JPS60215650A - グリセロ−ルアクリレ−トまたはメタクリレ−トの製造法 - Google Patents
グリセロ−ルアクリレ−トまたはメタクリレ−トの製造法Info
- Publication number
- JPS60215650A JPS60215650A JP7008984A JP7008984A JPS60215650A JP S60215650 A JPS60215650 A JP S60215650A JP 7008984 A JP7008984 A JP 7008984A JP 7008984 A JP7008984 A JP 7008984A JP S60215650 A JPS60215650 A JP S60215650A
- Authority
- JP
- Japan
- Prior art keywords
- methacrylate
- reaction
- acrylate
- mol
- acid
- 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
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 title claims abstract description 22
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 title claims description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 239000002253 acid Substances 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000243 solution Substances 0.000 claims abstract description 8
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 6
- 239000003377 acid catalyst Substances 0.000 claims abstract description 6
- 239000003112 inhibitor Substances 0.000 claims abstract description 6
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims abstract description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 235000011187 glycerol Nutrition 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract description 14
- 230000018044 dehydration Effects 0.000 abstract description 14
- 238000006297 dehydration reaction Methods 0.000 abstract description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 12
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 abstract description 6
- 150000003839 salts Chemical class 0.000 abstract description 5
- 239000007864 aqueous solution Substances 0.000 abstract description 4
- 239000000178 monomer Substances 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000011347 resin Substances 0.000 abstract description 3
- 229920005989 resin Polymers 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract description 2
- 125000003700 epoxy group Chemical group 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 239000010409 thin film Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 description 10
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- MIHQWNKDHBLQEZ-UHFFFAOYSA-N 3-tert-butyl-2-methylphenol Chemical compound CC1=C(O)C=CC=C1C(C)(C)C MIHQWNKDHBLQEZ-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7008984A JPS60215650A (ja) | 1984-04-10 | 1984-04-10 | グリセロ−ルアクリレ−トまたはメタクリレ−トの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7008984A JPS60215650A (ja) | 1984-04-10 | 1984-04-10 | グリセロ−ルアクリレ−トまたはメタクリレ−トの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60215650A true JPS60215650A (ja) | 1985-10-29 |
| JPH0410465B2 JPH0410465B2 (enrdf_load_stackoverflow) | 1992-02-25 |
Family
ID=13421462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7008984A Granted JPS60215650A (ja) | 1984-04-10 | 1984-04-10 | グリセロ−ルアクリレ−トまたはメタクリレ−トの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60215650A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4730081A (en) * | 1986-01-14 | 1988-03-08 | Halliburton Company | Vicinal diol containing monomers and methods of preparing |
| US5283360A (en) * | 1990-07-06 | 1994-02-01 | Atochem | Selective epoxidation of unsaturated (meth)acrylates, new functional (meth)acrylates, and polymers thereof |
| KR970042452A (ko) * | 1995-12-29 | 1997-07-24 | 황선두 | 2-히드록시알킬메타크릴레이트의 정제 회수방법 |
| CN101205184B (zh) | 2006-12-21 | 2010-09-22 | 江苏雷蒙化工科技有限公司 | 一种三醋酸甘油酯提纯方法 |
-
1984
- 1984-04-10 JP JP7008984A patent/JPS60215650A/ja active Granted
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4730081A (en) * | 1986-01-14 | 1988-03-08 | Halliburton Company | Vicinal diol containing monomers and methods of preparing |
| US5283360A (en) * | 1990-07-06 | 1994-02-01 | Atochem | Selective epoxidation of unsaturated (meth)acrylates, new functional (meth)acrylates, and polymers thereof |
| US5510516A (en) * | 1990-07-06 | 1996-04-23 | Atochem | Process for selective epoxidation of unsaturated (meth)acrylates, new functional (meth)acrylates obtained and their application to the synthesis of new polymers |
| EP0720978A1 (fr) * | 1990-07-06 | 1996-07-10 | Elf Atochem S.A. | Procédé d'ouverture de la fonction époxyde d'époxydes (méth)acryliques |
| KR970042452A (ko) * | 1995-12-29 | 1997-07-24 | 황선두 | 2-히드록시알킬메타크릴레이트의 정제 회수방법 |
| CN101205184B (zh) | 2006-12-21 | 2010-09-22 | 江苏雷蒙化工科技有限公司 | 一种三醋酸甘油酯提纯方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0410465B2 (enrdf_load_stackoverflow) | 1992-02-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |