Patent GB-1529762-A (GB)
Title: Process for synthesizing specific complete polyol mixed esters
IPC: C07B61/00
Filed: 1976-02-11
Abstract: 1529762 Polyol esters PROCTOR & GAMBLE CO 11 Feb 1976 [12 Feb 1975] 05389/76 Heading C2C (1) A process for preparing specific complete polyol mixed esters from polyol partial esters with substantially no ester group rearrangement comprising esterifying a polyol partial ester with  an acid anhydride in the presence of a catalyst selected from anhydrous ferric chloride, anhydrous zinc chloride, anhydrous stannic chloride and mixtures thereof, said polyol partial ester being selected from the group consisting of polyol partial esters derived from saturated aliphatic diols having hydroxyl groups unsymmetrically substituted with respect to the carbon chain and partial polyol esters derived from saturated aliphatic polyols containing at least three hydroxyl groups. Examples prepare: synthetic cocoa butter (predominantly 1Àpalmitoyl - 2 - oleoyl - 3 - stearoyl glycerol and 1; 3-distearoyl-2-oleoyl glycerol) from a mixed 1,3 - stearoyl/palmitoyl-diglyceride and oleic anhydride, oleic-benzoic anhydride, oleic-pnitrobenzoic anhydride and oleic-diethylphosphoric anhydride; 1,3-dipalmitin, 1,2-dipalmitin, 1,3-distearin, 1-palmitoyl-3-stearoyl-, 1- palmitoyl-3-lauroyl- and 1-behenoyl-3-stearoyl glycerols are esterified with oleic anhydride to place an oleoyl group on the free hydroxy group; 1,3-dipalmitoin is esterified with rapeseed oil fatty acid anhydride at the 2-position; 2- stearoyldiolein is prepared from 2-monostearoin and oleic anhydride ; an ester of formula is prepared from 1-monostearin andl-stearoyl-1,2 propylene glycol - 2 - succinate anhydride; 1,3- distearoyl - 2 - octadecylglutarate glycerol is prepared from 1,3-distearin and monooctadecyl glutarate anhydride; di(1,3-distearin)succinate is prepared from 1,3-distearin and 1,3-distearin- 2-succinate anhydride; oleoyl 4-stearoyloxybutyryl 1,2-propylene is prepared from 1,2-propylene glycol monooleate and 4-stearoyloxybutyric anhydride; 1-behenoyl-2-oleoyl propylene glycol is prepared from 1,2-propylene glycol 1- monobehenate and oleic anhydride; 1,4-distearoyl-2,3-dioleoyl erythritol is prepared from 1,4-distearoyl erythritol and oleic anhydride; 1,3-dipropanoyl-2-acetyl or 2-benzoyl glycerols are prepared from 1,3-dipropanoyl glycerol and acetic or benzoic anhydrides. The above italicized anhydrides are prepared by reacting the corresponding acids with acetic anhydride. The above-mentioned 1,3-stearoyl/palmitoyl-diglyceride is prepared by transesterification of hydrogenated palm oil with triacetin. 1,2- Propylene glycol monooleate is prepared from the glycol and acid conventionally. Ethyl lactate is reacted with dihydropyran to give the ether tetrahydropyranyl - 2 ethyl lactate which is reduced with LiAlH 4  to the 2-tetrahydropyranyl - 21 ether of 1,2 - propylene glycol which on transesterification with methyl behenate gives 1-behenoyl-2-tetrahydropyranyl-2<SP>1</SP> propylene glycol which in turn is cleared with boric acid in trimethyl borate to give 1,2-propylene glycol 1-monobehenate. 1,4-Distearoyl erythritol is prepared from erythritol and methyl stearate and purified via a urea complex.