The alcohols employed as the alcohol moiety of the ester should contain ether linkages such as ethylenoxy, propylenoxy or butylenoxy radicals. 0000005660 00000 n
Additional objects, it not specifically set forth herein, will be readily apparent from the detailed description of the invention which follows. More specifically, the invention is directed to improvements in the manufacture of esters of carboxylic acids by heating and reacting the carboxylic acids and the desired alcohols at an esterification temperature in the presence of a catalytic amount of a compound or mixture of compounds represented by the formula 0 OH H 1 R4 R1 R4 R1 and R3 R2 3 R2 where R R R and R are selected from the group consisting of H and lower aliphatic hydrocarbon radicals. Filed Oct. 4, 1962, Ser. Although the alkylene portion of such materials in the preferred form of the invention comprises an ethylene group, it should be understood that polyoxypropylene and polyoxybutylene glycols and ether and ester derivatives thereof are also contemplated. Usually about 0.1-5 of the catalyst will be employed and the amount used will depend'upon the activity of the catalyst and the particular acid and alcohol being combined to form the ester. Example II 550 grams of the methyl ether of polyoxyethylene glycol having a molecular weight of 550 was mixed with 275 grams of oleic acid and 4 grams of 2,5-ditertiary butyl hydroquinone was added to the mixture. Background Esters are an incredibly important functional group in organic chemistry. Operating temperatures can be lowered by the use of catalysts such as organic sulfonic acids and inorganic mineral acids, but these catalysts promote corrosion and the reaction must be conducted in special corrosion-resistant equipment or glass. Example: esterification of benzoic acid to methyl benzoate.
5 6 4. The reaction mixture was agitated and heated gradually to a temperature of C. at which point water was evolved from the mixture. 0000010064 00000 n
The alkyl phenol adducts of polyoxyalkylene glycol such as the alkyl phenolethylene oxide condensates can be coupled with carboxylic acids to produce highly active emulsifiers. 0000001578 00000 n
University of Texas, Rio Grande Valley • CHEMISTRY 206.
The tall oil fatty acid adduct of polyethylene glycol having 12-18 and preferably about 12-16 oxyethylene groups is an example of a monohydric alcohol which can be esterified with fatty acids in accordance with the method of the invention to provide particularly interesting derivatives.
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Esters are typically very pleasant smelling molecules and are therefore frequently used in the …
The improved method is particularly useful in the manufacture of esters of higher fatty acids having about -22 carbon atoms and monohydric and dihydric alcohols containing alkylenoxy radicals. Other substituted quinones and hydroquinones such as 2,5-diethyl quinone and 2,5-di(l,1,3,3-tetramethyl)butyl hydroquinone can also be employed in a similar fashion.
The Fischer Esterification A. hydroquinone is methyl hydroquinone. This preview shows page 1 - 2 out of 5 pages. 0000011086 00000 n
An improved method of manufacturing esters of higher fatty acids and ether-alcohols comprising: heating said higher fatty acids and alkyleneoxy alcohols in the presence of a catalytic amount of a material selected from the group consisting of ortho-substituted quinones having lower aliphatic hydrocarbon substitutents, ortho-substituted hydroquinones having lower aliphatic hydrocarbon substituents, and mixtures thereof to an esterification temperature whereby to promote the evolution of water from the catalyzed mixture. 5.5 Esterification pre-treatment in reactor PT1 ***Esterification pre-treatment is only necessary when using waste oil with FFA greater than 1 wt%, otherwise skip to procedure 4.iv*** 5.5.1 HEATING 1. No. Different o-substituents cause variations in activity of the substituted quinone or hydroquinone and generally as the carbon attached to the quinone or hydroquinone ring goes from primary to secondary to tertiary catalytic activity is enhanced. The product was a waxy solid which, when added to water, produced foam. Example I 1,000 grams of polyethylene glycol, having a molecular weight of 1,000 was melted and agitated with 500 grams of stearic acid in the presence of 7 grams of o-methyl hydroquinone.
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