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Acetone azine is the simplest ketazine. It is an intermediate in some
Hydrazine can be produced through acid-catalysed hydrolysis of acetone azine:.
: 2 H2O + CH3)2C=Nsub>2 → 2 (CH3)2CO + N2H4
hydrazine
Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly toxic unless handled in solution as, for example, hydrazin ...
manufacturing processes.
Synthesis
Acetone azine can be prepared fromacetone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscible wi ...
and hydrazine:
:2 (CH3)2CO + N2H4 → 2 H2O + CH3)2C=Nsub>2
It can also be produced from acetone (2 eq.), ammonia
Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogeno ...
(2 eq.) and hydrogen peroxide
Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3% ...
(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
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscible wi ...
. 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 prepareacetone hydrazone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour.
Acetone is miscible wi ...
and 2-diazopropane.
Hydrazine can be produced through acid-catalysed hydrolysis of acetone azine:.
: 2 H2O + CH3)2C=Nsub>2 → 2 (CH3)2CO + N2H4
References
{{reflist Azines (hydrazine derivatives)