Observation of a novel PFOS-precursor, the perfluorooctane sulfonamido ethanol-based phosphate (SAmPAP) diester, in marine sediments
Abstract
The environmental occurrence of perfluorooctane sulfonate (PFOS) can arise from its direct use as well as from transformation of precursors ((N-alkyl substituted) perfluorooctane sulfonamides; FOSAMs). Perfluorooctane sulfonamidoethanol-based phosphate (SAmPAP) esters are among numerous potential PFOS-precursors which have not been previously detected in the environment and for which little is known about their stability. Based on their high production volume during the 1970s-2002 and widespread use in food contact paper and packaging, SAmPAP esters may be potentially significant sources of PFOS. Here we report for the first time on the environmental occurrence of SAmPAP diester in marine sediments from an urbanized marine harbor in Vancouver, Canada. SAmPAP diester concentrations in sediment (40-200 pg/g dry weight) were similar to those of PFOS (71-180 pg/g). A significant (p < 0.05) correlation was observed between SAmPAP diester and N-ethyl perfluorooctane sulfonamido acetate (an anticipated degradation product of SAmPAP diester). ∑PFOS-precursor (FOSAM) concentrations in sediment (120-1100 pg/g) were 1.6-24 times greater than those of PFOS in sediment. Although SAmPAP diester was not detected in water, PFOS was observed at concentrations up to 710 pg/L. Among the per- and polyfluoroalkyl substances monitored in the present work, mean log-transformed sediment/water distribution coefficients ranged from 2.3 to 4.3 and increased with number of CF(2) units and N-alkyl substitution (in the case of FOSAMs). Overall, these results highlight the importance of FOSAMs as potentially significant sources of PFOS, in particular for urban marine environments.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
PFOS is known to be a final transformation product of some PFASs, including N-alkyl substituted perfluorooctane sulfonamides and N-ethyl perfluorooctane sulfonamido ethanol.
“This is because PFOS is known to be the final transformation product of some PFASs such as (N-alkyl substituted) perfluorooctane sulfonamides and N-ethyl perfluorooctane sulfonamido ethanol (D'eon et al., 2006;Benskin et al., 2012;Zhao et al., 2016).”
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 Benskin et al., 2012
PFOS precursors transform to PFOS in air, water (including wastewater treatment), and soils.
“The transformation of PFOS-precursors to PFOS happens in air, water (including waste water treatment), and soils.”
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 Benskin et al., 2012
DiSAmPAP was first detected in marine sediments in Vancouver, Canada, at a concentration comparable to PFOS.
“As a potential significant source of PFOS, DiSAmPAP was first detected in marine sediments in Vancouver, Canada, at a concentration comparable to PFOS (Benskin et al., 2012).”
From Biotransformation of perfluoroalkyl acid precursors from various environmental systems: advances and perspectives (2021) · cites this paper as Benskin et al., 2012
Cites
Global Distribution of Perfluorooctane Sulfonate in Wildlife
Giesy, J. P., & Kannan, K. (2001) · Environmental Science & Technology · doi:10.1021/es001834k · Cited by 2,750 · see citing works
Perfluoroalkyl Acids: A Review of Monitoring and Toxicological Findings
Lau, C., Anitole, K., Hodes, C., Lai, D., Pfahles-Hutchens, A., & Seed, J. (2007) · Toxicological Sciences · doi:10.1093/toxsci/kfm128 · Cited by 2,620 · see citing works
Sorption of Perfluorinated Surfactants on Sediments
Higgins, C. P., & Luthy, R. G. (2006) · Environmental Science & Technology · doi:10.1021/es061000n · Cited by 1,563 · see citing works
Perfluorinated compounds – Exposure assessment for the general population in western countries
Fromme, H., Tittlemier, S. A., Völkel, W., Wilhelm, M., & Twardella, D. (2008) · International Journal of Hygiene and Environmental Health · doi:10.1016/j.ijheh.2008.04.007 · Cited by 963 · see citing works
A global survey of perfluorinated acids in oceans
Yamashita, N., Kannan, K., Taniyasu, S., Horii, Y., Petrick, G., & Gamo, T. (2005) · Marine Pollution Bulletin · doi:10.1016/j.marpolbul.2005.04.026 · Cited by 639 · see citing works
Quantitative determination of perfluorochemicals in sediments and domestic sludge.
