TW200909404A - Process for production of 1,2,2,2-tetrafluoroethyl difluoromethyl ether (desflurane) - Google Patents
Process for production of 1,2,2,2-tetrafluoroethyl difluoromethyl ether (desflurane) Download PDFInfo
- Publication number
- TW200909404A TW200909404A TW097126467A TW97126467A TW200909404A TW 200909404 A TW200909404 A TW 200909404A TW 097126467 A TW097126467 A TW 097126467A TW 97126467 A TW97126467 A TW 97126467A TW 200909404 A TW200909404 A TW 200909404A
- Authority
- TW
- Taiwan
- Prior art keywords
- metal
- desflurane
- reactor
- range
- fluorination
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 70
- DPYMFVXJLLWWEU-UHFFFAOYSA-N desflurane Chemical compound FC(F)OC(F)C(F)(F)F DPYMFVXJLLWWEU-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 22
- 229960003537 desflurane Drugs 0.000 title abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 30
- 229910052751 metal Inorganic materials 0.000 claims abstract description 23
- 239000002184 metal Substances 0.000 claims abstract description 23
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 9
- 239000000758 substrate Substances 0.000 claims abstract description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 239000012808 vapor phase Substances 0.000 claims description 21
- 239000007789 gas Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- -1 pentafluoride Chemical compound 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 239000011159 matrix material Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 238000002309 gasification Methods 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- RPVUQXHGCXIWHO-UHFFFAOYSA-N 2-(difluoromethoxy)-1,1-difluoroethane Chemical compound FC(F)COC(F)F RPVUQXHGCXIWHO-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 claims 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims 1
- 229910052785 arsenic Inorganic materials 0.000 claims 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 1
- YBGKQGSCGDNZIB-UHFFFAOYSA-N arsenic pentafluoride Chemical compound F[As](F)(F)(F)F YBGKQGSCGDNZIB-UHFFFAOYSA-N 0.000 claims 1
- 230000000739 chaotic effect Effects 0.000 claims 1
- KJDVOYQUOWRVOA-UHFFFAOYSA-N difluoromethoxyethane Chemical compound CCOC(F)F KJDVOYQUOWRVOA-UHFFFAOYSA-N 0.000 claims 1
- 210000005069 ears Anatomy 0.000 claims 1
- FTIMWVSQXCWTAW-UHFFFAOYSA-N ruthenium Chemical compound [Ru].[Ru] FTIMWVSQXCWTAW-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 41
- 239000000047 product Substances 0.000 abstract description 13
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 abstract description 10
- 229960002725 isoflurane Drugs 0.000 abstract description 10
- 239000006227 byproduct Substances 0.000 abstract description 9
- 238000010924 continuous production Methods 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000376 reactant Substances 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012025 fluorinating agent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000003983 inhalation anesthetic agent Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910021561 transition metal fluoride Inorganic materials 0.000 description 2
- LEEHHJCQFUKQTC-UHFFFAOYSA-N 1,1,1,3,3-pentafluoro-3-(1,1,3,3,3-pentafluoropropoxy)propane Chemical compound FC(F)(F)CC(F)(F)OC(F)(F)CC(F)(F)F LEEHHJCQFUKQTC-UHFFFAOYSA-N 0.000 description 1
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000012777 commercial manufacturing Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 229960003132 halothane Drugs 0.000 description 1
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 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
- 230000001771 impaired effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- GIDBEKINLBHYLA-UHFFFAOYSA-I pentachlororuthenium Chemical compound Cl[Ru](Cl)(Cl)(Cl)Cl GIDBEKINLBHYLA-UHFFFAOYSA-I 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007430 reference method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1343MU2007 | 2007-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200909404A true TW200909404A (en) | 2009-03-01 |
Family
ID=40260165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097126467A TW200909404A (en) | 2007-07-13 | 2008-07-11 | Process for production of 1,2,2,2-tetrafluoroethyl difluoromethyl ether (desflurane) |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8378149B2 (enExample) |
| EP (1) | EP2167453A4 (enExample) |
| JP (1) | JP2010533211A (enExample) |
| CN (1) | CN101743215A (enExample) |
| AR (1) | AR070010A1 (enExample) |
| AU (1) | AU2008277290B2 (enExample) |
| BR (1) | BRPI0814554A2 (enExample) |
| CA (1) | CA2692874A1 (enExample) |
| MX (1) | MX2010000522A (enExample) |
| TW (1) | TW200909404A (enExample) |
| WO (1) | WO2009010908A2 (enExample) |
| ZA (1) | ZA201001059B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6886104B2 (ja) | 2016-12-29 | 2021-06-16 | セントラル硝子株式会社 | ハロゲン化α−フルオロエーテル類の製造方法 |
