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
CAS Number
  • 627-70-3 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
 4-01-00-03207
ChemSpider
  • 71417 checkY
ECHA InfoCard 100.010.009 Edit this at Wikidata
EC Number
  • 211-009-6
PubChem CID
  • 79085
UNII
  • Q18Y7G3ZPB checkY
CompTox Dashboard (EPA)
  • DTXSID1060845 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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)
Refractive index (nD)
 1.454
Hazards
GHS labelling:
Pictograms
 GHS02: Flammable GHS08: Health hazard GHS06: Toxic
Danger
Hazard statements
 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).
Infobox references
Chemical compound

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

Synthesis

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

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

  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.