JPS58140043A - 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 - Google Patents
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Info
- Publication number
- JPS58140043A JPS58140043A JP1817282A JP1817282A JPS58140043A JP S58140043 A JPS58140043 A JP S58140043A JP 1817282 A JP1817282 A JP 1817282A JP 1817282 A JP1817282 A JP 1817282A JP S58140043 A JPS58140043 A JP S58140043A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyalkyl
- reaction
- distillation
- methacrylate
- acrylate
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000005886 esterification reaction Methods 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 3
- 238000004821 distillation Methods 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- -1 alkyl methacrylate Chemical compound 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000002505 iron Chemical class 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 6
- 150000003839 salts Chemical class 0.000 abstract description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 239000012043 crude product Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 150000002506 iron compounds Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000032683 aging Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 235000014413 iron hydroxide Nutrition 0.000 description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical class [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 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
- 239000005711 Benzoic acid Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 208000031361 Hiccup Diseases 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 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
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- ZWZHJDRBENYHMK-UHFFFAOYSA-L iron(2+);2-methylprop-2-enoate Chemical compound [Fe+2].CC(=C)C([O-])=O.CC(=C)C([O-])=O ZWZHJDRBENYHMK-UHFFFAOYSA-L 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 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 class 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000126 substance Substances 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 true JPS58140043A (ja) | 1983-08-19 |
| JPS6241662B2 JPS6241662B2 (enrdf_load_stackoverflow) | 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 (enrdf_load_stackoverflow) |
Cited By (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 |
| JP2007521303A (ja) * | 2003-06-30 | 2007-08-02 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド | ビス（トリメチルシリルオキシ）シリルアルキルグリセロールメタクリレートの製造法 |
| JP2007521300A (ja) * | 2003-06-30 | 2007-08-02 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド | ビス（トリメチルシリルオキシ）シリルアルキルグリセロールメタクリレートの製造方法 |
| CN102584581A (zh) * | 2012-01-16 | 2012-07-18 | 常州海克莱化学有限公司 | 一种丙烯酸羟丙酯的制备工艺 |
| CN102584580A (zh) * | 2012-01-16 | 2012-07-18 | 常州海克莱化学有限公司 | 一种甲基丙烯酸羟丙酯的制备工艺 |
| CN102584579A (zh) * | 2012-01-16 | 2012-07-18 | 常州海克莱化学有限公司 | 一种甲基丙烯酸羟乙酯的制备工艺 |
| CN102584582A (zh) * | 2012-01-16 | 2012-07-18 | 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 |
-
1982
- 1982-02-09 JP JP1817282A patent/JPS58140043A/ja active Granted
Cited By (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 |
| JP2007521303A (ja) * | 2003-06-30 | 2007-08-02 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド | ビス（トリメチルシリルオキシ）シリルアルキルグリセロールメタクリレートの製造法 |
| JP2007521300A (ja) * | 2003-06-30 | 2007-08-02 | ジョンソン・アンド・ジョンソン・ビジョン・ケア・インコーポレイテッド | ビス（トリメチルシリルオキシ）シリルアルキルグリセロールメタクリレートの製造方法 |
| CN102584581A (zh) * | 2012-01-16 | 2012-07-18 | 常州海克莱化学有限公司 | 一种丙烯酸羟丙酯的制备工艺 |
| CN102584580A (zh) * | 2012-01-16 | 2012-07-18 | 常州海克莱化学有限公司 | 一种甲基丙烯酸羟丙酯的制备工艺 |
| CN102584579A (zh) * | 2012-01-16 | 2012-07-18 | 常州海克莱化学有限公司 | 一种甲基丙烯酸羟乙酯的制备工艺 |
| CN102584582A (zh) * | 2012-01-16 | 2012-07-18 | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6241662B2 (enrdf_load_stackoverflow) | 1987-09-03 |
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