Czonolysis as a method for establishing the position of olefinic linkages

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Abstract
Summary: Ozonolysis and chromatographic procedures as a method for determining the position of double bonds in olefinic acids are not entirely satisfactory. Ozonolysis is seriously limited because of the secondary reactions undergone by the ozonide. Chromatographic resolution of the decomposed ozonides of oleic acid yields the expected pelargonic and azelaic acids but also yields fractions that indicate double bonds which do not exist. Fractions corresponding to pimelic, sebacic, caprylic, suberic, and capric acids appeared. The “pimelic acid” fraction resulted from the reaction of ozone with an oxidizable or hydrolyzable solvent such as acetone, methanol, or tetrachloromethane. The “sebacic” and “caprylic acid” fractions were incompletely decomposed ozonide. The suberic and capric acid fractions however were real and are believed to have resulted from 8‐octadecenoic acid present in the oleic acid in amounts too small to be detected by the methods used to establish its purity.