Isomer Profiling of Perfluorinated Substances as a Tool for Source Tracking: A Review of Early Findings and Future Applications

  • Jonathan P. Benskin
  • Amila O. De Silva
  • Jonathan W. Martin
Chapter
Part of the Reviews of Environmental Contamination and Toxicology book series (RECT, volume 208)

Abstract

The ubiquitous detection of perfluorinated acids (PFAs) and their precursors (PFA precursors) in the global environment has led to concern over their effects in humans and wildlife. This is exacerbated by evidence of developmental toxicity (Lau et al. 2007; Apelberg et al. 2007; Fei et al. 2008), along with persistence, chain length-dependent bioaccumulation potential (Houde et al. 2006), and long-range transport potential (Wallington et al. 2006; Wania 2007; Armitage et al. 2006, 2009a, b). In the over half-century of global perfluorochemical manufacturing, the two most commonly used synthetic methods have produced products with very different isomeric purities. Despite the fact that both branched and linear PFA and PFA-precursor isomers exist in the environment, quantitative analysis of these chemicals is, for the most part, still conducted by eluting all isomers together and integrating them as a single peak. This practice has continued despite the fact that emerging literature suggests that more accurate and informative data can be generated by isomer-specific analysis.

References

  1. 3 M Co. (1999) U.S. Environmental Protection Agency Public Docket AR226-0550: fluorochemical use, distribution and release overview. U.S. Environmental Protection Agency, Office of Pollution Prevention and Toxic Substances, Washington, DCGoogle Scholar
  2. Ahrens L, Felizeter S, Sturm R, Zie Z, Ebinghaus R (2009) Polyfluorinated compounds in waste water treatment plant effluents and surface waters along the River Elbe, Germany. Mar Pollut Bull 58:1326–1333Google Scholar
  3. Apelberg BJ, Witter FR, Herbstman JB, Calafat AM, Halden RU, Needham LL, Goldman LR (2007) Cord serum concentrations of perfluorooctane sulfonate (PFOS) and perfluorooctanoate (PFOA) in relation to weight and size at birth. Environ Health Perspect 115:1670–1676Google Scholar
  4. Appel AG, Abd-Elghafar SF (1990) Toxicity, sublethal effects, and performance of sulfluramid against the German cockroach (Dictyoptera: Blattellidae). J Econ Entomol 83:1409–1414Google Scholar
  5. Armitage JM, Cousins IT, Buck RC, Prevedouros K, Russell MH, MacLeod M, Korzeniowski SH (2006) Modeling global-scale fate and transport of perfluorooctanoate emitted from direct sources. Environ Sci Technol 40:6969–6975Google Scholar
  6. Armitage JM, MacLeod M, Cousins IT (2009a) Modeling the global fate and transport of perfluorooctanoic acid (PFOA) and perfluorooctanoate (PFO) emitted from direct sources using a multispecies mass balance model. Environ Sci Technol 43:1134–1140Google Scholar
  7. Armitage JM, MacLeod M, Cousins IT (2009b) Comparative assessment of the global fate and transport pathways of long-chain perfluorocarboxylic acids (PFCAs) emitted from direct sources. Environ Sci Technol 43:5830–5836Google Scholar
  8. Arsenault G, Chittim B, Gu J, McAlees A, McCrindle R, Robertson V (2008a) Separation and fluorine nuclear magnetic resonance spectroscopic (19F NMR) analysis of individual branched isomers present in technical perfluorooctanesulfonic acid (PFOS). Chemosphere 73:S53–S59Google Scholar
  9. Arsenault G, Chittim B, McAlees A, McCrindle R, Riddell N, Yeo B (2008b) Some issues relating to the use of perfluorooctanesulfonate (PFOS) samples as reference standards. Chemosphere 70:616–625Google Scholar
  10. Balague J, Ameduri B, Boutevin B, Caporiccio G (1995) Synthesis of fluorinated telomers. Part 1: Telomerization of vinylidene fluoride with perfluoroalkyl iodides. J Fluorine Chem 70:215–223Google Scholar
