Murdoch University Research Repository

Welcome to the Murdoch University Research Repository

The Murdoch University Research Repository is an open access digital collection of research
created by Murdoch University staff, researchers and postgraduate students.

Learn more

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

Altarawneh, M.ORCID: 0000-0002-2832-3886 (2012) A theoretical study on the pyrolysis of perfluorobutanoic acid as a model compound for perfluoroalkyl acids. Tetrahedron Letters, 53 (32). pp. 4070-4073.

Link to Published Version: http://dx.doi.org/10.1016/j.tetlet.2012.05.109
*Subscription may be required

Abstract

The potential energy surface is mapped out for all plausible reactions in the self-decomposition of perfluorobutanoic acid (CF 3CF 2CF 2COOH) 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 (CF 3CF 2COF) and the closed-shell singlet CF 3CF 2CF:. Direct elimination of CO 2 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.

Item Type: Journal Article
Publisher: Elsevier BV
Copyright: © 2012 Elsevier Ltd.
URI: http://researchrepository.murdoch.edu.au/id/eprint/22653
Item Control Page Item Control Page