JPS6241662B2 - - Google Patents
Info
- Publication number
- JPS6241662B2 JPS6241662B2 JP1817282A JP1817282A JPS6241662B2 JP S6241662 B2 JPS6241662 B2 JP S6241662B2 JP 1817282 A JP1817282 A JP 1817282A JP 1817282 A JP1817282 A JP 1817282A JP S6241662 B2 JPS6241662 B2 JP S6241662B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyalkyl
- acrylate
- reaction
- ferric
- distillation
- 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
Links
- 238000004821 distillation Methods 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 238000005886 esterification reaction Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- -1 carboxylic acid iron salt Chemical class 0.000 description 7
- 238000000746 purification Methods 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 150000002506 iron compounds Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000005070 ripening Effects 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 235000014413 iron hydroxide Nutrition 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical group [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 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
- 238000001556 precipitation Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241000482268 Zea mays subsp. mays Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- IXPUJMULXNNEHS-UHFFFAOYSA-L copper;n,n-dibutylcarbamodithioate Chemical compound [Cu+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC IXPUJMULXNNEHS-UHFFFAOYSA-L 0.000 description 1
- ZOUQIAGHKFLHIA-UHFFFAOYSA-L copper;n,n-dimethylcarbamodithioate Chemical compound [Cu+2].CN(C)C([S-])=S.CN(C)C([S-])=S ZOUQIAGHKFLHIA-UHFFFAOYSA-L 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical group 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1817282A JPS58140043A (ja) | 1982-02-09 | 1982-02-09 | ２−ヒドロキシアルキルアクリレ−トまたは２−ヒドロキシアルキルメタクリレ−トの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1817282A JPS58140043A (ja) | 1982-02-09 | 1982-02-09 | ２−ヒドロキシアルキルアクリレ−トまたは２−ヒドロキシアルキルメタクリレ−トの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58140043A JPS58140043A (ja) | 1983-08-19 |
| JPS6241662B2 true JPS6241662B2 (de) | 1987-09-03 |
Family
ID=11964188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1817282A Granted JPS58140043A (ja) | 1982-02-09 | 1982-02-09 | ２−ヒドロキシアルキルアクリレ−トまたは２−ヒドロキシアルキルメタクリレ−トの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58140043A (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002088022A (ja) * | 2000-09-08 | 2002-03-27 | Nippon Shokubai Co Ltd | ヒドロキシアルキル（メタ）アクリレートの製造方法 |
| JP2002275126A (ja) * | 2001-01-10 | 2002-09-25 | Nippon Shokubai Co Ltd | ヒドロキシアルキル（メタ）アクリレートの製造方法 |
| US8373000B2 (en) * | 2003-06-30 | 2013-02-12 | Johnson & Johnson Vision Care, Inc. | Process for the production of bis(trimethylsilyloxy)silylalkylglycerol methacrylates |
| US6891055B2 (en) * | 2003-06-30 | 2005-05-10 | Diana Zanini | Process for the production of bis(trimethylsilyloxy)silylalkylglycerol methacrylates |
| CN102584582B (zh) * | 2012-01-16 | 2013-12-25 | 常州海克莱化学有限公司 | 一种丙烯酸羟基乙酯的制备工艺 |
| CN102584579B (zh) * | 2012-01-16 | 2013-12-25 | 常州海克莱化学有限公司 | 一种甲基丙烯酸羟基乙酯的制备工艺 |
| CN102584580B (zh) * | 2012-01-16 | 2014-03-05 | 常州海克莱化学有限公司 | 一种甲基丙烯酸羟基丙酯的制备工艺 |
| CN102584581B (zh) * | 2012-01-16 | 2014-03-05 | 常州海克莱化学有限公司 | 一种丙烯酸羟基丙酯的制备工艺 |
-
1982
- 1982-02-09 JP JP1817282A patent/JPS58140043A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58140043A (ja) | 1983-08-19 |
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