976-04-02 DE DE2614333A patent/DE2614333C2/de not_active Expired
- 1976-06-18 US US05/697,629 patent/US4081466A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2306189B1 (enExample) | 1983-01-07 |
| DE2614333A1 (de) | 1976-10-21 |
| NL7603413A (nl) | 1976-10-05 |
| US4081466A (en) | 1978-03-28 |
| JPS51127023A (en) | 1976-11-05 |
| GB1529514A (en) | 1978-10-25 |
| IT1058936B (it) | 1982-05-10 |
| FR2306189A1 (fr) | 1976-10-29 |
| DE2614333C2 (de) | 1985-10-03 |
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