CA2506455A1 - Selective reaction of hexafluoropropylene oxide with perfluoroacyl fluorides - Google Patents
Selective reaction of hexafluoropropylene oxide with perfluoroacyl fluorides Download PDFInfo
- Publication number
- CA2506455A1 CA2506455A1 CA002506455A CA2506455A CA2506455A1 CA 2506455 A1 CA2506455 A1 CA 2506455A1 CA 002506455 A CA002506455 A CA 002506455A CA 2506455 A CA2506455 A CA 2506455A CA 2506455 A1 CA2506455 A1 CA 2506455A1
- Authority
- CA
- Canada
- Prior art keywords
- cof
- hfpo
- product
- mixture
- monoaddition
- 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.)
- Abandoned
Links
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 title claims abstract description 86
- 150000002222 fluorine compounds Chemical class 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 title description 17
- 238000000034 method Methods 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 150000004673 fluoride salts Chemical class 0.000 claims abstract description 11
- 238000010923 batch production Methods 0.000 claims abstract description 6
- 239000002798 polar solvent Substances 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000001302 tertiary amino group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910005143 FSO2 Inorganic materials 0.000 claims 2
- 239000000047 product Substances 0.000 description 52
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 19
- 239000000376 reactant Substances 0.000 description 18
- 239000006227 byproduct Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000013459 approach Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- FDGCJTUAVVJFMB-UHFFFAOYSA-N 2,2,3,3,4,4,5,5-octafluorohexanedioyl difluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)=O FDGCJTUAVVJFMB-UHFFFAOYSA-N 0.000 description 2
- OIUVUINPJBFCCD-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluoro-4-fluorosulfonylbutanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O OIUVUINPJBFCCD-UHFFFAOYSA-N 0.000 description 2
- ZAKJNULOUJTZMO-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-3-(trifluoromethoxy)propanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)OC(F)(F)F ZAKJNULOUJTZMO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- JAAGVIUFBAHDMA-UHFFFAOYSA-M rubidium bromide Chemical compound [Br-].[Rb+] JAAGVIUFBAHDMA-UHFFFAOYSA-M 0.000 description 2
- WFUBYPSJBBQSOU-UHFFFAOYSA-M rubidium iodide Chemical compound [Rb+].[I-] WFUBYPSJBBQSOU-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VLIZXYVPNGFOFC-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-3-(1,1,2,2,3,3,4,4-octafluoro-4-fluorosulfonylbutoxy)propanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O VLIZXYVPNGFOFC-UHFFFAOYSA-N 0.000 description 1
- BKVHLZIOVHGSAZ-UHFFFAOYSA-N 2,2,3,3-tetrafluoro-3-[1,1,2,2,3,3-hexafluoro-3-(trifluoromethoxy)propoxy]propanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)OC(F)(F)C(F)(F)C(F)(F)OC(F)(F)F BKVHLZIOVHGSAZ-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- LYQFWZFBNBDLEO-UHFFFAOYSA-M caesium bromide Chemical compound [Br-].[Cs+] LYQFWZFBNBDLEO-UHFFFAOYSA-M 0.000 description 1
- XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Chemical compound [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical class FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/64—Separation; Purification; Stabilisation; Use of additives
-
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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)
