Biodegradation of Polyfluoroalkyl Phosphates as a Source of Perfluorinated Acids to the Environment
Abstract
Wastewater treatment plants (WWTPs) have been identified as a major source of perfluorocarboxylates (PFCAs) to aqueous environments. The observed increase in PFCA mass flows from WWTP influent to effluent suggests the biodegradation of commercial fluorinated materials within the WWTP. Commercial fluorinated surfactants are used as greaseproofing agents in food-contact paper products as well as leveling and wetting agents. As WWTPs are likely the major fate of these surfactants, their biodegradation may be a source of PFCA production. One class of commercial surfactants, the polyfluoroalkyl phosphates (PAPs), have been observed in WWTP sludge. While PAPs have been shown to degrade into PFCAs in a rat model, the present study investigates their microbial fate to determine whether the biodegradation of PAPs within a WWTP-simulated system will contribute to the load of PFCAs released. PAPs are applied commercially in mixed formulations of different chain lengths and substitution at the phosphate center. The effect of chain length and phosphate substitution on the biodegradation of PAPs was investigated by incubating mixtures of 4:2, 6:2, 8:2, and 10:2 monosubstituted PAPs (monoPAPs) in an aerobic microbial system and by separately incubating the 6:2 monoPAP and 6:2 disubstituted PAP (diPAP) for 92 days. Headspace sampling revealed production of the fluorotelomer alcohols (FTOHs) from the hydrolysis of the PAP phosphate ester linkages. Analysis of the aqueous phase revealed microbial transformation of the PAPs to the final PFCA products was possible. The majority of the oxidation products observed were consistent with previous investigations that have suggested fluorotelomer precursor compounds degrade predominantly via a beta-oxidation-like mechanism. However, in this study, the detection of odd-chain PFCAs suggests that other pathways may be important. The present study demonstrated microbially mediated biodegradation of PAPs to PFCAs. This observation, together with the diPAP concentrations observed in WWTP sludge, suggest PAPs-containing commercial products may be a significant contributor to the increased PFCA mass flows observed in WWTP effluents.
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Sequential hydrolysis of the phosphodiester bonds from triPAP was demonstrated with the detection of 6:2 diPAP, 6:2 monoPAP and 6:2 FTOH that then entered the FTOH degradation pathway.
“In the study, sequential hydrolysis of the phosphodiester bonds from triPAP was demonstrated with the detection of 6:2 diPAP, 6:2 monoPAP and 6:2 FTOH that then entered the FTOH degradation pathway.”
From A review of microbial degradation of per- and polyfluoroalkyl substances (PFAS): Biotransformation routes and enzymes (2023) · cites this paper as Lee et al., 2010
Microbial hydrolysis of 6:2 mono- and di-PAPs into 6:2 FTOH was demonstrated in WWTP activated sludge.
“The microbial hydrolysis of 6:2 mono- and di- PAPs into 6:2 FTOH was demonstrated in WWTP activated sludge (Lee et al., 2010).”
From A review of microbial degradation of per- and polyfluoroalkyl substances (PFAS): Biotransformation routes and enzymes (2023) · cites this paper as Lee et al., 2010
DiPAPs can degrade to more stable PFAAs.
“DiPAPs can degrade to more stable PFAAs”
From Release of per- and polyfluoroalkyl substances (PFAS) from a waste management facility fire to an urban creek (2022) · cites this paper as Lee et al., 2010
Microbial degradation of 6:2 PAP and 6:2 diPAP using WWTP aerobic microbes has been shown to produce 6:2 FTOH, which was then degraded further to PFHxA.
“Microbial degradation of the compounds 6:2 PAP and 6:2 diPAP using WWTP aerobic microbes has been shown to produce 6:2 FTOH, which was then degraded further to PFHxA [59].”
