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

Title: A theoretical study on the pyrolysis of perfluorobutanoic acid as a model compound for perfluoroalkyl acids
Creator: Altarawneh, Mohammednoor
Relation: Tetrahedron Letters Vol. 53, Issue 32, p. 4070-4073
Publisher Link: http://dx.doi.org/10.1016/j.tetlet.2012.05.109
Publisher: Pergamon
Resource Type: journal article
Date: 2012
Description: The potential energy surface is mapped out for all plausible reactions in the self-decomposition of perfluorobutanoic acid (CF₃CF₂CF₂COOH) 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.
Subject: perfluorobutanoic acid; pyrolysis; reaction rate constants; decarboxylation
Identifier: http://hdl.handle.net/1959.13/1327416
Identifier: uon:25659
Identifier: ISSN:0040-4039
Language: eng
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