Perfluoroalkyl Compounds

Persistent Organic Pollutants

Volumn , Issue , 2009, Pages 25-69

  Stock, Naomi L ^a,b   Muir, Derek C G ^c   Mabury, Scott ^b  

^a TRENT UNIVERSITY   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

^c ENVIRONMENT CANADA   (Canada)

Author keywords

Fluorotelomer alcohols (FTOHs); Fluorotelomer carboxylic acids fluorotelomer carboxylates; Perfluoroalkyl compounds; Perfluoroalkylsulfonic acids perfluoroalkylsulfonates (PFSAs); Perfluorocarboxylic acids perfluorocarboxylates (PFCAs); Polyfluorinated sulfonamides (FSAs)

Indexed keywords

CARBOXYLATION; SULFUR COMPOUNDS;

FLUOROTELOMER ALCOHOLS (FTOHS); FLUOROTELOMER CARBOXYLIC ACIDS; PERFLUOROALKYL COMPOUNDS; PERFLUOROALKYLSULFONIC ACIDS/PERFLUOROALKYLSULFONATES (PFSAS); PERFLUOROCARBOXYLIC ACID; POLYFLUORINATED SULFONAMIDES (FSAS);

AMIDES;

EID: 80053414527     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470684122.ch3     Document Type: Chapter

References (212)

1. Grondin, J., Sagnes, R., Commeyras, A. Perfluorosulfonic acids 3. Hammett acidity functions of perfluoroalkanesulfonic acids and of their mixtures with SBF5. B. Soc. Chim. Fr., 11-12: 1779-1782 (1976).
2. Tromp, T. K., Ko, M. K. W., Rodriguesz, J. M., Sze, N. D. Potential accumulation of a CFC- replacement degradation product in seasonal wetlands. Nature, 376: 327-330 (1995).
3. Boutonnet, J. C., Bingham, P., Calamari, D., de Rooij, C., Franklin, J., Kawano, T., et al. Environmental risk assessment of trifluoroacetic acid. Hum. Ecol. Risk Assess., 5: 59-124 (1999).
4. Kissa, E. Fluorinated Surfactants, Synthesis, Properties, Applications. Marcel Dekker, New York, 2001.
5. Moroi, Y., Yano, H., Shibata, O., Yonemitsu, T. Determination of acidity constants of per- fluoroalkanoic acids. Bull. Chem. Soc. Japan, 74: 667-672 (2001).
6. 3M Company. Fluorochemical use, distribution and release overview. US Environmental Protection Agency Public Docket AR-226-0550, St Paul, Minnesota, 1999.
7. Fluoropolymer Manufacturers Group. Detecting and quantifying low levels of fluoropolymer polymerization aids - a guidance document. Society of the Plastic Industry, Inc., Washington, DC, 2003.
8. DuPont. DuPont global PFOA strategy - comprehensive source reduction. Presentation to USEPA-OPPT, January 31, 2005. US Environmental Protection Agency Public Docket AR226- 1914, Washington, DC, 2005.
9. Simons, J. H. The electrochemical process for the production of fluorocarbons. J. Electrochem. Soc., 95: 47-59 (1949).
10. 3M Company. Phase-out plan for PFOSF-based products. US Environmental Protection Agency Public Docket OPPT-2002-0043, St Paul, Minnesota, 2000.
11. Renner, R. The long and short of perfluorinated replacements. Environ. Sci. Technol., 40: 12-13 (2006).
12. Brace, N. O. (DuPont). Addition of Perfluoroalkyl Iodides to Unsaturated Compounds and Products Produced Thereby. US Patent Number 3145222, 1961.
13. Blanchard, W. A., Rhode, J. C. (DuPont). Process for Preparing Perfluoroalkyl Iodides. US Patent Number 3226449, 1965.
14. Prevedouros, K., Cousins, I. T., Buck, R. C., Korzeniowski, S. H. Sources, fate and transport of perfluorocarboxylates. Environ. Sci. Technol., 40: 32-44 (2006).
15. 3M Company. Environmental and health assessment of perfluorooctane sulfonate and its salts. US Environmental Protection Agency Public Docket AR-226-1486, St Paul, Minnesota, 2003.
16. 3M Company. Production of PFOS derivatives (email letter). US Envronmental Protection Agency, AR-226-0997, Washington, DC, 2001.
17. Telomer Research Program. Telomer Research Program Update. Presented to USEPA-OPPT, November 25, 2002. US Environmental Protection Agency Public Docket AR226-1141, Washington, DC, 2002.
18. DuPont Global PFOA Strategy - comprehensive source reduction. Presentation to USEPA- OPPT, January 31, 2005. US Environmental Protection Agency Public Docket AR226-1914, Washington, DC, 2005.
19. Organisation for Economic Co-operation and Development (OECD). Results of the 2006 survey on production and use of PFOS, PFAS, PFOA, PFCA, their related substances and products/mixtures containing these substances. ENV/JM/MONO(2006)36, Environment Directorate, Organisation for Economic Co-operation and Development, Paris, 2006.
20. US Environmental Protection Agency. Perfluoroalkyl sulfonates, significant new use rule; final rule and supplemental proposed rule. Fed. Regist., 67: 11007-11013 (2002).
21. US Environmental Protection Agency. Toxic Substance Control Act (TSCA) Chemical Inventory, Washington, DC, 2002.
22. Lau, C., Buttenhoff, J. L., Rogers, J. M. The development toxicity of perfluoroalkyl acids and their derivative. Toxicol. Appl. Pharmacol., 198: 231-241 (2004).
23. Lau, C., Anitole, K., Hodes, C., Lai, D., Pfahles-Hutchens, A., Seed, J. Perfluoroalkyl acids: a review of monitoring and toxicological findings. Toxicol. Sci., 99: 366-394 (2007).
24. Kennedy, G. L., Butenhoff, J. L., Olsen, G. W., O'Connor, J. C., Seacat, A. M., Perkins, R. G., et al. The toxicology of perfluorooctanoate. Crit. Rev. Toxicol., 34: 351-384 (2004).
25. Hu, W., Jones, P. D., De Coen, W., Newsted, J. L., Giesy, J. P. Alterations in cell membrane properties caused by perfluorinated compounds. Comp. Biochem. Physiol. C: Pharmacol., 135C: 77-88 (2003).
26. Renner, R. Growing concern over perfluorinated chemicals. Environ. Sci. Technol., 35: 154A-160A (2001).
27. Jones, P. D., Hu, W., De Coen, W. Binding of perfluorinated fatty acids to serum proteins. Environ. Toxicol. Chem., 22: 2639-2649 (2003).
28. Han, X., Snow, T. A., Kemper, R. A., Jepson, G. W. Binding of perfluorooctanoic acid to rat and human plasma proteins. Chem. Res. Toxicol., 16: 775-781 (2003).
