GB782480A - Method of producing mono-esters of monocarboxylic acids with di- or tri-hydric alcohols - Google Patents

Method of producing mono-esters of monocarboxylic acids with di- or tri-hydric alcohols

Info

Publication number
GB782480A
GB782480A GB30616/55A GB3061655A GB782480A GB 782480 A GB782480 A GB 782480A GB 30616/55 A GB30616/55 A GB 30616/55A GB 3061655 A GB3061655 A GB 3061655A GB 782480 A GB782480 A GB 782480A
Authority
GB
United Kingdom
Prior art keywords
glycol
diethylene glycol
weight
tri
monocarboxylic acids
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
GB30616/55A
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.)
Olin Corp
Original Assignee
Olin Corp
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 Olin Corp filed Critical Olin Corp
Publication of GB782480A publication Critical patent/GB782480A/en
Expired legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • B01J31/08—Ion-exchange resins
    • B01J31/10—Ion-exchange resins sulfonated
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • B01J31/08—Ion-exchange resins
    • 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
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
    • C11C3/025—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol with a stoechiometric excess of glycerol
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/49—Esterification or transesterification

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Mono-esters of monocarboxylic acids with di- or tri-hydric alcohols are prepared by reacting at an elevated temperature at least 1 mol. of the alcohol with each mol. of acid in the presence of an acidic cation exchange resin. The molar ratio of alcohol to acid is preferably between 4 : 1 and 12 : 1. The reaction is preferably carried out at a temperature of 100 DEG to 200 DEG C. Preferably from 1 to 10 per cent by weight of exchange resin is used based on the total weight of the reactants. The exchange resin may contain sulphonic, carboxylic, phenolic or phosphoric polar groups, specified examples being those of the sulphonated coal, sulphonated phenol-formaldehyde or sulphonated polystyrene types. Between 10 and 50 per cent by weight (based on weight of total reactants) of an inert water-immiscible solvent may be present during the reaction. Solvents boiling between 100 DEG and 200 DEG C. are preferred, those specified being n-octane, 2 : 2 : 4-trimethylpentane, n - decane, toluene, xylene, ethylbenzene, cumene, para-cymene, trichloroethylene and tetrachloroethylene. The di- and tri-hydric alcohol reactants preferably contain from 2 to 8 carbon atoms, those specified being ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, trimethylene glycol, a -butylene glycol and glycerol. Specified monocarboxylic acids are acetic, propionic, butyric, 2-ethylhexanoic, lauric, palmitic, stearic, oleic, benzoic, toluic, phenylacetic, 2 : 4-dichlorophenoxyacetic and 2 : 4 : 5-trichlorophenoxyacetic acids. The examples describe the preparation of diethylene glycol monolaurate, diethylene glycol monooleate, diethylene glycol monostearate, diethylene glycol mono-(2 : 4 : 5-trichlorophenoxyacetate) and diethylene glycol monobenzoate. Diethylene glycol dilaurate is formed as a by-product.
GB30616/55A 1954-10-26 1955-10-26 Method of producing mono-esters of monocarboxylic acids with di- or tri-hydric alcohols Expired GB782480A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US782480XA 1954-10-26 1954-10-26

Publications (1)

Publication Number Publication Date
GB782480A true GB782480A (en) 1957-09-04

Family

ID=22142850

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30616/55A Expired GB782480A (en) 1954-10-26 1955-10-26 Method of producing mono-esters of monocarboxylic acids with di- or tri-hydric alcohols

Country Status (1)

Country Link
GB (1) GB782480A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0192035A2 (en) * 1985-01-21 1986-08-27 Henkel Kommanditgesellschaft auf Aktien Process for the pre-esterification of free fatty acids in raw fats and/or oils
EP1785478A1 (en) * 2004-07-13 2007-05-16 Revo International Inc. Process for producing fatty acid alkyl ester
JP2008037837A (en) * 2006-08-10 2008-02-21 Mitsubishi Rayon Co Ltd Method for producing monoester
WO2011151114A1 (en) * 2010-05-31 2011-12-08 Evonik Goldschmidt Gmbh Polyol partial esters for use in cosmetics

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0192035A2 (en) * 1985-01-21 1986-08-27 Henkel Kommanditgesellschaft auf Aktien Process for the pre-esterification of free fatty acids in raw fats and/or oils
EP0192035A3 (en) * 1985-01-21 1987-07-15 Henkel Kommanditgesellschaft Auf Aktien Process for the pre-esterification of free fatty acids in raw fats and/or oils
EP1785478A1 (en) * 2004-07-13 2007-05-16 Revo International Inc. Process for producing fatty acid alkyl ester
EP1785478A4 (en) * 2004-07-13 2009-08-19 Revo Internat Inc Process for producing fatty acid alkyl ester
JP2008037837A (en) * 2006-08-10 2008-02-21 Mitsubishi Rayon Co Ltd Method for producing monoester
WO2011151114A1 (en) * 2010-05-31 2011-12-08 Evonik Goldschmidt Gmbh Polyol partial esters for use in cosmetics

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