The preparation and properties of some nitrogen‐containing derivatives of petroselinic acid

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.