|Systematic IUPAC name
3D model (JSmol)
|Molar mass||112.17 g mol−1|
|Density||0.842 g cm−3|
|Melting point||−125 °C (−193 °F; 148 K)|
|Boiling point||133 °C (271 °F; 406 K)|
Refractive index (nD)
|GHS signal word||DANGER|
|H226, H302, H311, H315, H319, H335, H350|
|P201, P261, P280, P305+351+338, P308+313|
|Flash point||31 °C (88 °F; 304 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
- 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).
Hydrazine can be produced via acid-catalysed hydrolysis of acetone azine:
- 2 H2O + [(CH3)2C=N]2 → 2 (CH3)2CO + N2H4
- "Acetone azine MSDS (Santa Cruz Biotechnology)" (PDF).
- "Acetone azine MSDS (Sigma Aldrich)".
- Day, A. C.; Whiting, M. C. "Acetone Hydrazone". Org. Synth.; Coll. Vol., 6, p. 10
- US 3972878, Schirmann, Jean-Pierre; Jean Combroux & Serge Yvon Delavarenne, "Method for preparing azines and hydrazones", issued 1976-08-03 . US 3978049, Schirmann, Jean-Pierre; Pierre Tellier & Henri Mathais et al., "Process for the preparation of hydrazine compounds", issued 1976-08-31
- US 4724133, Schirmann, Jean-Pierre; Jean Combroux & Serge Y. Delavarenne, "Preparation of a concentrated aqueous solution of hydrazine hydrate", issued 1988-02-09
- Organic Syntheses, Coll. Vol. 6, p.392 (1988); Vol. 50, p.27 (1970). Link
- Gilbert, E. C. (1929), "Studies on Hydrazine. The Hydrolysis of Dimethylketazine and the Equilibrium between Hydrazine and Acetone", J. Am. Chem. Soc., 51 (11): 3394–3409, doi:10.1021/ja01386a032.