JP2004067684A - ヒドロフルオロエーテル類とその製法 - Google Patents
ヒドロフルオロエーテル類とその製法 Download PDFInfo
- Publication number
- JP2004067684A JP2004067684A JP2003205416A JP2003205416A JP2004067684A JP 2004067684 A JP2004067684 A JP 2004067684A JP 2003205416 A JP2003205416 A JP 2003205416A JP 2003205416 A JP2003205416 A JP 2003205416A JP 2004067684 A JP2004067684 A JP 2004067684A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- hydrofluoroethers
- cfx
- pfpe
- weight
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 229910001512 metal fluoride Inorganic materials 0.000 claims abstract description 5
- 229910004261 CaF 2 Inorganic materials 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- KEDSBJOHAWJRQU-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6-nonafluoro-6-(1,1,2,2,3,3,3-heptafluoropropyl)oxane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C1(F)OC(F)(F)C(F)(F)C(F)(F)C1(F)F KEDSBJOHAWJRQU-UHFFFAOYSA-N 0.000 claims description 3
- CJFUEPJVIFJOOU-UHFFFAOYSA-N 2-perfluorobutyltetrahydrofuran Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C1CCCO1 CJFUEPJVIFJOOU-UHFFFAOYSA-N 0.000 claims description 3
- 229910016569 AlF 3 Inorganic materials 0.000 claims description 2
- 229910016036 BaF 2 Inorganic materials 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 abstract 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract 1
- 239000010702 perfluoropolyether Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001263 acyl chlorides Chemical class 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000001265 acyl fluorides Chemical class 0.000 description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229910018287 SbF 5 Inorganic materials 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- -1 ether compound Chemical class 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910001504 inorganic chloride Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000012561 harvest cell culture fluid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C07C43/137—Saturated ethers containing hydroxy or O-metal groups containing halogen
-
- 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
- C07C43/126—Saturated ethers containing halogen having more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/125—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups
- C07C59/135—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/002—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds
- C08G65/005—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens
- C08G65/007—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from unsaturated compounds containing halogens containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
- C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/322—Polymers modified by chemical after-treatment with inorganic compounds containing hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyethers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT001731A ITMI20021731A1 (it) | 2002-08-01 | 2002-08-01 | Idrofluoroeteri aventi almeno un terminale idrogenato -ocfx'ch3 in cui x'=f, cf3 e loro processo di preparazione. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004067684A true JP2004067684A (ja) | 2004-03-04 |
| JP2004067684A5 JP2004067684A5 (enExample) | 2006-06-01 |
Family
ID=30130959
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003205416A Withdrawn JP2004067684A (ja) | 2002-08-01 | 2003-08-01 | ヒドロフルオロエーテル類とその製法 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7161030B2 (enExample) |
| EP (1) | EP1388554B1 (enExample) |
| JP (1) | JP2004067684A (enExample) |
| CA (1) | CA2435920A1 (enExample) |
| DE (1) | DE60316514T2 (enExample) |
| IT (1) | ITMI20021731A1 (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004359955A (ja) * | 2003-06-03 | 2004-12-24 | Solvay Solexis Spa | 撥油紙サイジング用（ペル）フルオロポリエーテルカルボン酸およびその使用 |
