Observation of a novel PFOS-precursor, the perfluorooctane sulfonamido ethanol-based phosphate (SAmPAP) diester, in marine sediments

Environmental Science and Technology

Volumn 46, Issue 12, 2012, Pages 6505-6514

  Benskin, Jonathan P ^a,b   Ikonomou, Michael G ^b   Gobas, Frank A P C ^c   Woudneh, Million B ^a   Cosgrove, John R ^a  

^a AXYS Analytical Services Ltd   (Canada)

^b INSTITUTE OF OCEAN SCIENCES   (Canada)

^c SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DEGRADATION PRODUCTS; DIESTERS; DIRECT USE; DISTRIBUTION COEFFICIENT; DRY WEIGHT; ENVIRONMENTAL OCCURRENCE; FOOD CONTACT; HIGH PRODUCTION VOLUMES; MARINE ENVIRONMENT; MARINE SEDIMENTS; PERFLUOROOCTANE SULFONAMIDE; PERFLUOROOCTANE SULFONATES; VANCOUVER , CANADA;

ALKYLATION; AMIDES; DEGRADATION; ESTERIFICATION; ESTERS; ETHANOL; SEDIMENTOLOGY; SEDIMENTS; SULFUR COMPOUNDS;

SUBMARINE GEOLOGY;

ORGANOPHOSPHATE; PERFLUOROOCTANESULFONIC ACID;

ACETATE; ALKANE; CONCENTRATION (COMPOSITION); CORRELATION; ESTER; ETHANOL; HARBOR; MARINE ENVIRONMENT; MARINE SEDIMENT; PHOSPHATE; SEDIMENT CHEMISTRY; STABILIZATION; URBAN AREA;

ARTICLE; CANADA; CONCENTRATION (PARAMETERS); DEGRADATION; MARINE ENVIRONMENT; SEDIMENT; SUBSTITUTION REACTION; URBAN AREA;

ALKANESULFONIC ACIDS; FLUOROCARBONS; GEOLOGIC SEDIMENTS; QUALITY CONTROL; SEAWATER; WATER POLLUTANTS, CHEMICAL;

BRITISH COLUMBIA; CANADA; VANCOUVER;

EID: 84862560381     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es300823m     Document Type: Article

References (57)