  11. Bastosa JK, Freitasa LAP, Pagliarussia RS, Merinoc RE (2001) A rapid quantitative method for the analysis of sulfluramid and its isomers in ant bait by capillary column gas chromatography. J Sep Sci 24:406–410Google Scholar
  12. Beesoon S, Webster G, Shoeib M, Harner T, Benskin JP, Martin JW (2009) Isomer profiles of perfluorinated compounds in house dust, pregnant women and cord serum: sources and transplacental transfer. Society of Environmental Toxicology and Chemistry 30th North American meeting, New Orleans, LA, USA, 19–23 NovGoogle Scholar
  13. Benskin JP, Bataineh M, Martin JW (2007) Simultaneous characterization of perfluoroalkyl carboxylate, sulfonate, and sulfonamide isomers by liquid chromatography–tandem mass spectrometry. Anal Chem 79:6455–6464Google Scholar
  14. Benskin JP, De Silva AO, Martin LJ, Arsenault G, McCrindle R, Riddell N, Mabury SA, Martin JW (2009a) Disposition of perfluorinated acid isomers in Sprague Dawley rats. Part 1: Single dose. Environ Toxicol Chem 28:542–554Google Scholar
  15. Benskin JP, Holt A, Martin JW (2009b) Isomer-specific biotransformation of a perfluorooctane sulfonate (PFOS)-precursor by cytochrome P450 isozymes and human liver microsomes. Environ Sci Technol 43:8566–8572Google Scholar
  16. Benskin JP, Arhens LWY, Yamashita N, Taniyasu S, Lam PKS, Tomy G, Muir DC, Scott B, Spencer C, Rosenberg B, Martin JW (2009c) Perfluorinated acid isomer profiles in ocean water. Society of Environmental Toxicology and Chemistry 30th North American meeting, New Orleans, LA, USA, 19–23 NovGoogle Scholar
  17. Bernett MK, Zisman WA (1967) Surface properties of perfluoro acids as affected by terminal branching and chlorine substitution. J Phys Chem 71:2075–2082Google Scholar
  18. Brace NO (1962) Long chain alkanoic and alkenoic acids with perfluoroalkyl terminal segments. J Org Chem 27:4491–4498Google Scholar
  19. Burns DC, Ellis DA, Li H, McMurdo CJ, Webster E (2008) Experimental pK a determination for perfluorooctanoic acid (PFOA) and the potential impact of pK a concentration dependence on laboratory-measured partitioning phenomena and environmental modeling. Environ Sci Technol 42:9283–9288Google Scholar
  20. Butenhoff J, Costa G, Elcombe C, Farrar D, Hansen K, Iwai H, Jung R, Kennedy G, Lieder P, Olsen G, Thomford P (2002) Toxicity of ammonium perfluorooctanoate in male cynomolgus monkeys after oral dosing for 6 months. Toxicol Sci 69:244–257Google Scholar
  21. Butt CM, Muir DC, Stirling I, Kwan M, Mabury SA (2007) Rapid response of Arctic ringed seals to changes in perfluoroalkyl production. Environ Sci Technol 41:42–49Google Scholar
  22. Chan E, Sandhu S, Benskin JP, Ralitsch M, Thibault N, Birkholz D, Martin JW (2009) Endogenous high-performance liquid chromatography/tandem mass spectrometry interferences and the case of perfluorohexane sulfonate (PFHxS) in human serum: Are we overestimating exposure? Rapid Commun Mass Spectrom 23:1405–1410Google Scholar
  23. Cheng J, Psillakis E, Hoffmann MR, Colussi AJ (2009) Acid dissociation versus molecular association of perfluoroalkyl oxoacids: environmental implications. J Phys Chem A 113:8152–8156Google Scholar
  24. Chu S, Letcher RJ (2009) Linear and branched perfluorooctane sulfonate isomers in technical product and environmental samples by in-port derivatization-gas chromatography–mass spectrometry. Anal Chem 81:4256–4262Google Scholar
  25. Cui L, Zhou QF, Liao CY, Fu JJ, Jiang GB (2009) Studies on the toxicological effects of PFOA and PFOS on rats using histological observation and chemical analysis. Arch Environ Contam Toxicol 56:338–349Google Scholar
