TWI328577B - - Google Patents
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- Publication number
- TWI328577B TWI328577B TW093116187A TW93116187A TWI328577B TW I328577 B TWI328577 B TW I328577B TW 093116187 A TW093116187 A TW 093116187A TW 93116187 A TW93116187 A TW 93116187A TW I328577 B TWI328577 B TW I328577B
- Authority
- TW
- Taiwan
- Prior art keywords
- fluorine
- containing alkyl
- reactor
- producing
- alkyl ether
- Prior art date
Links
- 150000001336 alkenes Chemical class 0.000 claims abstract description 14
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 13
- -1 fluoroalkyl ether Chemical compound 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 42
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 38
- 239000011737 fluorine Substances 0.000 claims description 38
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 19
- 150000005215 alkyl ethers Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 6
- CWIFAKBLLXGZIC-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-1-(2,2,2-trifluoroethoxy)ethane Chemical compound FC(F)C(F)(F)OCC(F)(F)F CWIFAKBLLXGZIC-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- PSQZJKGXDGNDFP-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)(F)F PSQZJKGXDGNDFP-UHFFFAOYSA-N 0.000 description 1
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- 101100348341 Caenorhabditis elegans gas-1 gene Proteins 0.000 description 1
- 229910021055 KNH2 Inorganic materials 0.000 description 1
- 101100447658 Mus musculus Gas1 gene Proteins 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 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
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003159342 | 2003-06-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200505840A TW200505840A (en) | 2005-02-16 |
| TWI328577B true TWI328577B (https=) | 2010-08-11 |
Family
ID=33508510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093116187A TW200505840A (en) | 2003-06-04 | 2004-06-04 | Method for producing fluorine-containing alkyl ether |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7193118B2 (https=) |
| EP (1) | EP1630151B1 (https=) |
| JP (1) | JP4635871B2 (https=) |
| KR (1) | KR101080670B1 (https=) |
| CN (1) | CN100528822C (https=) |
| AT (1) | ATE473956T1 (https=) |
| DE (1) | DE602004028119D1 (https=) |
| ES (1) | ES2348721T3 (https=) |
| TW (1) | TW200505840A (https=) |
| WO (1) | WO2004108644A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1882680A4 (en) * | 2005-05-17 | 2008-06-25 | Asahi Glass Co Ltd | PROCESS FOR PROCESSING A FLUORINATED ALKYL ETHER |
| EP2444385B1 (en) * | 2009-06-15 | 2014-12-10 | Daikin Industries, Ltd. | Method for producing fluorine-containing ether with high purity |
| CN103992213B (zh) * | 2014-05-24 | 2015-07-08 | 山东中氟化工科技有限公司 | 一种制备 1,1,2,2-四氟乙基-2,2,3,3-四氟丙基醚的方法 |
| CN104045524B (zh) * | 2014-07-10 | 2015-05-13 | 山东中氟化工科技有限公司 | 一种清洁生产氢氟醚的方法 |
| EP3415597A4 (en) | 2016-02-09 | 2019-10-30 | Agc Inc. | SOLVENT COMPOSITION, CLEANING METHOD, COATING FILM-FORMING COMPOSITION, AND COATING FILM-FORMING METHOD |
| US10717690B2 (en) * | 2017-06-22 | 2020-07-21 | Zeon Corporation | Method of manufacturing octafluorocyclopentene |
| CN117700306A (zh) * | 2023-12-12 | 2024-03-15 | 珠海市赛纬电子材料股份有限公司 | 氢氟醚的生产方法 |
| WO2025173746A1 (ja) * | 2024-02-15 | 2025-08-21 | Ａｇｃ株式会社 | フルオロポリマーの製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2973389A (en) * | 1957-07-24 | 1961-02-28 | Hoechst Ag | Fluorinated organic ethers |
| US3557294A (en) * | 1967-10-12 | 1971-01-19 | Allied Chem | Fluorinated ethers as inhalation convulsants |
| US3764706A (en) * | 1971-08-11 | 1973-10-09 | Airco Inc | Inhalation anesthetic |
| JP2563960B2 (ja) * | 1988-03-05 | 1996-12-18 | 株式会社トクヤマ | 含フッ素エーテル化合物及びその製造方法 |
| EP0344935A3 (en) * | 1988-05-19 | 1991-04-17 | E.I. Du Pont De Nemours And Company | Photo-assisted solution phase direct fluorination process improvement |
| JP3834096B2 (ja) * | 1996-03-29 | 2006-10-18 | 株式会社トクヤマ | 含フッ素アルキルエーテルの製造方法 |
| JP3482488B2 (ja) * | 2000-12-28 | 2003-12-22 | 独立行政法人産業技術総合研究所 | 含フッ素エーテル化合物の製造方法 |
-
2004
- 2004-06-03 DE DE602004028119T patent/DE602004028119D1/de not_active Expired - Lifetime
- 2004-06-03 WO PCT/JP2004/008075 patent/WO2004108644A1/ja not_active Ceased
- 2004-06-03 KR KR1020057019846A patent/KR101080670B1/ko not_active Expired - Fee Related
- 2004-06-03 CN CNB2004800152102A patent/CN100528822C/zh not_active Expired - Lifetime
- 2004-06-03 AT AT04735982T patent/ATE473956T1/de not_active IP Right Cessation
- 2004-06-03 JP JP2005506832A patent/JP4635871B2/ja not_active Expired - Fee Related
- 2004-06-03 ES ES04735982T patent/ES2348721T3/es not_active Expired - Lifetime
- 2004-06-03 EP EP04735982A patent/EP1630151B1/en not_active Expired - Lifetime
- 2004-06-04 TW TW093116187A patent/TW200505840A/zh not_active IP Right Cessation
-
2005
- 2005-12-05 US US11/293,200 patent/US7193118B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004108644A1 (ja) | 2004-12-16 |
| DE602004028119D1 (de) | 2010-08-26 |
| EP1630151B1 (en) | 2010-07-14 |
| US7193118B2 (en) | 2007-03-20 |
| TW200505840A (en) | 2005-02-16 |
| CN1798722A (zh) | 2006-07-05 |
| JPWO2004108644A1 (ja) | 2006-07-20 |
| CN100528822C (zh) | 2009-08-19 |
| ATE473956T1 (de) | 2010-07-15 |
| US20060094908A1 (en) | 2006-05-04 |
| EP1630151A4 (en) | 2006-10-11 |
| KR20060021295A (ko) | 2006-03-07 |
| JP4635871B2 (ja) | 2011-02-23 |
| ES2348721T3 (es) | 2010-12-13 |
| EP1630151A1 (en) | 2006-03-01 |
| KR101080670B1 (ko) | 2011-11-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |