Degradation of Perfluoroalkyl Ether Carboxylic Acids with Hydrated Electrons: Structure–Reactivity Relationships and Environmental Implications

Published on Feb 18, 2020in Environmental Science & Technology7.149
· DOI :10.1021/acs.est.9b05869
Michael J. Bentel1
Estimated H-index: 1
(UCR: University of California, Riverside),
Yaochun Yu3
Estimated H-index: 3
(UIUC: University of Illinois at Urbana–Champaign)
+ 5 AuthorsJinyong Liu9
Estimated H-index: 9
(UCR: University of California, Riverside)
This study explores structure–reactivity relationships for the degradation of emerging perfluoroalkyl ether carboxylic acid (PFECA) pollutants with ultraviolet-generated hydrated electrons (eaq–). The rate and extent of PFECA degradation depend on both the branching extent and the chain length of oxygen-segregated fluoroalkyl moieties. Kinetic measurements, theoretical calculations, and transformation product analyses provide a comprehensive understanding of the PFECA degradation mechanisms and pathways. In comparison to traditional full-carbon-chain perfluorocarboxylic acids, the distinct degradation behavior of PFECAs is attributed to their ether structures. The ether oxygen atoms increase the bond dissociation energy of the C–F bonds on the adjacent −CF2– moieties. This impact reduces the formation of H/F-exchanged polyfluorinated products that are recalcitrant to reductive defluorination. Instead, the cleavage of ether C–O bonds generates unstable perfluoroalcohols and thus promotes deep defluorinatio...
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