Physicochemical Properties and Aquatic Toxicity of Poly- and Perfluorinated Compounds

REFERENCES

• Renner , R. 2001 . Growing concern over perfluorinated chemicals . Environmental Science and Technology , 35 : 154A – 160A .
   PubMed Web of Science ®Google Scholar
• Renner , R. 2003 . Concerns over common perfluorinated surfactant . Environmental Science and Technology , 37 : 201A – 202A .
   PubMed Web of Science ®Google Scholar
• Rayne , S. and Forest , K. 2009 . Perfluoroalkyl sulfonic and carboxylic acids: A critical review of physicochemical properties, levels and patterns in waters and wastewaters, and treatment methods . Journal of Environmental Science and Health, Part A , 44 : 1145 – 1199 .
   Web of Science ®Google Scholar
• Key , B. D. , Howell , R. D. and Criddle , C. S. 1997 . Fluorinated organic in the biosphere . Environmental Science and Technology , 31 : 2445 – 2454 .
   Web of Science ®Google Scholar
• Kissa , E. 2001 . Fluorinated surfactants and repellants (2nd ed.) , New York : Marcel Decker .
   Google Scholar
• Giesy , J. P. and Kannan , K. 2002 . Perfluorochemical surfactants in the environment . Environmental Science and Technology , 36 : 146A – 152A .
   Web of Science ®Google Scholar
• Lau , C. , Butenhoff , J. L. and Rogers , J. M. 2004 . The developmental toxicity of perfluororalkyl acids and their derivatives . Toxicology and Applied Pharmacology , 198 : 231 – 241 .
   PubMed Web of Science ®Google Scholar
• Schultz , M. , Barofsky , D. and Field , J. 2003 . Fluorinated alkyl surfactants . Environmental Engineering Science , 20 : 487 – 501 .
   Web of Science ®Google Scholar
• Lehmler , H. 2005 . Synthesis of environmentally relevant fluorinated surfactants: A review . Chemosphere , 58 : 1471 – 1496 .
   PubMed Web of Science ®Google Scholar
• Prevedouros , K. , Cousins , I. T. , Buck , R. C. and Korzeniowski , S. H. 2006 . Sources, fate and transport of perfluorocarboxylates . Environmental Science and Technology , 40 : 32 – 44 .
   PubMed Web of Science ®Google Scholar
• Paul , A. G. , Jones , K. C. and Sweetman , A. J. 2009 . A first global production, emission, and environmental inventory for perfluorooctane sulfonate . Environmental Science and Technology , 43 : 386 – 392 .
   PubMed Web of Science ®Google Scholar
• 3M . 1999 . Fluorochemical use, distribution and release overview , AR226 – 0550 . St. Paul , MN : 3M Company .
   Google Scholar
• Powley , C. R. , George , S. W. , Russell , M. H. , Hoke , R. A. and Buck , R. C. 2008 . Polyfluorinated chemicals in a spatially and temporally integrated food web in the Western Arctic . Chemosphere , 70 : 664 – 672 .
   PubMed Web of Science ®Google Scholar
• Ellis , D. A. , Martin , J. W. , De Silva , A. O. , Mabury , S. A. , Hurley , M. D. , Sulbaek Andersen , M. P. and Wallington , T. J. 2004 . Degradation of fluorotelomer alcohols: A likely atmospheric source of perfluorinated carboxylic acids . Environmental Science and Technology , 38 : 3316 – 3321 .
   PubMed Web of Science ®Google Scholar
• Martin , J. W. , Mabury , S. A. and O’Brien , P. J. 2005 . Metabolic products and pathways of fluorotelomer alcohols in isolated rat hepatocytes . Chemico-Biological Interactions , 155 : 165 – 180 .
   PubMed Web of Science ®Google Scholar
• Wang , N. , Szostek , B. , Buck , R. C. , Folsom , P. W. , Sulecki , L. and Gannon , J. T. 2009 . 8–2 Fluorotelomer alcohol aerobic soil biodegradation: pathways, metabolites, and metabolite yields . Chemosphere , 75 : 1089 – 1096 .
