WO2004076439A1 - Verfahren zur herstellung von 4-fluor-1,3-dioxolan-2-on - Google Patents
Verfahren zur herstellung von 4-fluor-1,3-dioxolan-2-on Download PDFInfo
- Publication number
- WO2004076439A1 WO2004076439A1 PCT/EP2004/001345 EP2004001345W WO2004076439A1 WO 2004076439 A1 WO2004076439 A1 WO 2004076439A1 EP 2004001345 W EP2004001345 W EP 2004001345W WO 2004076439 A1 WO2004076439 A1 WO 2004076439A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ethylene carbonate
- dioxolan
- fluoro
- fluorine
- reaction
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/42—Halogen atoms or nitro radicals
Definitions
- the invention relates to a process for the preparation of 4-fluoro-1, 3-dioxolan-2-one with high selectivity.
- 4-fluoro-1, 3-dioxolan-2-one can be prepared by stoichiometric reaction of chloroethylene carbonate with potassium fluoride.
- the reaction time here is about 24 hours.
- JP 2000309583 describes a process for the preparation of 4-fluoro-1,3-dioxolan-2-one by reacting ethylene carbonate with fluorine. Since direct fluorination reactions are very exothermic, the ethylene carbonate is dissolved in organic solvents and the fluorine gas or a fluorine-containing gas mixture is introduced into the ethylene carbonate.
- the reaction temperature here is in the range from 20 to 100 ° C. Direct fluorinations are highly exothermic reactions, so care must be taken to keep the reaction temperature within manageable limits. According to JP 2000 309583, the gas phase introduced is cooled.
- the object of the invention is to provide a modified process for the preparation of 4-fluoro-1, 3-dioxolan-2-one.
- the process should be characterized by high selectivity and good temperature control.
- 3 to 20% by weight of 4-fluoro-1,3-dioxolan-2-one (based on the amount of ethylene carbonate) is added to ethylene carbonate.
- the solution can first be heated to about 35 ° C to dissolve the ethylene carbonate.
- Fluorine gas or a mixture containing fluorine in an inert gas is introduced into the reaction solution.
- Fluorine is used substoichiometrically based on the ethylene carbonate present in order to limit the formation of secondary components, for example amounts of fluorine in the range from 60 to 95 mol%, preferably 70 to 95 mol% (based on the ethylene carbonate present) are used.
- the reaction solution is cooled to a temperature of 15 to 45 ° C. during the entire reaction period.
- the temperature of the solution is only briefly above the melting point of ethylene carbonate (37-39 ° C) at the beginning of the fluorination.
- the temperature of the solution is below 90% of the fluorination time Melting point of ethylene carbonate. In one embodiment, the temperature of the solution is 20 to 35 ° C.
- the reaction solution obtained in this way is purified several times by distillation under vacuum. Fractions containing ethylene carbonate can be used as starting material for the process according to the invention. This means that the unreacted ethylene carbonate can be recycled in the process.
- the first amount of 4-fluoro-1,3-dioxolan-2-one required for the process according to the invention can be prepared by a known process.
- Another advantage of the process according to the invention is that no additional separate inert solvent is required, which has to be separated off again after the synthesis of the 4-fluoro-1,3-dioxolan-2-one. This simplifies the work-up of the reaction solution obtained.
- Ethylene carbonate has a melting point of 37-39 ° C, while 4-fluoro-1, 3-dioxolan- 2-one shows a melting point of about 17 ° C.
- the melting point can be lowered by adding 4-fluoro-1,3-dioxolan-2-one to ethylene carbonate.
- a mixture of 87% ethylene carbonate and 13% 4-fluoro-1,3-dioxolan-2-one shows a melting point of about 20 ° C.
- a fluorine / nitrogen gas mixture (5:95% by volume) was then introduced through a dip tube with a PTFE frit.
- the temperature of the solution is briefly above the melting point of ethylene carbonate. Over 90% of the fluorination time, the temperature of the solution is below the melting point of ethylene carbonate, preferably in the range from 30 to 35 ° C.
