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.
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PFOA and PFOS were the dominant PFAS compounds and were thought to be the final transformation products of other PFASs.
“Many studies found that perfluorooctanoic acid (PFOA) and perfluorooctanesulfonic acid (PFOS) were the dominant compounds and they were believed to be the final transformation products of other PFASs”
From Short- and long-chain perfluoroalkyl substances in the water, suspended particulate matter, and surface sediment of a turbid river (2016) · cites this paper as Dinglasan et al., 2004
Though these surfactants are less persistent in the environment than their perfluoroalkyl analogues, they have been shown to degrade to PFAAs which are highly persistent.
“Though these surfactants are less persistent in the environment than their perfluoroalkyl analogues, they have been shown to degrade to PFAAs which are highly persistent”
From Release of per- and polyfluoroalkyl substances (PFAS) from a waste management facility fire to an urban creek (2022) · cites this paper as Dinglasan et al., 2004
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- Authors
- Dinglasan, M. J. A., Ye, Y., Edwards, E. A., & Mabury, S. A.
- Affiliations
- Department of Chemistry, University of Toronto, 80 Saint George Street, Toronto, Ontario, Canada M5S 3H6, and Department of Chemical Engineering and Applied Chemistry, University of Toronto, 200 College Street, Toronto, Ontario, Canada M5S 3E5
- University of Toronto (CA)
- Corresponding author
- Mabury, Scott A.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-04-16
- Volume
- 38
- Issue
- 10
- Pages
- 2857-2864
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W2054851279
- Cited by
- 554
- References
- 17
- Citations by year
- 2026: 23 · 2025: 34 · 2024: 40 · 2023: 21 · 2022: 32 · 2021: 23 · 2020: 17 · 2019: 12 · 2018: 12 · 2017: 19 · 2016: 26 · 2015: 19 · 2014: 16 · 2013: 31 · 2012: 30
- FWCI
- 16.45
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Environmental Science & Technology (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Environmental Science › Environmental Chemistry › Per- and polyfluoroalkyl substances research
- Physical Sciences › Environmental Science › Environmental Chemistry › Environmental Chemistry and Analysis
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmaceutical Science › Fluorine in Organic Chemistry
- Keywords
- fluorotelomer alcohols, perfluorinated carboxylic acids, perfluorooctanoic acid, aerobic biodegradation, microbial degradation, fatty acid beta-oxidation, biotransformation, aquatic ecosystems, half-life
- MeSH terms
- Bacteria, Aerobic, Biodegradation, Environmental, Chromatography, Liquid, Decanoic Acids, Environmental Pollutants, Fatty Acids, Fatty Alcohols, Fluorocarbons, Fresh Water, Gas Chromatography-Mass Spectrometry, Oxidation-Reduction, Sewage, Geologic Sediments
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