CA2307593A1 - Continuous process for the production of carboxylic acid esters of alkylene glycol monoalkyl ethers - Google Patents
Continuous process for the production of carboxylic acid esters of alkylene glycol monoalkyl ethers Download PDFInfo
- Publication number
- CA2307593A1 CA2307593A1 CA002307593A CA2307593A CA2307593A1 CA 2307593 A1 CA2307593 A1 CA 2307593A1 CA 002307593 A CA002307593 A CA 002307593A CA 2307593 A CA2307593 A CA 2307593A CA 2307593 A1 CA2307593 A1 CA 2307593A1
- Authority
- CA
- Canada
- Prior art keywords
- carboxylic acid
- alkylene glycol
- acid esters
- glycol monoalkyl
- monoalkyl ethers
- 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
- -1 alkylene glycol monoalkyl ethers Chemical class 0.000 title abstract 2
- 150000001733 carboxylic acid esters Chemical class 0.000 title abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title abstract 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000010924 continuous production Methods 0.000 title 1
- 238000000034 method Methods 0.000 abstract 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention provides an improved method for the preparation of carboxylic acid esters of alkylene glycol monoalkyl ethers by the acid catalyzed esterification of the monoalkyl ether with a carboxylic acid. In a preferred embodiment of the invention, the carboxylic acid and alcohol are reacted in a reactor/column and the resulting ester product is distilled into an overhead decanter/extractor as a single phase.
A small amount of solvent, preferably a hydrocarbon is added to the mixture causing the resulting distillate to separate into two phases, one phase containing the desired product, the other containing primarily water.
The process described is applicable to both batch and continuous operation and is not constrained by the difficulty of separating closely boiling azeotropes and results in substantially higher production rates than achieved by current processes.
A small amount of solvent, preferably a hydrocarbon is added to the mixture causing the resulting distillate to separate into two phases, one phase containing the desired product, the other containing primarily water.
The process described is applicable to both batch and continuous operation and is not constrained by the difficulty of separating closely boiling azeotropes and results in substantially higher production rates than achieved by current processes.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1997/019827 WO1999023058A1 (en) | 1997-10-31 | 1997-10-31 | Continuous process for the production of carboxylic acid esters of alkylene glycol monoalkyl ethers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2307593A1 true CA2307593A1 (en) | 1999-05-14 |
| CA2307593C CA2307593C (en) | 2007-01-16 |
Family
ID=22261983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002307593A Expired - Fee Related CA2307593C (en) | 1997-10-31 | 1997-10-31 | Continuous process for the production of carboxylic acid esters of alkylene glycol monoalkyl ethers |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JP3986756B2 (en) |
| KR (1) | KR100532269B1 (en) |
| CA (1) | CA2307593C (en) |
| DE (2) | DE19782298B4 (en) |
| GB (1) | GB2345911B (en) |
| WO (1) | WO1999023058A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100710832B1 (en) * | 2006-03-31 | 2007-04-23 | (주) 청도정밀화학 | Improved preparation of high molecular weight alkoxypolyalkylene glycol (meth) acrylates |
| KR101134659B1 (en) * | 2010-09-06 | 2012-04-09 | 이수화학 주식회사 | Preparation method of Propylene glycol monomethyl ether acetate |
| CN106431831B (en) * | 2016-09-18 | 2018-12-18 | 昆明博鸿生物科技有限公司 | A kind of synthetic method of 5E- decene-1-alcohol and acetic acid 5E- ubidecarenone |
| CN108129317A (en) * | 2018-01-29 | 2018-06-08 | 淄博高新技术产业开发区精细化工和高分子材料研究院 | A kind of method for continuously recycling PGMEA from PGMEA/ aqueous solutions using azeotropic distillation |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3235531A1 (en) * | 1982-09-25 | 1984-03-29 | Chemische Werke Hüls AG, 4370 Marl | METHOD FOR THE ESTERIFICATION OF ACETIC ACID WITH ALCOHOLS CONTAINING 4 AND MORE C ATOMES, AND WITH GLYCOLETHERS |
| DE3475188D1 (en) * | 1983-03-17 | 1988-12-22 | Atlantic Richfield Company | |
| US5618973A (en) * | 1994-11-10 | 1997-04-08 | Union Carbide Chemicals & Plastics Technology Corporation | Esterification process |
-
1997
- 1997-10-31 DE DE19782298A patent/DE19782298B4/en not_active Expired - Fee Related
- 1997-10-31 JP JP2000518935A patent/JP3986756B2/en not_active Expired - Lifetime
- 1997-10-31 WO PCT/US1997/019827 patent/WO1999023058A1/en not_active Ceased
- 1997-10-31 KR KR10-2000-7004700A patent/KR100532269B1/en not_active Expired - Fee Related
- 1997-10-31 CA CA002307593A patent/CA2307593C/en not_active Expired - Fee Related
- 1997-10-31 GB GB0009596A patent/GB2345911B/en not_active Expired - Lifetime
- 1997-10-31 DE DE19782298T patent/DE19782298T1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA2307593C (en) | 2007-01-16 |
| GB2345911B (en) | 2001-07-18 |
| JP3986756B2 (en) | 2007-10-03 |
| DE19782298B4 (en) | 2005-02-17 |
| WO1999023058A1 (en) | 1999-05-14 |
| KR100532269B1 (en) | 2005-11-29 |
| GB2345911A (en) | 2000-07-26 |
| GB0009596D0 (en) | 2000-06-07 |
| KR20010031647A (en) | 2001-04-16 |
| JP2001521918A (en) | 2001-11-13 |
| DE19782298T1 (en) | 2000-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |