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

Research output: Contribution to journalArticlepeer-review

8 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 languageEnglish
Pages (from-to)872-880
Number of pages9
JournalIndustrial and Engineering Chemistry Research
Volume56
Issue number4
DOIs
Publication statusPublished - 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

Fingerprint

Dive into the research topics of 'Role of anhydride in the ketonization of carboxylic acid: Kinetic study on dimerization of hexanoic acid'. Together they form a unique fingerprint.

Cite this