Higgins, C., Field, J., Criddle, C., & Luthy, R. (2005) · Environmental Science and Technology · doi:10.1021/es048245p · Cited by 585 · see citing works
Identifying New Persistent and Bioaccumulative Organics Among Chemicals in Commerce
Howard, P. H., & Muir, D. C. G. (2010) · Environmental Science & Technology · doi:10.1021/es903383a · Cited by 434 · see citing works
Powley, C. R., George, S. W., Ryan, T. W., & Buck, R. C. (2005) · Analytical Chemistry · doi:10.1021/ac0508090 · Cited by 396 · see citing works
Martin, J. W., Ellis, D. A., Mabury, S. A., Hurley, M. D., & Wallington, T. J. (2005) · Environmental Science & Technology · doi:10.1021/es051362f · Cited by 318 · see citing works
You, C., Jia, C., & Pan, G. (2010) · Environmental Pollution · doi:10.1016/j.envpol.2010.01.009 · Cited by 313 · see citing works
Martin, J. W., Asher, B. J., Beesoon, S., Benskin, J. P., & Ross, M. S. (2010) · Journal of Environmental Monitoring · doi:10.1039/c0em00295j · Cited by 311 · see citing works
Self-citationD'eon, J. C., Hurley, M. D., Wallington, T. J., & Mabury, S. A. (2006) · Environmental Science & Technology · doi:10.1021/es0520767 · Cited by 300 · see citing works
Biodegradation of Polyfluoroalkyl Phosphates as a Source of Perfluorinated Acids to the Environment
Lee, H., D’eon, J., & Mabury, S. A. (2010) · Environmental Science & Technology · doi:10.1021/es9028183 · Cited by 288 · see citing works
Labadie, P., & Chevreuil, M. (2010) · Environmental Pollution · doi:10.1016/j.envpol.2010.10.039 · Cited by 274 · see citing works
D’eon, J. C., & Mabury, S. A. (2007) · Environmental Science & Technology · doi:10.1021/es070126x · Cited by 259 · see citing works
Ahrens, L., Yamashita, N., Yeung, L. W. Y., Taniyasu, S., Horii, Y., Lam, P. K. S., & Ebinghaus, R. (2009) · Environmental Science & Technology · doi:10.1021/es901213s · Cited by 259 · see citing works
Significant Residual Fluorinated Alcohols Present in Various Fluorinated Materials
Dinglasan-Panlilio, M. J. A., & Mabury, S. A. (2006) · Environmental Science & Technology · doi:10.1021/es051619+ · Cited by 243 · see citing works
Migration of fluorochemical paper additives from food-contact paper into foods and food simulants
Begley, T. H., Hsu, W., Noonan, G., & Diachenko, G. (2008) · Food Additives & Contaminants: Part A · doi:10.1080/02652030701513784 · Cited by 235 · see citing works
Distribution of perfluorinated compounds in aquatic systems in the Netherlands
Kwadijk, C. J. A. F., Korytár, P., & Koelmans, A. A. (2010) · Environmental Science & Technology · doi:10.1021/es100485e · Cited by 234 · see citing works
Tomy, G. T., Tittlemier, S. A., Palace, V. P., Budakowski, W. R., Braekevelt, E., Brinkworth, L., & Friesen, K. J. (2003) · Environmental Science & Technology · doi:10.1021/es034550j · Cited by 231 · see citing works
Temporal Trends of Perfluoroalkyl Concentrations in American Red Cross Adult Blood Donors, 2000–2010
Olsen, G. W., Lange, C. C., Ellefson, M. E., Mair, D. C., Church, T. R., Goldberg, C. L., Herron, R., Medhdizadehkashi, Z., Nobiletti, J. B., Rios, J. A., et al. (2012) · Environmental Science & Technology · doi:10.1021/es300604p · Cited by 221 · see citing works
D’eon, J. C., Crozier, P. W., Furdui, V. I., Reiner, E. J., Libelo, E. L., & Mabury, S. A. (2009) · Environmental Science & Technology · doi:10.1021/es900100d · Cited by 214 · see citing works
Estimating the contribution of precursor compounds in consumer exposure to PFOS and PFOA
