DE2323328C2 - Verfahren zur Abtrennung von Acrylsäure aus einer angesäuerten wäßrigen Butanol-Acrylsäure-Veresterungsablauge - Google Patents
Verfahren zur Abtrennung von Acrylsäure aus einer angesäuerten wäßrigen Butanol-Acrylsäure-VeresterungsablaugeInfo
- Publication number
- DE2323328C2 DE2323328C2 DE2323328A DE2323328A DE2323328C2 DE 2323328 C2 DE2323328 C2 DE 2323328C2 DE 2323328 A DE2323328 A DE 2323328A DE 2323328 A DE2323328 A DE 2323328A DE 2323328 C2 DE2323328 C2 DE 2323328C2
- Authority
- DE
- Germany
- Prior art keywords
- acrylic acid
- butanol
- butyl acrylate
- extraction
- waste liquor
- 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 title claims description 42
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims description 42
- 238000005886 esterification reaction Methods 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 14
- 230000032050 esterification Effects 0.000 title claims description 12
- 239000002699 waste material Substances 0.000 title claims description 12
- PRWNDQXXTXXMMW-UHFFFAOYSA-N butan-1-ol;prop-2-enoic acid Chemical compound CCCCO.OC(=O)C=C PRWNDQXXTXXMMW-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000926 separation method Methods 0.000 title claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 30
- 238000000605 extraction Methods 0.000 claims description 21
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 239000003791 organic solvent mixture Substances 0.000 claims description 2
- BWSJQWFZVLKZMC-UHFFFAOYSA-N butan-1-ol;butyl prop-2-enoate Chemical compound CCCCO.CCCCOC(=O)C=C BWSJQWFZVLKZMC-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 238000006243 chemical reaction Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture 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
- INUKYRAZZYGZEC-UHFFFAOYSA-N C(C=C)(=O)OCCCC.C(CCC)O.C(C=C)(=O)O Chemical compound C(C=C)(=O)OCCCC.C(CCC)O.C(C=C)(=O)O INUKYRAZZYGZEC-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
- Physical Water Treatments (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2323328A DE2323328C2 (de) | 1973-05-09 | 1973-05-09 | Verfahren zur Abtrennung von Acrylsäure aus einer angesäuerten wäßrigen Butanol-Acrylsäure-Veresterungsablauge |
| US05/467,255 US3962074A (en) | 1973-05-09 | 1974-05-06 | Process for separating acrylic acid from aqueous solutions |
| FR7415768A FR2228761B1 (enExample) | 1973-05-09 | 1974-05-07 | |
| GB2032374A GB1458705A (en) | 1973-05-09 | 1974-05-08 | Process for separating acrylic acid from aqueous solutions |
| BE144100A BE814762A (fr) | 1973-05-09 | 1974-05-09 | Procede de separation de l'acide acrylique de ses solutions aqueuses |
| JP49050801A JPS5018412A (enExample) | 1973-05-09 | 1974-05-09 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2323328A DE2323328C2 (de) | 1973-05-09 | 1973-05-09 | Verfahren zur Abtrennung von Acrylsäure aus einer angesäuerten wäßrigen Butanol-Acrylsäure-Veresterungsablauge |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2323328A1 DE2323328A1 (de) | 1974-11-21 |
| DE2323328C2 true DE2323328C2 (de) | 1982-04-01 |
Family
ID=5880379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2323328A Expired DE2323328C2 (de) | 1973-05-09 | 1973-05-09 | Verfahren zur Abtrennung von Acrylsäure aus einer angesäuerten wäßrigen Butanol-Acrylsäure-Veresterungsablauge |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3962074A (enExample) |
| JP (1) | JPS5018412A (enExample) |
| BE (1) | BE814762A (enExample) |
| DE (1) | DE2323328C2 (enExample) |
| FR (1) | FR2228761B1 (enExample) |
| GB (1) | GB1458705A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102015115916A1 (de) | 2014-09-23 | 2016-03-24 | Basf Se | Verfahren und Anlage zur Behandlung von bei der Acrolein- und/oder (Meth-)Acrylsäure-Herstellung anfallenden Nebenkomponenten |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS541124Y2 (enExample) * | 1975-06-04 | 1979-01-19 | ||
