DE3308879A1 - Verfahren zur herstellung von acrylsaeure- oder methacrylsaeureestern - Google Patents
Verfahren zur herstellung von acrylsaeure- oder methacrylsaeureesternInfo
- Publication number
- DE3308879A1 DE3308879A1 DE19833308879 DE3308879A DE3308879A1 DE 3308879 A1 DE3308879 A1 DE 3308879A1 DE 19833308879 DE19833308879 DE 19833308879 DE 3308879 A DE3308879 A DE 3308879A DE 3308879 A1 DE3308879 A1 DE 3308879A1
- Authority
- DE
- Germany
- Prior art keywords
- reactor
- alcohol
- column
- acrylic
- acrylic 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.)
- Withdrawn
Links
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims abstract description 77
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims description 26
- 230000008569 process Effects 0.000 title claims description 15
- 125000005397 methacrylic acid ester group Chemical group 0.000 title abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 84
- 238000006243 chemical reaction Methods 0.000 claims abstract description 47
- 238000011084 recovery Methods 0.000 claims abstract description 41
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000005886 esterification reaction Methods 0.000 claims abstract description 20
- 238000000746 purification Methods 0.000 claims abstract description 20
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 230000002378 acidificating effect Effects 0.000 claims abstract description 8
- 230000032050 esterification Effects 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 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 11
- 239000003456 ion exchange resin Substances 0.000 claims description 11
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 5
- 238000004140 cleaning Methods 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 2
- 239000011347 resin Substances 0.000 abstract description 5
- 229920005989 resin Polymers 0.000 abstract description 5
- 235000019441 ethanol Nutrition 0.000 description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
- 238000004821 distillation Methods 0.000 description 31
- 239000000203 mixture Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 12
- 239000012295 chemical reaction liquid Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 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
- 238000009835 boiling Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000002351 wastewater Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000003112 inhibitor Substances 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000005406 washing 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
- 239000004793 Polystyrene Substances 0.000 description 1
- 235000017284 Pometia pinnata Nutrition 0.000 description 1
- 240000007653 Pometia tomentosa Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- -1 aliphatic alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SEGBQNJGOCXIGC-FHERZECASA-N benzyl n-[(2s)-1-[(4-hydroxyoxolan-3-yl)amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound N([C@@H](CC(C)C)C(=O)NC1C(COC1)O)C(=O)OCC1=CC=CC=C1 SEGBQNJGOCXIGC-FHERZECASA-N 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 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
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000009466 transformation Effects 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)
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 (1)
| Publication Number | Publication Date |
|---|---|
| DE3308879A1 true DE3308879A1 (de) | 1983-09-29 |
Family
ID=12592143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833308879 Withdrawn DE3308879A1 (de) | 1982-03-17 | 1983-03-12 | Verfahren zur herstellung von acrylsaeure- oder methacrylsaeureestern |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS58159442A (enrdf_load_stackoverflow) |
| DE (1) | DE3308879A1 (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0289178A1 (en) * | 1987-04-16 | 1988-11-02 | Nippon Shokubai Kagaku Kogyo Co., Ltd | Process for producing methacrylic ester |
| EP0765859A1 (de) * | 1995-09-28 | 1997-04-02 | Basf Aktiengesellschaft | 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 |