  26. De Silva AO, Benskin JP, Martin LJ, Arsenault G, McCrindle R, Riddell N, Martin JW, Mabury SA (2009a) Disposition of perfluorinated acid isomers in Sprague-Dawley rats. Part 2: Subchronic dose. Environ Toxicol Chem 28:555–567Google Scholar
  27. De Silva AO, Mabury SA (2006) Isomer distribution of perfluorocarboxylates in human blood: potential correlation to source. Environ Sci Technol 40:2903–2909Google Scholar
  28. De Silva AO, Mabury SA (2004) Isolating isomers of perfluorocarboxylates in polar bears (Ursus maritimus) from two geographical locations. Environ Sci Technol 38:6538–6545Google Scholar
  29. De Silva AO, Muir DC, Mabury SA (2009b) Distribution of perfluorinated carboxylate isomers in select samples in the North American environment. Environ Toxicol Chem 28:1801–1814Google Scholar
  30. De Silva AO, Stock NL, Bonin J, Wong GW, Young C, Mabury SA (2008) Water solubility and octanol–water partition coefficient of perfluorooctylsulfonamides and fluorotelomer alcohols in: perfluorocarboxylate isomer analysis as a tool for source elucidation. PhD Thesis, Department of Chemistry, University of Toronto, ON, CanadaGoogle Scholar
  31. De Silva AO, Tseng PJ, Mabury SA (2009c) Toxicokinetics of perfluorocarboxylate isomers in rainbow trout. Environ Toxicol Chem 28:330–337Google Scholar
  32. D’eon JC, Hurley M, Wallington TJ, Mabury SA (2006) Atmospheric chemistry of N-methyl perfluorobutane sulfonamidoethanol, C4F9SO2N(CH3)CH2CH2OH: kinetics and mechanism of reaction with OH. Environ Sci Technol 40:1862–1868Google Scholar
  33. Dinglasan-Panlilio MJ, Mabury SA (2006) Significant residual fluorinated alcohols present in various fluorinated materials. Environ Sci Technol 40:1447–1453Google Scholar
  34. Ellis DA, Mabury SA, Martin JW, Muir DC (2001) Thermolysis of fluoropolymers as a potential source of halogenated organic acids in the environment. Nature 412:321–324Google Scholar
  35. Ellis DA, Martin JW, De Silva AO, Mabury SA, Hurley MD, Andersen MPS, Wallington TJ (2004) Degradation of fluorotelomer alcohols: a likely atmospheric source of perfluorinated carboxylic acids. Environ Sci Technol 38:3316–3321Google Scholar
  36. Ellis DA, Martin JW, Mabury SA, Hurley MD, Andersen MP, Wallington TJ (2003a) Atmospheric lifetime of fluorotelomer alcohols. Environ Sci Technol 37:3816–3820Google Scholar
  37. Ellis DA, Martin JW, Muir DC, Mabury SA (2003b) The use of 19F NMR and mass spectrometry for the elucidation of novel fluorinated acids and atmospheric fluoroacid precursors evolved in the thermolysis of fluoropolymers. Analyst 128:756–764Google Scholar
  38. Ellis DA, Webster E (2009) Response to comment on: aerosol enrichment of the surfactant PFO and mediation of the water–air transport of gaseous PFOA. Environ Sci Technol 43:1234–1235Google Scholar
  39. Fei C, McLaughlin JK, Lipworth L, Olsen J (2008) Prenatal exposure to perfluorooctanoate (PFOA) and perfluorooctanesulfonate (PFOS) and maternally reported developmental milestones in infancy. Environ Health Perspect 116:1391–1395Google Scholar
  40. Fluoropolymer Manufacturing Group (2002) Fluoropolymer manufacturers group presentation slides. U.S. EPA Administrative Record AR226-1094Google Scholar
  41. Furdui VI, Helm PA, Crozier PW, Lucaciu C, Reiner EI, Marvin CH, Whittle DM, Mabury SA, Tomy GT (2008) Temporal trends of perfluoroalkyl compounds with isomer analysis in Lake Trout from Lake Ontario (1979–2004). Environ Sci Technol 42:4739–4744Google Scholar
  42. Gauthier SA (2004) Aqueous photolysis of the 8:2 fluorotelomer alcohol and the determination of the water solubility of N-ethylperfluorooctanesulfoneamidoethyl alcohol. MSc Thesis, Department of Chemistry, University of Toronto, ON, CanadaGoogle Scholar
