JP2006510719A - ヘキサフルオロプロピレンオキシドとフッ化パーフルオロアシルとの選択的反応 - Google Patents
ヘキサフルオロプロピレンオキシドとフッ化パーフルオロアシルとの選択的反応 Download PDFInfo
- Publication number
- JP2006510719A JP2006510719A JP2004564820A JP2004564820A JP2006510719A JP 2006510719 A JP2006510719 A JP 2006510719A JP 2004564820 A JP2004564820 A JP 2004564820A JP 2004564820 A JP2004564820 A JP 2004564820A JP 2006510719 A JP2006510719 A JP 2006510719A
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- JP
- Japan
- Prior art keywords
- cof
- product
- hfpo
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- 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.)
- Pending
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- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 title claims abstract description 83
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 title claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 title abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 150000004673 fluoride salts Chemical class 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 239000002798 polar solvent Substances 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001033 ether group Chemical group 0.000 claims description 8
- 125000001302 tertiary amino group Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 238000010923 batch production Methods 0.000 claims description 6
- 230000003252 repetitive effect Effects 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002009 alkene group Chemical group 0.000 claims 1
- 150000003512 tertiary amines Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 56
- 238000007792 addition Methods 0.000 description 42
- 239000000376 reactant Substances 0.000 description 15
- 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
- -1 cation salts Chemical class 0.000 description 4
- 239000000463 material Substances 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
- 238000003682 fluorination reaction Methods 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical class FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000000630 rising effect Effects 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000004429 atom Chemical group 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010924 continuous production Methods 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
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 1
- WMFABESKCHGSRC-UHFFFAOYSA-N propanoyl fluoride Chemical compound CCC(F)=O WMFABESKCHGSRC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| JP2006510719A true JP2006510719A (ja) | 2006-03-30 |
| JP2006510719A5 JP2006510719A5 (https=) | 2006-11-09 |
Family
ID=32507252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004564820A Pending JP2006510719A (ja) | 2002-12-17 | 2003-10-23 | ヘキサフルオロプロピレンオキシドとフッ化パーフルオロアシルとの選択的反応 |
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=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010038902A1 (en) * | 2008-10-01 | 2010-04-08 | Daikin Industries, Ltd. | Production method of fluoroethercarboxylic acid fluoride and fluoroethercarboxylic acid |
| JP2020502314A (ja) * | 2016-12-14 | 2020-01-23 | ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． | （ペル）フルオロポリエーテルポリマー |
| US12209019B2 (en) | 2018-11-28 | 2025-01-28 | Hysilabs, Sas | Catalysed process of production of hydrogen from silylated derivatives as hydrogen carrier compounds |
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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 |
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| GB0514387D0 (en) * | 2005-07-15 | 2005-08-17 | 3M Innovative Properties Co | Aqueous emulsion polymerization of fluorinated monomers using a perfluoropolyether surfactant |
| 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 |
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| 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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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
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010038902A1 (en) * | 2008-10-01 | 2010-04-08 | Daikin Industries, Ltd. | Production method of fluoroethercarboxylic acid fluoride and fluoroethercarboxylic acid |
| JP2010083887A (ja) * | 2008-10-01 | 2010-04-15 | Daikin Ind Ltd | フルオロエーテルカルボン酸フルオライド及びフルオロエーテルカルボン酸の製造方法 |
| JP2020502314A (ja) * | 2016-12-14 | 2020-01-23 | ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． | （ペル）フルオロポリエーテルポリマー |
| JP7187456B2 (ja) | 2016-12-14 | 2022-12-12 | ソルベイ スペシャルティ ポリマーズ イタリー エス．ピー．エー． | （ペル）フルオロポリエーテルポリマー |
| US12209019B2 (en) | 2018-11-28 | 2025-01-28 | Hysilabs, Sas | Catalysed process of production of hydrogen from silylated derivatives as hydrogen carrier compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2506455A1 (en) | 2004-07-22 |
| 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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