Oxypropylation of fatty alcohols, and the sulfation products

Abstract

Abstract Reaction of propylene oxide, rather than ethylene oxide, with fatty alcohols, gives a higher yield (50%) of mono‐oxyalkylation product because the secondary alcohol formed is less reactive than the primary alcohol formed with ethylene oxide. Rate of further reaction is about half the rate of the parent primary alcohol. Distributuon of propylene oxide reaction products follows the Weibull‐Nycander equation. Analysis of reaction products was accomplished by gas‐liquid chromatography of the acetylated ether alcohol mixtures. Pure mono‐oxypropylated alcohols ROCH 2 CHOHCH 3 and in some cases dioxypropylated alcohols R[OCH 2 CH(CH 3 )] 2 OH were separated by fractional distillation. Individual ether alcohols and products with a known average number of oxypropyl groups were sulfated and evaluated in terms of Krafft point, critical micelle concentration, detergency, foam height and lime soap dispersing properties. Incorporation of one oxypropyl group was more effective than the same degree of oxyethylation, and improved solubility with no significant loss in foaming and detergency. Ether alcohol sulfates from propylene oxide are stable to alkaline hydrolysis and nearly equal to the sulfates from ethylene oxide in their stability to acid hydrolysis.