JPS6320415B2 - - Google Patents
Info
- Publication number
- JPS6320415B2 JPS6320415B2 JP17455781A JP17455781A JPS6320415B2 JP S6320415 B2 JPS6320415 B2 JP S6320415B2 JP 17455781 A JP17455781 A JP 17455781A JP 17455781 A JP17455781 A JP 17455781A JP S6320415 B2 JPS6320415 B2 JP S6320415B2
- Authority
- JP
- Japan
- Prior art keywords
- acrylic acid
- meth
- ester
- alcohol
- water
- 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
- 238000004821 distillation Methods 0.000 claims description 28
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 26
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 24
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 22
- 238000005886 esterification reaction Methods 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 20
- -1 acrylic ester Chemical class 0.000 claims description 17
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 12
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 11
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000002994 raw material Substances 0.000 claims description 7
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 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 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 claims description 2
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 44
- 235000019441 ethanol Nutrition 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 238000000926 separation method Methods 0.000 description 17
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 12
- 238000011084 recovery Methods 0.000 description 12
- 239000012071 phase Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000011550 stock solution Substances 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003729 cation exchange resin Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011973 solid acid 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- DXORWOXMIMWULJ-UHFFFAOYSA-N benzene-1,4-diol;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.OC1=CC=C(O)C=C1 DXORWOXMIMWULJ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 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
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17455781A JPS5877845A (ja) | 1981-11-02 | 1981-11-02 | アクリル酸エステルまたはメタクリル酸エステルの製造方法 |
| US06/393,484 US4464229A (en) | 1981-07-09 | 1982-06-29 | Process for producing acrylic or methacrylic esters |
| BR8203983A BR8203983A (pt) | 1981-07-09 | 1982-07-08 | Processo para produzir ester acrilico ou metacrilico |
| MX193511A MX163005B (es) | 1981-07-09 | 1982-07-08 | Procedimiento mejorado para producir un ester acrilico o metacrilico |
| FR8211987A FR2509294A1 (fr) | 1981-07-09 | 1982-07-08 | Procede de fabrication d'esters de l'acide acrylique ou methacrylique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17455781A JPS5877845A (ja) | 1981-11-02 | 1981-11-02 | アクリル酸エステルまたはメタクリル酸エステルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5877845A JPS5877845A (ja) | 1983-05-11 |
| JPS6320415B2 true JPS6320415B2 (zh) | 1988-04-27 |
Family
ID=15980634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17455781A Granted JPS5877845A (ja) | 1981-07-09 | 1981-11-02 | アクリル酸エステルまたはメタクリル酸エステルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5877845A (zh) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6357554A (ja) * | 1986-08-29 | 1988-03-12 | Mitsubishi Rayon Co Ltd | アクリル酸又はメタクリル酸のフエニルエステル類の製法 |
| JPH0764787B2 (ja) * | 1987-04-16 | 1995-07-12 | 株式会社日本触媒 | 高純度メタクリル酸エステルの製造方法 |
| ATE228109T1 (de) * | 1997-05-20 | 2002-12-15 | Union Carbide Chem Plastic | Verfahren zur raffination von butylacrylat |
| US6525206B1 (en) * | 2000-10-17 | 2003-02-25 | President And Fellows Of Harvard College | Compounds with high monoamine transporter affinity |
| TW201739730A (zh) * | 2015-12-18 | 2017-11-16 | 陶氏全球科技責任有限公司 | 用於純化甲基丙烯酸甲酯之方法 |
-
1981
- 1981-11-02 JP JP17455781A patent/JPS5877845A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5877845A (ja) | 1983-05-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4280010A (en) | Continuous production of alkyl acrylates free from ether | |
| US5811574A (en) | Continuous preparation of alkyl esters of (meth)acrylic acid and apparatus for this purpose | |
| US3776947A (en) | Continuous esterification process | |
| JP3934163B2 (ja) | アクリル酸ブチルの精製方法 | |
| US4012439A (en) | Continuous production of n-butylacrylate free from dibutylether | |
| JP6030564B2 (ja) | ブチルアクリレートの製造方法 | |
| CA1226550A (en) | Process for recovery of methacrylic acid | |
| US20150299093A1 (en) | Method for producing 2-octyl acrylate by direct esterification | |
| US5187309A (en) | Process for the continuous preparation of lower acrylates | |
| KR840001899B1 (ko) | 메틸 메타아크릴레이트의 정제방법 | |
| US4464229A (en) | Process for producing acrylic or methacrylic esters | |
| US9908838B2 (en) | Process for producing light (meth)acrylic esters | |
| JPS6357551A (ja) | Ｃ↓１−ｃ↓４脂肪族アルコ−ルのメタクリル酸エステルの連続製造方法 | |
| US8940925B2 (en) | Method for purifying the azeotropic fraction generated during the synthesis of N,N-dimethyl aminoethyl acrylate | |
| EP0916643B1 (en) | A process for preparing alkyl (meth)acrylates | |
| US5206421A (en) | Method for producing 4-hydroxybutyl (meth)acrylate | |
| JPS6320415B2 (zh) | ||
| US5637761A (en) | Process for the continuous preparation of esters of lower aliphatic carboxylic acids with lower alcohols | |
| JP2003521478A (ja) | 平衡律速反応を行う方法 | |
| US6172258B1 (en) | Process for the production and purification of n-butyl acrylate | |
| JPH0147454B2 (zh) | ||
| EP0060719B1 (en) | Process for the production of methyl acetate by esterifying methanol with acetic acid | |
| EP0455906A1 (en) | Recovery of acrylic acid and/or ethyl acrylate from black acid | |
| JP2022533439A (ja) | 高純度アルキルアクリレートを製造するための改良された方法 | |
| US4739108A (en) | Purification and esterification of methacrylic acid |