Acetoacetic acid

• 3- oxobutanoic acid
• 3- oxobutyric

Liquid or fixed

36-37 ° C and viscous liquid at room temperature

Miscible with water

Template: Infobox chemical / molecular formula search available

Acetoacetic acid is the trivial name of the 3 - oxobutanoic acid. The anion of the acid is called acetoacetate or acetoacetate.

Production and representation

Acetoacetic acid is prepared by saponification (hydrolysis) of ethyl acetoacetate, followed by reaction with acids. Another way of illustration, the oxidation of butyric acid with hydrogen peroxide.

The reaction of sodium ethyl acetate produced in a Claisen condensation of ethyl acetoacetate, which can be converted by ester cleavage into the pure acid.

Properties

Acetoacetic acid is present in a keto -enol tautomerism. As a result of the inductive effect of the keto group acetoacetic acid more acidic than the underlying butyric acid.

With elemental chlorine or bromine to acetoacetic acid into carbon dioxide, the corresponding hydrogen halide and chlorine acetone or bromoacetone decomposed.

Use

Pure acetoacetic acid is rarely used because they are easily decomposed under decarboxylation to carbon dioxide and acetone ( quickly at 100 ° C). More important are their esters and salts.

Biological Significance

Acetoacetic acid ( acetoacetate ) takes as its isomer 2- oxobutanoic acid as an intermediate in the metabolism, one of the ketone bodies and of particular importance in the catabolism during starvation or diet. This is arisen in the state of hunger, acetyl -CoA, an intermediate (3 -hydroxy -3-methylglutaryl -CoA), converted to the acetoacetate.