   PubMed Web of Science ®Google Scholar
• Liu , J. X. , Wang , N. , Szostek , B. , Buck , R. C. , Panciroli , P. K. , Folsom , P. W. , Sulecki , L. M. and Bellin , C. A. 2010 . 6–2 Fluorotelomer alcohol aerobic biodegradation in soil and mixed bacterial culture . Chemosphere , 78 : 437 – 444 .
   PubMed Web of Science ®Google Scholar
• 3M . 2000 . Sulfonated perfluorochemicals in the environment: Sources, dispersion, fate and effects , AR226 – 0545 . St. Paul , MN : 3M Company .
   Google Scholar
• 3M . 2000 . Sulfonated perfluorochemicals: U.S. release estimation: 1997 Part 1: Life-cycle waste stream estimates , AR226 – 0681 . St. Paul , MN : 3M Company .
   Google Scholar
• Lau , C. , Lindstrom , A. B. and Seed , J. 2009 . Perfluorinated chemicals 2008: PFAA days II meeting report and highlights . Reproductive Toxicology , 27 : 429 – 434 .
   PubMedGoogle Scholar
• Giesy , J. P. and Kannan , K. 2001 . Global distribution of perfluorooctane sulfonate in wildlife . Environmental Science and Technology , 35 : 1339 – 1342 .
   PubMed Web of Science ®Google Scholar
• Houde , M. , Martin , J. W. , Letcher , R. J. , Solomon , K. R. and Muir , D. C. G. 2006 . Biological monitoring of polyfluoroalkyl substances: A review . Environmental Science and Technology , 40 : 3463 – 3473 .
   PubMed Web of Science ®Google Scholar
• Lau , C. , Anitole , K. , Hodes , C. , Lai , D. , Pfahles-Hutchens , A. and Seed , J. 2007 . Perfluoroalkyl acids: A review of monitoring and toxicological findings . Toxicological Sciences , 99 : 366 – 394 .
   PubMed Web of Science ®Google Scholar
• Dreyer , A. , Weinberg , I. , Temme , C. and Ebinghaus , R. 2009 . Polyfluorinated compounds in the atmosphere of the Atlantic and Southern Oceans: Evidence for a global distribution . Environmental Science and Technology , 43 : 6507 – 6514 .
   PubMed Web of Science ®Google Scholar
• Kannan , K. , Corsolini , S. , Falandysz , J. , Fillmann , G. , Kumar , K. S. , Loganathan , B. G. , Mohd , M. A. , Olivero , J. , Van Wouwe , N. , Yang , J. H. and Aldous , K. M. 2004 . Perfluorooctanesulfonate and related fluorochemicals in human blood from several countries . Environmental Science and Technology , 38 : 4489 – 4495 .
   PubMed Web of Science ®Google Scholar
• D’eon , J. C. , Crozier , P. W. , Furdui , V. I. , Reiner , E. J. , Libelo , E. L. and Mabury , S. A. 2009 . Observation of a commercial fluorinated material, the polyfluoroalkyl phosphoric acid diesters, in human sera, wastewater treatment plant sludge, and paper fibers . Environmental Science and Technology , 43 : 4589 – 4594 .
   PubMed Web of Science ®Google Scholar
• Fromme , H. , Tittlemier , S. A. , Völkel , W. , Wilhelm , M. and Twardella , D. 2009 . Perfluorinated compounds–exposure assessment for the general population in western countries . International Journal of Hygiene and Environmental Health , 212 : 239 – 270 .
   PubMed Web of Science ®Google Scholar
• Jones , P. D. , Hu , W. , De Coen , W. , Newsted , J. L. and Giesy , J. P. 2003 . Binding of perfluorinated fatty acids to serum proteins . Environmental Toxicology and Chemistry , 22 : 2639 – 2649 .
   PubMed Web of Science ®Google Scholar
• Luebker , D. J. , Hansen , K. J. , Bass , N. M. , Butenhoff , J. L. and Seacat , A. M. 2002 . Interactions of fluorochemicals with rat liver fatty acid-binding protein . Toxicology , 176 : 175 – 185 .
