JPH0239496B2 - - Google Patents
Info
- Publication number
- JPH0239496B2 JPH0239496B2 JP57040854A JP4085482A JPH0239496B2 JP H0239496 B2 JPH0239496 B2 JP H0239496B2 JP 57040854 A JP57040854 A JP 57040854A JP 4085482 A JP4085482 A JP 4085482A JP H0239496 B2 JPH0239496 B2 JP H0239496B2
- Authority
- JP
- Japan
- Prior art keywords
- reactor
- alcohol
- acrylic acid
- ester
- 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 - Lifetime
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 80
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 73
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 71
- 238000006243 chemical reaction Methods 0.000 claims description 49
- 238000011084 recovery Methods 0.000 claims description 37
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 27
- 238000000746 purification Methods 0.000 claims description 22
- 238000005886 esterification reaction Methods 0.000 claims description 18
- 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 claims description 15
- 239000003456 ion exchange resin Substances 0.000 claims description 11
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 11
- 208000012839 conversion disease Diseases 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 6
- -1 acrylic ester Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 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
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims 1
- 235000019441 ethanol Nutrition 0.000 description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
- 150000002148 esters Chemical class 0.000 description 55
- 238000004821 distillation Methods 0.000 description 32
- 238000005406 washing Methods 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 14
- 230000018044 dehydration Effects 0.000 description 13
- 238000006297 dehydration reaction Methods 0.000 description 13
- 239000007788 liquid Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000012295 chemical reaction liquid Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002351 wastewater Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000003729 cation exchange resin Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- 239000005416 organic matter Substances 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 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
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000003679 aging effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000178 monomer Substances 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
- 229920001467 poly(styrenesulfonates) Polymers 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
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4085482A JPS58159442A (ja) | 1982-03-17 | 1982-03-17 | 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 |
| DE19833308879 DE3308879A1 (de) | 1982-03-17 | 1983-03-12 | Verfahren zur herstellung von acrylsaeure- oder methacrylsaeureestern |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4085482A JPS58159442A (ja) | 1982-03-17 | 1982-03-17 | 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 |
|---|---|
| JPS58159442A JPS58159442A (ja) | 1983-09-21 |
| JPH0239496B2 true JPH0239496B2 (fr) | 1990-09-05 |
Family
ID=12592143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4085482A Granted JPS58159442A (ja) | 1982-03-17 | 1982-03-17 | 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 (2)
| Country | Link |
|---|---|
| JP (1) | JPS58159442A (fr) |
| DE (1) | DE3308879A1 (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0680033B2 (ja) * | 1985-01-30 | 1994-10-12 | 日本油脂株式会社 | 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 |
| CA1308737C (fr) * | 1987-04-16 | 1992-10-13 | Syoichi Matsumoto | Procede d'obtention d'ester methacrylique |
| JPH0686406B2 (ja) * | 1989-04-21 | 1994-11-02 | 株式会社日本触媒 | アクリル酸エステルの製造方法 |
| JPH0686405B2 (ja) * | 1989-04-21 | 1994-11-02 | 株式会社日本触媒 | メタクリル酸エステルの製造方法 |
| DE19536178A1 (de) * | 1995-09-28 | 1997-04-03 | Basf Ag | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure |
| JPH09316034A (ja) * | 1996-05-29 | 1997-12-09 | Toagosei Co Ltd | （メタ）アクリル酸低級アルキルエステルの製造における低級アルキルアルコールの回収方法及びそのエステルの製造方法 |
| WO1998052903A1 (fr) * | 1997-05-20 | 1998-11-26 | Union Carbide Chemicals & Plastics Technology Corporation | Procedes pour realiser des reactions limitees a l'etat d'equilibre |
| DE10062754A1 (de) * | 2000-12-15 | 2002-06-20 | Mg Technologies Ag | Verfahren zum Herstellen eines Esters der Acrylsäure oder Methacrylsäure |
| FR2818639B1 (fr) * | 2000-12-26 | 2003-02-07 | Atofina | Procede perfectionne de fabrication d'esters carboxyliques insatures |
| JP4160087B2 (ja) | 2006-07-11 | 2008-10-01 | 株式会社日本触媒 | アクリル酸エステルの製造方法 |
| JP2015157800A (ja) * | 2014-01-22 | 2015-09-03 | 三洋化成工業株式会社 | 固体酸触媒反応装置及びエステルの製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS481369U (fr) * | 1971-05-17 | 1973-01-09 |
-
1982
- 1982-03-17 JP JP4085482A patent/JPS58159442A/ja active Granted
-
1983
- 1983-03-12 DE DE19833308879 patent/DE3308879A1/de not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS481369U (fr) * | 1971-05-17 | 1973-01-09 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3308879A1 (de) | 1983-09-29 |
| JPS58159442A (ja) | 1983-09-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4634784A (en) | Process for production of epichlorohydrin | |
| US5362918A (en) | Process for producing acetaldehyde dimethylacetal | |
| US4250328A (en) | Method for separation of an ester from a reaction mixture | |
| US4012439A (en) | Continuous production of n-butylacrylate free from dibutylether | |
| JPH0239496B2 (fr) | ||
| US8772534B2 (en) | Method of recovering (meth) acrylic acid ester | |
| US5187309A (en) | Process for the continuous preparation of lower acrylates | |
| US6392088B1 (en) | Process for the production of dimethylesters of unsaturated dicarboxylic anhydrides | |
| JP4048076B2 (ja) | ミカエル型付加物の分解方法 | |
| US4775447A (en) | Process for the production of 2,2-dimethoxypropane | |
| KR20100112534A (ko) | 카르복실산에스테르의 제조 방법 | |
| US3821286A (en) | Process for the production of methyl methacrylate | |
| JPS58183641A (ja) | （メタ）アクリル酸メチルの精製法 | |
| US20230416184A1 (en) | Optimized process for synthesizing alkyl methacrylate by reducing unwanted byproducts | |
| JPH10279523A (ja) | （メタ）アクリル酸エステルの製造方法 | |
| JPS61238745A (ja) | アリルアルコ−ルの製造法 | |
| US4968834A (en) | Recovery of acrylic acid and/or ethyl acrylate from black acid | |
| US5440004A (en) | Method and apparatus for the production of alkylene carbonate | |
| JPS6320415B2 (fr) | ||
| JPS6216937B2 (fr) | ||
| JPS58192851A (ja) | アクリル酸またはメタクリル酸と高級アルコ−ルとのエステル類の製法 | |
| JP3174406B2 (ja) | エチルアルコールの製造方法 | |
| US3957730A (en) | Recovery of pure 2-methyl-2-hydroxy-heptanone-6 | |
| NL7906650A (nl) | Werkwijze voor de bereiding van een diol. | |
| US4251460A (en) | Process for production of dimethylformamide |