Aerobic biotransformation of a novel highly functionalized polyfluoroether-based surfactant using activated sludge from a wastewater treatment plant

Abstract

A replacement fluorosurfactant has been recently introduced to the European market as an alternative to other per- and polyfluoroalkyl substances (PFAS) that have been phased-out or banned. Here, we incubated this novel fluorosurfactant (diFESOS, [F₇C₃OCHFCF₂SCH₂CH₂OC(O)]₂C₂H₃SO₃⁻) which contains ether and thioether insertions, and its known polyfluoroalkyl degradation products, an alcohol (FESOH) and carboxylic acid (FESCA), with activated sludge from a wastewater treatment plant under sulfur-limited conditions. Dosed chemicals and their transformation products were monitored using ultra-high performance liquid chromatography-tandem mass spectrometry, and gas chromatography-mass spectrometry. In addition to FESOH and FESCA, two smaller metabolites were identified: C₃F₇OCHFCOO⁻ (2H-3:2 PFECA) and perfluoropropanoic acid (PFPrA). 2H-3:2 PFECA presumably was a result of S-dealkylation of FESCA, which then resulted in the abiotic cleavage of two C–F bonds; no S-oxygenation was observed. Overall, the terminal products of this biotransformation likely have lower bioaccumulation potential than the parent fluorosurfactant based on comparison to other similar PFAS.