Acetone azine

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

Acetone azine[1][2]
Names
Preferred IUPAC name
1,2-di(propan-2-ylidene)hydrazine
Systematic IUPAC name
Acetone azine
Other names
Ketazine

Acetone ketazine
Dimethyl ketazine
2-Propanone, 2-(1-methylethylidene)hydrazone
Acetone isopropylidenehydrazone
Dipropan-2-ylidenehydrazine
Diisopropylidene hydrazine

N-(propan-2-ylideneamino)propan-2-imine
Identifiers
3D model (JSmol)
4-01-00-03207
ChemSpider
ECHA InfoCard 100.010.009
EC Number
  • 211-009-6
UNII
Properties
C6H12N2
Molar mass 112.17 g mol−1
Appearance Pale-yellow liquid
Density 0.842 g cm−3
Melting point −125 °C (−193 °F; 148 K)
Boiling point 133 °C (271 °F; 406 K)
1.454
Hazards
GHS pictograms
GHS Signal word Danger
H226, H302, H311, H315, H319, H335, H350
P201, P261, P280, P305+351+338, P308+313
NFPA 704 (fire diamond)
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Flash point 31 °C (88 °F; 304 K)
Related compounds
Related compounds
 Hydrazine

Acetone

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis
See also: Peroxide process

Acetone azine can be prepared from acetone and hydrazine:[3]

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.).[4] 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).[5]

Reactions

Acetone azine can be used to prepare acetone hydrazone[3] and 2-diazopropane.[6]

Hydrazine can be produced through acid-catalysed hydrolysis of acetone azine:[7]

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

References
  1. "Acetone azine MSDS (Santa Cruz Biotechnology)" (PDF).
  2. "Acetone azine MSDS (Sigma Aldrich)".
  3. Day, A. C.; Whiting, M. C. "Acetone Hydrazone". Organic Syntheses.; Collective Volume, 6, p. 10
  4. US 3972878, Schirmann, Jean-Pierre; Jean Combroux & Serge Yvon Delavarenne, "Method for preparing azines and hydrazones", issued 1976-08-03, assigned to Produits Chimiques Ugine Kuhlmann.US 3978049, Schirmann, Jean-Pierre; Pierre Tellier & Henri Mathais et al., "Process for the preparation of hydrazine compounds", issued 1976-08-31, assigned to Produits Chimiques Ugine Kuhlmann
  5. US 4724133, Schirmann, Jean-Pierre; Jean Combroux & Serge Y. Delavarenne, "Preparation of a concentrated aqueous solution of hydrazine hydrate", issued 1988-02-09, assigned to Atochem
  6. Organic Syntheses, Coll. Vol. 6, p.392 (1988); Vol. 50, p.27 (1970). Link
  7. 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.
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