JP6691220B2 - 過フッ素化ビニルエーテルの部分フッ素化飽和エーテル誘導体への変換 - Google Patents
過フッ素化ビニルエーテルの部分フッ素化飽和エーテル誘導体への変換 Download PDFInfo
- Publication number
- JP6691220B2 JP6691220B2 JP2018533250A JP2018533250A JP6691220B2 JP 6691220 B2 JP6691220 B2 JP 6691220B2 JP 2018533250 A JP2018533250 A JP 2018533250A JP 2018533250 A JP2018533250 A JP 2018533250A JP 6691220 B2 JP6691220 B2 JP 6691220B2
- Authority
- JP
- Japan
- Prior art keywords
- fluorinated
- ether
- ammonia
- vinyl ether
- partially fluorinated
- 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.)
- Expired - Fee Related
Links
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 title claims description 44
- 238000006243 chemical reaction Methods 0.000 title claims description 33
- 150000002170 ethers Chemical class 0.000 title claims description 32
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 86
- 238000000034 method Methods 0.000 claims description 83
- 229910021529 ammonia Inorganic materials 0.000 claims description 43
- 150000001412 amines Chemical class 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 28
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- -1 trifluoroethenyl Chemical group 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000001294 propane Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 80
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 150000001336 alkenes Chemical class 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 150000004985 diamines Chemical class 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000001033 ether group Chemical group 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- RJBJXVAPYONTFE-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F RJBJXVAPYONTFE-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 238000005915 ammonolysis reaction Methods 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/18—Preparation of carboxylic acid nitriles by reaction of ammonia or amines with compounds containing carbon-to-carbon multiple bonds other than in six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562387598P | 2015-12-24 | 2015-12-24 | |
| US62/387,598 | 2015-12-24 | ||
| PCT/US2016/067674 WO2017112629A1 (en) | 2015-12-24 | 2016-12-20 | Conversion of a perfluorinated vinyl ether into a partially fluorinated saturated ether derivative |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019500373A JP2019500373A (ja) | 2019-01-10 |
| JP2019500373A5 JP2019500373A5 (enExample) | 2019-03-28 |
| JP6691220B2 true JP6691220B2 (ja) | 2020-04-28 |
Family
ID=57910116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018533250A Expired - Fee Related JP6691220B2 (ja) | 2015-12-24 | 2016-12-20 | 過フッ素化ビニルエーテルの部分フッ素化飽和エーテル誘導体への変換 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US10723683B2 (enExample) |
| EP (1) | EP3394021B1 (enExample) |
| JP (1) | JP6691220B2 (enExample) |
| WO (1) | WO2017112629A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016148504A1 (ko) | 2015-03-17 | 2016-09-22 | 주식회사 베이글랩스 | 길이 측정 장치 및 길이 측정 시스템 |
| WO2017112445A2 (en) | 2015-12-24 | 2017-06-29 | 3M Innovative Properties Company | Methods for converting fluorinated compounds |
| CN111732500A (zh) * | 2020-05-29 | 2020-10-02 | 中船重工（邯郸）派瑞特种气体有限公司 | 一种氢氟醚的制备方法 |
| JP2023159878A (ja) * | 2022-04-20 | 2023-11-01 | ダイキン工業株式会社 | 精製された含フッ素エーテル化合物を含む組成物の製造方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3250808A (en) | 1963-10-31 | 1966-05-10 | Du Pont | Fluorocarbon ethers derived from hexafluoropropylene epoxide |
| DE3826807A1 (de) | 1988-08-06 | 1990-02-08 | Hoechst Ag | Verfahren zur herstellung von fluorierten carbonsaeurefluoriden |
| US5260492A (en) | 1992-12-21 | 1993-11-09 | E. I. Du Pont De Nemours And Company | Fluorinated monomers and polymers |
| 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 |
| GB0525978D0 (en) * | 2005-12-21 | 2006-02-01 | 3M Innovative Properties Co | Fluorinated Surfactants For Making Fluoropolymers |
| US7691282B2 (en) * | 2005-09-08 | 2010-04-06 | 3M Innovative Properties Company | Hydrofluoroether compounds and processes for their preparation and use |
| US8791254B2 (en) | 2006-05-19 | 2014-07-29 | 3M Innovative Properties Company | Cyclic hydrofluoroether compounds and processes for their preparation and use |
| JP2008230981A (ja) * | 2007-03-16 | 2008-10-02 | Daikin Ind Ltd | 高純度含フッ素アルキルエーテルの製造方法 |
| US8394989B2 (en) | 2007-09-27 | 2013-03-12 | 3M Innovative Properties Company | Fluorinated oxy-carboxylic acids, derivatives, and methods of preparation |
| GB0823120D0 (en) | 2008-12-19 | 2009-01-28 | 3M Innovative Properties Co | Method of making fluorinated alkoxy carboxylic acids and precursors thereof |
| GB0918616D0 (en) | 2009-10-23 | 2009-12-09 | 3M Innovative Properties Co | Method of preparing highly fluorinated carboxylic acids and their salts |
| GB0920718D0 (en) | 2009-11-26 | 2010-01-13 | 3M Innovative Properties Co | Method of preparing highly fluorinated carboxylic acids and their salts |
| WO2017112445A2 (en) | 2015-12-24 | 2017-06-29 | 3M Innovative Properties Company | Methods for converting fluorinated compounds |
-
2016
- 2016-12-20 US US16/065,502 patent/US10723683B2/en not_active Expired - Fee Related
- 2016-12-20 EP EP16831671.9A patent/EP3394021B1/en not_active Not-in-force
- 2016-12-20 JP JP2018533250A patent/JP6691220B2/ja not_active Expired - Fee Related
- 2016-12-20 WO PCT/US2016/067674 patent/WO2017112629A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP2019500373A (ja) | 2019-01-10 |
| US20180370888A1 (en) | 2018-12-27 |
| WO2017112629A1 (en) | 2017-06-29 |
| US10723683B2 (en) | 2020-07-28 |
| EP3394021B1 (en) | 2021-02-17 |
| EP3394021A1 (en) | 2018-10-31 |
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