| US4468328A (en) * | 1983-01-17 | 1984-08-28 | The Board Of Trustees Of The University Of Ill. | Purification of 12-O-tetradecanoylphorbol-13-acetate, phorbol, and 4α- |
| US5728872A (en) * | 1994-06-27 | 1998-03-17 | Lutz Riemenschneider | Stabilized acrylic acid compositions |
| FR2723089B1 (fr) * | 1994-07-28 | 1996-09-06 | Atochem Elf Sa | Procede de fabrication de l'acrylate de butyle par esterification directe |
| DE19600955A1 (de) * | 1996-01-12 | 1997-07-17 | Basf Ag | Verfahren zur Herstellung von Acrylsäure und deren Ester |
| DE19624674A1 (de) | 1996-06-20 | 1998-01-02 | Basf Ag | Verfahren zur Entsorgung von bei der Acrylsäure- oder Methacrylsäure-Herstellung anfallenden Nebenkomponenten |
| DE19709471A1 (de) * | 1997-03-07 | 1998-09-10 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäure |
| MY120051A (en) * | 1997-07-30 | 2005-08-30 | Mitsubishi Rayon Co | Process for purification of (meth)acrylic acid |
| DE19740252A1 (de) | 1997-09-12 | 1999-03-18 | Basf Ag | Verfahren zur Herstellung von Acrylsäure und Methacrylsäure |
| DE10127941A1 (de) | 2001-06-08 | 2002-05-29 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| US6737546B2 (en) * | 2001-11-13 | 2004-05-18 | Lurgi Ag | Extraction process for recovery of acrylic acid |
| GB0403592D0 (en) | 2004-02-18 | 2004-03-24 | Lucite Int Uk Ltd | A catalyst system |
| FR2884514B1 (fr) * | 2005-04-18 | 2007-06-22 | Arkema Sa | Procede perfectionne de fabrication de (meth) acrylates d'alkyle par esterification directe |
| CN101384539B (zh) * | 2005-12-26 | 2013-05-08 | 三菱丽阳株式会社 | 甲基丙烯酸的萃取方法 |
| SG190294A1 (en) | 2010-11-24 | 2013-06-28 | Lucite Int Uk Ltd | A process for the production of methacrylic acid and its derivatives and polymers produced therefrom |
| KR102013910B1 (ko) * | 2011-02-09 | 2019-08-23 | 루사이트 인터내셔널 유케이 리미티드 | (메트)아크릴산 및 그 유도체의 제조 방법 및 이들로부터 제조된 폴리머 |
| JP5659053B2 (ja) * | 2011-03-18 | 2015-01-28 | 三和油化工業株式会社 | 含浸液含有洗浄廃水のリサイクル方法 |
| CN105130060B (zh) * | 2015-09-17 | 2017-07-14 | 博天环境集团股份有限公司 | 一种废水处理方法 |
| KR20230066325A (ko) * | 2020-07-10 | 2023-05-15 | 아쿠아포터스 테크놀로지스 리미티드 | 염 회수 용액 및 이의 사용 방법 |
| CN113387493B (zh) * | 2021-04-15 | 2023-12-05 | 佳化化学科技发展（上海）有限公司 | 一种活性稀释剂生产中废水处理工艺 |
| CN117126051A (zh) * | 2022-05-19 | 2023-11-28 | 中国石油化工股份有限公司 | 制备（甲基）丙烯酸高级脂肪醇酯的方法 |
| CN117126048A (zh) * | 2022-05-19 | 2023-11-28 | 中国石油化工股份有限公司 | （甲基）丙烯酸水溶液的分离方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1568081A1 (de) * | 1966-02-19 | 1970-02-05 | Basf Ag | Verfahren zur Abtrennung von (Meth)acrylsaeure |
| US3809645A (en) * | 1973-04-03 | 1974-05-07 | Mitsubishi Rayon Co | Recovering methacrylic acid and methanol |
-
1973
- 1973-05-09 DE DE2323328A patent/DE2323328C2/de not_active Expired
-
1974
- 1974-05-06 US US05/467,255 patent/US3962074A/en not_active Expired - Lifetime
- 1974-05-07 FR FR7415768A patent/FR2228761B1/fr not_active Expired
- 1974-05-08 GB GB2032374A patent/GB1458705A/en not_active Expired
- 1974-05-09 BE BE144100A patent/BE814762A/xx not_active IP Right Cessation
- 1974-05-09 JP JP49050801A patent/JPS5018412A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102015115916A1 (de) | 2014-09-23 | 2016-03-24 | Basf Se | Verfahren und Anlage zur Behandlung von bei der Acrolein- und/oder (Meth-)Acrylsäure-Herstellung anfallenden Nebenkomponenten |
| US10093551B2 (en) | 2014-09-23 | 2018-10-09 | Basf Se | Process and plant for treatment of secondary components obtained in acrolein and/or (meth)acrylic acid production |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2228761A1 (enExample) | 1974-12-06 |
| GB1458705A (en) | 1976-12-15 |
| DE2323328A1 (de) | 1974-11-21 |
| JPS5018412A (enExample) | 1975-02-26 |
| BE814762A (fr) | 1974-11-12 |
| FR2228761B1 (enExample) | 1977-10-21 |
| US3962074A (en) | 1976-06-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8125 | Change of the main classification | ||
| D2 | Grant after examination | ||
| 8330 | Complete disclaimer |