Vestergren, R., Cousins, I. T., Trudel, D., Wormuth, M., & Scheringer, M. (2008) · Chemosphere · doi:10.1016/j.chemosphere.2008.08.011 · Cited by 194 · see citing works
Biomagnification of Perfluorinated Compounds in a Remote Terrestrial Food Chain: Lichen–Caribou–Wolf
Müller, C., Silva, A. O. D., Small, J. M., Williamson, M., Wang, X., Morris, A. D., Katz, S., Gamberg, M., & Muir, D. C. G. (2011) · Environmental Science & Technology · doi:10.1021/es201353v · Cited by 193 · 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
Armitage, J. M., Schenker, U., Scheringer, M., Martin, J. W., MacLeod, M., & Cousins, I. T. (2009) · Environmental Science & Technology · doi:10.1021/es901448p · Cited by 181 · see citing works
Plumlee, M. H., McNeill, K., & Reinhard, M. (2009) · Environmental Science & Technology · doi:10.1021/es803411w · Cited by 163 · see citing works
Long-Term Environmental Fate of Perfluorinated Compounds after Accidental Release at Toronto Airport
Awad, E., Zhang, X., Bhavsar, S. P., Petro, S., Crozier, P. W., Reiner, E. J., Fletcher, R., Tittlemier, S. A., & Braekevelt, E. (2011) · Environmental Science & Technology · doi:10.1021/es2001985 · Cited by 163 · see citing works
Rapid Response of Arctic Ringed Seals to Changes in Perfluoroalkyl Production
Butt, C. M., Muir, D. C. G., Stirling, I., Kwan, M., & Mabury, S. A. (2006) · Environmental Science & Technology · doi:10.1021/es061267m · Cited by 161 · see citing works
Sediment–water distribution of perfluorooctane sulfonate (PFOS) in Yangtze River Estuary
Pan, G., & You, C. (2010) · Environmental Pollution · doi:10.1016/j.envpol.2010.01.011 · Cited by 160 · see citing works
Ahrens, L., Xie, Z., & Ebinghaus, R. (2009) · Chemosphere · doi:10.1016/j.chemosphere.2009.11.038 · Cited by 158 · see citing works
Lee, H., & Mabury, S. A. (2011) · Environmental Science & Technology · doi:10.1021/es200167q · Cited by 153 · see citing works
Degradability of an Acrylate-Linked, Fluorotelomer Polymer in Soil
Washington, J. W., Ellington, J. J., Jenkins, T. M., Evans, J. J., Yoo, H., & Hafner, S. C. (2009) · Environmental Science & Technology · doi:10.1021/es9002668 · Cited by 152 · see citing works
Dietz, R., Bossi, R., Rigét, F. F., Sonne, C., & Born, E. W. (2008) · Environmental Science & Technology · doi:10.1021/es7025938 · Cited by 145 · see citing works
Bossi, R., Rigét, F. F., & Dietz, R. (2005) · Environmental Science & Technology · doi:10.1021/es0508469 · Cited by 139 · see citing works
Halogenated Contaminants in Farmed Salmon, Trout, Tilapia, Pangasius, and Shrimp
van Leeuwen, S. P. J., van Velzen, M. J. M., Swart, C., van der Veen, I., Traag, W. A., & de Boer, J. (2009) · Environmental Science & Technology · doi:10.1021/es803558r · Cited by 129 · see citing works
Shi, Y., Wang, J., Pan, Y., & Cai, Y. (2012) · Environmental Toxicology and Chemistry · doi:10.1002/etc.1758 · Cited by 113 · see citing works
Cai, M., Zhao, Z., Yang, H., Yin, Z., Hong, Q., Sturm, R., Ebinghaus, R., Ahrens, L., Cai, M., He, J., et al. (2011) · Environmental Pollution · doi:10.1016/j.envpol.2011.09.045 · Cited by 106 · see citing works
A review of spatial and temporal assessment of PFOS and PFOA contamination in China
Chen, C., Lü, Y., Zhang, X., Geng, J., Wang, T., Shi, Y., Hu, W., & Li, J. (2009) · Chemistry and Ecology · doi:10.1080/02757540902918321 · Cited by 90 · see citing works
Spatial distribution of polyfluoroalkyl compounds in seawater of the German Bight.
