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 PDF

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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
Application number
CA002307593A
Other languages
French (fr)
Other versions
CA2307593C (en
Inventor
H. Robert Gerberich
R. Jay Warner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Celanese International Corp
Original Assignee
Celanese International Corporation Under The Laws Of The State Of Delaware
H. Robert Gerberich
R. Jay Warner
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Celanese International Corporation Under The Laws Of The State Of Delaware, H. Robert Gerberich, R. Jay Warner filed Critical Celanese International Corporation Under The Laws Of The State Of Delaware
Publication of CA2307593A1 publication Critical patent/CA2307593A1/en
Application granted granted Critical
Publication of CA2307593C publication Critical patent/CA2307593C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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

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.
CA002307593A 1997-10-31 1997-10-31 Continuous process for the production of carboxylic acid esters of alkylene glycol monoalkyl ethers Expired - Fee Related CA2307593C (en)

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) DE19782298T1 (en)
GB (1) GB2345911B (en)
WO (1) WO1999023058A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100710832B1 (en) * 2006-03-31 2007-04-23 (주) 청도정밀화학 Improved production method of high molecular weight alkoxy poly alkylene glycol (meth)acrylate
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)

* Cited by examiner, † Cited by third party
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
EP0119833B1 (en) * 1983-03-17 1988-11-17 Arco Chemical Technology, Inc. Preparation of carboxylic acid esters of alkylene glycol monoalkyl ethers
US5618973A (en) * 1994-11-10 1997-04-08 Union Carbide Chemicals & Plastics Technology Corporation Esterification process

Also Published As

Publication number Publication date
GB0009596D0 (en) 2000-06-07
DE19782298T1 (en) 2000-11-30
GB2345911B (en) 2001-07-18
WO1999023058A1 (en) 1999-05-14
KR20010031647A (en) 2001-04-16
GB2345911A (en) 2000-07-26
DE19782298B4 (en) 2005-02-17
JP3986756B2 (en) 2007-10-03
KR100532269B1 (en) 2005-11-29
JP2001521918A (en) 2001-11-13
CA2307593C (en) 2007-01-16

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