GB928182A - Continuous esterification process - Google Patents

Continuous esterification process

Info

Publication number
GB928182A
GB928182A GB299959A GB299959A GB928182A GB 928182 A GB928182 A GB 928182A GB 299959 A GB299959 A GB 299959A GB 299959 A GB299959 A GB 299959A GB 928182 A GB928182 A GB 928182A
Authority
GB
United Kingdom
Prior art keywords
alcohol
ester
acid
reactor
distillation column
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
Application number
GB299959A
Inventor
Kenneth Wilfred Geddes
Robert Norman Maclean
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.)
Distillers Co Yeast Ltd
Distillers Co Ltd
Original Assignee
Distillers Co Yeast Ltd
Distillers Co Ltd
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 Distillers Co Yeast Ltd, Distillers Co Ltd filed Critical Distillers Co Yeast Ltd
Publication of GB928182A publication Critical patent/GB928182A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • 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
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/60—Maleic acid esters; Fumaric acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

An ester is prepared by a continuous process from an acid reactant which is less volatile than water and is a carboxylic acid, carboxylic acid anhydride or carboxylic ester-acid, and an alcohol which is more volatile than water and the ester produced and does not form an azeotrope with water, which comprises heating the acid reactant with an excess of the alcohol in a reactor to which the reactants are fed in counter current flow to produce an ester, withdrawing from the reactor a resulting mixture of the vapours of the alcohol and water, introducing the said mixture of vapours into a distillation column into which is also introduced as liquid reflux a feed of dry alcohol, passing as alcoholic reactant dry alcohol vapour from the head of the distillation column into the reactor, withdrawing water from the base of the distillation column, withdrawing from the reactor a liquid mixture of ester and alcohol, separating the ester from the alcohol and passing the separated alcohol to the distillation column. The reactor may be operated at 100 DEG -250 DEG C. and preferably comprises a series of zones, each zone having independent heating means whereby each zone may be operated at an optimum temperature. Suitably, the reactor may take the form of a bubble-cap fractionating column with steam heating coils in each section. The dry alcohol vapour from the distillation column head may be passed to the reactor via a compressor. Part of the vapour may be returned to the distillation column as reflux additional to that furnished by the dry alcohol feed. The separation of ester from alcohol may be effected by fractional distillation with or without the aid of steam. When an esterification catalyst, e.g. sulphuric acid or para-toluene sulphuric acid has been used, this is preferably removed before separation of the alcohol from the ester. Suitable apparatus is described in which methyl alcohol and molten phthalic acid or acid anhydride are continuously reacted in the presence of sulphuric acid to give dimethyl phthalate. Sebacic, maleic, stearic, adipic, isophthalic, terephthalic and isosebacic acids and maleic anhydride are other specified acid reactants. According to the Provisional Specification, the acid reactant may be in the form of an ester with an alcohol more volatile than the alcohol reactant.
GB299959A 1960-02-06 1959-01-28 Continuous esterification process Expired GB928182A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB429760A GB968083A (en) 1960-02-06 1960-02-06 Production of esters

Publications (1)

Publication Number Publication Date
GB928182A true GB928182A (en) 1963-06-12

Family

ID=9774505

Family Applications (2)

Application Number Title Priority Date Filing Date
GB299959A Expired GB928182A (en) 1960-02-06 1959-01-28 Continuous esterification process
GB429760A Expired GB968083A (en) 1960-02-06 1960-02-06 Production of esters

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB429760A Expired GB968083A (en) 1960-02-06 1960-02-06 Production of esters

Country Status (4)

Country Link
FR (2) FR1248225A (en)
GB (2) GB928182A (en)
IT (1) IT639996A (en)
NL (2) NL260453A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004078699A1 (en) * 2003-03-05 2004-09-16 Council Of Scientific And Industrial Research Method of producing dimethyl phthalate from naphthalene based chemicals
EP1849764A1 (en) 2006-04-28 2007-10-31 Board of Trustees of Michigan State University Process for reactive esterification distillation
CN105399623A (en) * 2014-09-16 2016-03-16 常州市松盛香料有限公司 Diethyl maleate preparation method

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102489172B1 (en) * 2019-07-04 2023-01-18 주식회사 엘지화학 Manufacturing unit of diester-based material and method of manufacturing the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004078699A1 (en) * 2003-03-05 2004-09-16 Council Of Scientific And Industrial Research Method of producing dimethyl phthalate from naphthalene based chemicals
EP1849764A1 (en) 2006-04-28 2007-10-31 Board of Trustees of Michigan State University Process for reactive esterification distillation
CN105399623A (en) * 2014-09-16 2016-03-16 常州市松盛香料有限公司 Diethyl maleate preparation method

Also Published As

Publication number Publication date
GB968083A (en) 1964-08-26
FR79176E (en) 1962-11-03
NL247818A (en)
NL260453A (en)
IT639996A (en)
FR1248225A (en) 1960-10-31

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