The cyanoethylation and infrared spectra of some ricinoleic acid derivatives

Abstract

Summary: Five ricinoleic acid derivatives have been cyanoethylated with acrylonitrile, namely, 4‐ricinoleoylmorpholine, 4‐ricinelaidoylmorpholine, 4‐(12‐hydroxystearoyl) morpholine, 1,12‐dihydroxy‐9‐octadecene and 1,12‐dihydroxyoctadecane, using benzyltrimethylammonium hydroxide as a cyanoethylation catalyst and water to retard the polymerization of acrylonitrile. Any polyacrylonitrile formed was readily precipitated out of an ethereal solution. Purification of the cyanoethylated products was accomplished by washing out the catalyst, rapid distillation under high vacuum, and crystallizations from methanol. In addition, 1,12‐bis(β‐cyanoethoxy)‐9‐octadecene was isomerized fromcis totrans form and crystallized successively from acetone and methanol. The infrared spectra of these compounds have been determined. It was found that the characteristic absorption for the nitrile group at 4.44 microns is about 67% greater in chloroform than in carbon tetrachloride and that it obeys Beer's law over a wide range of concentrations, thus permitting convenient infrared analysis of this type of compound. Some properties of these compounds are described.