| EP1215194A3 (de) * | 2000-12-15 | 2004-01-07 | mg technologies ag | Verfahren zum Herstellen eines Esters der Acrylsäure oder Methacrylsäure |
Families Citing this family (8)
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
Family Cites Families (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
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0289178A1 (en) * | 1987-04-16 | 1988-11-02 | Nippon Shokubai Kagaku Kogyo Co., Ltd | Process for producing methacrylic ester |
| US4956493A (en) * | 1987-04-16 | 1990-09-11 | Nippon Shokubai Kagaku Kogyo Co., Ltd. | Process for producing methacrylic ester |
| EP0765859A1 (de) * | 1995-09-28 | 1997-04-02 | Basf Aktiengesellschaft | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure |
| US5811574A (en) * | 1995-09-28 | 1998-09-22 | Basf Aktiengesellschaft | Continuous preparation of alkyl esters of (meth)acrylic acid and apparatus for this purpose |
| US5900125A (en) * | 1995-09-28 | 1999-05-04 | Basf Aktiengesellschaft | Continuous preparation of alkyl esters of (meth)acrylic acid and apparatus for this purpose |
| CN1084324C (zh) * | 1995-09-28 | 2002-05-08 | 巴斯福股份公司 | (甲基)丙烯酸的烷基酯的连续制备方法和所使用的设备 |
| WO1998052903A1 (en) * | 1997-05-20 | 1998-11-26 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for conducting equilibrium-limited reactions |
| EP1215194A3 (de) * | 2000-12-15 | 2004-01-07 | mg technologies ag | Verfahren zum Herstellen eines Esters der Acrylsäure oder Methacrylsäure |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58159442A (ja) | 1983-09-21 |
| JPH0239496B2 (enrdf_load_stackoverflow) | 1990-09-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69405138T2 (de) | Verfahren zur Herstellung von Acryl- und Methacrylsäureestern | |
| DE3520019C2 (enrdf_load_stackoverflow) | ||
| DE69609955T2 (de) | Rückgewinnung von essigsäure aus einer während eines carbonylierungsverfahrens gewonnenen verdünnten wässrigen lösung | |
| DE69010046T2 (de) | Reinigungs- und Herstellungsverfahren von Methylmethacrylat. | |
| EP0017866B1 (de) | Verfahren zur Gewinnung von wasserfreier oder weitgehend wasserfreier Ameisensäure | |
| DE69500874T2 (de) | Verfahren zum Herstellen von Butylacrylat durch direkte Veresterung | |
| DE3308879A1 (de) | Verfahren zur herstellung von acrylsaeure- oder methacrylsaeureestern | |
| DE2325990C2 (de) | Verfahren zur kontinuierlichen Herstellung von Acrylsäuremethyl- oder Acrylsäureäthylester | |
| DD295627A5 (de) | Verfahren zur kontinuierlichen Herstellung von niedrigsiedenden Acrylaten | |
| DE69801633T2 (de) | Ester coproduktion | |
| DE2201246B2 (de) | Verfahren zur Abwasserreinigung und Chemikalien-Wiedergewinnung bei der Natriumhydrogensulfit-Herstellung | |
| DE3819830A1 (de) | Verfahren zur herstellung von 1,2,5,6,9,10-hexabromcyclododecan | |
| DE68904760T2 (de) | Regeneration von erschoepften schwefelsaeuren mittels wasserstoffperoxyd. | |
| DE2657189B2 (de) | Verfahren zur Reinigung von NaBverfahrensphosphorsäure | |
| DE60205422T2 (de) | Verfahren zur Herstellung von 2-Ethylhexylacrylat | |
| DE2539045C2 (de) | Verfahren zur Extraktion eines Dialkylbenzol-dihydroperoxids | |
| EP0398095B1 (de) | Verfahren zur Herstellung von Phosphorsäure-tris(2-chlor(iso)-propyl)estern | |
| DE2657190A1 (de) | Verfahren zur reinigung von nassverfahrensphosphorsaeure | |
| DE2745918B2 (de) | Verfahren zur Herstellung von Terephthalsäure | |
| EP0056489A1 (de) | Verfahren zur kontinuierlichen Herstellung von Adipinsäure | |
| DE2043689A1 (de) | Verfahren zum Entwässern von Essigsaure | |
| DE2729627C2 (de) | Verfahren zur Herstellung von farblosen, als Weichmacher verwendbaren Carbonsäureestern | |
| DE2428081B2 (de) | Kontinuierliches Verfahren zum Reinigen von Glyoxal | |
| DE2938163C2 (enrdf_load_stackoverflow) | ||
| DE2837694A1 (de) | Verfahren und extraktionsmittel zur herstellung von reiner phosphorsaeure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: TUERK, D., DIPL.-CHEM. DR.RER.NAT. GILLE, C., DIPL |
|
| 8141 | Disposal/no request for examination |