JP4102188B2 - フルオロメチルヘキサフルオロイソプロピルエーテルの製造方法 - Google Patents
フルオロメチルヘキサフルオロイソプロピルエーテルの製造方法 Download PDFInfo
- Publication number
- JP4102188B2 JP4102188B2 JP2002551505A JP2002551505A JP4102188B2 JP 4102188 B2 JP4102188 B2 JP 4102188B2 JP 2002551505 A JP2002551505 A JP 2002551505A JP 2002551505 A JP2002551505 A JP 2002551505A JP 4102188 B2 JP4102188 B2 JP 4102188B2
- Authority
- JP
- Japan
- Prior art keywords
- ether
- alcohol
- acid
- fluoromethyl
- bis
- 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 - Fee Related
Links
- PBLGJMMEOGUSID-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(fluoromethyl)-2-[1,1,1,3,3,3-hexafluoro-2-(fluoromethyl)propan-2-yl]oxypropane Chemical compound FCC(C(F)(F)F)(C(F)(F)F)OC(CF)(C(F)(F)F)C(F)(F)F PBLGJMMEOGUSID-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- SGAMQLNREKTWEK-UHFFFAOYSA-N fluoro(fluoromethoxy)methane Chemical compound FCOCF SGAMQLNREKTWEK-UHFFFAOYSA-N 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 40
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 33
- DFEYYRMXOJXZRJ-UHFFFAOYSA-N sevoflurane Chemical compound FCOC(C(F)(F)F)C(F)(F)F DFEYYRMXOJXZRJ-UHFFFAOYSA-N 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 24
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 13
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000007848 Bronsted acid Substances 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 15
- 229960002078 sevoflurane Drugs 0.000 description 24
- 239000006227 byproduct Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000539 dimer Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 229920001774 Perfluoroether Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VXQMRCAROXZWJH-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-(2-fluoroethoxy)-2-[1,1,1,3,3,3-hexafluoro-2-(2-fluoroethoxy)propan-2-yl]oxypropane Chemical compound FCCOC(C(F)(F)F)(C(F)(F)F)OC(C(F)(F)F)(C(F)(F)F)OCCF VXQMRCAROXZWJH-UHFFFAOYSA-N 0.000 description 1
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- FZVWKTZOOXAZJS-UHFFFAOYSA-N CC(C)COC(C(F)(F)F)(C(F)(F)F)OC(C(F)(F)F)(C(F)(F)F)OCC(C)C Chemical compound CC(C)COC(C(F)(F)F)(C(F)(F)F)OC(C(F)(F)F)(C(F)(F)F)OCC(C)C FZVWKTZOOXAZJS-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- -1 fluoromethylhexafluoroisopropyl Chemical group 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 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
- C07C41/14—Preparation of ethers by exchange of organic parts on the ether-oxygen for other organic parts, e.g. by trans-etherification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0031301.5A GB0031301D0 (en) | 2000-12-21 | 2000-12-21 | Process for the production of fluoromethyl hexafluoroisopropyl ether |
| PCT/GB2001/005728 WO2002050003A1 (en) | 2000-12-21 | 2001-12-21 | Process for the production of fluoromethyl hexafluoroisopropyl ether |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004520308A JP2004520308A (ja) | 2004-07-08 |
| JP2004520308A5 JP2004520308A5 (enExample) | 2005-12-22 |
| JP4102188B2 true JP4102188B2 (ja) | 2008-06-18 |
Family
ID=9905629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002551505A Expired - Fee Related JP4102188B2 (ja) | 2000-12-21 | 2001-12-21 | フルオロメチルヘキサフルオロイソプロピルエーテルの製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7034190B2 (enExample) |
| EP (1) | EP1385811B1 (enExample) |
| JP (1) | JP4102188B2 (enExample) |
| AT (1) | ATE282018T1 (enExample) |
| AU (2) | AU1729202A (enExample) |
| BR (1) | BR0116752A (enExample) |
| CA (1) | CA2432596A1 (enExample) |
| DE (1) | DE60107121T2 (enExample) |
| ES (1) | ES2231387T3 (enExample) |
| GB (1) | GB0031301D0 (enExample) |
| WO (1) | WO2002050003A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4861161B2 (ja) | 2003-01-14 | 2012-01-25 | バクスター・インターナショナル・インコーポレイテッド | セボフルラン合成の廃棄物の流れから１，１，１，３，３，３−ヘキサフルオロイソプロパノールの回収のためのプロセス |
| EP2301935A1 (en) | 2005-07-09 | 2011-03-30 | AstraZeneca AB (Publ) | Heteroaryl benzamide derivatives for use as GLK activators in the treatment of diabetes |
| SA07280576B1 (ar) | 2006-10-26 | 2011-06-22 | استرازينيكا ايه بي | مركبات بنزويل أمينو سيكليل غير متجانسة بأعتبارها عوامل منشطة للجلوكوكيناز |
| CN101314560B (zh) * | 2008-07-02 | 2011-06-15 | 鲁南制药集团股份有限公司 | 七氟烷的合成方法 |
| CN101659603B (zh) | 2008-08-27 | 2014-05-07 | 中化蓝天集团有限公司 | 一种制备氟甲基-1,1,1,3,3,3-六氟异丙基醚的方法 |