- Epoxy Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/322,254 | 2002-12-17 | ||
| US10/322,254 US20040116742A1 (en) | 2002-12-17 | 2002-12-17 | Selective reaction of hexafluoropropylene oxide with perfluoroacyl fluorides |
| PCT/US2003/033958 WO2004060849A1 (en) | 2002-12-17 | 2003-10-23 | Selective reaction of hexafluoropropylene oxide with perfluoroacyl fluorides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2506455A1 true CA2506455A1 (en) | 2004-07-22 |
Family
ID=32507252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002506455A Abandoned CA2506455A1 (en) | 2002-12-17 | 2003-10-23 | Selective reaction of hexafluoropropylene oxide with perfluoroacyl fluorides |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20040116742A1 (https=) |
| EP (1) | EP1572616B1 (https=) |
| JP (1) | JP2006510719A (https=) |
| KR (1) | KR20050093781A (https=) |
| CN (1) | CN1726180A (https=) |
| AT (1) | ATE359257T1 (https=) |
| AU (1) | AU2003303552A1 (https=) |
| CA (1) | CA2506455A1 (https=) |
| DE (1) | DE60313213T2 (https=) |
| WO (1) | WO2004060849A1 (https=) |
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| US20060105219A1 (en) * | 2004-11-15 | 2006-05-18 | Anderson Robert D | Fuel cell component storage or shipment |
| US20060144791A1 (en) * | 2004-12-30 | 2006-07-06 | Debe Mark K | Platinum recovery from nanostructured fuel cell catalyst |
| US20060147791A1 (en) * | 2004-12-30 | 2006-07-06 | Debe Mark K | Platinum recovery from fuel cell stacks |
| CN101120467A (zh) * | 2005-02-16 | 2008-02-06 | 3M创新有限公司 | 燃料电池催化剂 |
| US7214740B2 (en) * | 2005-05-03 | 2007-05-08 | 3M Innovative Properties Company | Fluorinated ionomers with reduced amounts of carbonyl end groups |
| GB2427170A (en) * | 2005-06-17 | 2006-12-20 | 3M Innovative Properties Co | Fluoropolymer film having glass microspheres |
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| US7671112B2 (en) * | 2005-07-15 | 2010-03-02 | 3M Innovative Properties Company | Method of making fluoropolymer dispersion |
| GB0514398D0 (en) * | 2005-07-15 | 2005-08-17 | 3M Innovative Properties Co | Aqueous emulsion polymerization of fluorinated monomers using a fluorinated surfactant |
| GB0525978D0 (en) * | 2005-12-21 | 2006-02-01 | 3M Innovative Properties Co | Fluorinated Surfactants For Making Fluoropolymers |
| US20080015304A1 (en) * | 2006-07-13 | 2008-01-17 | Klaus Hintzer | Aqueous emulsion polymerization process for producing fluoropolymers |
| GB0523853D0 (en) | 2005-11-24 | 2006-01-04 | 3M Innovative Properties Co | Fluorinated surfactants for use in making a fluoropolymer |
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| US20070276103A1 (en) * | 2006-05-25 | 2007-11-29 | 3M Innovative Properties Company | Fluorinated Surfactants |
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| US8119750B2 (en) * | 2006-07-13 | 2012-02-21 | 3M Innovative Properties Company | Explosion taming surfactants for the production of perfluoropolymers |
| JP5431958B2 (ja) * | 2006-12-29 | 2014-03-05 | スリーエム イノベイティブ プロパティズ カンパニー | 耐久性のあるポリマー電解質薄膜を製造する方法 |
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| CN102834374B (zh) | 2010-04-16 | 2016-08-03 | 3M创新有限公司 | 质子传导材料 |
| EP2756024B1 (en) | 2011-10-03 | 2015-11-18 | Solvay Specialty Polymers Italy S.p.A. | Linear (per)fluoropolyethers with -cf(cf3)cof end groups and derivatives thereof |
| CN103857831B (zh) | 2011-10-10 | 2016-08-17 | 3M创新有限公司 | 催化剂电极及其制备和使用方法 |
