Role of anhydride in the ketonization of carboxylic acid: Kinetic study on dimerization of hexanoic acid

Yesol Woo; Yunsu Lee; Jae Wook Choi; Dong Jin Suh; Chang Ha Lee; Jeong Myeong Ha; Myung June Park

doi:10.1021/acs.iecr.6b04605

Role of anhydride in the ketonization of carboxylic acid: Kinetic study on dimerization of hexanoic acid

Yesol Woo, Yunsu Lee, Jae Wook Choi, Dong Jin Suh, Chang Ha Lee, Jeong Myeong Ha, Myung June Park

Department of Chemical and Biomolecular Engineering

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

(Chemical Equation Presented) Ketonization of hexanoic acid (CH₃ (CH₂)₄COOH) to produce 6-undecanone ((CH₃(CH₂)₄)₂ CO) 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)₄ CH₃) 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.

Original language	English
Pages (from-to)	872-880
Number of pages	9
Journal	Industrial and Engineering Chemistry Research
Volume	56
Issue number	4
DOIs	https://doi.org/10.1021/acs.iecr.6b04605
Publication status	Published - 2017 Feb 1

Bibliographical note

Funding Information:
This research was supported by C1 Gas Refinery Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (2016M3D3A1A01913280), and the Human Resources Development of the KETEP grant funded by the Korea government Ministry of Trade, Industry and Energy (No. 20154010200820).

Publisher Copyright:
© 2017 American Chemical Society.

All Science Journal Classification (ASJC) codes

Chemistry(all)
Chemical Engineering(all)
Industrial and Manufacturing Engineering

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10.1021/acs.iecr.6b04605

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title = "Role of anhydride in the ketonization of carboxylic acid: Kinetic study on dimerization of hexanoic acid",

abstract = "(Chemical Equation Presented) Ketonization of hexanoic acid (CH3 (CH2)4COOH) to produce 6-undecanone ((CH3(CH2)4)2 CO) 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)4 CH3) 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.",

author = "Yesol Woo and Yunsu Lee and Choi, {Jae Wook} and Suh, {Dong Jin} and Lee, {Chang Ha} and Ha, {Jeong Myeong} and Park, {Myung June}",

note = "Funding Information: This research was supported by C1 Gas Refinery Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (2016M3D3A1A01913280), and the Human Resources Development of the KETEP grant funded by the Korea government Ministry of Trade, Industry and Energy (No. 20154010200820). Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.iecr.6b04605",

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T1 - Role of anhydride in the ketonization of carboxylic acid

T2 - Kinetic study on dimerization of hexanoic acid

AU - Woo, Yesol

AU - Lee, Yunsu

AU - Choi, Jae Wook

AU - Suh, Dong Jin

AU - Lee, Chang Ha

AU - Ha, Jeong Myeong

AU - Park, Myung June

N1 - Funding Information: This research was supported by C1 Gas Refinery Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning (2016M3D3A1A01913280), and the Human Resources Development of the KETEP grant funded by the Korea government Ministry of Trade, Industry and Energy (No. 20154010200820). Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/2/1

Y1 - 2017/2/1

N2 - (Chemical Equation Presented) Ketonization of hexanoic acid (CH3 (CH2)4COOH) to produce 6-undecanone ((CH3(CH2)4)2 CO) 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)4 CH3) 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.

AB - (Chemical Equation Presented) Ketonization of hexanoic acid (CH3 (CH2)4COOH) to produce 6-undecanone ((CH3(CH2)4)2 CO) 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)4 CH3) 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.

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Role of anhydride in the ketonization of carboxylic acid: Kinetic study on dimerization of hexanoic acid

Abstract

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