Acetoacetic acid ethyl ester
3-Oxobutanoic acid ethyl ester
|Molar mass||130.14 g/mol|
with fruit or rum odour
|Density||1.021 g/cm3, liquid|
|Melting point||−45 °C (−49 °F; 228 K)|
|Boiling point||180.8 °C (357.4 °F; 453.9 K)|
|2.86 g/100 ml (20 °C)|
|Acidity (pKa)||10.68 (in H2O)
14.2 (in DMSO)
|EU classification||not listed|
|Flash point||70 °C (158 °F; 343 K)|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine and aminopyrine, and vitamin B1; as well as the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food.
The preparation of ethyl acetoacetate is a classic laboratory procedure. It is prepared via the Claisen condensation of ethyl acetate. Two moles of ethyl acetate condense to form one mole each of ethyl acetoacetate and ethanol.
Ethyl acetoacetate is subject to Keto-enol tautomerism. Ethyl acetoacetate is often used in the acetoacetic ester synthesis similar to diethyl malonate in the malonic ester synthesis or the Knoevenagel condensation. The protons alpha to carbonyl groups are acidic, and the resulting carbanion can undergo nucleophilic substitution. A subsequent thermal decarboxylation is also possible. Similar to the behavior of acetylacetone, the enolate of ethyl acetoacetate can also serve as a bidentate ligand. For example, it forms purple coordination complexes with iron(III) salts:
Ethyl acetoacetate can also be reduced to ethyl 3-hydroxybutyrate.
- Fructone, the ethylene glycol ketal of ethyl acetoacetate, an aroma compound
- Wilhelm Riemenschneider and Hermann M. Bolt "Esters, Organic" Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a09_565.pub2
- J. K. H. Inglis and K. C. Roberts (1926). "Ethyl Acetoacetate". Org. Synth.; Coll. Vol. 1, p. 235
- Carey, Francis A. (2006). Organic Chemistry (Sixth Edition ed.). New York, NY: McGraw-Hill. ISBN 0-07-111562-5.