Patent GB-925718-A (GB)
Title: Process for the production of sugar esters
IPC: C07H13/06
Filed: 1960-10-05
Abstract: Carboxylic acid esters and/or carbonic acid esters of non-reducing sugars and glycosides, acetals and ketals of sugars are prepared by interesterification of the sugar or sugar derivative with a carboxylic acid aryl ester and/or carbonic acid aryl ester.  The esterification is carried out at 40 DEG  to 190 DEG C. in one or more stages in the presence of a catalyst, optionally in the presence of a dispersion agent, e.g. a liquid aromatic hydrocarbon or a solvent in which the sugar is soluble.  The phenol produced, and any dispersion agent or solvent present, is removed by distillation.  In examples saccharose octolinoleic ester is obtained by reacting cane sugar with linoleic phenyl ester, saccharose octolauric acid ester is obtained by reacting cane sugar with lauric acid phenyl ester, the 3-stearic acid ester of 1,2-5,6-biscyclohexylidene glucose is obtained by reacting biscyclohexylidene glucose with stearic acid phenyl ester, saccharose monostearate, saccharose distearate, saccharose tristearate, saccharose pentastearate and saacharose heptastearate are obtained by reacting cane sugar with various proportions of stearic acid phenyl ester in one or several stages, saccharose monolinoleic acid ester is obtained by reacting cane sugar with lineolic acid phenyl ester, saccharose dilaurate is obtained by reacting cane sugar with lauric acid phenyl ester in two stages, saccharose disalicylate is obtained by reacting cane sugar with salicylic acid phenyl ester, saccharose trilaurate is obtained by reacting cane sugar with lauric acid phenyl ester, a dehydrated castor oil ester of saccharose is obtained by reacting cane sugar with dehydrated castor oil acid phenyl ester; similarly cane sugar is reacted with stearic acid cresyl ester, with stearic acido-chlorophenyl ester, and with lauric acid a -naphthyl ester, raffinose is reacted with stearic acid phenyl ester to obtain raffinose distearate and with lauric acid phenyl ester to obtain raffinose decalaurate; sucrose is reacted with a mixture of diphenyl carbonate and linoleic acid phenyl ester, with a mixture of adipic acid phenyl ester and linoleic acid phenyl ester, with adipic acid diphenyl ester, with a mixture of adipic acid diphenyl ester and diphenyl carbonate, with sebacic acid diphenyl ester, with fumaric acid diphenyl ester, with isophthalic acid diphenyl ester, with a mixture of stearic acid phenyl ester and adipic acid diphenyl ester, and with diphenyl carbonate; catalysts used in the examples are potassium carbonate, potassium hydroxide, potassium phenylate, and sodium hydroxide; solvents used in the examples are ligroin, methylene chloride, dimethylformamide and pyridine.  Other sugars mentioned are trehalose, glucoxylose, melezitose, gentianose and stachiose.  Other glycosides, acetal and ketals of sugars mentioned are methyl, ethyl, propyl, butyl and benzyl glycoside, bis-propylidene, bis-isobutylidene and bis-benzylidene glucose, fructose and sorbose, and diacetone, di(methyl ethyl ketone) and diethylketone glucose.  Lists of mono- and di-carboxylic acids from which the esters may be derived are given.  The catalysts may be metallic alkali and alkaline earth metals, oxides, hydroxides, alcoholates, phenolates, carbonates, phosphates and acetates of alkali and alkaline earth metals, sodium sucrose, triphenyl methyl sodium and potassium pyrrole.  Other solvents mentioned include diethylformamide, dimethyl and diethyl acetamide, dialkyl sulphoxides, pyrrolidone and tertiary amines.