Acetone azine
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| Acetone azine | |
|---|---|
| IUPAC name | acetone azine diisopropylidenehydrazine |
| Identifiers | |
| InChI | InChI=1/C6H12N2/c1-5(2)7-8-6(3)4/h1-4H3 |
| InChIKey | PFLUPZGCTVGDLV-UHFFFAOYAR |
| Standard InChI | InChI=1S/C6H12N2/c1-5(2)7-8-6(3)4/h1-4H3 |
| Standard InChIKey | PFLUPZGCTVGDLV-UHFFFAOYSA-N |
| CAS number | [] |
| EC number | |
| ChemSpider | |
| SMILES | |
| Properties[1] | |
| Chemical formula | C6H12N2 |
| Molar mass | 112.17 g mol−1 |
| Appearance | colourless liquid |
| Density | 0.8390 g cm−3 |
| Melting point |
−12.5 °C |
| Boiling point |
133 °C |
| Refractive index (nD) | 1.4535 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
Acetone azine, Me2C=N–N=CMe2, is the condensation product of two equivalents of acetone with one equivalent of hydrazine. It is an intermediate in the industrial production of hydrazine by the Atofina–PCUK cycle.[2]
On a laboratory scale, acetone azine is prepared by the direct reaction of acetone with hydrazine hydrate, with water being removed from the product by stirring with solid potassium hydroxide:[3][4] it is also commercially available. It is a useful precursor to acetone hydrazone[5][4] and hence to 2-diazopropane,[5][6][7] both of which must be prepared immediately before use and cannot be stored.[4][7]
References
- ↑ CRC Handbook of Chemistry and Physics, 62nd ed.; Weast, Robert C., Ed.; CRC Press: Boca Raton, FL, 1981; p C-74. ISBN 0-8493-0462-8.
- ↑ Schirmann, Jean-Pierre; Combroux, Jean; Delavarenne, Serge Yvon (Produits Chimiques Ugine Kuhlmann) Method for preparing azines and hydrazones. US Patent 3972878, issued 3 August 1976. Schirmann, Jean-Pierre; Tellier, Pierre; Mathais, Henri, et al. (Produits Chimiques Ugine Kuhlmann) Process for the preparation of hydrazine compounds. US Patent 3978049, issued 31 August 1976.
- ↑ Curtius, T.; Thun, K. J. Prakt. Chem. 1891, 44, 161.
- ↑ 4.0 4.1 4.2 Day, A. C.; Whiting, M. C. Acetone hydrazone. Org. Synth. 1970, 50, 3, <http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0010>; Coll. Vol., 6, 10.
- ↑ 5.0 5.1 Staudinger, H.; Gaule, A. Ber. Dtsch. Chem. Ges. 1916, 49, 1897.
- ↑ Day, A. C.; Raymond, P.; Southam, R. M.; Whiting, M. C. J. Chem. Soc. C 1966, 467.
- ↑ 7.0 7.1 Andrews, S. D.; Day, A. C.; Raymond, P.; Whiting, M. C. 2-Diazopropane. Org. Synth. 1970, 50, 27, <http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv6p0392>; Coll. Vol., 6, 392.
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