29. Van den Heuvel, J., Kuslikis, B., Van Rafelgham, M. Tissue distribution, metabolism, and elimination of perfluorooctanoic acid in male and female rats. Biochem. Toxicol., 6: 83-92 (1991).
30. Kudo, N., Katakura, M., Sato, Y., Kawashima, Y. Sex hormone-regulated renal transport of perfluorooctanoic acid. Chem. Biol. Interac., 139: 301-316 (2002).
31. Ikeda, T., Aiba, K., Fukuda, K., Tanaka, M. The induction of peroxisome proliferation in rat liver by perfluorinated fatty acids, metabolically inhert derivatives of fatty acids. J. Biochem., 98: 475-482 (1985).
32. Sohlenius, A. K., Lundgren, B., Depierre, J. W. Perfluorooctanoic acids has persistent effects on peroxisome proliferation and related paramets in mouse liver. J. Biochem. Toxicol., 7: 205-212 (1992).
33. Sohlenius, A. K., Eriksson, A. M., Hogstrom, C., Kimland, M., Depierre, J. W. Perfluorooctane sulfonic acid is a potent inducer of peroxisomal fatty-acid beta-oxidation and other activities known to be affected by peroxisome proliferators in mouse liver. Pharmacol. Toxicol., 72: 90-93 (1993).
34. Intrasuksri, U., Feller, D. R. Comparison of the effects of selected monocarboxylic, dicarboxylic and perfluorinated fatty acids on peroxisome proliferation in primary cultured rat hepatocytes. Biochem. Pharm., 42: 184-188 (1991).
35. Biegel, L. B.,Liu, R. C. M., Hurtt, M. E., Cook, J. C. Effects of ammonium perfluorooctanoate on Leydig cell function: in vitro, in vivo and ex vivo studies. Toxicol. Appl. Pharmacol., 134: 18-25 (1995).
36. Griffith, F. D., Long, J. E. Animal toxicity studies with ammonium perfluorooctanoate. Am. Ind. Hygiene Ass. J., 41: 576-583 (1980).
37. Upham, B. L., Deocamp, N. D., Wurl, B., Troskp, J. E. Inhibition of gap junction intercellular communication by perfluorinated fatty acids is dependent on the chain length of the fluorinated tail. Int. J. Cancer, 78: 491-495 (1998).
38. Hu, W., Jones, P. D., Upham, B. L., Trosko, J. E., Lau, C., Giesy, J. P. Inhibition of gap junction intercellular communication by perfluorinated compounds in rate liver and dolphin kidney epithelial cell lines in vitro and Sprague-Dawley rates in vivo. Toxicol. Sci., 68:429-436 (2002).
39. US Environmental Protection Agency. Draft risk assessment of potential human health effects associated with PFOA and its salts. US Environmental Protection Agency Public Docket SAB- 06-006, Washington, DC, May 3, 2006.
40. Kudo, N., Iwase, Y., Okayachi, H., Yamakawa, Y., Kawashima, Y. Induction of hepatic peroxisome proliferation by 8-2 telomer alcohol feeding in mice: formation of perfluorooctanoic acid in the liver. Toxicol. Sci., 86: 231-238 (2005).
41. Ishibashi, H., Ishida, H., Matsuoka, M., Tominaga, N., Arizono, K. Estrogenic effects of fluorotelomer acohols for human estrogen receptor isoforms alpha and beta in vitro. Biol. Pham. Bull., 30: 1358-1359 (2007).
42. Case, M. T., York, R. G., Christian, M. S. Rat and rabbit oral developmental toxicology studies with two perfluorinated compounds. Int. J. Toxicol., 20: 101-109 (2001).
43. Berthiaume, J., Wallace, K. B. Perfluorooctanoate, perfluorooctanesulfonate, and N-ethyl perfluorooctanesulfonamido ethanol; peroxisome proliferation and mitochondrial biogenesis. Toxicol. Lett., 129: 23-32 (2002).
44. Phillips, M. M., Dinglasan-Panlilio, M. J. A., Mabury, S. A., et al. Fluorotelomer acids are more toxic than perfluorinated acids. Environ. Sci. Technol., 41: 7159-7163. (2007).
45. Key, B. D., Howell, R. D., Criddle, C. S. Fluorinated organics in the biosphere. Environ. Sci. Technol., 31: 2445-2454 (1991).
46. Pauling, L. The Nature of the Chemical Bond. Cornell University Press, Ithaca, New York, 1960.
47. Smart, B. E. Fluorine substituent effects (on bioactivity). J. Fluorine Chem., 109: 3-11 (2001).
48. Smart, B. E. Fluorocarbons. In The Chemistry of Functional Groups. The Chemistry of Halides, Pseudo Halides and Azides (eds S. Patai and Z. Rappoport). John Wiley & Sons, Ltd, Chichester, 1983, pp. 603-655.
49. Kirsch, P. Modern Fluoroorganic Chemistry. John Wiley & Sons Inc., New York, 2004.
50. Key, B. D., Howell, R. D., Criddle, C. S. Fluorinated organics in the biosphere. Environ. Sci. Technol., 31: 2445-2454 (1997).
51. Eaton, D. F., Smart, B. E. Are fluorocarbon chains stiffer than hydrocarbon chains?. J Am. Chem. Soc., 112: 2821-2823 (1991).
52. Bunn, C. W., Howells, E. R. Structures of molecules and crystals of fluorocarbons. Nature, 174: 549-551 (1954).
53. Wang, J., Ober, C. K. Solid state crystalline and liquid crystalline structure of semifluorinated 1- bromoalkane compounds. Liq. Cryst., 26: 637-648 (1999).
54. 19F NMR to interpret the structural properties of perfluorocarboxylate acids: a possible correlation with their environmental disposition. J. Phys. Chem. A, 108: 10099-10106 (2004).
55. 19F NMR COSY and NOESY connections in the spectra of perfluorooctanoic acid: RF-palmitic acid-F13 and diethyl perfluorosuberate. Mag. Res. Chem., 43: 528-534. (2005).
56. 17O NMR study of polyfluorinated alcohols and ethers. J. Fluorine Chem., 31: 183-196 (1986).
57. Napoli, M., Krotz, L., Scipioni, A., Seraglia, R., Traldi, P. Mass spectrometry of some C6F13- compounds and their C6H13-analogs. Rapid Commun. Mass Sp., 7: 789-794 (1993).
58. Ellis, D. A., Mabury, S. A. Chemical ionization pathways of polyfluorinated chemicals - a connection to environmental atmospheric processes. J.Am. Soc. Mass Spectrom., 14: 1177-1191 (2003).