- the reaction solution was purified by first adding acetone to it. Then it was neutralized with potassium hydrogen carbonate with stirring. The suspension obtained was suction filtered through a suction filter and the residue was washed again with acetone. The solution obtained was distilled several times under vacuum. 1839 g (17.34 mol) of 4-fluoro-1, 3-dioxolan-2-one were obtained accordingly. After deducting the amounts of 4-fluorine-1,3-dioxolan-2-one originally contained, the yield for 4-fluoro-1,3-dioxolan-2-one is 63.9% based on the amount of fluorine used.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006501829A JP4791952B2 (ja) | 2003-02-26 | 2004-02-13 | 4−フルオロ−1,3−ジオキソラン−2−オンの製造方法 |
KR1020057015765A KR101158121B1 (ko) | 2003-02-26 | 2004-02-13 | 4-플루오로-1,3-디옥솔란-2-온의 제조 방법 |
EP04710797A EP1599459B1 (de) | 2003-02-26 | 2004-02-13 | Verfahren zur herstellung von 4-fluor-1,3-dioxolan-2-on |
CA2517395A CA2517395C (en) | 2003-02-26 | 2004-02-13 | A process for the preparation of 4-fluoro-1,3-dioxolan-2-one |
DE502004005133T DE502004005133D1 (de) | 2003-02-26 | 2004-02-13 | Verfahren zur herstellung von 4-fluor-1,3-dioxolan-2-on |
US11/210,868 US7745648B2 (en) | 2003-02-26 | 2005-08-25 | Process for preparing 4-fluoro-1,3-dioxolan-2-one |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10308149A DE10308149A1 (de) | 2003-02-26 | 2003-02-26 | Verfahren zur Herstellung von 4-Fluor-1, 3-dioxolan-2-on |
DE10308149.6 | 2003-02-26 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/210,868 Continuation US7745648B2 (en) | 2003-02-26 | 2005-08-25 | Process for preparing 4-fluoro-1,3-dioxolan-2-one |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004076439A1 true WO2004076439A1 (de) | 2004-09-10 |
Family
ID=32841893
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2004/001345 WO2004076439A1 (de) | 2003-02-26 | 2004-02-13 | Verfahren zur herstellung von 4-fluor-1,3-dioxolan-2-on |
Country Status (10)
Country | Link |
---|---|
US (1) | US7745648B2 (de) |
EP (1) | EP1599459B1 (de) |
JP (1) | JP4791952B2 (de) |
KR (1) | KR101158121B1 (de) |
CN (1) | CN100343245C (de) |
AT (1) | ATE374760T1 (de) |
CA (1) | CA2517395C (de) |
DE (2) | DE10308149A1 (de) |
TW (1) | TWI311991B (de) |
WO (1) | WO2004076439A1 (de) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7268238B2 (en) | 2005-01-24 | 2007-09-11 | Ulsan Chemical Co., Ltd. | Manufacturing method and apparatus of 4-fluoroethylene carbonate |
CN100444458C (zh) * | 2004-06-21 | 2008-12-17 | 索尼株式会社 | 电池 |
WO2011020830A1 (en) * | 2009-08-20 | 2011-02-24 | Solvay Fluor Gmbh | Process for the destillative purification of fluoroethylene carbonate |
EP2854147A1 (de) | 2013-09-30 | 2015-04-01 | Solvay SA | Elektrolytzusammensetzungen mit fluorierten Carbonaten |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE530537T1 (de) * | 2007-09-24 | 2011-11-15 | Evonik Degussa Gmbh | VERFAHREN ZUR HERSTELLUNG VON MONOCHLORETHYLENCARBONAT UND ZU DESSEN ANSCHLIEßENDER UMWANDLUNG IN VINYLENCARBONAT |
JP2011515446A (ja) * | 2008-03-27 | 2011-05-19 | ゾルファイ フルーオル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 特定の吸収剤を使用するhfが低減されたフッ素化有機カーボネートの製造 |
CN101981022A (zh) * | 2008-03-27 | 2011-02-23 | 苏威氟有限公司 | 用于从含hf的有机碳酸酯中除去hf的方法 |
TW201012796A (en) * | 2008-09-02 | 2010-04-01 | Solvay Fluor Gmbh | Method for removal of contaminants |
EP2196464A1 (de) | 2008-12-15 | 2010-06-16 | Solvay Fluor GmbH | Behälter mit fluorierten organischen Carbonaten |
TW201105646A (en) * | 2009-05-28 | 2011-02-16 | Solvay Fluor Gmbh | Process for the preparation of 4-fluoro-4-R-5-R'-1,3-dioxolane-2-ones |
TW201121938A (en) * | 2009-09-28 | 2011-07-01 | Solvay Fluor Gmbh | Manufacture of difluoroethylene carbonate, trifluoroethylene carbonate and tetrafluoroethylene carbonate |
TW201118065A (en) | 2009-09-28 | 2011-06-01 | Solvay Fluor Gmbh | Continuous preparation of carbonates |