1. Olsen, G. W.; Lange, C. C.; Ellefson, M. E.; Mair, D. C.; Church, T. R.; Goldberg, C. L.; Herron, R. M.; Medhdizadekashi, Z.; Nobiletti, J. B.; Rios, J. A.; Reagen, W. K.; Zobel, L. R. Temporal trends of perfluoroalkyl concentrations in American Red Cross adult blood donors. Environ. Sci. Technol. 2012, DOI: 10.1021/es300604p.
2. Chen, C. L.; Lu, Y. L.; Zhang, X.; Geng, J.; Wang, T. Y.; Shi, Y. J.; Hu, W. Y.; Li, J. A review of spatial and temporal assessment of PFOS and PFOA contamination in China. Chem. Ecol. 2009, 25, 163-177.
3. Giesy, J. P.; Kannan, K. Global distribution of perfluorooctane sulfonate in wildlife. Environ. Sci. Technol. 2001, 35, 1339-1342. (Pubitemid 32862501)
4. Yamashita, N.; Kannan, K.; Taniyasu, S.; Horii, Y.; Petrick, G.; Gamo, T. A global survey of perfluorinated acids in oceans. Mar. Pollut. Bull. 2005, 51, 658-668. (Pubitemid 41608817)
5. Lau, C.; Anitole, K.; Hodes, C.; Lai, D.; Pfahles-Hutchens, A.; Seed, J. Perfluoroalkyl acids: A review of monitoring and toxicological findings. Toxicol. Sci. 2007, 99, 366-394. (Pubitemid 351753056)
6. Ministry of Environmental Protection of China. Additional Information on Production and Use of PFOS; Stockholm Convention on Persistent Organic Pollutants: Stockholm, Sweden, 2008.
7. Butt, C. M.; Muir, D. C. G.; Stirling, I.; Kwan, M.; Mabury, S. A. Rapid response of arctic ringed seals to changes in perfluoroalkyl production. Environ. Sci. Technol. 2007, 41, 42-49. (Pubitemid 46047821)
8. Hart, K.; Gill, V. A.; Kannan, K. Temporal Trends (1992-2007) of Perfluorinated chemicals in northern sea otters (Enhydra lutris kenyoni) from South-Central Alaska. Arch. Environ. Contam. Toxicol. 2009, 56, 607-614.
9. Bossi, R.; Riget, F. F.; Dietz, R. Temporal and spatial trends of perfluorinated compounds in ringed seal (Phoca hispida) from Greenland. Environ. Sci. Technol. 2005, 39, 7416-7422. (Pubitemid 41407469)
10. Dietz, R.; Bossi, R.; Riget, F. F.; Sonne, C.; Born, E. W. Increasing perfluoroalkyl contaminants in east greenland polar bears (Ursus maritimus): A new toxic threat to the Arctic bears. Environ. Sci. Technol. 2008, 42, 2701-2707. (Pubitemid 351485627)
11. Reiner, J. L.; O'Connell, S. G.; Moors, A. J.; Kucklick, J. R.; Becker, P. R.; Keller, J. M. Spatial and temporal trends of perfluorinated compounds in Beluga Whales (Delphinapterus leucas) from Alaska. Environ. Sci. Technol. 2011, 45, 8129-8136.
12. Long, M.; Bossi, R.; Bonefeld-Jørgensen, E. C. Level and temporal trend of perfluoroalkyl acids in Greenlandic Inuit. Int. J. Circumpolar Health 2012, 71, 17998.
13. Martin, J. W.; Asher, B. J.; Beesoon, S.; Benskin, J. P.; Ross, M. S. PFOS or PreFOS? Are perfluorooctane sulfonate precursors (PreFOS) important determinants of human and environmental perfluorooctane sulfonate (PFOS) exposure? J. Environ. Monit. 2010, 12, 1979-2004.
14. 2OH: Kinetics and mechanism of reaction with OH. Environ. Sci. Technol. 2006, 40, 1862-1868.
15. Plumlee, M. H.; McNeill, K.; Reinhard, M. Indirect photolysis of perfluorochemicals: hydroxyl radical-initiated oxidation of N-ethyl perfluorooctane sulfonamido acetate (N-EtFOSAA) and other perfluoroalkanesulfonamides. Environ. Sci. Technol. 2009, 43, 3662-3668.
16. Tomy, G. T.; Tittlemier, S. A.; Palace, V. P.; Budakowski, W. R.; Braekevelt, E.; Brinkworth, L.; Friesen, K. Biotransformation of N-ethyl perfluorooctanesulfonamide by rainbow trout (Onchorhynchus mykiss) liver microsomes. Environ. Sci. Technol. 2004, 38, 758-762. (Pubitemid 38168742)
17. Lange, C. C. The aerobic biodegradation of N-EtFOSE alcohol by the microbial activity present in municipal wastewater treatment sludge. U.S. Environmental Protection Agency Docket AR-226-058; 2000.
18. Fluorochemical Use, Distribution and Release Overview; U.S. EPA Public Docket AR226-0550; 3M Company: St. Paul, MN, May 26, 1999.
19. Weppner, W. A. Correspondence from William A. Weppner to Oscar Hernandez; U.S. Environmental Protection Agency Docket AR226-004; 2000.
20. 3M Co. Sulfonated Perf luorochemicals: U. S. Release Estimation - 1997 Part 1: Life-cycle waste stream estimates - Final report for 3M specialty materials prepared by Battelle Memorial Institute; U.S. Environmental Protection Agency docket AR 226-0681; 2000.