  43. Goss KU (2008a) Correction: the pK a values of PFOA and other highly fluorinated carboxylic acids. Environ Sci Technol 42:5032Google Scholar
  44. Goss KU (2008b) The pK a values of PFOA and other highly fluorinated carboxylic acids. Environ Sci Technol 42:456–458Google Scholar
  45. Grottenmuller R, Knaup W, Probst A, Dullinger B (2003) Process for the preparation of perfluorocarboxylic acids. US Patent 6,515,172 B2Google Scholar
  46. Haszeldine RN (1953) Reactions of fluorocarbon radicals. Part 12. The synthesis of fluorocarbons and of fully fluorinated iodo-, bromo-, and chloroalkanes. J Chem Soc 3761–3768Google Scholar
  47. Haug LS, Thomsen C, Becher G (2009) Time trends and the influence of age and gender on serum concentrations of perfluorinated compounds in archived human samples. Environ Sci Technol 43:2131–2136Google Scholar
  48. Holzer J, Midasch O, Rauchfuss K, Kraft M, Reupert R, Angerer J, Kleeschulte P, Marschall N, Wilhelm M (2008) Biomonitoring of perfluorinated compounds in children and adults exposed to perfluorooctanoate-contaminated drinking water. Environ Health Perspect 116:651–657Google Scholar
  49. Houde M, Czub G, Small JM, Backus S, Wang X, Alaee M, Muir DC (2008) Fractionation and bioaccumulation of perfluorooctane sulfonate (PFOS) isomers in a Lake Ontario food web. Environ Sci Technol 42:9397–9403Google Scholar
  50. Houde M, Martin JW, Letcher RJ, Solomon KR, Muir DC (2006) Biological monitoring of polyfluoroalkyl substances: a review. Environ Sci Technol 40:3463–3473Google Scholar
  51. Hu W, Jones PD, Upham BL, Trosko JE, Lau C, Giesy JP (2002) Inhibition of gap junctional intercellular communication by perfluorinated compounds in rat liver and dolphin kidney epithelial cell lines in vitro and Sprague-Dawley rats in vivo. Toxicol Sci 68:429–436Google Scholar
  52. Johansson N, Eriksson P, Viberg H (2009) Neonatal exposure to PFOS and PFOA in mice results in changes in proteins which are important for neuronal growth and synaptogenesis in the developing brain. Toxicol Sci 108:412–418Google Scholar
  53. Jones PD, Hu W, De Coen W, Newsted JL, Giesy JP (2003) Binding of perfluorinated fatty acids to serum proteins. Environ Toxicol Chem 22:2639–2649Google Scholar
  54. Ju X, Jin Y, Sasaki K, Saito N (2008) Perfluorinated surfactants in surface, subsurface water and microlayer from Dalian Coastal waters in China. Environ Sci Technol 42:3538–3542Google Scholar
  55. Karrman A, Langlois I, van Bavel B, Lindstrom G, Oehme M (2007) Identification and pattern of perfluorooctane sulfonate (PFOS) isomers in human serum and plasma. Environ Int 33:782–788Google Scholar
  56. Katakura M, Kudo N, Tsuda T, Hibino Y, Mitsumoto A, Kawashima Y (2007) Rat organic anion transporter 3 and organic anion transporting polypeptide 1 mediate perfluorooctanoic acid transport. J Health Sci 53:77–83Google Scholar
  57. Katsushima A, Hisamoto I, Nagai M (1970) US Patent 3,525,758Google Scholar
  58. Katsushima A, Hisamoto I, Nagai M, Fukui T, Kato T (1976) Method for water and oil repellent treatment. Japanese Patent 0831272 (in Japanese)Google Scholar
  59. Kestner T (3 M Co.) (1997) U.S. Environmental Protection Agency Public Docket AR226-0564: fluorochemical isomer distribution by 19F-NMR spectroscopy. U.S. Environmental Protection Agency, Office of Pollution Prevention and Toxic Substances, Washington, DCGoogle Scholar
  60. Kissa E (2005) Fluorinated surfactants and repellents, 2nd edn. Marcel Dekker, NewYorkGoogle Scholar
  61. Korkowski P, Kestner T (1999) Chemical characterization of FOSA & PFOSA samples by 1H and 19F NMR spectroscopy. Provided by 3 M Co, 21 Jan 2009Google Scholar
  62. Kudo N, Katakura M, Sato Y, Kawashima Y (2002) Sex hormone-regulated renal transport of perfluorooctanoic acid. Chem Biol Interact 139:301–316Google Scholar
  63. Kutsuna S, Hori J (2008) Experimental determination of Henry’s law constant of perfluorooctanoic acid (PFOA) at 298 K by means of an inert-gas stripping method with a helical plate. Atmos Environ 42:8883–8892Google Scholar
  64. Langlois I (2006) Mass spectrometric isomer characterization of perfluorinated compounds in technical mixture, water, and human blood. PhD Thesis, Department of Chemistry, University of Basel, SwitzerlandGoogle Scholar
  65. Langlois I, Berger U, Zencak Z, Oehme M (2007) Mass spectral studies of perfluorooctane sulfonate derivatives separated by high-resolution gas chromatography. Rapid Commun Mass Spectrom 21:3547–3553Google Scholar
  66. Langlois I, Oehme M (2006) Structural identification of isomers present in technical perfluorooctane sulfonate by tandem mass spectrometry. Rapid Commun Mass Spectrom 20:844–850Google Scholar
  67. Lau C, Anitole K, Hodes C, Lai D, Pfahles-Hutchens A, Seed J (2007) Perfluoroalkyl acids: a review of monitoring and toxicological findings. Toxicol Sci 99:366–394Google Scholar
  68. Lee JJ, Schultz IR (2010) Sex differences in the uptake and disposition of perfluorooctanoic acid in fathead minnows after oral dosing. Environ Sci Technol 44:491–497Google Scholar
  69. Lehmler HJ (2005) Synthesis of environmentally relevant fluorinated surfactants – a review. Chemosphere 58:1471–1496Google Scholar
  70. Lieder PH, Chang SC, York RG, Butenhoff JL (2009) Toxicological evaluation of potassium perfluorobutanesulfonate in a 90-day oral gavage study with Sprague-Dawley rats. Toxicology 255:45–52Google Scholar
  71. Lloyd AS, Bailey VA, Hird SJ, Routledge A, Clarke DB (2009) Mass spectral studies towards more reliable measurement of perfluorooctanesulfonic acid and other perfluorinated chemicals (PFCs) in food matrices using liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 23:2923–2938Google Scholar
  72. Lopez-Fontan JL, Sarmiento F, Schulz PC (2005) The aggregation of sodium perfluorooctanoate in water. Colloid Polym Sci 283:862–871Google Scholar
  73. Loveless SE, Finlay C, Everds NE, Frame SR, Gillies PJ, O’Connor JC, Powley CR, Kennedy GL (2006) Comparative responses of rats and mice exposed to linear/branched, linear, or branched ammonium perfluorooctanoate (APFO). Toxicol 220:203–217Google Scholar
  74. Luebker DJ, York RG, Hansen KJ, Moore JA, Butenhoff JL (2005) Neonatal mortality from in utero exposure to perfluorooctanesulfonate (PFOS) in Sprague-Dawley rats: dose–response, and biochemical and pharamacokinetic parameters. Toxicology 215:149–169Google Scholar
  75. Lv G, Wang L, Liu S, Li S (2009) Determination of perfluorinated compounds in packaging materials and textiles using pressurized liquid extraction with gas chromatography–mass spectrometry. Anal Sci 25:425–429Google Scholar
  76. Martin JW, Ellis DA, Mabury SA, Hurley MD, Wallington TJ (2006) Atmospheric chemistry of perfluoroalkanesulfonamides: kinetic and product studies of the OH radical and Cl atom initiated oxidation of N-ethyl perfluorobutanesulfonamide. Environ Sci Technol 40:864–872Google Scholar
  77. Martin JW, Kannan K, Berger U, de Voogt P, Field J, Franklin J, Giesy JP, Harner T, Muir DC, Scott B, Kaiser M, Jarnberg U, Jones KC, Mabury SA, Schroeder H, Simcik M, Sottani C, van Bavel B, Karrman A, Lindstrom G, van Leeuwen SP (2004) Analytical challenges hamper perfluoroalkyl research. Environ Sci Technol 38:248A–255AGoogle Scholar
  78. Martin JW, Mabury SA, O'Brien PJ (2005) Metabolic products and pathways of fluorotelomer alcohols in isolated rat hepatocytes. Chem Biol Interact 155:165–180Google Scholar
  79. McMurdo CJ, Ellis DA, Webster E, Butler J, Christensen RD, Reid LK (2008) Aerosol enrichment of the surfactant PFO and mediation of the water–air transport of gaseous PFOA. Environ Sci Technol 42:3969–3974Google Scholar
  80. Millauer H (1974) US Patent 3,829,512Google Scholar
  81. Ochoa-Herrera V, Sierra-Alvarez R, Somogyi A, Jacobsen NE, Wysocki VH, Field JA (2008) Reductive defluorination of perfluorooctane sulfonate. Environ Sci Technol 42:3260–3264Google Scholar
  82. OECD (2002) OECD document ENV/JM/RD(2002)17/FINAL: hazard assessment of PFOS. Organisation for Economic Co-operation and Development Environment Directorate, ParisGoogle Scholar
  83. Ohmori K, Kudo N, Katayama K, Kawashima Y (2003) Comparison of the toxicokinetics between perfluorocarboxylic acids with different carbon chain length. Toxicology 184:135–140Google Scholar
  84. Olsen GW, Burris JM, Ehresman DJ, Froehlich JW, Seacat AM, Butenhoff JL, Zobel LR (2007) Half-life of serum elimination of perfluorooctanesulfonate, perfluorohexanesulfonate, and perfluorooctanoate in retired fluorochemical production workers. Environ Health Perspect 115:1298–1305Google Scholar
  85. Olsen GW, Chang SC, Noker PE, Gorman GS, Ehresman DJ, Lieder PH, Butenhoff JL (2009) A comparison of the pharmacokinetics of perfluorobutanesulfonate (PFBS) in rats, monkeys, and humans. Toxicology 256:65–74Google Scholar
  86. Parsons JR, Sáez M, Dolfing J, de Voogt P (2008) Biodegradation of perfluorinated compounds. Rev Environ Contam Toxicol 196:53–71Google Scholar
  87. Paul AG, Jones KC, Sweetman AJ (2009) A first global production, emission, and environmental inventory for perfluorooctane sulfonate. Environ Sci Technol 43:386–392Google Scholar
  88. Perrin DD, Dempsey B, Serjeant EP (1981) pK a prediction for organic acids and bases. Chapman and Hall, LondonGoogle Scholar
  89. Plumlee MH, McNeill K, Reinhard M (2009) Indirect photolysis of perfluorochemicals: hydroxyl radical-initiated oxidation of N-ethyl perfluorooctane sulfonamido acetate (NEtFOSAA) and other perfluoroalkane sulfonamides. Environ Sci Technol 43:3662–3668Google Scholar
  90. Powley CR, George SW, Russell MH, Hoke RA, Buck RC (2008) Polyfluorinated chemicals in a spatially and temporally integrated food web in the Western Arctic. Chemosphere 70:664–672Google Scholar
  91. Prevedouros K, Cousins IT, Buck RC, Korzeniowski SH (2006) Sources, fate and transport of perfluorocarboxylates. Environ Sci Technol 40:32–44Google Scholar
  92. Rayne S, Forest K, Friesen KJ (2009) Computational approaches may underestimate pK(a) values of longer-chain perfluorinated carboxylic acids: implications for assessing environmental and biological effects. J Environ Sci Health A Tox Hazard Subst Environ Eng 44:317–326Google Scholar
  93. Rayne S, Forest K, Friesen KJ (2008a) Relative gas-phase free energies for the C3 through C8 linear and branched perfluorinated sulfonic acids: implications for kinetic versus thermodynamic control during synthesis of technical mixtures and predicting congener profile inputs to environmental systems. J Mol Struct: Theochem 869:81–83Google Scholar
  94. Rayne S, Forest K, Friesen KJ (2008b) Congener-specific numbering systems for the environmentally relevant C4 through C8 perfluorinated homologue groups of alkyl sulfonates, carboxylates, telomer alcohols, olefins, and acids, and their derivatives. J Environ Sci Health A Tox Hazard Subst Environ Eng 43:1391–1401Google Scholar
  95. Reagen WK, Lindstrom KR, Jacoby CB, Purcell RG, Kestner TA, Payfer RM, Miller JW (2007) Environmental characterization of 3 M electrochemical fluorination derived perfluorooctanoate and perfluorooctanesulfonate. Society of Environmental Toxicology and Chemistry 28th North American meeting, Milwaukee, WI, USA, 11–15 NovGoogle Scholar
  96. Rhoads KR, Janssen EM, Luthy RG, Criddle CS (2008) Aerobic biotransformation and fate of N-ethyl perfluorooctane sulfonamidoethanol (N-EtFOSE) in activated sludge. Environ Sci Technol 42:2873–2879Google Scholar
  97. Riddell N, Arsenault G, Benskin JP, Chittim B, Martin JW, McAlees A, McCrindle R (2009) Branched perfluorooctane sulfonate isomer quantification and characterization in real samples by HPLC/ESI-MS(/MS). Environ Sci Technol 43:7902–7908Google Scholar
  98. Ruisheng Y (2008) Additional information of production and use of PFOS. Fax from Ministry of Environmental Protection of China. Stockholm Convention Secretatiat, Geneva, Switzerland. http://chm.pops.int/Portals/0/Repository/addinfo_2008/UNEP-POPS-POPRC-SUB-F08-PFOS-ADIN-CHI.English.pdf Google Scholar
  99. Rylander C, Brustad M, Falk H, Sandanger TM (2009a) Dietary predictors and plasma concentrations of perfluorinated compounds in a coastal population from northern Norway. J Environ Pub Health 2009:1–10Google Scholar
  100. Rylander C, Duong Trong P, Odland JO, Sandanger TM (2009b) Perfluorinated compounds in delivering women from south central Vietnam. J Environ Monit 11:2002–2008Google Scholar
  101. Santoro MA (2009) Activities at 3 M and Dyneon LLC to develop PFC alternatives. Workshop on managing perfluorinated chemicals and transitioning to safer alternatives, Geneva, Switzerland, February 12–13Google Scholar
  102. Savu PM (1994) Fluorinated higher carboxylic acids. In: Kirk-Othmer encyclopedia of chemical technology, John Wiley & Sons, USAGoogle Scholar
  103. Seacat AM, Thomford PJ, Hansen KJ, Clemen LA, Eldridge SR, Elcombe CR, Butenhoff JL (2003) Sub-chronic dietary toxicity of potassium perfluorooctanesulfonate in rats. Toxicology 183:117–131Google Scholar
  104. Seacat AM, Thomford PJ, Hansen KJ, Olsen GW, Case MT, Butenhoff JL (2002) Subchronic toxicity studies on perfluorooctanesulfonate potassium salt in cynomolgus monkeys. Toxicol Sci 68:249–264Google Scholar
  105. Senthil Kumar K, Zushi Y, Masunaga S, Gilligan M, Sajwan SS (2009) Perfluorinated organic contaminants in sediment and aquatic wildlife, including sharks, from Georgia, USA. Mar Pollut Bull 58:601–634Google Scholar
  106. Sharpe RL, Benskin JP, Laarman AL, MacLeod SM, Martin JW, Wong CS, Goss GG (2010) Perfluorooctane sulfonate toxicity, isomer-specific accumulation, and maternal transfer in zebrafish (Danio rerio) and rainbow trout (Oncorhynchus mykiss). Environ Toxicol Chem (in press)Google Scholar
  107. Shelton K (2009) DuPont approach to PFOA stewardship. Presentation at international workshop on managing perfluorinated chemicals and transitioning to safer alternatives, Geneva, Switzerland, 12–13 FebGoogle Scholar
  108. Shin-ya S (2009) PFC activities at Asahi. Presentation at international workshop on managing perfluorinated chemicals and transitioning to safer alternatives, Geneva, Switzerland, 12–13 FebGoogle Scholar
  109. Simons JH (1949) Electrochemical process for the production of fluorocarbons. J Electrochem Soc 95:47–59Google Scholar
  110. Skutlarek D, Exner M, Färber H (2006) Perfluorinated surfactants in surface and drinking waters. Environ Sci Pollut Res 13:299–307Google Scholar
  111. Smart BE (2001) Fluorine substituent effects (on bioactivity). J Fluorine Chem 109:3–8Google Scholar
  112. Stevenson L (2002) U.S. Environmental Protection Agency Public Docket AR-2261150: comparative analysis of fluorochemicals in human serum samples obtained commercially. U.S. Environmental Protection Agency, Office of Pollution Prevention and Toxic Substances, Washington, DCGoogle Scholar
  113. Tomy GT, Tittlemier SA, Palace VP, Budakowski WR, Braekevelt E, Brinkworth L, Friesen K (2004) Biotransformation of N-ethyl perfluorooctanesulfonamide by rainbow trout (Oncorhynchus mykiss) liver microsomes. Environ Sci Technol 38:758–762Google Scholar
  114. Vanden Heuvel JP, Thompson JT, Frame SR, Gillies PJ (2006) Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha. Toxicol Sci 92:476–489Google Scholar
  115. Vyas SM, Kania-Korwel I, Lehmler HJ (2007) Differences in the isomer composition of perfluorooctanesulfonyl (PFOS) derivatives. J Environ Sci Health A Tox Hazard Subst Environ Eng 42:249–255Google Scholar
  116. Wallington TJ, Hurley MD, Xia J, Wuebbles DJ, Sillman S, Ito A, Penner JE, Ellis DA, Martin J, Mabury SA, Nielsen OJ, Sulbaek Andersen MP (2006) Formation of C7F15COOH (PFOA) and other perfluorocarboxylic acids during the atmospheric oxidation of 8:2 fluorotelomer alcohol. Environ Sci Technol 40:924–930Google Scholar
  117. Wang Y, Arsenault G, Riddell N, McCrindle R, McAlees A, Martin JW (2009) Perfluorooctane sulfonate (PFOS) precursors can be metabolized enantioselectively: principle for a new PFOS source tracking tool. Environ Sci Technol 43:8283–8289Google Scholar
  118. Wania F (2007) A global mass balance analysis of the source of perfluorocarboxylic acids in the Arctic Ocean. Environ Sci Technol 41:4529–4535Google Scholar
  119. Wellington Laboratories (2005) Certificate of analysis/documentation for T-PFOS. Obtained Mar 2006 from Wellington Laboratories, Guelph, ON, CanadaGoogle Scholar
  120. Wellington Laboratories (2007) Certificate of analysis/documentation for br-PFOSK. Obtained Jan 2008 from Wellington Laboratories, Guelph, ON, CanadaGoogle Scholar
  121. Wellington Laboratories (2008) Certificate of analysis/documentation for individual PFOS/PFOA isomers. Obtained Sept 2008 from Wellington Laboratories, Guelph, ON, CanadaGoogle Scholar
  122. Wendling L (2003) U.S. Environmental Protection Agency Public Docket OPPT-2003-0012-0007: environmental, health and safety measures relating to perfluorooctanoic acid and its salts (PFOA). U.S. Environmental Protection Agency, Office of Pollution Prevention and Toxic Substances, Washington, DCGoogle Scholar
  123. White SS, Kato K, Jia LT, Basden BJ, Calafat AM, Hines EP, Stanko JP, Wolf CJ, Abbott BD, Fenton SE (2009) Effects of perfluorooctanoic acid on mouse mammary gland development and differentiation resulting from cross-foster and restricted gestational exposures. Reprod Toxicol 29:289–298Google Scholar
  124. Xu L, Krenitsky DM, Seacat AM, Butenhoff JL, Anders MW (2004) Biotransformation of N-ethyl-N-(2-hydroxyethyl)perfluorooctanesulfonamide by rat liver microsomes, cytosol, and slices and by expressed rat and human cytochromes P450. Chem Res Toxicol 17:767–775Google Scholar
  125. Yamamoto T, Noma Y, Sakai S, Shibata Y (2007) Photodegradation of perfluorooctane sulfonate by UV irradiation in water and alkaline 2-propanol. Environ Sci Technol 41:5660–5665Google Scholar
  126. Young CJ, Furdui VI, Franklin J, Koerner RM, Muir DC, Mabury SA (2007) Perfluorinated acids in Arctic snow: new evidence for atmospheric formation. Environ Sci Technol 41:3455–3461Google Scholar
  127. Zushi Y, Tamada M, Kanai Y, Masunaga S (2010) Time trends of perfluorinated compounds from the sediment core of Tokyo Bay, Japan (1950s–2004). Environ Pollut 158:756–763Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Jonathan P. Benskin
    • 1
  • Amila O. De Silva
    • 2
  • Jonathan W. Martin
    • 1
  1. 1.Division of Analytical and Environmental Toxicology, Department of Laboratory Medicine and PathologyUniversity of AlbertaEdmontonCanada
  2. 2.Environment Canada, Water Science and Technology DirectorateBurlingtonCanada

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