59. Stock, N. L., Ellis, D. A., Deleebeeck, L., Muir, D. C. G., Mabury, S. A. Vapour pressures of the fluorinated telomer alcohols - limitations of estimation methods. Environ. Sci. Technol., 38: 1693-1699 (2004).
60. Waterland, R. L., Hurley, M. D., Misner, J. A., Wallington, T. J., Melo, S. M. L., Strong, K., et al. Gas phase UV and IR adsorption spectra of CF3CH2CH2OH and F(CF2CF2)xCH2CH2OH (x = 2, 3, 4). J. Fluorine Chem., 126: 1288-1296 (2005).
61. Arp, H. P. H., Niederer, C., Goss, K.-U. Predicting the partitioning behaviour of various highly fluorinated compounds. Environ. Sci. Technol., 40: 7298-7304 (2006).
62. Gladysz, J. A., Curran, D. P., Horvath, I. T. (eds) Handbook of Fluorous Chemistry. John Wiley & Sons, Inc., New York, 2004.
63. Erkoc, S., Erkoc, F. Structural and electronic properties of PFOS and LiPFOS. J. Molec. Structs- Theochem., 549: 289-293 (2001).
64. Kaiser, M. A., Cobranchi, D. A., Chai Kao, C.-P., Krusic, J., Marchione, A. A., Buck, R. C. Physicochemical properties of 8-2 fluorinated telomer B alcohol. J. Chem. Engng Data, 912-916 (2004).
65. Liu, J., Lee, L. Solubility and sorption by soils of 8:2 fluorotelomer alcohol in water and cosolvent systems. Environ. Sci. Technol., 39: 7535-7540 (2005).
66. De Silva, A. O., Stock, N. L., Bonin, J. L., Wong, G. W.-Y., Mabury, S. A. Water solubility and octanol-water partition coefficient of perfluorooctylsulfonamices and fluorotelomer alcohols. J. Chem. Eng. Data, 2008 (to be submitted).
67. Prokop, H. W., Zhou, H.-J., Xu, S.-Q., Wu, C.-H., Liu, C. C. Analysis of the products from the electrochemical fluorination of octanoyl chloride. J. Fluorine Chem., 43: 277-290 (1989).
68. US Environmental Protection Agency. Draft hazard assessment of perfluorooctanoic acid and its salts. Office of Pollution Prevention and Toxics, Risk Assessment Division, Washington, DC, February 20, 2002.
69. Kauck, E. A., Diesslin, A. R. Some properties of perfluorocarboxylic acids. Ind. Engng Chem., 43: 2332-2334 (1951).
70. 3M Company. Sulfonated perfluorochemicals in the environment: sources, dispersion, fate and effects. US Environmental Protection Agency Public Docket AR-226-602, St Paul, Minnisota, 2000.
71. Lei, Y. D., Wania, F., Mathers, D., Mabury, S. A. Determination of vapor pressures, octanol-air, and water-air partition coefficients for polyfluorinated sulfonamide, sulfonamidoethanols, and telomer alcohols. J. Chem. Engng Data, 49: 1013-1022 (2004).
72. Krusic, P. J., Marchione, A. A., Davidson, F., Kaiser, M. A., Kao, C.-P. C., Richardson, R. E., et al. Vapour pressures and intramolecular hydrogen bonding in fluorotelomer alcohols. J. Phys. Chem. A, 109: 6232-6241 (2005).
73. Cobranchi, D. P., Botelho, M. W. B., Buck, R. C., Kaiser, M. A. Vapor pressure determinations of 8-2 fluorotelomer alcohol and 1-H perfluorooctane by capillary gas chromatography. Relative retention time versus headspace methods. J. Chromatogr. A, 1108: 248-251 (2006).
74. Shoeib, M., Harner, T., Ikonomou, M., Kannan, K. Indoor and outdoor air concentration and phase partitioning of perfluoroalkyl sulphonamides and polybrominated diphenyl ethers. Environ. Sci. Technol., 38: 1313-1320 (2004).
75. 3M Company. Determination of vapor pressure curve by dynamic method for U1463 (Et FOSE). US Environmental Protection Agency Public Docket AR226-346, Washington, DC, 1998.
76. Kaiser, M. A., Larsen, B. S., Kao, C.-P. C., Buck, R. C. Vapor pressures of perfluorooctanoic, - nonanoic, -decanoic, -undecanoic, and-dodecanoic acids. J. Chem. Engng Data, 50: 1841-1843 (2005).
77. Goss, K.-U., Bronner, G., Harner, T., Hertel, M., Schmidt, T. C. The partition behaviour of fluorotelomer alcohols and olefins. Environ. Sci. Technol., 40: 3572-3577 (2006).
78. Li, H., Ellis, D. A., Mackay, D. Measurement of low air-water partition coefficients of organic acids by evaporation from a water surface. J. Chem. Engng Data, 52: 1580-1584 (2007).
79. Sullivan, R. C., Mabury, S. A. Sorption of perfluorinated carboxylates and sulfonates to soil. Society of Environmental Toxicology and Chemistry (SETAC), Baltimore, Maryland, November 11-15, (2001).
80. Higgins, C. P., Luthy, R. G. Sorption of perfluorinated surfactants on sediments. Environ. Sci. Technol., 40: 7251-7256 (2006).
81. Muir, D. C. G., Smithwick, M., Brandsma, S., Bujas, T., Small, J. M., Martin, J. W., et al. Uptake, transformation and elimination of fluorotelomer alcohols and PFOSA by rainbow trout (Oncorhynchus mykiss). Society of Environmental Toxicology and Chemistry (SETAC), The Hague, The Netherlands, May 7-11, (2006).
82. Furdui, V. I., Stock, N. L., Ellis, D. A., Butt, C., Whittle, D. M., Crozier, P. W., et al. Per- fluoroalkyl contaminants in lake trout from the Great Lakes. Environ. Sci. Technol., 41: 1554-1559 (2007).
83. Martin, J. W., Mabury, S. A., Solomon, K., Muir, D. C. G. Dietary accumulation and tissue distribution of perfluorinated acids in juvenile rainbow trout (Oncorhynchus mykiss). Environ. Toxicol. Chem., 22: 189-195 (2003).
84. Martin, J., Mabury, S., Solomon, K., Muir, D. Bioconcentration and tissue distribution of perfluorinated acids in rainbow trout (Oncorhynchus mykiss). Environ. Toxicol. Chem., 22: 196-204 (2003).
85. Moody, C. A., Martin, J. W., Kwan, W. C., Muir, D. C. G., Mabury, S. A. Monitoring perfluorinated surfactants in biota and surface water samples following an accidental release of fire-fighting foam into Etobicoke Creek. Environ. Sci. Tecnol., 36: 545-551 (2002).
