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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
Other names
Biocide 470F[citation needed]
Methylacetopyronone[citation needed]
Identifiers
3D model (JSmol)
Abbreviations DHAA
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.541 Edit this at Wikidata
EC Number
  • 208-293-9
E number E265 (preservatives)
MeSH dehydroacetic+acid
UNII
  • InChI=1S/C8H8O4/c1-4-3-6(10)7(5(2)9)8(11)12-4/h3,11H,1-2H3 ☒N
    Key: JEQRBTDTEKWZBW-UHFFFAOYSA-N ☒N
  • CC(=O)C1=C(O)OC(C)=CC1=O
Properties
C8H8O4
Molar mass 168.148 g·mol−1
Appearance White crystals
Melting point 109 °C; 228 °F; 382 K
Boiling point 270 °C; 518 °F; 543 K
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302
P264, P270, P301+P312, P330, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Dehydroacetic acid is an organic compound which has several industrial applications. The compound is classified as a pyrone derivative. It presents as an odorless, colorless to white crystalline powder, almost insoluble in water and moderately soluble in most organic solvents.[2]

Preparation

It is prepared by the base-catalysed dimerization of diketene.[3] Commonly used organic bases include imidazole, DABCO, and pyridine.[4]

Uses

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

References

  1. ^ a b Merck Index, 11th Edition, 2855
  2. ^ Jilalat, Alae Eddine; et al. (2017). "DEHYDROACETIC ACID (Part 1): CHEMICAL AND PHARMACOLOGICAL PROPERTIES". Journal Marocain de Chimie Hétérocyclique. 16 (1): 1–47. ISSN 1114-7792. Retrieved July 3, 2017.
  3. ^ 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
  4. ^ Clemens, Robert J.; Witzeman, J. Stewart (1993). Agreda, Victor H.; Zoeller, Joseph R. (eds.). Acetic Acid and its Derivatives. New York: Marcel Dekker, Inc. p. 202. ISBN 9780824787929.
  5. ^ Harold William Rossmoore. Handbook of Biocide and Preservative Use, p. 341. ISBN 0-7514-0212-5
  6. ^ 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.
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