Acetone azine

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 Edit this at Wikidata
EC Number
  • 211-009-6
UNII
  • InChI=1S/C6H12N2/c1-5(2)7-8-6(3)4/h1-4H3 checkY
    Key: PFLUPZGCTVGDLV-UHFFFAOYSA-N checkY
  • N(\N=C(/C)C)=C(\C)C
Properties
C6H12N2
Molar mass 112.176 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 labelling:
GHS02: Flammable GHS08: Health hazard GHS06: Toxic
Danger
H226, H302, H311, H315, H319, H335, H350
P201, P261, P280, P305+P351+P338, P308+P313
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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 fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
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).

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

Synthesis

[edit]
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 a 1:6 azeotrope with water.[5]

Reactions

[edit]

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

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

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

References

[edit]
  1. ^ "Acetone azine MSDS (Santa Cruz Biotechnology)" (PDF).
  2. ^ "Acetone azine MSDS (Sigma Aldrich)".
  3. ^ a b Day, A. C.; Whiting, M. C. (1970). "Acetone Hydrazone". Organic Syntheses: 3; Collected Volumes, vol. 6, 1988, p. 10.
  4. ^ US 3972878, Schirmann, Jean-Pierre; Combroux, Jean & Delavarenne, Serge Yvon, "Method for preparing azines and hydrazones", issued 1976-08-03, assigned to Produits Chimiques Ugine Kuhlmann .US 3978049, Schirmann, Jean-Pierre; Tellier, Pierre & Mathais, Henri 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; Combroux, Jean & Delavarenne, Serge Y., "Preparation of a concentrated aqueous solution of hydrazine hydrate", issued 1988-02-09, assigned to Atochem 
  6. ^ Andrews, S. D.; Day, A. C.; Raymond, P.; Whiting, M. C. (1970). "2-Diazopropane". Organic Syntheses: 27; Collected Volumes, vol. 6, 1988, p. 392.
  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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