86. Taniyasu, S., Kannan, K., Horii, Y., Hanari, N., Yamashita, N. A survey of perfluorooctane sulfonate and related perfluorinated organic compounds in water, fish, birds, and humans from Japan. Environ. Sci. Technol., 37: 2634-2639 (2003).
87. Tomy, G. T., Budakowski, W., Halldorson, T., Helm, P. A., Stern, G. A., Friesen, K., et al. Fluorinated organic compounds in an Eastern Arctic marine food web. Environ. Sci. Technol., 38: 6475-6481 (2004).
88. Kannan, K., Tao, L., Sinclair, E., Pastva, S. D., Jude, D. J., Giesy, J. P. Perfluorinated compounds in aquatic organisms at various trophic levels in a Great Lakes food chain. Arch. Environ. Contam. Toxicol., 48: 559-566 (2005).
89. Houde, M., Bujas, T. A. D., Small, J. M., Wells, R. S., Fair, P. A., Bossart, G. D., et al. Biomagnification of perfluoroalkyl compounds in the bottlenose dolphin (Tursiops truncatus) food web. Environ. Sci. Technol., 40: 4138-4144 (2006).
90. Moody, C. A., Field, J. A. Determination of perfluorocarboxylates in groundwater impacted by fire-fighting activity. Environ. Sci. Technol., 33: 2800-2806 (1999).
91. Boudreau, T. M., Wilson, C. J., Cheong, W. J., Sibley, P. K., Mabury, S. A., Muir, D. C. G., et al. Response of the zooplankton community and environmental fate of perfluorooctane sulfonic acid in aquatic microcosms. Environ. Toxicol. Chem., 22: 2739-2745 (2003).
92. Hanson, M. L., Small, J. M., Sibley, P. K., Boudreau, T. M., Brain, R. A., Mabury, S. A., et al. Microcosm evaluation of the fate, toxicity, and risk to aquatic macrophytes from perfluor- ooctanoic acid (PFOA). Arch. Environ. Contam. Toxicol., 49: 307-316 (2005).
93. van Leeuwen, S., Karrman, A., van Bavel, B., de Boer, J., Lindstrom, G. Struggle for quality and determination of perfluorinated contaminants in environmental and human samples. Environ. Sci. Technol., 40: 7854-7860 (2006).
94. Martin, J. W., Kannan, K., Berger, U., de Voogt, P., Field, J. A., Franklin, J., et al. Analytical challenges hamper perfluoroalkyl research. Environ. Sci. Technol., 38: 248A-255A (2004).
95. Yamashita, N., Kannan, K., Taniyasu, S., Horii, Y., Okazawa, T., Petrick, G., et al. Analysis of perfluorinated acids at parts-per-quadrillion levels in seawater using liquid chromatography- tandem mass spectrometry. Environ. Sci. Technol., 38: 5522-5528 (2004).
96. Villagrasa, M., Lopez de Alda, M., Barcelo, D. Environmental analysis of fluorinated alkyl substances by liquid chromatography-(tandem) mass spectrometry: a review. Anal. Bioanal. Chem., 386: 953-972 (2006).
97. van Leeuwen, S., de Boer, J. Extraction and clean-up strategies for the analysis of poly- and perfluoroalkyl substances in environmental and human matrices. J. Chromatogr. A., 1153: 172-185 (2007).
98. Schultz, M. M., Barofsky, D. F., Field, J. A. Quantitative determination of fluorotelomer sulfonates in groundwater by LC-MS/MS. Environ. Sci. Technol., 38: 1828-1835 (2004).
99. Martin, J. W., Muir, D. G. C., Moody, C. A., Ellis, D. A., Kwan, W. C., Solomon, K. R., et al. Collection of airborne fluorinated organics and analysis by gas chromatography/chemical ionization mass spectrometry. Anal. Chem., 74: 584-590 (2002).
100. Stock, N. L., Lau, F. K., Ellis, D. A., Martin, J. W., Muir, D. G. C., Mabury, S. A. Polyfluorinated telomer alcohols and sulfonamides in the North American troposphere. Environ. Sci. Technol., 38: 991-996 (2004).
101. Shoeib, M., Harner, T., Vlahos, P. Perfluorinated chemicals in the arctic atmosphere. Environ. Sci. Technol., 40: 7577-7583 (2006).
102. Jahnke, A., Ahrens, L., Ebinghaus, R., Berger, U., Barber, J. L., Temme, C. An improved method for the analysis of volatile polyfluorinated alkyl substances in environmental air samples. Anal. Bioanal. Chem., 387: 965-975 (2007).
103. Dinglasan, M. J. A., Ye, Y., Mabury, S. A., Edwards, E. A. Fluorotelomer alcohol biodegradation yields poly- and perfluorinated acids. Environ. Sci. Technol., 38: 2857-2864 (2004).
104. Wang, N., Szostek, B., Buck, R. C., Folsom, P. W., Sulecki, M., Capka, V., et al. Fluorotelomer alcohol biodegradation - direct evidence that perfluorinated carbon chain breaks down. Environ. Sci. Technol., 39: 7516-7528 (2005).
105. Hansen, K., Clemen, L., Ellefson, M., Johnson, H. Compound specific quantitative characterization of organic fluorochemicals in biological matrices. Environ. Sci. Technol., 35: 766-770 (2001).
106. Giesy, J., Kannan, K. Global distribution of perfluorooctane sulfonate in wildlife. Environ. Sci. Technol., 35: 1339-1342 (2001).
107. 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., 41: 42-49 (2007).
108. Kannan, K., Corsolini, S., Falandysz, J., Fillmann, G., Kumar, K. S., Loganathan, B. G., et al. Perfluorooctane sulfonate and related fluorochemicals in human blood from several countries. Environ. Sci. Technol., 38: 4489-4495 (2004).
109. Martin, J. W., Whittle, D. M., Muir, D. G. C., Mabury, S.A. Perfluoroalkyl contaminants in a food web from Lake Ontario. Environ. Sci. Technol., 38: 5379-5385 (2004).
110. Hansen, K. J., Johnson, H. O., Eldridge, J. S., Butenhoff, J. L., Dick, L. A. Quantitative characterization of trace levels of PFOS and PFOA in the Tennessee River. Environ. Sci. Technol., 36: 1681-1685 (2002).
111. de Voogt, P., Saez, M. Analytical chemistry of perfluoroalkylated substances. TrAC, 25: 326-342 (2006).
112. Yamashita, N., Kannan, K., Taniyasu, S., Horii, Y., Petrick, G., Gamo, T. A global survey of perfluorinated acids in oceans. Mar. Pollut. Bull., 51: 658-668 (2005).
113. Young, C., Furdui,V.I., Franklin, J., Koerner, R.M., Muir, D.C.G., Mabury, S.A. Perfluorinated acids in arctic snow: new evidence for atmospheric formation. Environ. Sci. Technol., 41: 3455-3461 (2007).
