Dehydroacetic acid
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This article is missing information about etymology/history of discovery (where does the dehydro come from?); biocide mechanism of action; pKa. Please expand the article to include this information. Further details may exist on the talk page. (August 2022)
Chemical compound
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
[edit ]It is prepared by the base-catalysed dimerization of diketene.[3] Commonly used organic bases include imidazole, DABCO, and pyridine.[4]
Uses
[edit ]Industrially, dehydroacetic acid has several uses which include the following:
- as a fungicide and bactericide. The sodium salt, sodium dehydroacetate, is often used in place of dehydroacetic acid because of its greater solubility in water.
- as a food preservative to prevent pickle bloating in squash and strawberries.[5] When used as a food additive, dehydroacetic acid is referred to using the International Numbering System for Food Additives or E number 265.
- as a plasticizer in synthetic resins.[1]
- as an antienzyme in toothpastes.
- as a precursor for dimethyl-4-pyridones. The compounds are synthesized when dehydroacetic acid is exposed to aqueous solutions containing primary amines.[6]
References
[edit ]- ^ a b Merck Index, 11th Edition, 2855
- ^ 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.
- ^ 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
- ^ 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.
- ^ Harold William Rossmoore. Handbook of Biocide and Preservative Use, p. 341. ISBN 0-7514-0212-5
- ^ 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 .