From An investigation into per- and polyfluoroalkyl substances (PFAS) in nineteen Australian wastewater treatment plants (WWTPs) (2019) · cites this paper as [59]
Cites
Fluorotelomer Alcohol BiodegradationDirect Evidence that Perfluorinated Carbon Chains Breakdown
Wang, N., Szostek, B., Buck, R. C., Folsom, P. W., Sulecki, L. M., Capka, V., Berti, W. R., & Gannon, J. T. (2005) · Environmental Science & Technology · doi:10.1021/es0506760 · Cited by 260 · see citing works
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Buck, R. C., Franklin, J., Berger, U., Conder, J. M., Cousins, I. T., de Voogt, P., Jensen, A. A., Kannan, K., Mabury, S. A., & van Leeuwen, S. P. (2011) · Integrated Environmental Assessment and Management · doi:10.1002/ieam.258 · Cited by 4,641 · see citing works
Self-citationPer- and polyfluoroalkyl substances in the environment
Evich, M. G., Davis, M. J. B., McCord, J. P., Acrey, B., Awkerman, J. A., Knappe, D. R. U., Lindstrom, A. B., Speth, T. F., Tebes-Stevens, C., Strynar, M. J., et al. (2022) · Science · doi:10.1126/science.abg9065 · Cited by 2,157 · see citing works
Risk to human health related to the presence of perfluoroalkyl substances in food
Panel), E. P. O. C. I. T. F. C. (. C., Schrenk, D., Bignami, M., Bodin, L., Chipman, J. K., del Mazo, J., Grasl‐Kraupp, B., Hogstrand, C., Hoogenboom, L. (., Leblanc, J., et al. (2020) · EFSA Journal · doi:10.2903/j.efsa.2020.6223 · Cited by 989 · see citing works
Wang, Z., Cousins, I. T., Scheringer, M., & Hungerbühler, K. (2013) · Environment International · doi:10.1016/j.envint.2013.08.021 · Cited by 924 · see citing works
Trends in Exposure to Polyfluoroalkyl Chemicals in the U.S. Population: 1999−2008
Kato, K., Wong, L.-Y., Jia, L. T., Kuklenyik, Z., & Calafat, A. M. (2011) · Environmental Science & Technology · doi:10.1021/es1043613 · Cited by 777 · see citing works
Wang, Z., Cousins, I. T., Scheringer, M., Buck, R. C., & Hungerbühler, K. (2014) · Environment International · doi:10.1016/j.envint.2014.04.013 · Cited by 735 · see citing works
Post, G. B., Cohn, P. D., & Cooper, K. R. (2012) · Environmental Research · doi:10.1016/j.envres.2012.03.007 · Cited by 639 · see citing works
A review of emerging technologies for remediation of PFASs
Ross, I., McDonough, J., Miles, J., Storch, P., Thelakkat Kochunarayanan, P., Kalve, E., Hurst, J., S. Dasgupta, S., & Burdick, J. (2018) · Remediation Journal · doi:10.1002/rem.21553 · Cited by 606 · see citing works
Microbial degradation of polyfluoroalkyl chemicals in the environment: A review
Liu, J., & Mejia Avendaño, S. (2013) · Environment International · doi:10.1016/j.envint.2013.08.022 · Cited by 525 · see citing works
Houtz, E. F., Sutton, R., Park, J.-S., & Sedlak, M. (2016) · Water Research · doi:10.1016/j.watres.2016.02.055 · Cited by 374 · see citing works
Bolan, N., Sarkar, B., Yan, Y., Li, Q., Wijesekara, H., Kannan, K., Tsang, D. C. W., Schauerte, M., Bosch, J., Noll, H., et al. (2021) · Journal of Hazardous Materials · doi:10.1016/j.jhazmat.2020.123892 · Cited by 375 · see citing works
Review of the fate and transformation of per- and polyfluoroalkyl substances (PFASs) in landfills
Hamid, H., Li, L. Y., & Grace, J. R. (2018) · Environmental Pollution · doi:10.1016/j.envpol.2017.12.030 · Cited by 343 · see citing works
Wang, N., Liu, J., Buck, R. C., Korzeniowski, S. H., Wolstenholme, B. W., Folsom, P. W., & Sulecki, L. M. (2011) · Chemosphere · doi:10.1016/j.chemosphere.2010.11.003 · Cited by 333 · see citing works
Coggan, T. L., Moodie, D., Kolobaric, A., Szabo, D., Shimeta, J., Crosbie, N. D., Lee, E., Fernandes, M., & Clarke, B. O. (2019) · Heliyon · doi:10.1016/j.heliyon.2019.e02316 · Cited by 327 · see citing works
“7 was then degraded further to PFHxA [59].”
