Reaction of Propane Sultone with Sodium Salts of Higher Fatty Acids in Alcoholic Solvents

Abstract

The reaction of propane sultone with sodium salts of higher fatty acids in alcoholic solvents was investigated. it is clear that the following side reactions occur;(1) (I) (2) (II) And these resulted strongly acidic substances (I and II) promote the decomposition of APS (sodium γ-acyloxypropane sulfonate);RCOOCH2CH2CH2SO3Na+H2O→RCOOH+HOCH2CH2CH2SO3Na (3) RCOOCH2CH2CH2SO3Na+CH3OH→RCOOCH3+HOCH2CH2CH2SO3Na (4) Sodium salts of I and II did not promote the reaction (3) or (4). Therefore, APS was not decomposed under neutralization of I and II after a definite reaction time.From the results in methanol, it was made clear that the yield of APS greatly depends on occur-rence of the reactions (2) and (4). In isopropanol and tert-butanol, such decomposition was difficult to occur. Using sodium oleate as the salt of higher fatty acid, the yields of APS in methanol, isopropanol and tert-butanol were 67, 84 and 91%, respectively.