GB1001895A - Production of unsymmetrical esters of polycarboxylic acids - Google Patents

Abstract

Unsymmetrical phenyl or substituted phenyl esters of a di-, or poly-carboxylic acid are prepared by heating (a) an intramolecular anhydride of a polycarboxylic acid free from olefinic unsaturation, (b) a phenol, (c) a tert.-aliphatic amine and (d) an alkyl, aralkyl or alkenyl halide in which the halogen atom is chlorine, bromine or iodine. The components (a), (b) and (c) may be heated together first to form, at least partially, an amine salt of a monoester and the halide is then introduced. Anhydrides mentioned are phthalic, trimellitic, pyromellitic, succinic, glutaric and adipic, chlorophthalic, chlorosuccinic, and dodecyl succinic anhydrides; phenols may be phenol, alkyl and aryl substituted phenols; the amines may be <FORM:1001895/C2/1> in which R1, R2, and R3 are like or unlike aliphatic groups; and the halide may be R1X in which R1 is an aralkyl, alkyl, or alkenyl group and particularly alkyl halides prepared from petroleum fractions boiling at 30 DEG C. to 300 DEG C. The reactions may take place with or without a solvent such as a monohaloalkane. Examples describe the preparation of t-butylphenyl octyl phthalate, n-butyl phenyl phthalate, ethyl phenyl phthalate, n-octyl phenyl succinate, octylphenyl n-octyl phthalate, dibenzyl diphthalate, n-octyl cresyl phthalate, benzyl cresyl phthalate, amyl nonyl - phthenyl phthalate, dodecyl cresyl phthalate, hexadecyl phenyl phthalate, benzyl nonylphenyl phthalate, benzyl phenylphthalate, n-octyl phenyl phthalate and allyl phenyl phthalate. The esters are used as plasticizers for polyvinyl chloride resins.