BackgroundEnvironmental Mass Spectrometry: Emerging Contaminants and Current Issues
Richardson, S. D. (2012) · Analytical Chemistry · doi:10.1021/ac202903d · Cited by 323 · see citing works
Per- and polyfluorinated substances (PFASs): Environmental challenges
Krafft, M. P., & Riess, J. G. (2015) · Current Opinion in Colloid & Interface Science · doi:10.1016/j.cocis.2015.07.004 · Cited by 294 · see citing works
Harding-Marjanovic, K. C., Houtz, E. F., Yi, S., Field, J. A., Sedlak, D. L., & Alvarez-Cohen, L. (2015) · Environmental Science & Technology · doi:10.1021/acs.est.5b01219 · Cited by 295 · see citing works
Phong Vo, H. N., Ngo, H. H., Guo, W., Hong Nguyen, T. M., Li, J., Liang, H., Deng, L., Chen, Z., & Hang Nguyen, T. A. (2020) · Journal of Water Process Engineering · doi:10.1016/j.jwpe.2020.101393 · Cited by 291 · see citing works
Berhanu, A., Mutanda, I., Taolin, J., Qaria, M. A., Yang, B., & Zhu, D. (2023) · Science of The Total Environment · doi:10.1016/j.scitotenv.2022.160010 · Cited by 294 · see citing works
Per- and Polyfluoroalkyl Substances in Landfill Leachate: Patterns, Time Trends, and Sources
Benskin, J. P., Li, B., Ikonomou, M. G., Grace, J. R., & Li, L. Y. (2012) · Environmental Science & Technology · doi:10.1021/es302471n · Cited by 258 · see citing works
Eriksson, U., Haglund, P., & Kärrman, A. (2017) · Journal of Environmental Sciences · doi:10.1016/j.jes.2017.05.004 · Cited by 225 · see citing works
De Silva, A. O., Spencer, C., Scott, B. F., Backus, S., & Muir, D. C. G. (2011) · Environmental Science & Technology · doi:10.1021/es200135c · Cited by 214 · see citing works
D’eon, J. C., & Mabury, S. A. (2011) · Environmental Health Perspectives · doi:10.1289/ehp.1002409 · Cited by 193 · see citing works
Self-citationZhang, S., Szostek, B., McCausland, P. K., Wolstenholme, B. W., Lu, X., Wang, N., & Buck, R. C. (2013) · Environmental Science & Technology · doi:10.1021/es4000824 · Cited by 198 · see citing works
Xiao, F., Halbach, T. R., Simcik, M. F., & Gulliver, J. S. (2012) · Water Research · doi:10.1016/j.watres.2012.03.027 · Cited by 191 · see citing works
Yao, Y., Zhao, Y., Sun, H., Chang, S., Zhu, L., Alder, A. C., & Kannan, K. (2018) · Environmental Science & Technology · doi:10.1021/acs.est.7b04971 · Cited by 177 · see citing works
Analysis of perfluoroalkyl substances in waters from Germany and Spain
Llorca, M., Farré, M., Picó, Y., Müller, J., Knepper, T. P., & Barceló, D. (2012) · Science of The Total Environment · doi:10.1016/j.scitotenv.2012.05.011 · Cited by 170 · see citing works
Benskin, J. P., Ikonomou, M. G., Gobas, F. A. P. C., Begley, T. H., Woudneh, M. B., & Cosgrove, J. R. (2013) · Environmental Science & Technology · doi:10.1021/es304336r · Cited by 169 · see citing works
Fujii, Y., Harada, K. H., & Koizumi, A. (2013) · Chemosphere · doi:10.1016/j.chemosphere.2013.06.049 · Cited by 162 · see citing works
Houtz, E., Wang, M., & Park, J.-S. (2018) · Environmental Science & Technology · doi:10.1021/acs.est.8b04028 · Cited by 145 · see citing works
Occurrence of perfluorinated compounds in raw water from New Jersey public drinking water systems
Post, G. B., Louis, J. B., Lippincott, R. L., & Procopio, N. A. (2013) · Environmental Science & Technology · doi:10.1021/es402884x · Cited by 130 · see citing works
Allred, B. M., Lang, J. R., Barlaz, M. A., & Field, J. A. (2015) · Environmental Science & Technology · doi:10.1021/acs.est.5b01040 · Cited by 124 · see citing works
Aerobic biotransformation of polyfluoroalkyl phosphate esters (PAPs) in soil
Liu, C., & Liu, J. (2016) · Environmental Pollution · doi:10.1016/j.envpol.2016.01.069 · Cited by 121 · see citing works
Uptake, accumulation and metabolism of PFASs in plants and health perspectives: A critical review
Jiao, X., Shi, Q., & Gan, J. (2021) · Critical Reviews in Environmental Science and Technology · doi:10.1080/10643389.2020.1809219 · Cited by 121 · see citing works
Filipovic, M., & Berger, U. (2015) · Chemosphere · doi:10.1016/j.chemosphere.2014.07.082 · Cited by 91 · see citing works