CN101717389B (zh) * | 2009-10-29 | 2013-01-09 | 江苏华盛精化工股份有限公司 | 氟代碳酸乙烯酯的除酸除水方法 |
KR20150064073A (ko) * | 2012-10-09 | 2015-06-10 | 솔베이(소시에떼아노님) | 정제 플루오로치환 유기 카보네이트의 제조 |
KR20150064748A (ko) | 2012-10-09 | 2015-06-11 | 솔베이(소시에떼아노님) | 플루오르화 유기 카보네이트의 정제 방법 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000309583A (ja) * | 1999-04-28 | 2000-11-07 | Kanto Denka Kogyo Co Ltd | 4−フルオロ−1,3−ジオキソラン−2−オンの製造方法 |
Family Cites Families (6)
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JPS62290072A (ja) | 1986-06-09 | 1987-12-16 | Matsushita Electric Ind Co Ltd | 有機電解質二次電池 |
CA2087390A1 (en) * | 1992-02-12 | 1993-08-13 | Jack E. Richman | Preparation of fluorinated functional compounds |
JPH07312227A (ja) | 1994-05-17 | 1995-11-28 | Mitsubishi Chem Corp | リチウム二次電池 |
CA2267263A1 (en) * | 1996-10-03 | 1998-04-09 | National Research Council Of Canada | Electrolyte comprising fluoro-ethylene carbonate and propylene carbonate, for alkali metal-ion secondary battery |
JP4431212B2 (ja) | 1999-06-02 | 2010-03-10 | 関東電化工業株式会社 | 含フッ素環状炭酸エステルの製造方法 |
JP2004161638A (ja) | 2002-11-11 | 2004-06-10 | Mitsubishi Chemicals Corp | フッ素含環状化合物の製造方法 |
-
2003
- 2003-02-26 DE DE10308149A patent/DE10308149A1/de not_active Withdrawn
- 2003-12-19 TW TW092136083A patent/TWI311991B/zh not_active IP Right Cessation
-
2004
- 2004-02-13 EP EP04710797A patent/EP1599459B1/de not_active Expired - Lifetime
- 2004-02-13 AT AT04710797T patent/ATE374760T1/de active
- 2004-02-13 DE DE502004005133T patent/DE502004005133D1/de not_active Expired - Lifetime
- 2004-02-13 CA CA2517395A patent/CA2517395C/en not_active Expired - Fee Related
- 2004-02-13 JP JP2006501829A patent/JP4791952B2/ja not_active Expired - Fee Related
- 2004-02-13 CN CNB2004800039400A patent/CN100343245C/zh not_active Expired - Fee Related
- 2004-02-13 KR KR1020057015765A patent/KR101158121B1/ko not_active IP Right Cessation
- 2004-02-13 WO PCT/EP2004/001345 patent/WO2004076439A1/de active IP Right Grant
-
2005
- 2005-08-25 US US11/210,868 patent/US7745648B2/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000309583A (ja) * | 1999-04-28 | 2000-11-07 | Kanto Denka Kogyo Co Ltd | 4−フルオロ−1,3−ジオキソラン−2−オンの製造方法 |
Non-Patent Citations (3)
Title |
---|
DATABASE WPI Section Ch Week 200112, Derwent World Patents Index; Class B03, AN 2001-106329, XP002284419 * |
HASEGAWA, MASARU ET AL: "Electroorganic synthesis under solvent-free conditions. Highly regioselective anodic monofluorination of cyclic ethers, lactones, and a cyclic carbonate", TETRAHEDRON LETTERS (2002), 43(8), 1503-1505, XP004334975 * |
PATENT ABSTRACTS OF JAPAN vol. 2000, no. 14 5 March 2001 (2001-03-05) * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100444458C (zh) * | 2004-06-21 | 2008-12-17 | 索尼株式会社 | 电池 |
US7268238B2 (en) | 2005-01-24 | 2007-09-11 | Ulsan Chemical Co., Ltd. | Manufacturing method and apparatus of 4-fluoroethylene carbonate |
WO2011020830A1 (en) * | 2009-08-20 | 2011-02-24 | Solvay Fluor Gmbh | Process for the destillative purification of fluoroethylene carbonate |
EP2854147A1 (de) | 2013-09-30 | 2015-04-01 | Solvay SA | Elektrolytzusammensetzungen mit fluorierten Carbonaten |
Also Published As
Publication number | Publication date |
---|---|
US20060036102A1 (en) | 2006-02-16 |
JP2006519191A (ja) | 2006-08-24 |
CN100343245C (zh) | 2007-10-17 |
CN1747946A (zh) | 2006-03-15 |
TW200502229A (en) | 2005-01-16 |
KR20050105487A (ko) | 2005-11-04 |
TWI311991B (en) | 2009-07-11 |
DE10308149A1 (de) | 2004-09-09 |
US7745648B2 (en) | 2010-06-29 |
KR101158121B1 (ko) | 2012-06-19 |
EP1599459B1 (de) | 2007-10-03 |
CA2517395A1 (en) | 2004-09-10 |
ATE374760T1 (de) | 2007-10-15 |
JP4791952B2 (ja) | 2011-10-12 |
EP1599459A1 (de) | 2005-11-30 |
DE502004005133D1 (de) | 2007-11-15 |
CA2517395C (en) | 2011-11-22 |
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