Journal article
A theoretical study on the pyrolysis of perfluorobutanoic acid as a model compound for perfluoroalkyl acids
Tetrahedron Letters, Vol.53(32), pp.4070-4073
2012
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.
Details
- Title
- A theoretical study on the pyrolysis of perfluorobutanoic acid as a model compound for perfluoroalkyl acids
- Authors/Creators
- M. Altarawneh (Author/Creator)
- Publication Details
- Tetrahedron Letters, Vol.53(32), pp.4070-4073
- Publisher
- Elsevier BV
- Identifiers
- 991005545207607891
- Copyright
- © 2012 Elsevier Ltd.
- Murdoch Affiliation
- Murdoch University
- Language
- English
- Resource Type
- Journal article
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- Citation topics
- 3 Agriculture, Environment & Ecology
- 3.60 Herbicides, Pesticides & Ground Poisoning
- 3.60.1998 PFAS Toxicity
- Web Of Science research areas
- Chemistry, Organic
- ESI research areas
- Chemistry