Phenyloctadecanol and surface‐active derivatives

Abstract

Phenyloctadecanol from the Friedel‐Crafts reaction, like phenylstearic acid, is a viscous oil and a mixture of several position isomers. Gasliquid chromatography of the acetophenone homologs formed by CrO3 oxidation showed it to be a mixture of 13 position homologs, with substitution of the phenyl group at carbon atoms 5–17. A crystalline 17‐phenyloctadecanol was isolated. Reaction of oily phenyloctadecanol with dioxane‐SO3 sulfated the primary alcohol group to give sodium phenyloctadecyl sulfate CH3 (CH2)xCH (C6H5) (CH2)y CH2OSO3Na, where x + y = 15. Reaction of phenyloctadecanol with 2.4 moles of SO3 gave an impure p‐sulfophenyloctadecyl sulfate, hydrolyzed to sodium p‐sulfophenyloctadecanol CH3(CH2)xCH (p‐Cin6) H4SO3Na) (CH2)yCH2OH, and sulfated again with dioxane‐SO3 to disodium p‐sulfophenyl‐octadecyl sulfate CH3(CH2)xCH(p‐C6H4SO3Na) (CH2)yCH2OSO3Na. Foam, detergency, and other surface‐active properties were compared with those of the p‐sulfo anda‐sulfo derivatives of oily phenylstearic acid.