title: Fluorotelomer alcohol biodegradation yields poly- and perfluorinated acids.
abstract: The widespread detection of environmentally persistent perfluorinated acids (PFCAs) such as perfluorooctanoic acid (PFOA) and its longer chained homologues (C9>C15) in biota has instigated a need to identify potential sources. It has recently been suggested that fluorinated telomer alcohols (FTOHs) are probable precursor compounds that may undergo transformation reactions in the environment leading to the formation of these potentially toxic and bioaccumulative PFCAs. This study examined the aerobic biodegradation of the 8:2 telomer alcohol (8:2 FTOH, CF3(CF2)7CH2CH2OH) using a mixed microbial system. The initial measured half-life of the 8:2 FTOH was approximately 0.2 days mg(-1) of initial biomass protein. The degradation of the telomer alcohol was monitored using a gas chromatograph equipped with an electron capture detector (GC/ECD). Volatile metabolites were identified using gas chromatography/ mass spectrometry (GC/MS), and nonvolatile metabolites were identified and quantified using liquid chromatography/ tandem mass spectrometry (LC/MS/MS). Telomer acids (CF3(CF2)7CH2COOH; CF3(CF2)6CFCHCOOH) and PFOA were identified as metabolites during the degradation, the unsaturated telomer acid being the predominant metabolite measured. The overall mechanism involves the oxidation of the 8:2 FTOH to the telomer acid via the transient telomer aldehyde. The telomer acid via a beta-oxidation mechanism was furthertransformed, leading to the unsaturated acid and ultimately producing the highly stable PFOA. Telomer alcohols were demonstrated to be potential sources of PFCAs as a consequence of biotic degradation. Biological transformation may be a major degradation pathway for fluorinated telomer alcohols in aquatic systems.
authors.affiliation: Department of Chemistry, University of Toronto, 80 Saint George Street, Toronto, Ontario, Canada M5S 3H6.
authors.forename: Mary Joyce A
authors.initials: MJ
authors.lastname: Dinglasan
authors.forename: Yun
authors.initials: Y
authors.lastname: Ye
authors.forename: Elizabeth A
authors.initials: EA
authors.lastname: Edwards
authors.forename: Scott A
authors.initials: SA
authors.lastname: Mabury
mesh_terms: D001420:Bacteria, Aerobic / Q000378:metabolism; D001673:Biodegradation, Environmental; D002853:Chromatography, Liquid / Q000379:methods; D003652:Decanoic Acids / Q000737:chemistry / Q000378:metabolism; D004785:Environmental Pollutants / Q000378:metabolism; D005227:Fatty Acids / Q000737:chemistry / Q000378:metabolism*; D005233:Fatty Alcohols / Q000737:chemistry / Q000378:metabolism*; D005466:Fluorocarbons / Q000737:chemistry / Q000378:metabolism*; D005618:Fresh Water; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D019015:Geologic Sediments; D010084:Oxidation-Reduction; D012722:Sewage
chemical_list: D003652:Decanoic Acids; D004785:Environmental Pollutants; D005227:Fatty Acids; D005233:Fatty Alcohols; D005466:Fluorocarbons; D012722:Sewage; C036567:perfluorodecanoic acid