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Koch reaction information


The Koch reaction is an organic reaction for the synthesis of tertiary carboxylic acids from alcohols or alkenes. The reaction is a strongly acid-catalyzed carbonylation using carbon monoxide, and typically occurs at high pressures ranging from 50 to 5,000 kPa, often requiring temperatures several hundred degrees higher than room temperature. Generally the reaction is conducted with strong mineral acids such as sulfuric acid, HF or BF3.[1] Large scale operations for the fine chemical industry produce almost 150,000 tonnes of Koch acids and their derivatives annually[2] but also generate a great deal of waste, motivating ongoing attempts to use metal, solid acid, and other novel catalysts to enable the use of milder reaction conditions. Formic acid, which readily decomposes to carbon monoxide in the presence of acids or relatively low heat, is often used instead of carbon monoxide directly; this procedure was developed shortly after the Koch reaction and is more commonly referred to as the Koch–Haaf reaction. This variation allows for reactions at nearly standard room temperature and pressure. Some commonly industrially produced Koch acids include pivalic acid, 2,2-dimethylbutyric acid and 2,2-dimethylpentanoic acid.

The Koch reaction
  1. ^ Koch, H.; Haaf, W. Ann. 1958, "618", 251–266.(doi:10.1002/jlac.19586180127)
  2. ^ Weissermel, K., Jargen-Arpe, H. In "Syntheses involving carbon monoxide", Industrial Organic Chemistry; VCH Publishers: New York, NY; pp. 141–145. (ISBN 978-3527320028)

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