Acetone azine is the simplest

ketazine Azines are a functional class of organic compounds with the connectivity RR'C=N-N=CRR'. These compounds are the product of the condensation of hydrazine with ketones and aldehydes, although in practice they are often made by alternative routes ...

. It is an intermediate in some

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, hydrazine ...

manufacturing processes.

Synthesis

Acetone azine can be prepared from

acetone 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 miscib ...

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 nitrogenous was ...

(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 Acetone imine, or 2-propanimine is an organic compound and an imine with the chemical formula (CH3)2CNH. It is a volatile and flammable liquid at room temperature. It is the simplest ketimine. This compound is mainly of academic interest. Sy ...

, 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 Condensation is the change of the state of matter from the gas phase into the liquid phase, and is the reverse of vaporization. The word most often refers to the water cycle. It can also be defined as the change in the state of water vapor to ...

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. Acetone azine chem

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)