Low-Temperature Mineralization of Fluorotelomers with Diverse Polar Head Groups

Richard J. Monsky, Yuli Li, K. N. Houk*, William R. Dichtel*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Per- and polyfluoroalkyl substances (PFAS) are persistent environmental pollutants linked to harmful health effects. Currently employed PFAS destruction methods are energy-intensive and often produce shorter-chain and recalcitrant partially fluorinated byproducts. We report the mineralization of five fluorotelomer compounds via a base-mediated degradation using NaOH and mild temperatures (120 °C) in a mixture of DMSO:H2O (8:1 v/v). The studied fluorotelomers have varying polar head groups-carboxylic acids, sulfonic acids, alcohols, and phosphonic acids, which are the most common polar head groups used in commercial and industrial applications. The degradation intermediates and byproducts were characterized using 1H, 13C, and 19F NMR spectroscopy. Density functional theory computations at the M06-2X/6-311 + G(2d,p)-SMD-(DMSO) level were consistent with the observed intermediates and guided an overall mechanistic hypothesis. Degradation of each fluorotelomer occurs through a similar process, in which the nonfluorinated carbons and the first fluorinated carbon are cleaved from the remaining perfluoroalkyl fragment, which degrades through previously identified pathways. These findings provide important insight into PFAS degradation processes and suggest that PFAS containing at least one C-H bond within or adjacent to its fluoroalkyl chain can be degraded under these mild conditions. Many PFAS in current use as well as recalcitrant fluorinated byproducts generated from other PFAS degradation methods are candidates for this approach.

Original languageEnglish (US)
Pages (from-to)17150-17157
Number of pages8
JournalJournal of the American Chemical Society
Volume146
Issue number25
DOIs
StatePublished - Jun 26 2024

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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