| US10683252B2 (en) | 2016-12-29 | 2020-06-16 | Central Glass Company, Limited | Production method for 1,2,2,2-tetrafluoroethyl difluoromethyl ether (desflurane) |
| JP2019064948A (ja) * | 2017-09-29 | 2019-04-25 | セントラル硝子株式会社 | １，２，２，２−テトラフルオロエチルジフルオロメチルエーテル（デスフルラン）の製造方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2478362A (en) * | 1948-06-15 | 1949-08-09 | Kinetic Chemicals Inc | Distillation process for separating products of perchloro-ethylene fluorination |
| US3535388A (en) * | 1969-05-12 | 1970-10-20 | Air Reduction | 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether |
| US3897502A (en) * | 1971-10-22 | 1975-07-29 | Airco Inc | Process for making fluorinated ethers |
| DE2361058A1 (de) | 1973-12-07 | 1975-06-19 | Hoechst Ag | 1.2.2.2-tetrafluoraethyl-chlorfluormethylaether und verfahren zu dessen herstellung |
| DE2546532C2 (de) * | 1975-10-17 | 1977-11-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Trichlormethyl-trifluormethylbenzolen |
| US4436942A (en) * | 1977-10-27 | 1984-03-13 | Occidental Chemical Corporation | Process for the catalyzed fluorination of haloalkyl aromatic compounds |
| FR2501064A1 (fr) * | 1980-12-29 | 1982-09-10 | Ugine Kuhlmann | Catalyseurs de fluoruration en phase gazeuse des hydrocarbures chlores et chlorofluores aliphatiques, a base d'oxyde de chrome depose sur charbon actif, et procedes de fluoruration utilisant ces catalyseurs |
| US4762856A (en) * | 1987-02-02 | 1988-08-09 | Boc, Inc. | Anesthetic composition and method of using the same |
| US4874901A (en) | 1988-05-06 | 1989-10-17 | Boc, Inc. | Process for the production of polyfluorinated ethers |
| US5015781A (en) * | 1988-05-06 | 1991-05-14 | Boc, Inc. | Anesthetic compound and method of preparing |
| JPH01301636A (ja) | 1988-05-31 | 1989-12-05 | Central Glass Co Ltd | １，２，２，２−テトラフルオロエチルジフルオロメチルエーテルの製造法 |
| US5026924A (en) * | 1989-03-14 | 1991-06-25 | Anaquest, Inc. | Process for production of 1,2,2,2-tetrafluoroethyl difluoromethyl ether |
| GB9023370D0 (en) * | 1990-10-26 | 1990-12-05 | Rhone Poulenc Chemicals | Synthesis of fluorinated substituted ethanes |
| EP0712826A1 (en) * | 1994-11-17 | 1996-05-22 | Elf Atochem North America, Inc. | 1,1,1-Trifluoroethane synthesis using a supported lewis acid |
| ES2155201T3 (es) * | 1995-10-10 | 2001-05-01 | Ici Plc | Procedimiento para la recuperacion de fluoruro de hidrogeno. |
| JP2001511194A (ja) * | 1997-01-08 | 2001-08-07 | ハーキュリーズ・インコーポレーテッド | 炭化水素樹脂の製造用触媒としてのフッ化固体酸 |
| US6074985A (en) * | 1999-08-03 | 2000-06-13 | Elf Atochem North America, Inc. | Fluorination catalysts |
| JP3837628B2 (ja) * | 2000-09-08 | 2006-10-25 | 独立行政法人産業技術総合研究所 | １−クロロ−１，１，２，２−テトラフロロ−２−メトキシエタン及びその製造方法 |
| US6635231B2 (en) * | 2001-03-06 | 2003-10-21 | Lithdyne International | Preparation of arsenic pentafluoride |
| US6800786B1 (en) * | 2002-09-25 | 2004-10-05 | Baxter International, Inc. | Preparation of desflurane |
| WO2006055749A1 (en) * | 2004-11-17 | 2006-05-26 | Minrad Inc. | Process for production of 1,2,2,2-tetrafluoro ethyl difluoro methyl ether |
| EP1843996B1 (en) * | 2005-01-12 | 2013-04-10 | Halocarbon Products Corporation | Synthesis of fluorinated ethers |
| HUE025953T2 (en) | 2005-02-15 | 2016-04-28 | Halocarbon Prod Corp | Separation / purification of desflurane from hydrogen fluoride |
-
2008
- 2008-07-11 EP EP08789277A patent/EP2167453A4/en not_active Withdrawn
- 2008-07-11 AU AU2008277290A patent/AU2008277290B2/en not_active Ceased
- 2008-07-11 WO PCT/IB2008/052801 patent/WO2009010908A2/en not_active Ceased
- 2008-07-11 BR BRPI0814554-7A2A patent/BRPI0814554A2/pt not_active IP Right Cessation
- 2008-07-11 MX MX2010000522A patent/MX2010000522A/es active IP Right Grant
- 2008-07-11 CA CA 2692874 patent/CA2692874A1/en not_active Abandoned
- 2008-07-11 JP JP2010516622A patent/JP2010533211A/ja not_active Ceased
- 2008-07-11 AR ARP080103001A patent/AR070010A1/es not_active Application Discontinuation
- 2008-07-11 US US12/668,984 patent/US8378149B2/en not_active Expired - Fee Related
- 2008-07-11 CN CN200880024550A patent/CN101743215A/zh active Pending
- 2008-07-11 TW TW097126467A patent/TW200909404A/zh unknown
-
2010
- 2010-02-12 ZA ZA201001059A patent/ZA201001059B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US8378149B2 (en) | 2013-02-19 |
| ZA201001059B (en) | 2010-10-27 |
| MX2010000522A (es) | 2010-04-01 |
| US20100185020A1 (en) | 2010-07-22 |
| AU2008277290A1 (en) | 2009-01-22 |
| CA2692874A1 (en) | 2009-01-22 |
| JP2010533211A (ja) | 2010-10-21 |
| AR070010A1 (es) | 2010-03-10 |
| CN101743215A (zh) | 2010-06-16 |
| BRPI0814554A2 (pt) | 2015-01-06 |
| WO2009010908A3 (en) | 2009-12-30 |
| WO2009010908A2 (en) | 2009-01-22 |
| EP2167453A2 (en) | 2010-03-31 |
| EP2167453A4 (en) | 2013-03-06 |
| AU2008277290B2 (en) | 2013-09-05 |
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