GB741492A - Process for the manufacture of plasticizers - Google Patents

Abstract

Plasticizers for vinyl resins and cellulose derivatives are made by epoxidizing an oleic acid ester of a mono- or poly-hydric alcohol or an oleyl alcohol ester of a mono- or poly-basic carboxylic acid and treating the resultant epoxide, optionally in the presence of an esterification catalyst with a mono- or poly-basic carboxylic acid or its anhydride (see Group IV (b)). In examples, oleyl butyrate is epoxidized with hydrogen peroxide in the presence of formic acid and esterified with (1) butyric, (2) benzoic, and (6) adipic acids; in (3), (4) and (5) mixed lower paraffin oxidation fatty acids (acid No. 480) are used to esterify respectively epoxides obtained from butyl oleate with performic acid, oleyl oleate with hydrogen peroxide and formic acid and dioleyl phthalate, the products of (1), (2), (5) and (6) being compatible with polyvinyl chloride, e.g. 1-5 times as much resin as ester may be used, of (2) and (4) with nitrocellulose, of (3) with mixed styrenebutadiene resins and of (4) with benzyl cellulose.ALSO:Ester plasticizers are made by epoxidizing an oleic acid ester of a mono- or poly-hydric alcohol or an oleyl alcohol ester of a mono- or poly-basic carboxylic acid and treating the resultant epoxide, optionally in the presence of an esterification catalyst, with a mono- or poly-basic carboxylic acid or its anhydride. Epoxidizing is effected with organic per-acids or hydrogen peroxide in the presence of carboxylic acids. In the second stage the epoxide is esterified, at least 2 mols. of a mono- or one mol. of a di-basic acid being required per mol. of epoxide, reaction temperatures may exceed 200 DEG C. and water formed should be removed. Specified alcohols are ethanol, butanol, cyclohexanol, octanol, 2-ethyl hexanol, dodecanol, stearyl and oleyl alcohol, mixtures of lower alcohols obtainable by reduction of acids made by oxidizing paraffins, mixtures of oxo alcohols made from olefines, mixtures of guerbet alcohols, butoxy - ethanol, 6 - chloro - hexanol, tetrahydro-furfuryl alcohol, benzyl alcohol, phenyl and phenoxy ethanol, glycol, 1,4-butandiol, 1,4-hexandiol, diglycol, glycerol, trimethylol ethane, pentaerythritol and dipentaerythritol. Specified acids for the epoxidizing reaction are acetic, butyric, caproic, lauric, stearic and oleic acid, mixtures of C4-11 paraffin oxidation acids, butoxy-, octyl-, phenyl- and phenoxy-acetic acids, benzoic, naphthoic, succinic, maleic, adipic, sebacic, diglycollic, phthalic and terephthalic acids. Anhydrides of these acids may be used in the second stage. In examples oleyl butyrate is epoxdized with hydrogen peroxide in the presence of formic acid and esterified with (1) butyric, (2) benzoic and (6) adipic acids, in (3), (4) and (5) mixed lower paraffin oxidation fatty acids (acid No. 480) are used to esterify respectively epoxides obtained from butyl oleate with performic acid, oleyl oleate with hydrogen peroxide and formic acid and dioleyl phthalate.