| JP2009528415A (ja) * | 2006-03-02 | 2009-08-06 | ソルヴェイ ソレクシス エス．ピー．エー． | 熱伝導流体 |
| JP2010523617A (ja) * | 2007-04-10 | 2010-07-15 | ソルヴェイ・ソレクシス・エッセ・ピ・ア | カルボニルパーフルオロポリエーテルを調製する方法 |
| JP2010540742A (ja) * | 2007-10-05 | 2010-12-24 | ソルヴェイ・ソレクシス・エッセ・ピ・ア | ポリオールペルフルオロポリエーテル誘導体を製造する方法 |
| JP2022019839A (ja) * | 2019-09-26 | 2022-01-27 | ダイキン工業株式会社 | フルオロポリエーテル基含有化合物 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20050188A1 (it) * | 2005-02-10 | 2006-08-11 | Solvay Solexis Spa | Composizioni acquose contenenti sali di-carbossilici perfluoropolieterei per il trattamento oleorepellente della carta |
| US20090176148A1 (en) * | 2008-01-04 | 2009-07-09 | 3M Innovative Properties Company | Thermal management of electrochemical cells |
| CN102675058A (zh) * | 2012-04-28 | 2012-09-19 | 太仓中化环保化工有限公司 | 端羟基全氟聚醚化合物的制备方法 |
| US10988425B2 (en) | 2019-02-18 | 2021-04-27 | Honeywell International Inc. | One step process for manufacturing trifluoroiodomethane from trifluoroacetyl halide, hydrogen, and iodine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3342875A (en) * | 1962-03-26 | 1967-09-19 | Du Pont | Hydrogen capped fluorocarbon polyethers |
| BE1007822A5 (fr) * | 1993-12-10 | 1995-10-31 | Solvay | Support pour un catalyseur d'hydrogenation, systeme catalytique comprenant ce support et procede d'hydrodechloration d'hydrocarbures chlorofluores. |
| US5658962A (en) * | 1994-05-20 | 1997-08-19 | Minnesota Mining And Manufacturing Company | Omega-hydrofluoroalkyl ethers, precursor carboxylic acids and derivatives thereof, and their preparation and application |
| US6046368A (en) * | 1998-03-17 | 2000-04-04 | 3M Innovative Properties Company | Catalytic process for making hydrofluoroethers |
| JP2001085058A (ja) * | 1999-09-20 | 2001-03-30 | Hitachi Ltd | 非水電解液及びこれを用いたリチウム１次電池及びリチウム２次電池及び電気化学キャパシタ及び高分子電解質及びこれを用いたポリマ２次電池 |
-
2002
- 2002-08-01 IT IT001731A patent/ITMI20021731A1/it unknown
-
2003
- 2003-07-24 CA CA002435920A patent/CA2435920A1/en not_active Abandoned
- 2003-07-29 EP EP03017181A patent/EP1388554B1/en not_active Expired - Lifetime
- 2003-07-29 DE DE60316514T patent/DE60316514T2/de not_active Expired - Fee Related
- 2003-07-31 US US10/630,697 patent/US7161030B2/en not_active Expired - Fee Related
- 2003-08-01 JP JP2003205416A patent/JP2004067684A/ja not_active Withdrawn
-
2006
- 2006-10-27 US US11/588,325 patent/US20070106092A1/en not_active Abandoned
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004359955A (ja) * | 2003-06-03 | 2004-12-24 | Solvay Solexis Spa | 撥油紙サイジング用（ペル）フルオロポリエーテルカルボン酸およびその使用 |
| JP2009528415A (ja) * | 2006-03-02 | 2009-08-06 | ソルヴェイ ソレクシス エス．ピー．エー． | 熱伝導流体 |
| JP2010523617A (ja) * | 2007-04-10 | 2010-07-15 | ソルヴェイ・ソレクシス・エッセ・ピ・ア | カルボニルパーフルオロポリエーテルを調製する方法 |
| JP2010540742A (ja) * | 2007-10-05 | 2010-12-24 | ソルヴェイ・ソレクシス・エッセ・ピ・ア | ポリオールペルフルオロポリエーテル誘導体を製造する方法 |
| JP2022019839A (ja) * | 2019-09-26 | 2022-01-27 | ダイキン工業株式会社 | フルオロポリエーテル基含有化合物 |
| CN114466881A (zh) * | 2019-09-26 | 2022-05-10 | 大金工业株式会社 | 含氟代聚醚基化合物 |
| JP7236001B2 (ja) | 2019-09-26 | 2023-03-09 | ダイキン工業株式会社 | フルオロポリエーテル基含有化合物 |
| US12281200B2 (en) | 2019-09-26 | 2025-04-22 | Daikin Industries, Ltd. | Fluoropolyether group-containing compound |
Also Published As
| Publication number | Publication date |
|---|---|
| US7161030B2 (en) | 2007-01-09 |
| EP1388554A3 (en) | 2004-03-31 |
| US20040024249A1 (en) | 2004-02-05 |
| EP1388554B1 (en) | 2007-09-26 |
| CA2435920A1 (en) | 2004-02-01 |
| ITMI20021731A1 (it) | 2004-02-02 |
| US20070106092A1 (en) | 2007-05-10 |
| EP1388554A2 (en) | 2004-02-11 |
| DE60316514D1 (de) | 2007-11-08 |
| DE60316514T2 (de) | 2008-07-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20060411 |
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| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20060411 |
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