Liu, Y., Robey, N. M., Bowden, J. A., Tolaymat, T. M., da Silva, B. F., Solo-Gabriele, H. M., & Townsend, T. G. (2021) · Environmental Science & Technology Letters · doi:10.1021/acs.estlett.0c00819 · Cited by 89 · see citing works
Benskin, J. P., Ikonomou, M. G., Gobas, F. A. P. C., Woudneh, M. B., & Cosgrove, J. R. (2012) · Environmental Science & Technology · doi:10.1021/es300823m · Cited by 72 · see citing works
Dauchy, X., Boiteux, V., Rosin, C., & Munoz, J.-F. (2012) · Bulletin of Environmental Contamination and Toxicology · doi:10.1007/s00128-012-0704-x · Cited by 66 · see citing works
Sun, H., Zhang, X., Wang, L., Zhang, T., Li, F., He, N., & Alder, A. C. (2012) · Environmental Science and Pollution Research · doi:10.1007/s11356-011-0727-6 · Cited by 62 · see citing works
Guo, R., Megson, D., Myers, A. L., Helm, P. A., Marvin, C., Crozier, P., Mabury, S., Bhavsar, S. P., Tomy, G., Simcik, M., et al. (2016) · Chemosphere · doi:10.1016/j.chemosphere.2016.08.126 · Cited by 58 · see citing works
Self-citationAirborne precursors predict maternal serum perfluoroalkyl acid concentrations
Makey, C. M., Webster, T. F., Martin, J. W., Shoeib, M., Harner, T., Dix-Cooper, L., & Webster, G. M. (2017) · Environmental Science & Technology · doi:10.1021/acs.est.7b00615 · Cited by 54 · see citing works
Dauchy, X., Boiteux, V., Rosin, C., & Munoz, J.-F. (2012) · Bulletin of Environmental Contamination and Toxicology · doi:10.1007/s00128-012-0705-9 · Cited by 53 · see citing works
Peter, L. G., & Lee, L. S. (2025) · Environmental Science & Technology · doi:10.1021/acs.est.4c09490 · Cited by 40 · see citing works
Methodology for studying biotransformation of polyfluoroalkyl precursors in the environment
Ruan, T., Lin, Y., Wang, T., Jiang, G., & Wang, N. (2015) · TrAC Trends in Analytical Chemistry · doi:10.1016/j.trac.2014.11.017 · Cited by 37 · see citing works
Biotransformation of 8:2 polyfluoroalkyl phosphate diester in gilthead bream (Sparus aurata)
Zabaleta, I., Bizkarguenaga, E., Izagirre, U., Negreira, N., Covaci, A., Benskin, J. P., Prieto, A., & Zuloaga, O. (2017) · Science of The Total Environment · doi:10.1016/j.scitotenv.2017.07.241 · Cited by 34 · see citing works
Hsu, J.-Y., Hsu, J.-F., Ho, H.-H., Chiang, C.-F., & Liao, P.-C. (2013) · Chemosphere · doi:10.1016/j.chemosphere.2013.06.047 · Cited by 32 · see citing works
Rand, A. A., & Mabury, S. A. (2012) · Environmental Science & Technology · doi:10.1021/es3008485 · Cited by 30 · see citing works
Self-citationAlghamdi, W., Marchiandi, J., Szabo, D., Samandra, S., & Clarke, B. O. (2022) · Journal of Hazardous Materials Advances · doi:10.1016/j.hazadv.2022.100167 · Cited by 19 · see citing works
- Authors
- Lee, H., D’eon, J., & Mabury, S. A.
- Affiliations
- University of Toronto (CA)
- Corresponding author
- Mabury, Scott A.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-03-31
- Volume
- 44
- Issue
- 9
- Pages
- 3305-3310
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W2079139182
- Cited by
- 288
- References
- 1
- Citations by year
- 2026: 24 · 2025: 27 · 2024: 19 · 2023: 19 · 2022: 19 · 2021: 18 · 2020: 17 · 2019: 9 · 2018: 14 · 2017: 17 · 2016: 13 · 2015: 15 · 2014: 14 · 2013: 23 · 2012: 19
- FWCI
- 16.94
- 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
- Physical Sciences › Environmental Science › Pollution › Pharmaceutical and Antibiotic Environmental Impacts
- Keywords
- perfluorocarboxylic acids, biodegradation, wastewater treatment plants, fluorinated surfactants, fluorotelomer alcohols, phosphate ester hydrolysis, fatty acid beta-oxidation, microbial transformation, chain length effects, phosphate substitution
- MeSH terms
- Acids, Animals, Biodegradation, Environmental, Fluorine, Humans, Hydrolysis, Industrial Waste, Paper, Phosphates, Surface-Active Agents, Water Microbiology, Water Pollutants, Chemical, Fluorine Compounds, Water Purification, Rats
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