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 (enExample) |
| EP (1) | EP1572616B1 (enExample) |
| JP (1) | JP2006510719A (enExample) |
| KR (1) | KR20050093781A (enExample) |
| CN (1) | CN1726180A (enExample) |
| AT (1) | ATE359257T1 (enExample) |
| AU (1) | AU2003303552A1 (enExample) |
| CA (1) | CA2506455A1 (enExample) |
| DE (1) | DE60313213T2 (enExample) |
| WO (1) | WO2004060849A1 (enExample) |
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| 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 |
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| JP7369774B2 (ja) | 2018-12-21 | 2023-10-26 | スリーエム イノベイティブ プロパティズ カンパニー | 触媒毒を低減したフルオロポリマーアイオノマー及びそれからの物品 |
| WO2020261089A1 (en) | 2019-06-28 | 2020-12-30 | 3M Innovative Properties Company | Functionalized triazine compounds, compositions comprising such compounds and cured fluoropolymer articles |
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| 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 EP EP03814614A patent/EP1572616B1/en not_active Expired - Lifetime
- 2003-10-23 KR KR1020057011074A patent/KR20050093781A/ko not_active Withdrawn
- 2003-10-23 WO PCT/US2003/033958 patent/WO2004060849A1/en not_active Ceased
- 2003-10-23 AT AT03814614T patent/ATE359257T1/de not_active IP Right Cessation
- 2003-10-23 JP JP2004564820A patent/JP2006510719A/ja active Pending
- 2003-10-23 CN CNA2003801059233A patent/CN1726180A/zh active Pending
- 2003-10-23 DE DE60313213T patent/DE60313213T2/de not_active Expired - Fee Related
- 2003-10-23 CA CA002506455A patent/CA2506455A1/en not_active Abandoned
- 2003-10-23 AU AU2003303552A patent/AU2003303552A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20040116742A1 (en) | 2004-06-17 |
| EP1572616A1 (en) | 2005-09-14 |
| ATE359257T1 (de) | 2007-05-15 |
| AU2003303552A1 (en) | 2004-07-29 |
| JP2006510719A (ja) | 2006-03-30 |
| EP1572616B1 (en) | 2007-04-11 |
| CN1726180A (zh) | 2006-01-25 |
| KR20050093781A (ko) | 2005-09-23 |
| DE60313213D1 (de) | 2007-05-24 |
| DE60313213T2 (de) | 2007-12-20 |
| WO2004060849A1 (en) | 2004-07-22 |
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