Ahrens, L., Felizeter, S., & Ebinghaus, R. (2009) · Chemosphere · doi:10.1016/j.chemosphere.2009.03.052 · Cited by 89 · see citing works
Hart, K., Gill, V. A., & Kannan, K. (2008) · Archives of Environmental Contamination and Toxicology · doi:10.1007/s00244-008-9242-2 · Cited by 76 · see citing works
Reiner, J. L., O’Connell, S. G., Moors, A. J., Kucklick, J. R., Becker, P. R., & Keller, J. M. (2011) · Environmental Science & Technology · doi:10.1021/es103560q · Cited by 76 · see citing works
Labadie, P., & Chevreuil, M. (2011) · Environmental Pollution · doi:10.1016/j.envpol.2011.07.028 · Cited by 72 · see citing works
Friesen, E. N., Ikonomou, M. G., Higgs, D. A., et al. (2008) · Environmental Science & Technology · doi:10.1021/es0714843 · Cited by 48 · see citing works
Self-citationLevel and temporal trend of perfluoroalkyl acids in Greenlandic Inuit
Long, M., Bossi, R., & Bonefeld‐Jørgensen, E. C. (2012) · International Journal of Circumpolar Health · doi:10.3402/ijch.v71i0.17998 · Cited by 40 · see citing works
Ding, H., Peng, H., Yang, M., & Hu, J. (2012) · Journal of Chromatography A · doi:10.1016/j.chroma.2012.01.004 · Cited by 36 · see citing works
Commercial Fluorosurfactants and their Metabolites in Human Blood
Robinson, S. (2011) · TSpace (University of Toronto) · Cited by 3 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
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
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
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
Zhao, P., Xia, X., Dong, J., Xia, N., Jiang, X., Li, Y., & Zhu, Y. (2016) · Science of The Total Environment · doi:10.1016/j.scitotenv.2016.05.221 · Cited by 322 · see citing works
Zhang, W., Pang, S., Lin, Z., Mishra, S., Bhatt, P., & Chen, S. (2021) · Environmental Pollution · doi:10.1016/j.envpol.2020.115908 · Cited by 280 · 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
Self-citationFate and transport of per- and polyfluoroalkyl substances (PFASs) in the vadose zone
Sharifan, H., Bagheri, M., Wang, D., Burken, J. G., Higgins, C. P., Liang, Y., Liu, J., Schaefer, C. E., & Blotevogel, J. (2021) · Science of The Total Environment · doi:10.1016/j.scitotenv.2021.145427 · Cited by 180 · 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
Self-citationMicrobial biotransformation of aqueous film-forming foam derived polyfluoroalkyl substances
Choi, Y. J., Helbling, D. E., Liu, J., Olivares, C. I., & Higgins, C. P. (2022) · Science of The Total Environment · doi:10.1016/j.scitotenv.2022.153711 · Cited by 79 · see citing works
Ye, F., Tokumura, M., Islam, M. S., Zushi, Y., Oh, J., & Masunaga, S. (2014) · Water Research · doi:10.1016/j.watres.2014.09.014 · Cited by 64 · see citing works
Liu, Y., Pereira, A. S., Beesoon, S., Vestergren, R., Berger, U., Olsen, G. W., Glynn, A., & Martin, J. W. (2015) · Environment International · doi:10.1016/j.envint.2014.11.014 · Cited by 45 · see citing works
Glaser, D., Lamoureux, E., Opdyke, D., LaRoe, S., Reidy, D., & Connolly, J. (2021) · Integrated Environmental Assessment and Management · doi:10.1002/ieam.4414 · Cited by 39 · 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
Zhang, S., Peng, H., Mu, D., Zhao, H., & Hu, J. (2018) · Environmental Pollution · doi:10.1016/j.envpol.2017.12.021 · Cited by 36 · 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
Self-citation
- Authors
- Benskin, J. P., Ikonomou, M. G., Gobas, F. A. P. C., Woudneh, M. B., & Cosgrove, J. R.
- Affiliations
- Fisheries and Oceans Canada (CA)
- Simon Fraser University (CA)
- AXYS Technologies (Canada) (CA)
- Corresponding author
- Benskin, Jonathan P.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-05-31
- Volume
- 46
- Issue
- 12
- Pages
- 6505-6514
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W2320485669
- Cited by
- 72
- References
- 47
- Citations by year
- 2026: 2 · 2025: 5 · 2024: 3 · 2023: 6 · 2022: 7 · 2021: 5 · 2020: 6 · 2019: 2 · 2018: 5 · 2017: 8 · 2016: 4 · 2015: 1 · 2014: 11 · 2013: 6 · 2012: 1
- FWCI
- 4.85
- 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 › Health, Toxicology and Mutagenesis › Toxic Organic Pollutants Impact
- Physical Sciences › Environmental Science › Environmental Chemistry › Environmental Chemistry and Analysis
- Keywords
- PFOS, perfluorooctane sulfonamide, marine sediment, degradation products, per- and polyfluoroalkyl substances
- MeSH terms
- Fluorocarbons, Quality Control, Seawater, Water Pollutants, Chemical, Alkanesulfonic Acids, Geologic Sediments
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review