JPS58159442A - 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 - Google Patents
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Info
- Publication number
- JPS58159442A JPS58159442A JP4085482A JP4085482A JPS58159442A JP S58159442 A JPS58159442 A JP S58159442A JP 4085482 A JP4085482 A JP 4085482A JP 4085482 A JP4085482 A JP 4085482A JP S58159442 A JPS58159442 A JP S58159442A
- 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.)
- Granted
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 74
- 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 title claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 82
- 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 73
- 238000006243 chemical reaction Methods 0.000 claims abstract description 50
- 238000011084 recovery Methods 0.000 claims abstract description 39
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000000746 purification Methods 0.000 claims abstract description 26
- 238000005886 esterification reaction Methods 0.000 claims abstract 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 abstract description 15
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 11
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 230000002378 acidificating effect Effects 0.000 claims abstract description 7
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 7
- 230000032050 esterification Effects 0.000 claims abstract description 6
- -1 acrylic ester Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 74
- 238000000034 method Methods 0.000 abstract description 15
- 239000002994 raw material Substances 0.000 abstract description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract description 5
- 208000012839 conversion disease Diseases 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 description 72
- 150000002148 esters Chemical class 0.000 description 50
- 238000004821 distillation Methods 0.000 description 35
- 238000005406 washing Methods 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- 239000007788 liquid Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- 230000018044 dehydration Effects 0.000 description 13
- 238000006297 dehydration reaction Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- 239000012295 chemical reaction liquid Substances 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002351 wastewater Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000003729 cation exchange resin Substances 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000005416 organic matter Substances 0.000 description 3
- 239000012074 organic phase 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000007086 side reaction 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
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000011259 mixed solution 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
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 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
- 235000014102 seafood Nutrition 0.000 description 1
- 238000000926 separation method 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
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 true JPS58159442A (ja) | 1983-09-21 |
| JPH0239496B2 JPH0239496B2 (enrdf_load_stackoverflow) | 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 (enrdf_load_stackoverflow) |
| DE (1) | DE3308879A1 (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61176555A (ja) * | 1985-01-30 | 1986-08-08 | Nippon Oil & Fats Co Ltd | 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 |
| JPH01139547A (ja) * | 1987-04-16 | 1989-06-01 | Nippon Shokubai Kagaku Kogyo Co Ltd | 高純度メタクリル酸エステルの製造方法 |
| JPH02279655A (ja) * | 1989-04-21 | 1990-11-15 | Nippon Shokubai Kagaku Kogyo Co Ltd | アクリル酸エステルの製造方法 |
| JPH02279654A (ja) * | 1989-04-21 | 1990-11-15 | Nippon Shokubai Kagaku Kogyo Co Ltd | メタクリル酸エステルの製造方法 |
| 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 |
| JP2002255896A (ja) * | 2000-12-26 | 2002-09-11 | Atofina | 不飽和カルボン酸エステルの改良された製造方法 |
| US7491841B2 (en) | 2006-07-11 | 2009-02-17 | Nippon Shokubai Co., Ltd. | Process for producing acrylic ester |
| 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 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1308737C (en) * | 1987-04-16 | 1992-10-13 | Syoichi Matsumoto | Process for producing methacrylic ester |
| DE19536178A1 (de) * | 1995-09-28 | 1997-04-03 | Basf Ag | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure |
| WO1998052903A1 (en) * | 1997-05-20 | 1998-11-26 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for conducting equilibrium-limited reactions |
| DE10062754A1 (de) * | 2000-12-15 | 2002-06-20 | Mg Technologies Ag | Verfahren zum Herstellen eines Esters der Acrylsäure oder Methacrylsäure |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS481369U (enrdf_load_stackoverflow) * | 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 (enrdf_load_stackoverflow) * | 1971-05-17 | 1973-01-09 |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61176555A (ja) * | 1985-01-30 | 1986-08-08 | Nippon Oil & Fats Co Ltd | 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 |
| JPH01139547A (ja) * | 1987-04-16 | 1989-06-01 | Nippon Shokubai Kagaku Kogyo Co Ltd | 高純度メタクリル酸エステルの製造方法 |
| JPH02279655A (ja) * | 1989-04-21 | 1990-11-15 | Nippon Shokubai Kagaku Kogyo Co Ltd | アクリル酸エステルの製造方法 |
| JPH02279654A (ja) * | 1989-04-21 | 1990-11-15 | Nippon Shokubai Kagaku Kogyo Co Ltd | メタクリル酸エステルの製造方法 |
| 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 |
| JP2002255896A (ja) * | 2000-12-26 | 2002-09-11 | Atofina | 不飽和カルボン酸エステルの改良された製造方法 |
| US7491841B2 (en) | 2006-07-11 | 2009-02-17 | Nippon Shokubai Co., Ltd. | Process for producing acrylic ester |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3308879A1 (de) | 1983-09-29 |
| JPH0239496B2 (enrdf_load_stackoverflow) | 1990-09-05 |
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