Microbial Defluorination of Unsaturated Per- and Polyfluorinated Carboxylic Acids under Anaerobic and Aerobic Conditions: A Structure Specificity Study
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High Resolution Image Download MS PowerPoint Slide The recently discovered microbial reductive defluorination of two C 6 branched and unsaturated fluorinated carboxylic acids (FCAs) provided valuable insights into the environmental fate of per- and polyfluoroalkyl substances (PFASs) and potential bioremediation strategies. However, a systematic investigation is needed to further demonstrate the role of C═C double bonds in the biodegradability of unsaturated PFASs. Here, we examined the structure-biodegradability relationships of 13 FCAs, including nine commercially available unsaturated FCAs and four structurally similar saturated ones, in an anaerobic defluorinating enrichment and an activated sludge community. The anaerobic and aerobic transformation/defluorination pathways were elucidated. The results showed that under anaerobic conditions, the α,β-unsaturation is crucial for FCA biotransformation via reductive defluorination and/or hydrogenation pathways. With sp 2 C–F bonds being substituted by C–H bonds, the reductive defluorination became less favorable than hydrogenation. Moreover, for the first time, we reported enhanced degradability and defluorination capability of specific unsaturated FCA structures with trifluoromethyl (−CF 3 ) branches at the α/β-carbon. Such FCA structures can undergo anaerobic abiotic defluorination in the presence of reducing agents and significant aerobic microbial defluorination. Given the diverse applications and emerging concerns of fluorochemicals, this work not only advances the fundamental understanding of the fate of unsaturated PFASs in natural and engineered environments but also may provide insights into the design of readily degradable fluorinated alternatives to existing PFAS compounds.
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α,β unsaturation is critical for anaerobic reductive defluorination of unsaturated PFAS, and unsaturated fluorinated carboxylic acids with α/β-trifluoromethyl branches have enhanced degradability.
“Another study investigated the role of carbon–carbon double bonds in the biodegradation of unsaturated PFAS, showing that α,β unsaturation is critical for anaerobic reductive defluorination and highlighting the enhanced degradability of unsaturated fluorinated carboxylic acids with α/β-trifluoromethyl branches [76].”
From The EU’s Per- and Polyfluoroalkyl Substances (PFAS) Ban: A Case of Policy over Science (2023) · cites this paper as [76]
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- Authors
- Yu, Y., Che, S., Ren, C., Jin, B., Tian, Z., Liu, J., & Men, Y.
- Affiliations
- University of California, Riverside (US)
- Northeastern University (US)
- Corresponding author
- Men, Yujie
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2022-04-04
- Volume
- 56
- Issue
- 8
- Pages
- 4894-4904
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- PMC
- PMC9465985
- OpenAlex
- W4224275005
- Cited by
- 143
- References
- 47
- Citations by year
- 2026: 38 · 2025: 45 · 2024: 36 · 2023: 18 · 2022: 6
- FWCI
- 9.30
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Environmental Science & Technology (publishedVersion, cc-by-nc-nd)
- PubMed Central (publishedVersion, cc-by-nc-nd)
- PubMed (publishedVersion)
- eScholarship (California Digital Library) (submittedVersion, cc-by-nc-nd)
- Funders
- National Institute of Environmental Health Sciences (1R01ES032668-01)
- National Science Foundation (1931941)
- Strategic Environmental Research and Development Program (ER20-1541)
- Topics
- Physical Sciences › Environmental Science › Environmental Chemistry › Per- and polyfluoroalkyl substances research
- Physical Sciences › Environmental Science › Pollution › Microbial bioremediation and biosurfactants
- Physical Sciences › Environmental Science › Environmental Chemistry › Environmental Chemistry and Analysis
- Keywords
- reductive defluorination, C=C double bond, hydrogenation, activated sludge, anaerobic enrichment cultures, trifluoromethyl group, bioremediation
- MeSH terms
- Anaerobiosis, Biodegradation, Environmental, Carboxylic Acids, Fluorocarbons, Sewage
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