Process for the hydration of epoxy esters

Hydroxy carboxylic esters are prepared by hydrating an epoxy ester with a concentrated aqueous solution of a strong acid, and separating the hydroxy esters from the reaction mixture. The epoxy esters may be mono-, di-, or polycarboxylic esters of, for example, acrylic, polyacrylic, 2,3-epoxypropionic, stearic, oleic, 9,10-epoxystearic, ricinoleic, pelargonic, azelaic, sebacic, adipic, succinic, phthalic, benzoic, dimerized or trimerized linoleic, tetrahydrophthalic, cyclohexanecarboxylic, nicotinic, quinolinic and diepoxystearic acids with alcohols such as methanol, ethanol, ethylene glycol, glycerol, glycidol, methylol cyclohexane, 2,3-epoxybutanediol, 1-octadecanol, 9,10-epoxy-1-octadecanol, oleyl, linoleyl, 9,10,12,13-diepoxy-1-octadecanol and ricinoleyl alcohols. The acids used include sulphuric, nitric, perchloric, methanesulphonic, benzenesulphonic, naphthalene sulphonic, trifluoroacetic and fluoboric acids and the reaction may be in an inert solvent. Examples describe the hydration of glycidyl stearate in various solvents any with various acids to produce mono- and di-stearic (2,3-dihydroxypropyl) stearates; and of methyl 9,10-epoxystearate, glycidyl oleate, diglycidyl sebacate, glycidyl ricinoleate, and epoxidized soyabean oil. The product bis-(2,3-dihydroxy propyl) sebacate is claimed as a new product.