Acetone azine

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Acetone azine[1][2]
Acetone azine.png
Identifiers
CAS number 627-70-3 YesY
PubChem 79085
ChemSpider 71417 YesY
EC number 211-009-6
Beilstein Reference 4-01-00-03207
Jmol-3D images Image 1
Properties
Molecular formula C
6
H
12
N
2
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)
Refractive index (nD) 1.454
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H226, H302, H311, H315, H319, H335, H350
GHS precautionary statements P201, P261, P280, P305+351+338, P308+313
EU classification Toxic T Harmful Xn
R-phrases R45, R21/22, R10, R36/37/38
S-phrases S53, S26, S36/37, S45
NFPA 704
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 fuel Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 31 °C (88 °F; 304 K)
Related compounds
Related compounds Hydrazine

Acetone

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

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

Synthesis[edit]

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[edit]

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

Acetone azine chem.png

Hydrazine can be produced via 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)". 
  2. ^ "Acetone azine MSDS (Sigma Aldrich)". 
  3. ^ a b Day, A. C.; Whiting, M. C., Acetone Hydrazone, Org. Synth. ; Coll. Vol. 6: 10 
  4. ^ 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 
  5. ^ US 4724133, Schirmann, Jean-Pierre; Jean Combroux & Serge Y. Delavarenne, "Preparation of a concentrated aqueous solution of hydrazine hydrate", issued 1988-02-09 
  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 .