114. Furdui, V. I., Crozier, P. W., Reiner, E. J., Mabury, S. A. Optimized trace level analysis of perfluorinated carboxylic and sulfonic acids. Organohalogen Cpds, 211-214 (2005).
115. Schroeder, H. Determination of fluorinated surfactants and their metabolites in sewage sludge samples by liquid chromatography with mass sectrometry and tandem mass spectrometry after pressurised liquid extraction and separation on fluorine-modified reversed-phase sorbents. J. Chromatogr. A, 1020: 131-151 (2003).
116. Langlois, I., Oehme, M. Structural identification of isomers present in technical perfluorooctane sulfonate by tandem mass spectrometry. Rapid Commun. Mass Sp., 20: 844-850 (2006).
117. Benskin, J. P., Bataineh, M., Martin, J. W. Simultaneous characterization of perfluoroalkyl carboxylate, sulfonate and sulfonamide isomers by liquid chromatography-tandem mass spectrometry. Anal. Chem., 79: 6455-6464 (2007).
118. Boulanger, B., Peck, A. M., Schoor, J. L., Hornbuckle, C. K. Mass budget of perfluorooctane surfactants in Lake Ontario. Environ. Sci. Technol., 39: 74-79 (2005).
119. De Silva, A. O., Mabury, S. A. Isolating isomers of perfluorocarboxylates in polar bears (Ursus maritimus) from two geographical locations. Environ. Sci. Technol., 38: 6538-6545 (2004).
120. De Silva, A. O., Mabury, S. A. Isomer distribution of perfluorocarboxylates in human blood: potential correlation to source. Environ. Sci. Technol., 40: 2903-2909 (2006).
121. Scott, B. F., Moody, C. A., Spencer, C., Small, J. M., Muir, D. C. G., Mabury, S. A. Analysis for perfluorocarboxylic acids/anions in surface waters and precipitation using GC/MS and analysis of PFOS from large volume samples. Environ Sci Technol., 40: 6405-6410 (2006).
122. Scott, B. F., Spencer, C., Mabury, S. A., Muir, D. C. G. Poly and perfluorinated carboxylates in North American precipitation. Environ. Sci. Technol., 40: 7167-7173 (2006).
123. Taves, D. R. Evidence that there are two forms of fluoride in human serum. Nature, 16: 1050-1051 (1968).
124. 19F NMR. Anal. Chem., 73: 2200-2206 (2001).
125. Wickbold, R. Die photometrische trubunoptitration zur bestimmeng kleinster sulfatmengen. Agnew. Chem., 66: 173 (1954).
126. Miyake, Y., Yamashita, N., Rostkowski, P., So, M. K., Taniyasu, S., Lam, P. K. S., et al. Determination of trace levels of total fluorine in water using combustion ion chromatography for fluorine: a mass balance approach to determine individual perfluorinated chemicals in water. J. Chromatogr. A, 1143: 98-104 (2007).
127. Miyake, Y., Yamashita, N., So, M. K., Rostkowski, P., Taniyasu, S., Lam, P. K. S., et al. Trace analysis of total fluorine in human blood using combustion ion chromatography for fluorine: a mass balance approach for the determination of known and unknown organofluorine compounds. J. Chromatogr. A, 1154: 214-221 (2007).
128. Arsenault, G., Chittim, B., McAlees, A., McCrindle, R., Riddell, N., Yeo, B. Some issues relating to the use of perfluorooctanesulfonate (PFOS) samples as references standards. Chemosphere, 70: 616-625 (2008).
129. Olsen, G. W., Church, T. R., Miller, J. P., Hansen, K. J., Lundberg, J. K., Armitage, J. M., et al. Perfluorooctanesulfonate and other fluorochemicals in the serum of American Red Cross adult blood donors. Environ. Health Perspect., 111: 1892-1901 (2003).
130. Olsen, G. W., Huang, H.-Y., Helzlsouer, K. J., Hansen, K. J., Butenhoff, J. L., Mandel, J. H. Historical comparison of perfluorooctanesulfonate, perfluorooctanoate and other fluorochem- icals in human blood. Environ. Health Perspect., 113: 539-545 (2005).
131. Guruge, K. S., Taniyasu, S., Yamashita, N., Wijeratna, S., Mohotti, K. M., Seneviratne, H. R., et al. Perfluorinated organic compounds in human blood serum and seminal plasma: a study of urban and rural tea worker populations in Sri Lanka. J. Environ. Monitor, 7: 371-377 (2005).
132. Yeung, L. W. Y., So, M. K., Jiang, G., Taniyasu, S., Yamashita, N., Song, M., et al. Perfluoro- octanesulfonate and related fluorochemicals in human blood samples from China. Environ. Sci. Technol., 40: 715-720 (2006).
133. Calafat, A. M., Kuklenyik, Z., Caudill, S. P., Rediy, J. A., Needham, L. L. Perfluorochemicals in pooled serum samples from United States residents in 2001 and 2002. Environ. Sci. Technol., 40: 2128-2134 (2006).
134. Olsen G.W. Schmickler M.N. Tierens J.M. Logan P.W. Burris J.M. Burlew M.M., et al. Descriptive summary of serum fluorochemical levels among employee participants of the year 2000 Antwerp Fluorochemical Medical Surveillance Program. US Environmental Protection Agency Public Docket AR-226-1030-0206, St Paul, Minnesota 2001.
135. Olsen, G. W., Burris, J. M., Ehresman, D. J., Froehlich, J. W., Seacat, A. M., Butenhoff, J. L., et al. Half-life of serum elimination of perfluorooctanesulfonate, perfluorohexanesulfonate, and perfluorooctanoate in retired fluorochemical production workers. Environ. Health Perspect., 115: 1298-1305 (2007).
136. Houde, M., Martin, J. W., Letcher, R., Solomon, K., Muir, D. C. G. Biological monitoring of perfluoroalkyl substances: a review. Environ. Sci. Technol., 40: 3463-3473 (2006).
137. Inoue, K., Okada, F., Ito, R., Kato, S., Sasaki, S., Nakajima, S., et al. Perfluorooctane sulfonate (PFOS) and related perfluorinated compounds in human blood and cord blood samples: assessment of PFOS exposure in a susceptible population during pregnancy. Environ. Health Perspect., 112: 1204-1207 (2004).
138. So, M. K., Yamashita, N., Taniyasu, S., Jiang, Q., Giesy, J. P., Chen, K., et al. Health risks in infants associated with exposure to perfluorinated compounds in human breastmilk from Zhoushan. China. Environ. Sci. Technol., 40: 2924-2929 (2006).
139. Tittlemier, S. A., Pepper, K., Seymour, C., Moisey, J., Bronson, R., Cao, X.-L., et al. Dietary exposure of Canadians to perfluorinated carboxylates and perflurooctane sulfonate via consumption of meat, fish, fast foods and food items prepared in their packaging. J. Agric. Food Chem., 55: 3203-3210 (2007).
140. Washburn, S. T., Bingman, T. S., Braithwaite, S. K., Buck, R. C., Buxton, L. W., Clewell, H. J., et al. Exposure assessment and risk characterization for perfluorooctanoate in selected consumer articles. Environ. Sci. Technol., 39: 3904 (2005).
141. Dinglasan-Panlilio, M. J. A., Mabury, S. A. Significant residual fluorinated alcohols present in various fluorinated materials. Environ. Sci. Technol., 40: 1447-1453 (2006).
142. Larsen, B. S., Stchur, P., Szostek, B., Bachmura, S. F., Rowand, R. C., Prickett, K. B., et al. Method development for the determination of residual fluorotelomer raw material and per- fluorooctanoate in fluorotelomer-based products by gas chromatography and liquid chromatography mass spectrometry. J. Chromatogr. A, 1110: 117-124 (2006).
143. Begley, T. H., White, K., Honigfort, P., Twaroski, M. L., Neches, R., Walker, R. A. Perfluor- ochemicals: potential sources of and migration from food packaging. Food Addit. Contam., 22: 1023-1031 (2005).
144. Tittlemier, S. A., Pepper, K., Edwards, L. Concentrations of perfluorooctanesulfonamides in Canadian total diet study composite food samples collected between 1992 and 2004. J. Agric. Food Chem., 54: 8385-8389 (2006).
145. Falandysz, J., Taniyasu, S., Gulkowska, A., Yamashita, N. Is fish a major source of fluorinated surfactants and repellents in humans living on the Baltic Coast? Environ. Sci. Technol., 40: 748-751 (2006).
146. 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., 41: 4799-4805 (2007).
147. Loveless, S. E., Finlay, C., Everds, N. E., Frame, S. R., Gillies, P. J., O'Connor, J. C., et al. Comparative responses of rats and mice exposed to linear/branched, linear, or branched ammonium perfluorooctanoate (APFO). Toxicol., 220: 203-216 (2006).
148. Hekster, F. M., Laane, R. W. P. M., de Voogt, P. Environmental and toxicity effects of perfluoroalkylated substances. Rev. Environ. Contam. Toxicol., 179: 99-121 (2003).
149. Dinglasan-Panlilio, M. J. A., Edwards, E., Mabury, S. A.Biodegradation of fluorotelomer monomers - importance of linkages. Presented at the Society of Environmental Toxicology and Chemistry (SETAC), Annual North American Meeting, Montreal, Quebec, Canada, November 5-9, 2006.
150. Telomer Research Program. Letter of Intent. US Environmental Protection Agency Public Docket OPPT 2003-0012-0013, Washington, DC, 2003.
151. Ellis, D. A., Mabury, S. A., Martin, J. W., Muir, D. G. C. Thermolysis of fluoropolymers as a potential source of halogenated organic acids in the environment. Nature, 412: 321-324 (2001).
152. 19F NMR and mass spectrometry for the elucidation of novel fluorinated acids and atmospheric fluoroacid precursors evolved in the thermolysis of fluoropolymers. Analyst, 128: 756-764 (2003).
153. Ellis, D. A., Martin, J. W., DeSilva, A. O., Mabury, S. A., Hurley, M. D., Sulbeck Andersen, M. D., et al. Degradation of fluorotelomer alcohols: a likely source of perfluorinated carboxylic acids. Environ. Sci. Technol., 38: 3316-3321 (2004).
154. Wallington, T. J., Hurley, M. D., Xia, J., Wuebbles, D. J., Sillman, S., Ito, A., et al. Formation of C7F15COOH (PFOA) and other perfluorocarboxylic acids during the atmospheric oxidation of 8:2 fluorotelomer alcohol. Environ. Sci. Technol., 40: 924-930 (2006).
155. Gauthier, S. A., Mabury, S. A. Aqueous photolysis of 8:2 fluorotelomer alcohol. Environ. Toxicol. Chem., 24: 1837-1846 (2005).
156. Hagen, D. F., Belisle, J., Johnson, J. D., Venkateswarlu, P. Characterization of fluorinated metabolites by a gas chromatographic-helium microwave plasma detector - the biotransformation of 1H, 1H, 2H, 2H-perfluorodecanol to perfluorooctanoate. Anal. Biochem., 118: 336-343 (1981).
157. Martin, J. W., Mabury, S. A., O'Brien, P. J. Metabolic products and pathways of fluorotelomer alcohols in isolated rat hepatocytes. Chem. Biol. Interac., 155: 165-180 (2005).
158. Xu, L., Krenitsky, D. M., Seacat, A. M., Butenhoff, J. L., Anders, M. W. Biotransformation of N- ethyl-N-(2-hydroxyethyl)perfluorooctanesulfonamide by rat liver microsomes, cytosol, and slices and by expressed rat and human cyctochromes P450. Chem. Res. Toxicol., 17: 767-775 (2004).
159. Tomy, G. T., Tittlemier, S. A., Palace, V. P., Budakowski, W. R., Braekevelt, E., Brinkworth, L., et al. Biotransformation of N-ethyl perfluorooctane sulfonamide by rainbow trout (Onchor- hynchus mykiss) liver microsomes. Environ. Sci. Technol., 38: 758-762 (2004).
160. 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., 40: 864-872 (2006).
161. D'eon, J. C., Hurley, M. D., Wallington, T. J., Mabury, S. A. Atmospheric chemistry of N-methyl perfluorobutane sulfonamidoethanol. C4F9SO2N(CH3)CH2CH2OH: kinetics and mechanism of reaction with OH. Environ. Sci. Technol., 40: 1862-1868 (2006).
162. Ellis, D. A., Martin, J. W., Mabury, S. A., Hurley, M. D., Sulbeck Andersen, M. D., Wallington, T. J. Atmospheric lifetime of fluorotelomer alcohols. Environ. Sci. Technol., 37: 3816-3820 (2003).
163. Armitage, J., Cousins, I. T., Buck, R. C., Prevedouros, K., Russell, M. H., Macleod, M., et al. Modeling global-scale fate and transport of perfluorooctanoate from direct sources. Environ. Sci. Technol., 40: 6969-6975 (2006).
164. Wania, F. A global mass balance analysis of the source of perfluorocarboxylic acids in the Arctic Ocean. Environ. Sci. Technol., 41: 4529-4535 (2007).
165. So, M. K., Taniyasu, S., Yamashita, N., Giesy, J. P., Zheng, J., Fang, Z., et al. Perfluorinated compounds in coastal waters of Hong Kong, south China and Korea. Environ. Sci. Technol., 38: 4056-4063 (2004).
166. Stock, N. L., Furdui, V. I., Muir, D. C. G., Mabury, S. A. Perfluoroalkyl contaminants in the Canadian Arctic: evidence of atmospheric transport and local contamination. Environ. Sci. Technol., 41: 3529-3536 (2007).
167. Shoeib, M., Harner, T., Wilford, B. H., Jones, K. C., Zhu, J. Perfluorinated sulfonamides in indoor and outdoor air and indoor dust: occurrence, partitioning, and human exposure. Environ. Sci. Technol., 39: 6599-6606 (2005).
168. Berger, U., Barber, J. L., Jahnke, A., Temme, C., Jones, K. C.Analysis of fluorinated alkyl compounds in air samples from England. In Fluoros: An International Symcposium on Fluorinated Organics in the Environment, Toronto, Ontario, Canada, August 18-19, 2005.
169. Jahnke, A., Ahrens, L., Ebinghaus, R., Temme, C. Urban versus remote air concentrations of fluorotelomer alcohols and other polyfluorinated alkyl substances in Germany. Environ. Sci. Technol., 41: 745-752 (2007).
170. Sasaki, K., Harada, K., Saito, N., Tsutsui, T., Nakanishi, S., Tsuzuki, H., et al. Impacts of airborne perfluorooctane sulfonate on the human body burden and the ecological system. Bull. Environ. Contam. Toxicol., 71: 408-413 (2003).
171. Barton, C. A., Butler, L. E., Zarzecki, C. J., Flaherty, J., Kaiser, M. Characterizing perfluorooctanoate in ambient air near the fence line of a manufacturing facility: comparing modeled and monitored values. J. Air Waste Managmt Ass., 56: 48-55 (2006).
172. Loewen, M., Halldorson, T., Wong, F., Tomy, G. Fluorotelomer carboxylic acids and PFOS in rainwater from an urban centre in Canada. Environ. Sci. Technol., 39: 2944-2951 (2005).
173. Moody, C. A., Field, J. A. Perfluorinated surfactants and the environmental implications of their use in fire-fighting foams. Environ. Sci. Technol., 34: 3864-3870 (2000).
174. Moody, C. A., Herbert, G. N., Strauss, S. H., Field, J. A. Occurrence and persistence of perfluorooctanesulfonate and other perfluorinated surfactants in groundwater at a firetraining area at Wurtsmith Air Force Base, Michigan. USA. J. Environ. Monitor, 5: 341-345 (2003).
175. Saito, N., Sasaki, K., Nakatome, K., Harada, K., Yoshinaga, T., Koizumi, A. Perfluorooctane sulfonate concentrations in surface water in Japan. Arch. Environ. Contam. Toxicol., 45: 149-158 (2003).
176. Saito, N., Harada, K., Inoue, K., Sasaki, K., Yoshinaga, T., Koizumi, A. Perfluorooctanoate and perfluorooctane sulfonate concentrations in surface water in Japan. J. Occup. Health., 46:49-59 (2004).
177. Tseng, C.-L., Liu, L.-L., Chen, C.-M., Ding, W.-H. Analysis of perfluorooctanesulfonate and related fluorochemicals in water and biological tissue samples by liquid chromatography-ion trap mass spectrometry. J. Chromatogr. A, 1105: 119-126 (2006).
178. Skutlarek, D., Exner, M., Farber, H. Perfluorinated surfactants in surface and drinking waters. Environ. Sci. Pollut. Res., 13: 299-307 (2006).
179. Boulanger, B., Vargo, J., Schnoor, J., Hornbuckle, K. C. Detection of perfluorooctane surfactants in Great Lakes water. Environ. Sci. Technol., 38: 4064-4070 (2004).
180. Simcik, M. F., Dorweiler, K. J. Ratio of perfluorochemical concentrations as a tracer of atmospheric deposition to waters. Environ. Sci. Technol., 39: 8678-8683 (2005).
181. Sinclair, E., Mayack, D. T., Roblee, K., Yamashita, N., Kannan, K. Occurrence of perfluoroalkyl surfactants in water, fish and birds from New YorkState. Arch. Environ. Contam. Toxicol., 50: 398-410 (2006).
182. Taniyasu, S., Kannan, K., So, M. K., Gulkowska, A., Sinclair, E., Okazawa, T., et al. Analysis of fluorotelomer alcohols, fluorotelomer acids, and short- and long-chain perfluorinated acids in water and biota. J. Chromatogr. A, 1093: 89-97 (2005).
183. Field, J. A., Simonich, S., Barfosky, D. Comment on 'Detection of perfluorooctane surfactants in Great Lakes water' and 'Mass budget of perfluorooctane surfactants in Lake Ontario'. Environ. Sci. Technol., 39: 3883-3884 (2005).
184. Szostek, B., Prickett, K. B., Buck, R. C. Determination of fluorotelomer alcohols by liquid chromatography/tandem mass spectrometry in water. Rapid Commun. Mass Spectrom., 20: 2837-2844 (2006).
185. Higgins, C. P., Field, J. A., Criddle, C. S., Luthy, R. G. Quantitative determination of perfluorochemicals in sediment and domestic sludge. Environ. Sci. Technol., 39: 3946-3956 (2005).
186. Nakata, H., Kannan, K., Nasu, T., Cho, H.-S., Sinclair, E., Takemura, A. Perfluorinated contaminants in sediments and aquatic organisms collected from shallow water and tidal flat areas of the Ariake Sea. Japan: environmental fate of perfluorooctane sulfonate in aquatic ecosystems. Environ. Sci. Technol., 40: 4916-4921 (2006).
187. Martin, J. W., Smithwick, M., Braune, B. M., Hoekstra, P. F., Muir, D. C. G., Mabury, S. A. Identification of long-chain perfluorinated acids in biota from the Canadian Arctic. Environ. Sci. Technol., 38: 373-380 (2004).
188. Kannan, K., Hansen, K. J., Wade, T. L., Giesy, J. P. Perfluorooctane sulfonate in oysters, Crassostrea virginica, from the Gulf of Mexico and the Chesapeake Bay. Arch. Environ. Contam. Toxicol., 42: 313-318 (2002).
189. Van de Vijver, K. I., Hoff, P. T., Van Dongen, W., Esmans, E. L., Blust, R., De Coen, W. Exposure patterns of perfluorooctane sulfonate in aquatic invertebrates from the Western Scheldt Estuary and the southern North Sea. Environ. Toxicol. Chem., 22: 2037-2041 (2003).
190. Kannan, K., Corsolini, S., Falandysz, J., Oehme, G., Focardi, S., Giesy, J. P. Perfluorooctane- sulfonate and related fluorinated hydrocarbons in marine mammals, fishes and birds from coasts of the Baltic and Mediterranean Seas. Environ. Sci. Technol., 36: 3210-3216 (2002).
191. Hoff, P. T., Van Campernhout, K., Van de Vijver, K., Covaci, A., Bervoets, L., Moens, L., et al. Perfluorooctane sulfonic acid and organohalogen pollutants in liver of three freshwater fish species in Flanders (Belgium): relationship with biochemical and organismal effects. Environ. Pollut., 137: 324-333 (2005).
192. Bossi, R., Riget, F. F., Dietz, R., Sonne, C., Fauser, P., Dam, M., et al. Preliminary screening of perfluorooctane sulfonate (PFOS) and other fluorochemicals in fish, birds and marine mammals from Greenland and the Faroe Island. Environ. Pollut., 136: 323-329 (2005).
193. Keller, J. M., Kannan, K., Taniyasu, S., Yamashita, N., Day, R. D., Arendt, M. D., et al. Perfluorinated compounds in the plasma of loggerhead and Kemp's ridley sea turtles from the southeastern coast of the United States. Environ. Sci. Technol., 39: 9101-9108 (2005).
194. Kannan, K., Franson, J. C., Bowerman, W. W., Hansen, K. J., Jones, P. D., Giesy, J. P. Perfluorooctane sulfonate in fish-eating water birds including bald eagles and albatrosses. Environ. Sci. Technol., 35: 3065-3070 (2001).
195. Kannan, K., Choi, J.-W., Iseki, N., Senthilkumar, K., Kim, D. H., Masunaga, S., et al. Concentrations of perfluorinated acids in livers of birds from Japan and Korea. Chemosphere, 49: 225-231 (2002).
196. Verreault, J., Houde, M., Gabrielsen, G. W., Berger, U., Haukas, M., Letcher, R., et al. Perfluorinated alkyl substances in plasma, liver, brain, and eggs of glaucous gulls (Larus hyperboreus) from the Norwegian Arctic. Environ. Sci. Technol., 39: 7439-7444 (2005).
197. Butt, C. M., Mabury, S.A., Muir, D. C. G., Braune, B. M. Temporal trends of perfluorinated alkyl compounds in seabirds from the Candian Arctic: prevalence of long-chained perfluorinated carboxylates. Environ. Sci. Technol., 41: 3521-3528 (2007).
198. Hoff, P. T., Scheirs, J., Van de Vijver, K., Van Dongen, W., Esmans, E. L., Blust, R., et al. Biochemical effect evaluation of perfluorooctane sulfonic acid-contaminated wood mice (Apodemus sylvaticus). Environ. Health Perspect., 112: 681-686 (2004).
199. Kannan, K., Koistinen, J., Beckmen, K., Evans, T., Gorzelany, J., Hansen, K., et al. Accumulation of perfluorooctane sulfonate in marine mammals. Environ. Sci. Technol., 35: 1593-1598 (2001).
200. Van de Vijver, K. I., Hoff, P. T., Das, K., Van Dongen, W., Esmans, E. L., Jauniaux, T., et al. Perfluorinated chemicals infiltrate ocean waters: link between exposure levels and stable isotope ratios in marine mammals. Environ. Sci. Technol., 37: 5545-5550 (2003).
201. Van de Vijver, K., Hoff, P. T., Das, K., Van Dongen, W., Esmans, E. L., Siebert, U., et al. Baseline study of perfluorochemicals in harbour porpoises (Phocoenaphocoena) from Northern Europe. Mar. Pollut. Bull., 48: 992-999 (2004).
202. Bossi, R., Riget, F. F., Dietz, R. Temporal and spatial trends of perfluorinated compounds in ringed seal (Phoca hispida) from Greenland. Environ. Sci. Technol., 39: 7416-7422 (2005).
203. Houde, M., Wells, R. S., Fair, P. A., Bossart, G. D., Hohn, A. A., Rowles, T. K., et al. Polyfluorinated compounds in free-ranging bottlenose dolphins (Tursiops truncatus) from the Gulf of Mexico and the Atlantic Ocean. Environ. Sci. Technol., 39: 6591-6598 (2005).
204. Smithwick, M., Mabury, S. A., Solomon, K., Sonne, C., Martin, J. W., Born, E. W., et al. Circumpolar study of perfluoroalkyl contaminants in polar bears (Ursus maritimus). Environ. Sci. Technol., 39: 5517-5523 (2005).
205. Smithwick, M., Muir, D. C. G., Mabury, S. A., Solomon, K., Martin, J. W., Sonne, C., et al. Perfluoroalkyl contaminants in liver tissue from East Greenland polar bears (Ursus maritimus). Environ. Tox. Chem., 24: 981-986 (2005).
206. Kannan, K., Yun, S. H., Evans, T. J. Chlorinated, brominated, and perfluorinated contaminants in livers of polar bears from Alaska. Environ. Sci. Technol., 39: 9057-9063 (2005).
207. Houde, M., Balmer, B. C., Brandsma, S., Wells, R. S., Rowles, T. K., Solomon, K., et al. Perfluorinated alkyl compounds in relation with life-history and reproductive parameters in bottlenose dolphins (Tursiops truncatus) from Sarasota Bay, Florida. USA. Environ. Toxicol. Chem., 25: 2405-2412 (2006).
208. Smithwick, M., Norstrom, R. J., Mabury, S. A., Solomon, K., Evans, T. J., Stirling, I., et al. Temporal trends of perfluoroalkyl contaminants in polar bears (Ursus maritimus) from two locations in the North American Arctic, 1972-2002. Environ. Sci. Technol., 40: 1139-1143 (2006).
209. Ellis, D. A., Martin, J. W., De Silva, A. O., Mabury, S. A., Hurley, M. D., Sulbaek Andersen, M. P., et al. Degradation of fluorotelomer alcohols: a likely atmospheric source of perfluorinated carboxylic acids. Environ. Sci. Technol., 38: 3316-3321 (2004).
210. Smithwick, M. M., Mabury, S. A., Solomon, K. R., Sonne, C., Martin, J. W., Born, E. W., et al. Circumpolar study of perfluorlakyl contaminants in polar bears (Ursus maritimus). Environ. Sci. Technol., 39: 5517-5523 (2005).
211. Holmstrom, K. E., Jarnberg, U., Bignert, A. Temporal trends of PFOS and PFOA in guillemot eggs from the Baltic Sea, 1968-2003. Environ. Sci. Technol., 39: 80-84 (2005).
212. Verreault, J., Berger, U., Gabrielsen, G. W. Trend of perfluorinated alkyl substances in herring gull eggs from two coastal colonies in northern Norway: 1983-2003. Environ. Sci. Technol., 41: 6671-6677 (2007).