JPS59181239A - 含フツ素アクリル酸エステル又はメタクリル酸エステルの製造方法 - Google Patents
含フツ素アクリル酸エステル又はメタクリル酸エステルの製造方法Info
- Publication number
- JPS59181239A JPS59181239A JP5451183A JP5451183A JPS59181239A JP S59181239 A JPS59181239 A JP S59181239A JP 5451183 A JP5451183 A JP 5451183A JP 5451183 A JP5451183 A JP 5451183A JP S59181239 A JPS59181239 A JP S59181239A
- Authority
- JP
- Japan
- Prior art keywords
- fluorine
- alcohol
- ester
- sulfuric acid
- reaction
- 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.)
- Granted
Links
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 24
- 239000011737 fluorine Substances 0.000 title claims description 24
- 229910052731 fluorine Inorganic materials 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 title 1
- -1 acrylic ester Chemical class 0.000 title 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000005416 organic matter Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- VLHYAWNCTMZTSC-UHFFFAOYSA-N 1,1,3,3,3-pentafluoropropan-1-ol Chemical compound OC(F)(F)CC(F)(F)F VLHYAWNCTMZTSC-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- TXOZSRCVHASUCW-UHFFFAOYSA-N 1,3,3,3-tetrafluoropropan-1-ol Chemical compound OC(F)CC(F)(F)F TXOZSRCVHASUCW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000013040 bath agent Substances 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000013308 plastic optical fiber Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5451183A JPS59181239A (ja) | 1983-03-30 | 1983-03-30 | 含フツ素アクリル酸エステル又はメタクリル酸エステルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5451183A JPS59181239A (ja) | 1983-03-30 | 1983-03-30 | 含フツ素アクリル酸エステル又はメタクリル酸エステルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59181239A true JPS59181239A (ja) | 1984-10-15 |
| JPH0470300B2 JPH0470300B2 (enrdf_load_stackoverflow) | 1992-11-10 |
Family
ID=12972663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5451183A Granted JPS59181239A (ja) | 1983-03-30 | 1983-03-30 | 含フツ素アクリル酸エステル又はメタクリル酸エステルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59181239A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63196544A (ja) * | 1987-02-10 | 1988-08-15 | Osaka Yuki Kagaku Kogyo Kk | フツ素化アルキル（メタ）アクリレ−ト類の製造方法 |
| WO2001004081A1 (fr) * | 1999-07-09 | 2001-01-18 | Daikin Industries, Ltd. | Methode de preparation d'un polyfluoroalkyl ester et methode de production d'un copolymere acrylique fluore au moyen de l'ester ainsi obtenu |
| WO2005102983A1 (ja) * | 2004-04-26 | 2005-11-03 | Daikin Industries, Ltd. | 含フッ素アクリル酸エステルの製造方法 |
| US7135592B2 (en) * | 2004-07-30 | 2006-11-14 | Unimatec Co., Ltd. | Process for producing polyfluoroalkyl ester of unsaturated carboxylic acid |
| US7700800B2 (en) | 2005-03-15 | 2010-04-20 | Tokuyama Corporation | Method for producing fluorine-containing alkyl (meth)acrylate |
| CN105732384A (zh) * | 2014-12-11 | 2016-07-06 | 浙江蓝天环保高科技股份有限公司 | 一种含氟醇的甲基丙烯酸酯的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57118535A (en) * | 1981-01-16 | 1982-07-23 | Toray Ind Inc | Preparation of fluoroalkyl alpha-chloroacrylate |
| JPS588042A (ja) * | 1981-07-09 | 1983-01-18 | Nippon Shokubai Kagaku Kogyo Co Ltd | アクリル酸メチルの蒸留方法 |
| JPS5848446A (ja) * | 1981-09-18 | 1983-03-22 | Fujitsu Ltd | 薄膜抵抗回路体の製造方法 |
-
1983
- 1983-03-30 JP JP5451183A patent/JPS59181239A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57118535A (en) * | 1981-01-16 | 1982-07-23 | Toray Ind Inc | Preparation of fluoroalkyl alpha-chloroacrylate |
| JPS588042A (ja) * | 1981-07-09 | 1983-01-18 | Nippon Shokubai Kagaku Kogyo Co Ltd | アクリル酸メチルの蒸留方法 |
| JPS5848446A (ja) * | 1981-09-18 | 1983-03-22 | Fujitsu Ltd | 薄膜抵抗回路体の製造方法 |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63196544A (ja) * | 1987-02-10 | 1988-08-15 | Osaka Yuki Kagaku Kogyo Kk | フツ素化アルキル（メタ）アクリレ−ト類の製造方法 |
| WO2001004081A1 (fr) * | 1999-07-09 | 2001-01-18 | Daikin Industries, Ltd. | Methode de preparation d'un polyfluoroalkyl ester et methode de production d'un copolymere acrylique fluore au moyen de l'ester ainsi obtenu |
| JP2001019663A (ja) * | 1999-07-09 | 2001-01-23 | Daikin Ind Ltd | ポリフルオロアルキルエステル類の製造方法およびこのエステルを用いる含フッ素アクリル共重合体の製造方法 |
| US6660803B1 (en) | 1999-07-09 | 2003-12-09 | Daikin Industries, Ltd. | Method of preparing (perfluoroalkyl) ethyl acrylic esters and methods of preparing copolymers using said esters |
| WO2005102983A1 (ja) * | 2004-04-26 | 2005-11-03 | Daikin Industries, Ltd. | 含フッ素アクリル酸エステルの製造方法 |
| JPWO2005102983A1 (ja) * | 2004-04-26 | 2008-03-13 | ダイキン工業株式会社 | 含フッ素アクリル酸エステルの製造方法 |
| US7135592B2 (en) * | 2004-07-30 | 2006-11-14 | Unimatec Co., Ltd. | Process for producing polyfluoroalkyl ester of unsaturated carboxylic acid |
| US7700800B2 (en) | 2005-03-15 | 2010-04-20 | Tokuyama Corporation | Method for producing fluorine-containing alkyl (meth)acrylate |
| CN105732384A (zh) * | 2014-12-11 | 2016-07-06 | 浙江蓝天环保高科技股份有限公司 | 一种含氟醇的甲基丙烯酸酯的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0470300B2 (enrdf_load_stackoverflow) | 1992-11-10 |
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