   PubMed Web of Science ®Google Scholar
• Martin , J. W. , Mabury , S. A. , Solomon , K. R. and Muir , D. C. 2003 . Dietary accumulation of perfluorinated acids in juvenile rainbow trout (Oncorhynchus mykiss) . Environmental Toxicology and Chemistry , 22 : 189 – 195 .
   PubMed Web of Science ®Google Scholar
• Martin , J. W. , Mabury , S. A. , Solomon , K. R. and Muir , D. C. G. 2003 . Bioconcentration and tissue distribution of perfluorinated acids in rainbow trout (Oncorhynchus mykiss) . Environmental Toxicology and Chemistry , 22 : 196 – 204 .
   PubMed Web of Science ®Google Scholar
• Kennedy , G. L. , Butenhoff , J. L. , Olsen , G. W. , O’Connor , J. C. , Seacat , A. M. , Perkins , R. G. , Biegel , L. B. , Murphy , S. R. and Farrar , D. G. 2004 . The toxicology of perfluorooctanoate . Critical Reviews in Toxicology , 34 : 351 – 384 .
   PubMed Web of Science ®Google Scholar
• Andersen , M. E. , Butenhoff , J. L. , Shang , S. C. , Farrar , D. G. , Kennedy , G. L. and Lau , C. 2008 . Perfluoroalkyl acids and related chemistries—toxicokinetics and modes of action . Toxicological Sciences , 102 : 3 – 14 .
   PubMed Web of Science ®Google Scholar
• Jensen , A. A. and Leffers , H. 2008 . Emerging endocrine disrupters: Perfluoroalkylated substances . International Journal of Andrology , 31 : 161 – 169 .
   PubMed Web of Science ®Google Scholar
• Olsen , G. W. , Butenhoff , J. L. and Zobel , L. R. 2009 . Perfluoroalkyl chemicals and human fetal development: An epidemiologic review with clinical and toxicological perspectives . Reproductive Toxicology , 27 : 212 – 230 .
   PubMed Web of Science ®Google Scholar
• Shinoda , K. , Hato , M. and Hayashi , T. 1972 . The physico-chemical properties of aqueous solutions of fluorinated surfactants . The Journal of Physical Chemistry , 76 : 909 – 914 .
   Web of Science ®Google Scholar
• Kunieda , H. and Shinoda , K. 1976 . Krafft points, critical micelle concentrations, surface tension, and solubilizing power of aqueous solutions of fluorinated surfactants . The Journal of Physical Chemistry , 80 : 2468 – 2470 .
   Web of Science ®Google Scholar
• NICNAS . 2005 . Potassium perfluorobutane sulfonate: Hazard assessment. Australia Retrieved from http://www.nicnas.gov.au/Publications/CAR/Other/Potassium_Perfluorobutane_Sulfonate_PDF.pdf
   Google Scholar
• Organization for Economic Cooperation and Development . 2002 . Hazard assessment of perfluorooctane sulfonate (PFOS) and its salts ENV/JM/RD(2002)17/FINAL. Joint Meeting of the Chemicals Committee and the Working Party on Chemicals, Pesticides, and Biotechnology, Environment Directorate. Paris: OECD. Retrieved from http://www.oecd.org/dataoecd/23/18/2382880.pdf
   Google Scholar
• Minnesota Pollution Control Agency . 2007 . Surface water quality criterion for perfluorooctane sulfonic acid STS Project 200604796
   Google Scholar
• 3M . 2001 . Solubility of PFOS in water , St. Paul , MN : 3M Company . 3M Environmental Laboratory, Project Number E00-1716
   Google Scholar
• 3M . 2001 . Solubility of PFOS in natural seawater and an aqueous solution of 3.5% sodium chloride , St. Paul , MN : 3M Company . 3M Environmental Laboratory, Lab Project Number E00-1716
   Google Scholar
• 3M . 2001 . Solubility of PFOS in octanol , St. Paul , MN : 3M Company . 3M Environmental Laboratory, Laboratory Project Number E00-1716
   Google Scholar
• 3M Environmental Laboratory . 2001 . Characterization study of PFOA (lot #332), primary standard: Test control reference #TCR-99030–030. Phase: Solubility Determination , St. Paul , MN : 3M Company .
