Acetone azine

Acetone azine is the simplest ketazine. It is an intermediate in some hydrazine manufacturing processes.

Synthesis

Acetone azine can be prepared from acetone and hydrazine:
It can also be produced from acetone, ammonia and hydrogen peroxide. The first step is the formation of acetone imine, Me₂C=NH; this is then oxidized by hydrogen peroxide through a complex mechanism to give 3,3-dimethyloxaziridine, which reacts with a further molecule of ammonia to produce acetone hydrazone. The hydrazone then condenses with a further molecule of acetone to produce the azine. The acetone azine product is distilled out of the reaction mixture as a 1:6 azeotrope with water.

Acetone azine can be used to prepare acetone hydrazone and.
Hydrazine can be produced through acid-catalysed hydrolysis of acetone azine: