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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:

2 (CH<sub>3</sub>)<sub>2</sub>CO + N<sub>2</sub>H<sub>4</sub> → 2 H<sub>2</sub>O + [(CH<sub>3</sub>)<sub>2</sub>C=N]<sub>2</sub>

It can also be produced from acetone (2 eq.), ammonia (2 eq.) and hydrogen peroxide (1 eq.). The first step is the formation of acetone imine, Me<sub>2</sub>C=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.

Reactions

Acetone azine can be used to prepare acetone hydrazone and .

Hydrazine can be produced through acid-catalysed hydrolysis of acetone azine:

2 H<sub>2</sub>O + [(CH<sub>3</sub>)<sub>2</sub>C=N]<sub>2</sub> → 2 (CH<sub>3</sub>)<sub>2</sub>CO + N<sub>2</sub>H<sub>4</sub>

References