   Google Scholar
• Kaiser , M. A. , Cobranchi , D. P. , Kao , C. P. C. , Krusic , P. J. , Marchione , A. A. and Buck , R. C. 2004 . Physicochemical properties of 8–2 fluorinated Telomer B alcohol . Journal of Chemical and Engineering Data , 49 : 912 – 916 .
   Web of Science ®Google Scholar
• Liu , J. and Lee , L. S. 2005 . Solubility and sorption by soils of 8:2 fluorotelomer alcohol in water and cosolvent systems . Environmental Science and Technology , 39 : 7535 – 7540 .
   PubMed Web of Science ®Google Scholar
• Liu , J. and Lee , L. S. 2007 . Effect of fluorotelomer alcohol chain length on aqueous solubility and sorption by soils . Environmental Science and Technology , 41 : 5357 – 5362 .
   PubMed Web of Science ®Google Scholar
• Fischer-Drowos , S. G. , Betz , L. R. , Dibussolo , J. M. , Miscavige , J. A. and Madhoun , N. M. 2007 . Melting point and aqueous solubility determination of 2H-hexadecafluoro-2-decenoic acid (C10F16H2O2) . Journal of Chemical and Engineering Data , 52 : 759 – 761 .
   Web of Science ®Google Scholar
• Bhhatarai , B. and Gramatica , P. 2010 . Prediction of aqueous solubility, vapor pressure and critical micelle concentration for aquatic partitioning of perfluorinated chemicals . Environmental Science and Technology , 45 : 8120 – 8128 .
   PubMed Web of Science ®Google Scholar
• Crowder , G. A. , Taylor , Z. L. , Reed , T. M. and Young , J. A. 1967 . Vapor pressures and triple point temperatures for several pure fluorocarbons . Journal of Chemical and Engineering Data , 12 : 481 – 485 .
   Web of Science ®Google Scholar
• Mousat , A. H. N. 1978 . Study of vapor pressure and critical properties of perfluoro-n-hexane . Journal of Chemical and Engineering Data , 23 : 133 – 134 .
   Web of Science ®Google Scholar
• Dias , A. M. A. , Gonçalves , C. M. B. , Caço , A. I. , Santos , L. M. N. B. F. , Piñeiro , M. M. , Vega , L. F. , Coutinho , J. A. P. and Marrucho , I. M. 2005 . Densities and vapor pressures of highly fluorinated compounds . Journal of Chemical and Engineering Data , 50 : 1328 – 1333 .
   Web of Science ®Google Scholar
• Steele , W. V. , Chirico , R. D. , Knipmeyer , S. E. and Nguyen , A. 1997 . Vapor pressure, heat capacity, and density along the saturation line, measurements for dimethyl isophthalate, dimethyl carbonate, 1,3,5-triethylbenzene, pentafluorophenol, 4-tert-butylcatechol, a-methylstyrene, and N,N’-bis(2-hydroxyethyl)ethylenediamine . Journal of Chemical and Engineering Data , 42 : 1008 – 1020 .
   Web of Science ®Google Scholar
• Steele , W. V. , Chirico , R. D. , Knipmeyer , S. E. and Nguyen , A. 1997 . Vapor pressure, heat capacity, and density along the saturation line, measurements for cyclohexanol, 2-cyclohexen-1-one, 1,2-dichloropropane, 1,4-di-tert-butylbenzene, (±)-2-ethylhexanoic acid, 2-(methylamino)ethanol, perfluoro-n-heptane, and sulfolane . Journal of Chemical and Engineering Data , 42 : 1021 – 1036 .
   Web of Science ®Google Scholar
• Steele , W. V. , Chirico , R. D. , Knipmeyer , S. E. and Nguyen , A. 2002 . Vapor pressure, heat capacity, and density along the saturation line: Measurements for benzenamine, butylbenzene, sec-butylbenzene, tert-butylbenzene, 2,2-dimethylbutanoic acid, tridecafluoroheptanoic acid, 2-butyl-2-ethyl-1,3-propanediol, 2,2,4-trimethyl-1,3-pentanediol, and 1-chloro-2-propanol . Journal of Chemical and Engineering Data , 47 : 648 – 666 .
