Dehydroacetic acid

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Dehydroacetic acid[1]
Kekulé, skeletal formula of dehydroacetic acid
Names
Preferred IUPAC name
3-Acetyl-2-hydroxy-6-methyl-4H-pyran-4-one[citation needed]
Other names
Biocide 470F[citation needed]
Methylacetopyronone[citation needed]
Identifiers
3D model (JSmol)
Abbreviations DHAA
ChemSpider
ECHA InfoCard 100.007.541
EC Number 208-293-9
E number E265 (preservatives)
MeSH dehydroacetic+acid
UNII
Properties
C8H8O4
Molar mass 168.15 g·mol−1
Appearance White crystals
Melting point 109 °C; 228 °F; 382 K
Boiling point 270 °C; 518 °F; 543 K
Hazards
Harmful Xn
R-phrases (outdated) R22
S-phrases (outdated) (S2)
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dehydroacetic acid is an organic compound which has several industrial applications. The compound is classified as a pyrone derivative.

Preparation[edit]

It is prepared by the base-catalysed dimerization of diketene.[2] Useful catalysts include tertiary amines, imidazole, DABCO, and pyridine. [3]

Uses[edit]

Industrially, dehydroacetic acid has several uses which include the following:

References[edit]

  1. ^ a b Merck Index, 11th Edition, 2855
  2. ^ Raimund Miller, Claudio Abaecherli, Adel Said, Barry Jackson "Ketenes" in Ullmann's Encyclopedia of Industrial Chemistry, 2001, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a15_063
  3. ^ Clemens, Robert J.; Witzeman, J. Stewart (1993). Agreda, Victor H.; Zoeller, Joeseph R., eds. Acetic Acid and its Derivatives. New York: Marcel Dekker, Inc. p. 202. ISBN 9780824787929. 
  4. ^ Handbook of Biocide and Preservative Use, Harold William Rossmoore, p. 341 ISBN 0-7514-0212-5
  5. ^ Cook, Denys (1963). "The Preparation, Properties, and Structure of 2,6-bis-(Alkyamino)-2,5-heptadien-4-ones". Canadian Journal of Chemistry. 41 (6): 1435–1440. doi:10.1139/v63-195.