21. Dinglasan-Panlilio, M. J. A.; Mabury, S. A. Significant residual fluorinated alcohols present in various fluorinated materials. Environ. Sci. Technol. 2006, 40, 1447-1453. (Pubitemid 43376382)
22. Begley, T. H.; Hsu, W.; Noonan, G.; Diachenko, G. Migration of fluorochemical paper additives from food-contact paper into foods and food simulants. Food Addit. Contam., Part A 2008, 25, 384-390.
23. Lee, H.; Mabury, S. A. A pilot survey of legacy and current commercial fluorinated chemicals in human sera from United States donors in 2009. Environ. Sci. Technol. 2011, 45, 8067-8074.
24. U.S. Environmental Protection Agency (USEPA). Perfluoroalkyl Sulfonates; Significant new use rule (SNUR). U.S. Environmental Protection Agency docket EPA-HQ-OPPT-2002-0043; 2002.
25. Howard, P. H.; Muir, D. C. G. Identifying new persistent and bioaccumulative organics among chemicals in commerce. Environ. Sci. Technol. 2010, 44, 2277-2285.
26. Robinson, S. J. Commercial Fluorosurfactants and Their Metabolites in Human Blood. MSc Thesis, University of Toronto, Toronto, ON, Canada, 2011.
27. D'Eon, J. C.; Crozier, P. W.; Furdui, V. I.; Reiner, E. J.; Libelo, E. L.; Mabury, S. A. Observation of a commercial fluorinated material, the polyfluoroalkyl phosphoric acid diesters, in human sera, wastewater treatment plant sludge, and paper fibers. Environ. Sci. Technol. 2009, 43, 4589-4594.
28. Ding, H.; Peng, H.; Yang, M.; Hu, J. Simultaneous determination of mono- and disubstituted polyfluoroalkyl phosphates in drinking water by liquid chromatography-electrospray tandem mass spectrometry. J. Chromatogr., A 2012, 1227, 245-252.
29. D'Eon, J. C.; Mabury, S. A. Production of perfluorinated carboxylic acids (PFCAs) from the biotransformation of polyfluoroalkyl phosphate surfactants (PAPS): Exploring routes of human contamination. Environ. Sci. Technol. 2007, 41, 4799-4805. (Pubitemid 47047424)
30. Lee, H.; D'Eon, J, C.; Mabury, S. A. Biodegradation of polyfluoroalkyl phosphates as a source of perfluorinated acids to the environment. Environ. Sci. Technol. 2010, 44, 3305-3310.
31. D'Eon, J, C.; Mabury, S. A. Exploring indirect sources of human exposure to perfluoroalkyl carboxylates (PFCAs): Evaluating uptake, elimination, and biotransformation of polyfluoroalkyl phosphate esters (PAPs) in the rat. Environ. Health Perspect. 2011, 119, 344-350.
32. Higgins, C. P.; Field, J. A.; Criddle, C. S.; Luthy, R. G. Quantitative determination of perfluorochemicals in sediments and domestic sludge. Environ. Sci. Technol. 2005, 39, 3946-3956. (Pubitemid 40770221)
33. Ahrens, L.; Yamashita, N.; Yeung, L. W. Y.; Taniyasu, S.; Horii, Y.; Lam, P. K. S.; Ebinghaus, R. Partitioning behavior of per- and polyfluoroalkyl compounds between pore water and sediment in two sediment cores from Tokyo Bay, Japan. Environ. Sci. Technol. 2009, 43, 6969-6975.
34. Higgins, C. P.; Luthy, R. G. Sorption of perfluorinated surfactants on sediments. Environ. Sci. Technol. 2006, 40, 7251-7256. (Pubitemid 44871834)
35. Kwadijk, C.; Korytar, P.; Koelmans, A. A. Distribution of perfluorinated compounds in aquatic systems in The Netherlands. Environ. Sci. Technol. 2010, 44, 3746-3751.
36. Ahrens, L.; Xie, Z. Y.; Ebinghaus, R. Distribution of perfluoroalkyl compounds in seawater from Northern Europe, Atlantic Ocean, and Southern Ocean. Chemosphere 2010, 78, 1011-1016.
37. Labadie, P.; Chevreuil, M. Biogeochemical dynamics of perfluorinated alkyl acids and sulfonates in the River Seine (Paris, France) under contrasting hydrological conditions. Environ. Pollut. 2011, 159, 3634-3639.
38. Powley, C. R.; George, S. W.; Ryan, T. W.; Buck, R. C. Matrix effect-free analytical methods for determination of perfluorinated carboxylic acids in environmental matrixes. Anal. Chem. 2005, 77, 6353-6358. (Pubitemid 41436973)
39. Benskin, J. P.; Ikonomou, M. G.; Woudneh, M. B.; Cosgrove, J. R. Rapid characterization of perfluoralkyl carboxylate, sulfonate, and sulfonamide isomers by high performance liquid chromatography-tandem mass spectrometry. J. Chromatogr., A, accepted.
40. Cai, M.; Zhao, Z.; Yang, H.; Yin, Z.; Hong, Q.; Sturm, R.; Ebinghaus, R.; Ahrens, L.; He, J.; Xie, Z. Spatial distribution of per- and polyfluoroalkyl compounds in coastal waters from the East to South China Sea. Environ. Pollut. 2012, 161, 162-169.
