Patent GB-1383636-A (GB)
Title: Process for synthesizing specific complete mixed polyol esters
IPC: C07C67/08
Filed: 1973-04-06
Abstract: 1383636 Complete mixed polyol esters PROCTER & GAMBLE CO 6 April 1973 [7 April 1972] 16609/73 Heading C2C [Also in Division C5] Specific complete mixed polyol esters are prepared from partial polyol esters by esterification with an acid anhydride at -30‹ F. to 350‹ F. in the presence of a catalytic amount of a perfluoroalkyl (or cycloalkyl), sulphonic acid or anhydride or disulphonic acid. The polyol may be an aliphatic diol with the hydroxyl groups unsymmetrically substituted with respect to the carbon chain or an aliphatic polyol containing at least three hydroxyl groups, the diol or polyol having been partially esterified with a C 8  to C 22  monocarboxylic acid and, in each case, is partially esterified with an acidic lipid anhydride of the formula X.OC.O.CO.X or R.CO.OY in which X is a C 7  to C 21  alkyl or alkenyl group, or a residue of an alkyl or alkenyl half-ester of a dicarboxylic acid of the formula or a residue of a monoacyl diol half-ester of a  dicarboxylic acid of the formula or a residue of a diacyl glyceride half-ester of a dicarboxylic acid of the formula  or a residue of a monoacyl derivative of a primary monohydroxy monocarboxylic acid of the formula  in which R is a C 7  to C 21  alkyl or alkenyl group, R<SP>1</SP> is a C 2  to C 4  alkylene group, R<SP>2</SP> is a C 1  to C 4  alkylene group, or is absent, R<SP>3</SP> is a C 2  to C 5  alkylene group, Z is hydrogen or a methyl  group, Y is benzoyl, p-nitrobenzoyl or an alkyl phosphoryl group of the formula in which R<SP>4</SP> is a C 1  to C 5  alkyl or phenyl group. A specific complete mixed polyol ester made by the process is synthetic cocoa butter produced by acylating the 2-hydroxyl group of 1-palmitoyl-3-stearoyl glycerol with oleic anhydride and subsequent purification. The 1- palmitoyl-3-stearoyl glycerol is prepared by reacting substantially completely hydrogenated palm oil with glycerol in the presence of triacetin and sodium methoxide catalyst. Other examples are: mixed triglycerides of palmitic, oleic, stearic and behenic acids (Ex. II), 1,3 - di - palmitoyl partial glyceride ester and the complete esters obtained by further esterification with palmitic, stearic, oleic, palmitoleic, linoleic, linolenic or erucic acid (Ex. III), the anhydride from stearoyl propylene glycol hydrogen succinate and the complete ester derived by further reaction with 1 monostearin (Ex. V), similarly the octadecyl glutarate anhydride and the 1,3-di-stearyl-2-octadecyl glutaryl glyceride ester (Ex. VI), the anhydride of 1,3-distearin-2-hydrogen succinate and di- (l,3-distearin)succinate obtained by further esterification with 1,3-distearin (Ex. VII), stearoyl-4-hydroxy butyric anhydride and its esterification product with propylene glycol mono-oleate (Ex. VIII), tetrahydropyranyl ethyl lactate and reduction with lithium aluminium hydride to 2-tetrahydropyranyl propylene glycol, esterification to 1-behenic-2- tetrahydropyranyl propylene glycol eater, cleavage with boric acid to 1-propylene glycol monobehenate and final esterification to 1- behenoyl-2-oleoyl propylene glycol (Ex. IX), 1,4-distearoyl erythritol as a urea adduct (Ex. X), and 1,3-propyl-2-methyl glyceride ester or 1,3-propyl-2-benzoyl glyceride ester by reaction with acetic anhydride or benzoic anhydride respectively. The acid anhydrides used in Examples I, III, V-VIII are made from acetic anhydride and the corresponding acid.