Supriya Ghosh

Acetone azine

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Related compounds  Hydrazine Acetone
Appearance  Pale-yellow liquid
Acetone azine httpsuploadwikimediaorgwikipediacommonsthu

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

Contents

Synthesis

Acetone azine can be prepared from acetone and hydrazine:

2 (CH3)2CO + N2H4 → 2 H2O + [(CH3)2C=N]2

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, 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 its azeotrope with water (n(H2O)/n(azine) ≈ 6).

Reactions

Acetone azine can be used to prepare acetone hydrazone and 2-diazopropane.

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

2 H2O + [(CH3)2C=N]2 → 2 (CH3)2CO + N2H4

References

Acetone azine Wikipedia


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