Chemistry:Acetone azine

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Acetone azine[1][2]
Aceto azine Structural Formula V1.svg
Acetone azine Ball and Stick.png
Acetone azine Space Fill.png
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
3D model (JSmol)
4-01-00-03207
ChemSpider
EC Number
  • 211-009-6
Properties
C6H12N2
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 GHS02: Flammable GHS08: Health hazard GHS06: Toxic
GHS Signal word DANGER
H226, H302, H311, H315, H319, H335, H350
P201, P261, P280, P305+351+338, P308+313
NFPA 704 (fire diamond)
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 fuelHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial 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
Tracking categories (test):

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]

Acetone azine chem.png

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)". http://datasheets.scbt.com/sc-233803.pdf. 
  2. ↑ "Acetone azine MSDS (Sigma Aldrich)". http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=UK&language=EN&productNumber=273155&brand=ALDRICH&PageToGoToURL=null. 
  3. ↑ 3.0 3.1 Day, A. C.; Whiting, M. C.. "Acetone Hydrazone". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv6p0010. ; Collective Volume, 6, pp. 10 
  4. ↑ Schirmann, Jean-Pierre; Jean Combroux & Serge Yvon Delavarenne, "Method for preparing azines and hydrazones", US patent 3972878, issued 1976-08-03.Schirmann, Jean-Pierre; Pierre Tellier & Henri Mathais et al., "Process for the preparation of hydrazine compounds", US patent 3978049, issued 1976-08-31
  5. ↑ Schirmann, Jean-Pierre; Jean Combroux & Serge Y. Delavarenne, "Preparation of a concentrated aqueous solution of hydrazine hydrate", US patent 4724133, 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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