Alkyl azelaaldehydates of high purity from alkyl soyates: Preparation and properties

Abstract

AbstractReductive ozonolysis of appropriate alkyl soyates in various participating media producted methyl, ethyl,n‐propyl, isopropyl andn‐butyl azelaaldehydates in good yield and high purity (98+%). The participating media examined were: methyl, ethyl,n‐propyl andn‐butyl alcohols; mixtures of an alcohol and acetic acid; water; and mixtures of water and acetic acid. Any combination of solvent and ester, except methanol‐methyl soyate, allowed good separation by fractional distillation of ester and acetal impurities from the azelaaldehydate. A preparative method was developed by which high purity ethyl azelaaldehydate is produced from soybean oil by reductive ozonolysis in water. The only major impurity by this method was ethyl hydrogen azelate, which was easily removed with a bicarbonate wash. After a single fractional distillation with a short Vigreux column, the azelaaldehydate was obtained in 78% yield and 98+% purity. Physical properties and spectral (IR, NMR and mass spectroscopy) and chromatographic data were determined for the pure alkyl azelaaldehydates. Several of these properties were also determined for acetal and diester byproducts.