The hydrolysis of fatty acid chlorides

Abstract

Summary Fatty acid chlorides of octanoic, decanoic, lauric, myristic, palmitic, stearic, oleic, elaidic, and linoleic acids were hydrolyzed at 25° C, in water and the amounts of unchanged acid chlorides determined after different periods of reaction. Contrary to expectations, the chlorides of the longer chain fatty acids, palmitic and stearic, reacted at a more rapid rate than the chlorides of the shorter chain fatty acids. Lauryl chloride appears to be more resist‐ant to hydrolysis than either the chlorides of the lower molecular weight octanoic and decanoic acids or the chlorides of the higher molecular weight myristic to stearic acids. The chlorides of the unsaturated acids, oleic, elaidic, and linoleic, are hydrolyzed less rapidly than stearyl chloride. However, elaidyl and myristyl chlorides exhibit the same relative rates of hydrolysis during the first two hours of reaction. Myristyl chloride hydrolyzes more rapidly than elaidyl chloride after the first two hours. The addition of either hydrochloric acid or free fatty acids to the reaction mixture was found to have no pronounced effect on the hydrolysis of the acid chlorides.