41. Ahrens, L.; Felizeter, S.; Ebinghaus, R. Spatial distribution of polyfluoroalkyl compounds in seawater of the German Bight. Chemosphere 2009, 76, 179-184.
42. Martin, J. W.; Ellis, D. A.; Mabury, S. A.; Hurley, M. D.; Wallington, T. J. Atmospheric chemistry of perfluoroalkanesulfonamides: kinetic and product studies of the OH radical and Cl atom initiated oxidation of N-Ethyl perfluorobutanesulfonamide. Environ. Sci. Technol. 2006, 40, 864-872. (Pubitemid 43222173)
43. Friesen, E. N.; Ikonomou, M. G.; Higgs, D. A.; Pee Ang, K.; Dubetz, C. Use of terrestrial based lipids in aquaculture feeds and the effects on flesh organohalogen and fatty acid concentrations in farmed Atlantic salmon. Environ. Sci. Technol. 2008, 42, 3519-3523. (Pubitemid 351694054)
44. Shi, Y.; Wang, J.; Pan, Y.; Cai, Y. Tissue distribution of perfluorinated compounds in farmed freshwater fish and human exposure by consumption. Environ. Toxicol. Chem. 2012, 31, 717-723.
45. van Leeuwen, S. P. J.; van Velzen, M. J. M.; Swart, C. P.; van der Veen, I.; Traag, W. A.; de Boer, J. Halogenated contaminants in farmed salmon, trout, tilapia, pangasius, and shrimp. Environ. Sci. Technol. 2009, 43, 4009-4015.
46. Pan, G.; You, C. Sediment-water distribution of perfluorooctane sulfonate (PFOS) in Yangtze River Estuary. Environ. Pollut. 2010, 158, 1363-1367.
47. You, C.; Jia, C. X.; Pan, G. Effect of salinity and sediment characteristics on the sorption and desorption of perfluorooctane sulfonate at sediment-water interface. Environ. Pollut. 2010, 158, 1343-1347.
48. Mulvana, D.; Henion, J. Report prepared for the 3M Medical Department. Qualitative investigation of the in vitro metabolism of T-6292, T-6293, T-6294 and T-6295 by rat and human hepatocytes using ion spray LC/MS and LC/MS/MS. U.S. Environmental Protection Agency Docket AR-226-0328; 1996.
49. Poon, G.; Lowes, S. Report prepared for the 3M Medical Department. Additional characterization of metabolites of T-6292, T-6293 and T-6294 from rat and human hepatocytes by turbo ion spray LC/MS and LC/MS/MS. Semi-Quantitative analysis of T-6295 in rat and human hepatocytes incubated with T-6292, T-6293 and T-6294 by LC/MS/MS. U.S. Environmental Protection Agency Docket AR-226-0328; 1998.
50. Washington, J. W.; Ellington, J.; Jenkins, T. M.; Evans, J. J.; Yoo, H.; Hafner, S. C. Degradability of an acrylate-linked, fluorotelomer polymer in soil. Environ. Sci. Technol. 2009, 43, 6617-6623.
51. Awad, E.; Zhang, X.; Bhavsar, S. P.; Petro, S.; Crozier, P. W.; Reiner, E. J.; Fletcher, R.; Tittlemier, S. A.; Braekevelt, E. Long-term environmental fate of perfluorinated compounds after accidental release at Toronto airport. Environ. Sci. Technol. 2011, 45, 8081-8089.
52. Labadie, P.; Chevreuil, M. Partitioning behaviour of perfluorinated alkyl contaminants between water, sediment and fish in the Orge River (nearby Paris, France). Environ. Pollut. 2011, 159, 391-397.
53. Vestergren, R.; Cousins, I. T.; Trudel, D.; Wormuth, M.; Scheringer, M. Estimating the contribution of precursor compounds in consumer exposure to PFOS and PFOA. Chemosphere 2008, 73, 1617-1624.
54. Fromme, H.; Tittlemier, S. A.; Volkel, W.; Wilhelm, M.; Twardella, D. Perfluorinated compounds - Exposure assessment for the general population in western countries. Int. J. Hyg. Environ. Health A 2009, 212, 239-270.
55. Armitage, J. M.; Schenker, U.; Scheringer, M.; Martin, J. W.; MacLeod, M.; Cousins, I. T. Modeling the global fate and transport of perfluorooctane sulfonate (PFOS) and precursor compounds in relation to temporal trends in wildlife exposure. Environ. Sci. Technol. 2009, 43, 9274-9280.
56. Müller, C. E.; De Silva, A. O.; Small, J.; Williamson, M.; Wang, X.; Morris, A.; Katz, S.; Gamberg, M.; Muir, D. C. Biomagnification of perfluorinated compounds in a remote terrestrial food chain: Lichen-Caribou-wolf. Environ. Sci. Technol. 2011, 45, 8665-8673.
57. United Nations Environment Program Secretariat of the Stockholm Convention on Persistent Organic Pollutants. The Nine New POPs; An introduction to the nine chemicals added to the Stockholm Convention by the Conference of the Parties at its fourth meeting, Aug 2010. http://chm.pops.int/Programmes/ NewPOPs/Publications/tabid/695/language/en-US/Default.aspx.