Azine

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File:General structural formula of azines.svg
The generic formula of an azine. For an aldazine, R2, R4 = H.

Azines are a functional class of organic compounds with the connectivity Template:Chem2. These compounds are the product of the condensation of hydrazine with ketones and aldehydes, although in practice they are often made by alternative routes. Ketazines are azines derived from ketones.[1] For example, acetone azine is the simplest ketazine. Aldazines are azines derived from aldehydes.[2]

Preparation

The usual method of industrial production is the peroxide process, starting from the ketone, ammonia, and hydrogen peroxide.[3]

File:Pechiney-Ugine-Kuhlmann process.png

In the laboratory, azines are typically prepared by condensation of hydrazine with two equivalents of a carbonyl.[4]

Azines are also produced when chalcone reacts with a hydrazone to produce 3,5-diphenyl-1H-pyrazole,[5] in a conversion also carried out with hydrazine hydrate.[6][7]

File:Lasri condensation reaction.svg

Reactions

Azines characteristically undergo hydrolysis to hydrazines. The reaction proceeds by the intermediacy of a hydrazone:

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Azines have been used as precursors to hydrazones:[4][8]

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They are also precursors to diazo compounds.[9][8][10]

File:Acetone azine chem.png

The coordination chemistry of azines (as ligands) has also been studied.[11][12][13]

Acetone is used to derivatize hydrazine into acetone azine for analysis by gas chromatography. This method is used to determine trace levels of hydrazine in drinking water[14] and pharmaceuticals.[15]

Applications

Ketazines are also important intermediates in the industrial production of hydrazine hydrate by the peroxide process.[3] In the presence of an oxidant, ammonia and ketones react to give hydrazine via ketazine:

2 Me(Et)C=O + 2 NH3 + H2O2 → Me(Et)C=NN=C(Et)Me + 2 H2O

The ketazine can be hydrolyzed to the hydrazine and regenerate the ketone:

Me(Et)C=NN=C(Et)Me + 2 H2O → 2 Me(Et)C=O + N2H4

Ketazines have been also used as sources of hydrazine produced in situ, for example in the production of herbicide precursor 1,2,4-triazole.[16]

References

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  1. ↑ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "ketazines". Script error: No such module "CS1 identifiers".Script error: No such module "TemplatePar".
  2. ↑ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "aldazines". Script error: No such module "CS1 identifiers".Script error: No such module "TemplatePar".
  3. ↑ a b Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. Script error: No such module "CS1 identifiers"..
  4. ↑ a b Script error: No such module "Citation/CS1"..
  5. ↑ Script error: No such module "Citation/CS1".
  6. ↑ Script error: No such module "Citation/CS1".
  7. ↑ Script error: No such module "Citation/CS1".
  8. ↑ a b Script error: No such module "Citation/CS1".
  9. ↑ Script error: No such module "Citation/CS1".
  10. ↑ Script error: No such module "Citation/CS1".; Script error: No such module "citation/CS1"...
  11. ↑ Script error: No such module "Citation/CS1".
  12. ↑ Script error: No such module "Citation/CS1".
  13. ↑ Script error: No such module "Citation/CS1".
  14. ↑ Script error: No such module "Citation/CS1".
  15. ↑ Script error: No such module "Citation/CS1".
  16. ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Nagata, Nobuhiro; Nishizawa, Chiharu & Kurai, Toshikiyo, "Method of producing 1,2,4-triazole", published Script error: No such module "auto date formatter"., assigned to Mitsubishi Gas Chemical Co. Script error: No such module "Check for unknown parameters"..

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Further reading

  • Script error: No such module "Citation/CS1".
  • <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Eichenhofer, Kurt-Wilhelm & Schliebs, Reinhard, "Production of ketazines", published Script error: No such module "auto date formatter"., assigned to Bayer Script error: No such module "Check for unknown parameters"..
  • <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Schirmann, Jean-Pierre; Combroux, Jean & Delavarenne, Serge Yvon, "Method for preparing azines and hydrazones", published Script error: No such module "auto date formatter"., assigned to Produits Chimiques Ugine Kuhlmann Script error: No such module "Check for unknown parameters"..
  • <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Schirmann, Jean-Pierre; Tellier, Pierre & Mathais, Henri et al., "Process for the preparation of hydrazine compounds", published Script error: No such module "auto date formatter"., assigned to Produits Chimiques Ugine Kuhlmann Script error: No such module "Check for unknown parameters"..
  • <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Schirmann, Jean-Pierre; Combroux, Jean & Delavarenne, Serge Yvon, "Method for making azines", published Script error: No such module "auto date formatter"., assigned to Produits Chimiques Ugine Kuhlmann Script error: No such module "Check for unknown parameters"..
  • <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Schirmann, Jean-Pierre; Combroux, Jean & Delavarenne, Serge Y., "Preparation of a concentrated aqueous solution of hydrazine hydrate", published Script error: No such module "auto date formatter"., assigned to Atochem Script error: No such module "Check for unknown parameters"..
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