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| WO2014105407A1 (en) | 2012-12-28 | 2014-07-03 | 3M Innovative Properties Company | Electrode and method of making the same |
| JP2017501544A (ja) | 2013-12-17 | 2017-01-12 | スリーエム イノベイティブ プロパティズ カンパニー | 膜電極接合体及びその製造方法 |
| WO2015095021A1 (en) | 2013-12-17 | 2015-06-25 | 3M Innovative Properties Company | Membrane electrode assembly and methods of making the same |
| JP6846359B2 (ja) | 2015-05-26 | 2021-03-24 | スリーエム イノベイティブ プロパティズ カンパニー | 酸素発生触媒電極並びにそれを製造及び使用する方法 |
| EP3455322B1 (en) | 2016-05-09 | 2021-03-03 | 3M Innovative Properties Company | Hydrofluoroolefins and methods of using same |
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| US11560632B2 (en) | 2018-09-27 | 2023-01-24 | 3M Innovative Properties Company | Membrane, membrane electrode assembly, and water electrolyzer including the same |
| EP3659964A1 (en) | 2018-11-28 | 2020-06-03 | Hysilabs, SAS | Catalysed process of production of hydrogen from silylated derivatives as hydrogen carrier compounds |
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| CN111333502B (zh) * | 2018-12-19 | 2022-11-01 | 中蓝晨光化工研究设计院有限公司 | 一种分离全氟二酰氟同分异构体的方法 |
| CN113228356B (zh) | 2018-12-21 | 2025-03-25 | 3M创新有限公司 | 减少催化剂中毒的含氟聚合物离聚物及由其制得的制品 |
| CN113993944B (zh) | 2019-06-28 | 2024-01-30 | 3M创新有限公司 | 官能化三嗪化合物、包含此类化合物的组合物以及固化的含氟聚合物制品 |
| CN113950505B (zh) * | 2019-06-28 | 2023-05-30 | 3M创新有限公司 | 羟基官能化三嗪化合物、包含此类化合物的可固化含氟聚合物组合物以及由其制得的固化制品 |
| CN116375609A (zh) * | 2023-03-15 | 2023-07-04 | 北京科太亚洲生态科技股份有限公司 | 一种高性能树脂单体合成工艺 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3250808A (en) * | 1963-10-31 | 1966-05-10 | Du Pont | Fluorocarbon ethers derived from hexafluoropropylene epoxide |
| US4749526A (en) * | 1986-09-12 | 1988-06-07 | Minnesota Mining And Manufacturing Co. | Process for preparing fluoraliphatic ether-containing carbonyl fluoride compositions |
| US7285349B2 (en) * | 2003-10-30 | 2007-10-23 | 3M Innovative Properties Company | Polymer electrolyte membrane and method of making |
| US7060738B2 (en) * | 2003-12-11 | 2006-06-13 | 3M Innovative Properties Company | Polymer electrolytes crosslinked by ultraviolet radiation |
-
2002
- 2002-12-17 US US10/322,254 patent/US20040116742A1/en not_active Abandoned
-
2003
- 2003-10-23 CN CNA2003801059233A patent/CN1726180A/zh active Pending
- 2003-10-23 WO PCT/US2003/033958 patent/WO2004060849A1/en not_active Ceased
- 2003-10-23 DE DE60313213T patent/DE60313213T2/de not_active Expired - Fee Related
- 2003-10-23 AU AU2003303552A patent/AU2003303552A1/en not_active Abandoned
- 2003-10-23 JP JP2004564820A patent/JP2006510719A/ja active Pending
- 2003-10-23 KR KR1020057011074A patent/KR20050093781A/ko not_active Withdrawn
- 2003-10-23 CA CA002506455A patent/CA2506455A1/en not_active Abandoned
- 2003-10-23 AT AT03814614T patent/ATE359257T1/de not_active IP Right Cessation
- 2003-10-23 EP EP03814614A patent/EP1572616B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006510719A (ja) | 2006-03-30 |
| US20040116742A1 (en) | 2004-06-17 |
| EP1572616A1 (en) | 2005-09-14 |
| DE60313213T2 (de) | 2007-12-20 |
| CN1726180A (zh) | 2006-01-25 |
| EP1572616B1 (en) | 2007-04-11 |
| WO2004060849A1 (en) | 2004-07-22 |
| AU2003303552A1 (en) | 2004-07-29 |
| DE60313213D1 (de) | 2007-05-24 |
| ATE359257T1 (de) | 2007-05-15 |
| KR20050093781A (ko) | 2005-09-23 |
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| Publication | Publication Date | Title |
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