A theoretical study on the pyrolysis of perfluorobutanoic acid as a model compound for perfluoroalkyl acids
Altarawneh, M. (2012) A theoretical study on the pyrolysis of perfluorobutanoic acid as a model compound for perfluoroalkyl acids. Tetrahedron Letters, 53 (32). pp. 4070-4073.
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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.
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|Copyright:||© 2012 Elsevier Ltd.|
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