A theoretical study on the pyrolysis of perfluorobutanoic acid as a model compound for perfluoroalkyl acids

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13 Citations (Scopus)

Abstract

The potential energy surface is mapped out for all plausible reactions in the self-decomposition of perfluorobutanoic acid (CF3CF 2CF2COOH) as a model compound for the notoriously toxic and bio-accumulative perfluoroalkyl acids. Initial decomposition of perfluorobutanoic acid is found to be controlled by HF elimination and the formation of an α-lactone intermediate. The fate of this intermediate is predicted to be dominated by two competing channels, namely formation of pentafluoropropanoyl fluoride (CF3CF2COF) and the closed-shell singlet CF3CF2CF:. Direct elimination of CO2 through decarboxylation is found to be retarded by strong hyperconjugation effects induced by fluorine atoms on the carbon chain. The results presented herein provide insightful information towards a comprehensive understanding of the decomposition of perfluoroalkyl acids in thermal systems.

Original languageEnglish
Pages (from-to)4070-4073
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number32
DOIs
Publication statusPublished - Aug 8 2012
Externally publishedYes

Keywords

  • Decarboxylation
  • Perfluorobutanoic acid
  • Pyrolysis
  • Reaction rate constants

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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