| JP5434236B2 (ja) | 2009-04-28 | 2014-03-05 | セントラル硝子株式会社 | フルオロメチルヘキサフルオロイソプロピルエーテルの製造方法 |
| US8729313B2 (en) | 2011-08-15 | 2014-05-20 | Baxter International Inc. | Process for the manufacturing of sevoflurane |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4250334A (en) | 1979-12-26 | 1981-02-10 | Baxter Travenol Laboratories, Inc. | Method of synthesizing fluoromethylhexafluoroisopropyl ether |
| GB9126355D0 (en) | 1991-12-11 | 1992-02-12 | Ici Plc | Production of hydrofluorocarbons |
| GB9600072D0 (en) * | 1996-01-04 | 1996-03-06 | Ici Plc | Process for the production of fluoromethylhexafluoroisopropylether |
-
2000
- 2000-12-21 GB GBGB0031301.5A patent/GB0031301D0/en not_active Ceased
-
2001
- 2001-12-21 US US10/451,266 patent/US7034190B2/en not_active Expired - Fee Related
- 2001-12-21 EP EP01271343A patent/EP1385811B1/en not_active Expired - Lifetime
- 2001-12-21 ES ES01271343T patent/ES2231387T3/es not_active Expired - Lifetime
- 2001-12-21 JP JP2002551505A patent/JP4102188B2/ja not_active Expired - Fee Related
- 2001-12-21 CA CA002432596A patent/CA2432596A1/en not_active Abandoned
- 2001-12-21 AU AU1729202A patent/AU1729202A/xx active Pending
- 2001-12-21 BR BR0116752-9A patent/BR0116752A/pt not_active IP Right Cessation
- 2001-12-21 AT AT01271343T patent/ATE282018T1/de not_active IP Right Cessation
- 2001-12-21 WO PCT/GB2001/005728 patent/WO2002050003A1/en not_active Ceased
- 2001-12-21 DE DE60107121T patent/DE60107121T2/de not_active Expired - Fee Related
- 2001-12-21 AU AU2002217292A patent/AU2002217292B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| CA2432596A1 (en) | 2002-06-27 |
| ES2231387T3 (es) | 2005-05-16 |
| JP2004520308A (ja) | 2004-07-08 |
| BR0116752A (pt) | 2003-12-30 |
| US20040073070A1 (en) | 2004-04-15 |
| DE60107121T2 (de) | 2005-03-17 |
| GB0031301D0 (en) | 2001-01-31 |
| WO2002050003A1 (en) | 2002-06-27 |
| AU1729202A (en) | 2002-07-01 |
| EP1385811A1 (en) | 2004-02-04 |
| US7034190B2 (en) | 2006-04-25 |
| EP1385811B1 (en) | 2004-11-10 |
| AU2002217292B2 (en) | 2006-05-25 |
| DE60107121D1 (de) | 2004-12-16 |
| ATE282018T1 (de) | 2004-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0042412A1 (en) | PROCESS FOR SYNTHESIS OF FLUOROMETHYLHEXAFLUOROISOPROPYL ETHER. | |
| EP0822172B2 (en) | Process for preparing fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether | |
| JPWO1997030961A1 (ja) | フルオロメチル−１，１，１，３，３，３−ヘキサフルオロイソプロピルエ−テルの製造方法 | |
| CN110950776A (zh) | 有机碱催化丙烯腈水合制备3-羟基丙腈的方法 | |
| EP0876320B1 (en) | Process for the production of fluoromethylhexafluoroisopropylether | |
| JP4102188B2 (ja) | フルオロメチルヘキサフルオロイソプロピルエーテルの製造方法 | |
| JPH0667875B2 (ja) | アルキルグリコレートの製造方法 | |
| EP0487035B1 (en) | Process for the preparation of diethers | |
| JP3807514B2 (ja) | ジトリメチロールプロパンの製造方法 | |
| JPH0782192A (ja) | ネオペンチルグリコールの製造法 | |
| JPH04504862A (ja) | シトラールの製造方法 | |
| EP1381586B1 (en) | Process for the purification of fluoromethyl hexafluoroisopropyl ether | |
| JPWO2009057466A1 (ja) | ジトリメチロールプロパンの製造方法 | |
| US6111139A (en) | Process for the preparation of trifluoropropanal | |
| US3225102A (en) | Allenic aldehydes | |
| GB2143526A (en) | Preparing 3,3,3-trifluoro-2-trifluoromethylpropene | |
| US6894197B2 (en) | Process for producing fluorinated alcohol | |
| JP2756373B2 (ja) | １，１，１−トリフルオロ−３−ニトロ−２−プロペンの製造方法 | |
| SU548594A1 (ru) | Способ получени пропаргилового спирта | |
| JP6299905B1 (ja) | セボフルランの製造方法 | |
| JP2017214336A (ja) | エステル化合物の製造方法 | |
| WO1998054117A1 (en) | Chemical compounds having two terminal trifluoromethyl groups | |
| JP2025124500A (ja) | ホルムアルデヒドガスの製造方法 | |
| US3236901A (en) | Allenic alcohols and process of manufacturing them | |
| TWI585074B (zh) | 雙三羥甲基丙烷之製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20041202 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20041202 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20070704 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20070710 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20071009 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20071025 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080110 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20080219 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20080321 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110328 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |