KR20100103643A - 플루오로메틸 1,1,1,3,3,3-헥사플루오로이소프로필 에테르(세보플루란)의 정제 방법 - Google Patents
플루오로메틸 1,1,1,3,3,3-헥사플루오로이소프로필 에테르(세보플루란)의 정제 방법 Download PDFInfo
- Publication number
- KR20100103643A KR20100103643A KR1020107016600A KR20107016600A KR20100103643A KR 20100103643 A KR20100103643 A KR 20100103643A KR 1020107016600 A KR1020107016600 A KR 1020107016600A KR 20107016600 A KR20107016600 A KR 20107016600A KR 20100103643 A KR20100103643 A KR 20100103643A
- Authority
- KR
- South Korea
- Prior art keywords
- crude
- seboflurane
- hfip
- ppm
- seboflavone
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 65
- OOKYWAXNZYBZER-UHFFFAOYSA-N 3-amino-3-(4-ethoxy-3-methoxyphenyl)propanoic acid Chemical compound CCOC1=CC=C(C(N)CC(O)=O)C=C1OC OOKYWAXNZYBZER-UHFFFAOYSA-N 0.000 title claims abstract description 5
- DFEYYRMXOJXZRJ-UHFFFAOYSA-N sevoflurane Chemical compound FCOC(C(F)(F)F)C(F)(F)F DFEYYRMXOJXZRJ-UHFFFAOYSA-N 0.000 title claims description 12
- 229960002078 sevoflurane Drugs 0.000 title claims description 12
- 238000000746 purification Methods 0.000 title description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 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 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 58
- 239000012071 phase Substances 0.000 claims description 42
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 30
- 239000008346 aqueous phase Substances 0.000 claims description 24
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 22
- 238000004508 fractional distillation Methods 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
- 239000000047 product Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 229930040373 Paraformaldehyde Natural products 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 229920002866 paraformaldehyde Polymers 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 230000005484 gravity Effects 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229930003944 flavone Natural products 0.000 description 3
- 235000011949 flavones Nutrition 0.000 description 3
- SGAMQLNREKTWEK-UHFFFAOYSA-N fluoro(fluoromethoxy)methane Chemical compound FCOCF SGAMQLNREKTWEK-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000000066 reactive distillation Methods 0.000 description 3
- VNXYDFNVQBICRO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-methoxypropane Chemical compound COC(C(F)(F)F)C(F)(F)F VNXYDFNVQBICRO-UHFFFAOYSA-N 0.000 description 2
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 150000002212 flavone derivatives Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 2
- KHFGPBNEILANTD-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2,3,3,4,4,4-hexafluorobutane Chemical compound FC(F)(F)C(F)(F)C(F)(Cl)C(Cl)(Cl)Cl KHFGPBNEILANTD-UHFFFAOYSA-N 0.000 description 1
- LWRNQOBXRHWPGE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,7,8,8a-heptadecafluoro-8-(trifluoromethyl)naphthalene Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(F)C2(F)C(C(F)(F)F)(F)C(F)(F)C(F)(F)C(F)(F)C21F LWRNQOBXRHWPGE-UHFFFAOYSA-N 0.000 description 1
- FQERLIOIVXPZKH-UHFFFAOYSA-N 1,2,4-trioxane Chemical compound C1COOCO1 FQERLIOIVXPZKH-UHFFFAOYSA-N 0.000 description 1
- -1 Hexafluoroisopropyl Chemical group 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 229920001218 Pullulan Polymers 0.000 description 1
- 239000004373 Pullulan Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003398 denaturant Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003983 inhalation anesthetic agent Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000019423 pullulan Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
-
- 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
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/38—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/965,137 US7732647B2 (en) | 2007-12-27 | 2007-12-27 | Process for the purification of fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether (sevoflurane) |
| US11/965,137 | 2007-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20100103643A true KR20100103643A (ko) | 2010-09-27 |
Family
ID=40799288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020107016600A Ceased KR20100103643A (ko) | 2007-12-27 | 2008-12-22 | 플루오로메틸 1,1,1,3,3,3-헥사플루오로이소프로필 에테르(세보플루란)의 정제 방법 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7732647B2 (enExample) |
| EP (1) | EP2231574B1 (enExample) |
| JP (1) | JP2011515329A (enExample) |
