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Isobutyric acid
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Isobutyric acid
Isobutyric acid, also known as 2-methylpropanoic acid or isobutanoic acid, is a carboxylic acid with structural formula (CH3)2CHCOOH. It is an isomer of butyric acid. It is classified as a short-chain fatty acid. Deprotonation or esterification gives derivatives called isobutyrates.
Isobutyric acid is a colorless liquid with a somewhat unpleasant odor. It is soluble in water and organic solvents. It is found naturally in carobs (Ceratonia siliqua), in vanilla, and in the root of Arnica dulcis, and as an ethyl ester in croton oil.
Isobutyric acid is manufactured by the oxidation of isobutyraldehyde, which is a byproduct of the hydroformylation of propylene.
It can also be prepared by the high pressure hydrocarboxylation (Koch reaction) from propylene:
Isobutyric acid can also be manufactured commercially using engineered bacteria with a sugar feedstock.
Many routes are known including the hydrolysis of isobutyronitrile with alkalis and the oxidation of isobutanol with potassium dichromate in the presence of sulfuric acid. In the presence of proton donors, the action of sodium amalgam on methacrylic acid also gives isobutyric acid.
The acid reacts as a typical carboxylic acid: it can form amide, ester, anhydride, and chloride derivatives. Its acid chloride is commonly used as the intermediate to obtain the others. When heated with a chromic acid solution it is oxidized to acetone. Alkaline potassium permanganate oxidizes it to α-hydroxyisobutyric acid, (CH3)2C(OH)-CO2H.
Isobutyric acid and its volatile esters are present naturally in a wide variety of foods and, at varying concentrations, can impart a range of flavors. The compound's safety as a food additive was reviewed by an FAO and WHO panel, who concluded that there were no concerns at the likely levels of intake.
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Isobutyric acid
Isobutyric acid, also known as 2-methylpropanoic acid or isobutanoic acid, is a carboxylic acid with structural formula (CH3)2CHCOOH. It is an isomer of butyric acid. It is classified as a short-chain fatty acid. Deprotonation or esterification gives derivatives called isobutyrates.
Isobutyric acid is a colorless liquid with a somewhat unpleasant odor. It is soluble in water and organic solvents. It is found naturally in carobs (Ceratonia siliqua), in vanilla, and in the root of Arnica dulcis, and as an ethyl ester in croton oil.
Isobutyric acid is manufactured by the oxidation of isobutyraldehyde, which is a byproduct of the hydroformylation of propylene.
It can also be prepared by the high pressure hydrocarboxylation (Koch reaction) from propylene:
Isobutyric acid can also be manufactured commercially using engineered bacteria with a sugar feedstock.
Many routes are known including the hydrolysis of isobutyronitrile with alkalis and the oxidation of isobutanol with potassium dichromate in the presence of sulfuric acid. In the presence of proton donors, the action of sodium amalgam on methacrylic acid also gives isobutyric acid.
The acid reacts as a typical carboxylic acid: it can form amide, ester, anhydride, and chloride derivatives. Its acid chloride is commonly used as the intermediate to obtain the others. When heated with a chromic acid solution it is oxidized to acetone. Alkaline potassium permanganate oxidizes it to α-hydroxyisobutyric acid, (CH3)2C(OH)-CO2H.
Isobutyric acid and its volatile esters are present naturally in a wide variety of foods and, at varying concentrations, can impart a range of flavors. The compound's safety as a food additive was reviewed by an FAO and WHO panel, who concluded that there were no concerns at the likely levels of intake.
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