Acetone azine

Acetone azine[1][2]
Names
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
627-70-3 YesY
4-01-00-03207
ChemSpider 71417 YesY
EC Number 211-009-6
Jmol interactive 3D Image
PubChem 79085
Properties
C
6H
12N
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)
1.454
Hazards
GHS pictograms
GHS signal word DANGER
H226, H302, H311, H315, H319, H335, H350
P201, P261, P280, P305+351+338, P308+313
T 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
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

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 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 via 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. 1 2 Day, A. C.; Whiting, M. C. "Acetone Hydrazone". Org. Synth.; Coll. Vol. 6, p. 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.
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