Role of Anhydride in the Ketonization of Carboxylic Acid: Kinetic Study on Dimerization of Hexanoic Acid

Ketonization of hexanoic acid (CH3(CH2)4COOH) to produce 6-undecanone ((CH3(CH2)4)2CO) was performed and the reaction pathway was investigated through a kinetic study. Unlike studies suggesting β-keto acid as an undetectable intermediate of ketonization, hexanoic anhydride ((CH3(CH2)4)­COOCO­(CH2)4C...

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Published in:Industrial & engineering chemistry research 2017-02, Vol.56 (4), p.872-880
Main Authors: Woo, Yesol, Lee, Yunsu, Choi, Jae-Wook, Suh, Dong Jin, Lee, Chang-Ha, Ha, Jeong-Myeong, Park, Myung-June
Format: Article
Language:English
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Summary:Ketonization of hexanoic acid (CH3(CH2)4COOH) to produce 6-undecanone ((CH3(CH2)4)2CO) was performed and the reaction pathway was investigated through a kinetic study. Unlike studies suggesting β-keto acid as an undetectable intermediate of ketonization, hexanoic anhydride ((CH3(CH2)4)­COOCO­(CH2)4CH3) was observed to form as a result of the condensation of two hexanoic acid molecules by the loss of a water molecule. In order to investigate the role of hexanoic anhydride on the ketonization reaction, this kinetic study compared the performances of the reaction rate equations under different models for the reaction mechanism. Results indicate that ketonization occurs by the condensation of two hexanoic acid molecules producing hexanoic anhydride, followed by decarboxylation to produce 6-undecanone. By contrast, the formation of a β-keto acid is not observed in any experimental attempt.
ISSN:0888-5885
1520-5045
DOI:10.1021/acs.iecr.6b04605