This publication contains a comprehensive review of literature on petroselinic acid and its derivatives. All known sources of petroselinic acid including its synthetic derivation have been explored and described. The different plant species, whose seeds offer an oil reported to contain petroselinic acid, have been listed and the amounts of oil and their prevalent fatty acid components given. Its method of isolation from the naturally occurring triglycerides and identification have been discussed. The descriptions of characteristics and properties of petroselinic acid and its various derivatives are also included. In many cases they have been compared to oleic acid and other related fatty acids and their derivatives. The various methods of chemical modification of petroselinic acid have been, investigated and the derivatives obtained have been summarized in tabular form. Some potential uses for petroselinic acid and the products obtained from it have also been discussed. This review was designed to show that is known about petroselinic acid to date, and perhaps to create further interest in research on this unique naturally occurring octadecenoic acid.

Summary Methyl vinyl ketone was found to be an active dienophile for the modification of the eleostearate

Petroselinonitrile was prepared by distilling the ammonolysis products of petroselinic acid over phosphorus pentoxide, and also from parsley seed oil without first isolating the petroselinic acid. A high‐boiling antioxidant was employed during the reaction to control polymerization. The reaction by‐products were segregated from the pure petroselinonitrile by urea complexing. Petroselinamide was obtained from petroselinic acid by the acidolysis of urea. Although it was not possible to reduce the petroselinonitrile by catalytic hydrogenation without affecting the ethylenic linkage or without producing a mixture of the primary, secondary, and tertiary amines, petroselinonitrile was converted to primary petroselinylmine in good yields by reduction with metallic sodium and alcohol in toluene. The hydrochloride and the acetyl derivative of the pure primary amine have also been prepared.

Summary The addition products obtained by the Diels‐Alder reaction of acrylonitrile with the methyl, ethyl, and butyl eleostearates have been prepared in good yields and purified by means of high‐vacuum distillation. It has been possible to saturate preferentially by hydrogenation both the cyclic and exocyclic double bonds of the acrylonitrile adducts without material reduction of the nitrile group. Also the acrylonitrile adduct of tung oil has been prepared. All these adducts have been intercompared with DOP and evaluated as primary plasticizers for vinyl chloride‐vinyl acetate copolymer. These products, with the exception of the nonhydrogenated ethyl and butyl derivatives, were found to be satisfactory as primary plasticizers. The results obtained indicate that hydrogenation greatly improves the compatibility of the adducts without changing their other plasticizing characteristics appreciably. The outstanding characteristic of all the adducts is their high plasticizing efficiency, as reflected by their low modulus at 100% elongation.

SummaryEight derivatives of tung oil, namely, the methyl vinyl ketone, dimethyl maleate, methyl acrylate, and acrylonitrile adducts, and their hydrogenated products, were prepared and screened as softeners for Buna‐N rubber with dibutyl sebacate, as the control. Five of the eight products evaluated yielded stocks that met the low‐temperature flexibility requirements (−40°C.) of the automotive industry. In all cases the stocks prepared from the unhydrogenated derivatives were superior in plasticizing efficiency to the stocks prepared from their hydrogenated counterparts or to those prepared from the control.