Perfluorinated alkyl acids (PFAAs) are some of the most environmentally persistent organic compounds known to date. A completely oxidized polar group and strong hydrophobic C-F bonds (~116 kcal/mol) contribute toward the insusceptibility of these molecules to degradation in orthodox environmental conditions. Increasing concerns over the environmental and health impacts of these molecules have warranted the exploration of their possible degradation mechanisms. Several experimental methods have been developed to oxidize and activate PFAAs however; a consensus on the mechanistic pathways following the generation of the PFAA radical has yet to be reached. To this end, we investigated various pathways involved in the breakdown of model PFAA using Density Functional Theory (DFT) computations. Our preliminary computational work suggests varying solution conditions, including pH, the nature of the oxidant and temperature impact the resulting degradation mechanism. We will highlight several mechanistic pathways, possessing a predictive capacity for PFAA breakdown intermediates commonly observed in a variety of PFAA oxidation schemes including electrochemical and persulfate oxidation.  Elucidation of PFOA degradation pathways provide insights into not only the crucial reaction steps involved but also the potential chemical processes or materials that could facilitate faster degradation kinetics.<br/>

Perfluorinated alkyl acid degradation mechanisms probed by chemical computations

251st National Meeting (2016)

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