| KR (1) | KR20100103643A (enExample) |
| CN (1) | CN102066300B (enExample) |
| BR (1) | BRPI0821708A2 (enExample) |
| CA (1) | CA2710218C (enExample) |
| HU (1) | HUE028167T2 (enExample) |
| WO (1) | WO2009085247A2 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101455449B1 (ko) * | 2009-06-15 | 2014-10-27 | 다이킨 고교 가부시키가이샤 | 고순도 불소 함유 에테르의 제조 방법 |
| US8987524B2 (en) | 2009-08-10 | 2015-03-24 | Solvay Fluor Gmbh | Process for the manufacture of Sevoflurane |
| CN105664883B (zh) * | 2009-09-01 | 2020-09-08 | 蓝区技术有限公司 | 用于气体处理的系统和方法 |
| EP2673256B1 (en) | 2011-02-10 | 2015-04-08 | Solvay SA | Process for the manufacture of fluoromethoxymalonic acid derivatives |
| EP2626341A1 (en) | 2012-02-10 | 2013-08-14 | Solvay Sa | Manufacture of hexafluoroisopropanol |
| EP2889355B1 (en) * | 2013-12-26 | 2017-04-19 | Central Glass Company, Limited | Azeotropic mixture-like composition, heat transfer composition, cleaner, high-temperature heat pump device, and heat transfer method |
| CN105523903B (zh) * | 2016-01-30 | 2017-07-18 | 华东医药（西安）博华制药有限公司 | 一种七氟烷的纯化方法 |
| US10035745B1 (en) | 2016-07-30 | 2018-07-31 | Baxter International Inc. | Methods of purifying crude sevoflurane |
| JP6299905B1 (ja) * | 2017-02-06 | 2018-03-28 | セントラル硝子株式会社 | セボフルランの製造方法 |
Family Cites Families (10)
| 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 |
| JP2865554B2 (ja) * | 1994-04-08 | 1999-03-08 | セントラル硝子株式会社 | 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ーテルのガスクロマトグラフ分析 |
| GB9600072D0 (en) | 1996-01-04 | 1996-03-06 | Ici Plc | Process for the production of fluoromethylhexafluoroisopropylether |
| JP4087488B2 (ja) * | 1998-03-03 | 2008-05-21 | セントラル硝子株式会社 | 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ーテルの精製方法 |
| US6100434A (en) | 1999-03-26 | 2000-08-08 | Abbott Laboratories | Method for synthesizing sevoflurane and an intermediate thereof |
| US6469219B1 (en) * | 2000-03-16 | 2002-10-22 | Halocarbon Products Corporation | Production of fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether |
| GB0031310D0 (en) | 2000-12-21 | 2001-01-31 | Ici Plc | Process for the purification of fluoromethyl hexafluoroisopropyl ether |
| JP2007518078A (ja) * | 2004-01-05 | 2007-07-05 | ヘイロウカーボン プロダクツ コーポレイション | プロセス中及び完成セボフルランの両方の分析のクロマトグラフ法 |
| WO2007001916A2 (en) * | 2005-06-27 | 2007-01-04 | Dow Global Technologies, Inc. | Window envelopes with optical character readable window film patches |
| CA2618345C (en) | 2005-08-04 | 2012-03-06 | Halocarbon Products Corporation | Purification of fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether (sevoflurane) |
-
2007
- 2007-12-27 US US11/965,137 patent/US7732647B2/en not_active Expired - Fee Related
-
2008
- 2008-12-22 EP EP08868102.8A patent/EP2231574B1/en not_active Not-in-force
- 2008-12-22 JP JP2010540655A patent/JP2011515329A/ja active Pending
- 2008-12-22 CN CN2008801226629A patent/CN102066300B/zh not_active Expired - Fee Related
- 2008-12-22 CA CA2710218A patent/CA2710218C/en not_active Expired - Fee Related
- 2008-12-22 BR BRPI0821708-4A patent/BRPI0821708A2/pt not_active IP Right Cessation
- 2008-12-22 WO PCT/US2008/013981 patent/WO2009085247A2/en not_active Ceased
- 2008-12-22 KR KR1020107016600A patent/KR20100103643A/ko not_active Ceased
- 2008-12-22 HU HUE08868102A patent/HUE028167T2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009085247A2 (en) | 2009-07-09 |
| JP2011515329A (ja) | 2011-05-19 |
| WO2009085247A3 (en) | 2012-10-04 |
| CA2710218C (en) | 2016-06-07 |
| US20090171128A1 (en) | 2009-07-02 |
| US7732647B2 (en) | 2010-06-08 |
| BRPI0821708A2 (pt) | 2015-06-16 |
| EP2231574A2 (en) | 2010-09-29 |
| CN102066300B (zh) | 2013-12-25 |
| HUE028167T2 (en) | 2016-12-28 |
| EP2231574A4 (en) | 2014-03-05 |
| CN102066300A (zh) | 2011-05-18 |
| EP2231574B1 (en) | 2015-10-07 |
| WO2009085247A8 (en) | 2015-08-27 |
| CA2710218A1 (en) | 2009-07-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20100723 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20131108 Comment text: Request for Examination of Application |
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| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20150401 Patent event code: PE09021S01D |
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| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20151028 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20150401 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |