G. Maerker, E. T. Haeberer, W. Ault
Sep 1, 1964
Citations
0
Influential Citations
12
Citations
Journal
Journal of the American Oil Chemists’ Society
Abstract
Esters of 9,10-epoxystearic aeid (epoxidized oleic acid), dissolved in 1,4-dioxane, were treated at 15C, first with aqueoiis acid and then with water to convert them to 9,10-dihydroxystearates in high yields. Ester functions remained intact. Glycidyl 9,10-epoxystearate, ethylene glycolbis-9,10-epoxystearate and catecholbis-9,10-epoxystearate were converted to the corresponding tetrahydroxy esters by this method. Treatment of methyl 9,10-epoxystearate with diluted (24%) fluoboric acid gave methyl 9,10-dihydroxystearate in 89% yield. Under similar conditions glycidyl stearate did not react and the internal epoxy group of glycidyl 9,10-epoxystea-rate was hydrated preferentially. Hydration of methyl 9,10-epoxystearate with coned H2SO4 led to the formation of considerable amt of byproducts, principally methyl 9(10)-ketostearate. Side reactions were inhibited by diluting the acid-catalyst.