Acetone azine
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Names | |||
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Systematic IUPAC name
Acetone azine | |||
Other names
Ketazine Acetone ketazine | |||
Identifiers | |||
627-70-3 | |||
4-01-00-03207 | |||
ChemSpider | 71417 | ||
EC Number | 211-009-6 | ||
Jmol interactive 3D | Image | ||
PubChem | 79085 | ||
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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) | ||
Refractive index (nD) |
1.454 | ||
Hazards | |||
GHS pictograms | |||
GHS signal word | DANGER | ||
H226, H302, H311, H315, H319, H335, H350 | |||
P201, P261, P280, P305+351+338, P308+313 | |||
EU classification (DSD) |
T Xn | ||
R-phrases | R45, R21/22, R10, R36/37/38 | ||
S-phrases | S53, S26, S36/37, S45 | ||
NFPA 704 | |||
Flash point | 31 °C (88 °F; 304 K) | ||
Related compounds | |||
Related compounds |
Hydrazine | ||
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
- ↑ "Acetone azine MSDS (Santa Cruz Biotechnology)" (PDF).
- ↑ "Acetone azine MSDS (Sigma Aldrich)".
- 1 2 Day, A. C.; Whiting, M. C. "Acetone Hydrazone". Org. Synth.; Coll. Vol. 6, p. 10
- ↑ 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
- ↑ US 4724133, Schirmann, Jean-Pierre; Jean Combroux & Serge Y. Delavarenne, "Preparation of a concentrated aqueous solution of hydrazine hydrate", issued 1988-02-09
- ↑ Organic Syntheses, Coll. Vol. 6, p.392 (1988); Vol. 50, p.27 (1970). Link
- ↑ 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.