IX. On benzoline, a new organic salt-base from bitter almond oil

Abstract

When pure oil of bitter almonds is left some days in contact with a strong solution of ammonia, at the ordinary temperature of the air, it is slowly, but in the end completely converted into a white crystalline substance, insoluble in water, but readily soluble in hot alcohol. The solidification of the oil is complete, and there is no secondary product. This substance was examined by M. Laurent, who conferred upon it the name of hydrobenzamide , and assigned to it the formula C 42 H 18 N 2 ; it is generated by the union of the elements of two equivalents of ammonia with those of three equivalents of hydruret of benzoyle, and the separation of six equivalents of water. 3 eq. bitter almond oil . C 42 H 18 O 6 2 eq. ammonia...... H 6 N 2 / C 42 H 24 N 2 O 6 }= { Hydrobenzamide C 42 H 18 N 2 6 eq. water... H 6 O 6 / C 42 H 24 N 2 O 6 Acids decompose hydrobenzamide immediately, with separation of bitter almond oil and formation of salt of ammonia; with alkalies the case is different, solution of potash, even at a boiling heat, occasioning, as remarked by M. Laurent, no perceptible change. I found however that when the boiling was prolonged for some hours, a change was induced resembling that undergone by furfurolamide under similar circumstances. A few brownish crystalline flocks appear in the solution, and after cooling, the cake of resin-like substance is found harder and less fusible than hydrobenzamide which has been melted and left to solidify. This change is unaccompanied by any notable alteration of weight, although a faint odour of bitter almond oil is disengaged during the whole course of the ebullition. The new substance is an organic salt-base, having the same composition as hydrobenzamide itself; it might perhaps with propriety be called benzoline .