   Web of Science ®Google Scholar
• Steele , W. V. , Chirico , R. D. , Knipmeyer , S. E. and Nguyen , A. 2002 . Measurements of vapor pressure, heat capacity, and density along the saturation line for cyclopropane carboxylic acid, N,N-diethylethanolamine, 2,3-dihydrofuran, 5-hexen-2-one, perfluorobutanoic acid, and 2-phenylpropionaldehyde . Journal of Chemical and Engineering Data , 47 : 715 – 724 .
   Web of Science ®Google Scholar
• Kaiser , M. A. , Larsen , B. S. , Kao , C. P. C. and Buck , R. C. 2005 . Vapor pressures of perfluorooctanoic, -nonanoic, -decanoic, -undecanoic, and -dodecanoic acids . Journal of Chemical and Engineering Data , 50 : 1841 – 1843 .
   Web of Science ®Google Scholar
• Scott , L. S. 1986 . Determination of activity coefficients by accurate measurement of boiling point diagram . Fluid Phase Equilibria , 26 : 149 – 163 .
   Web of Science ®Google Scholar
• Washburn , S. T. , Bingman , T. S. , Braithwaite , S. K. , Buck , R. C. , Buxton , L. W. , Clewell , H. J. , Haroun , L. A. , Kester , J. E. , Rickard , R. W. and Shipp , A. M. 2005 . Exposure assessment and risk characterization for perfluorooctanoate in selected consumer articles . Environmental Science and Technology , 39 : 3904 – 3910 .
   PubMed Web of Science ®Google Scholar
• Barton , C. A. , Botelho , M. A. and Kaiser , M. A. 2008 . Solid vapor pressure and enthalpy of sublimation for perfluorooctanoic acid . Journal of Chemical and Engineering Data , 53 : 939 – 941 .
   Web of Science ®Google Scholar
• Barton , C. A. , Botelho , M. A. and Kaiser , M. A. 2009 . Solid vapor pressure and enthalpy of sublimation for ammonium perfluorooctanoate . Journal of Chemical and Engineering Data , 54 : 752 – 755 .
   Web of Science ®Google Scholar
• Lei , Y. D. , Wania , F. , Mathers , D. and Mabury , S. A. 2004 . Determination of vapor pressures, octanol-air, and water-air partition coefficients for polyfluorinated sulfonamide, sulfonamidoethanols, and telomer alcohols . Journal of Chemical and Engineering Data , 49 : 1013 – 1022 .
   Web of Science ®Google Scholar
• Shoeib , M. , Harner , T. , Ikonomou , M. and Kannan , K. 2004 . Indoor and outdoor air concentrations and phase partitioning of perfluoroalkyl sulfonamides and polybrominated diphenyl ethers . Environmental Science and Technology , 38 : 1313 – 1320 .
   PubMed Web of Science ®Google Scholar
• Wania , F. , Shiu , W.-Y. and Mackay , D. 1994 . Measurement of the vapor pressure of several low-volatility organochlorine chemicals at low temperatures with a gas saturation method . Journal of Chemical and Engineering Data , 39 : 572 – 577 .
   Web of Science ®Google Scholar
• Stock , N. L. , Ellis , D. A. , Deleebeeck , L. , Muir , D. C. G. and Mabury , S. A. 2004 . Vapor pressures of the fluorinated telomer alcohols: Limitations of estimation methods . Environmental Science and Technology , 38 : 1693 – 1699 .
   PubMed Web of Science ®Google Scholar
• Krusic , P. J. , Marchione , A. A. , Davidson , F. , Kaiser , M. A. , Kao , C. C. , Richardson , R. E. , Botelho , M. , Waterland , R. L. and Buck , R. C. 2005 . Vapor pressure and intramolecular hydrogen bonding in fluorotelomer alcohols . The Journal of Physical Chemistry A , 109 : 6232 – 6241 .
   PubMed Web of Science ®Google Scholar
• Goss , K. , Bronner , G. , Harner , T. , Hertel , M. and Schmidt , T. C. 2006 . The partition behavior of fluorotelomer alcohols and olefins . Environmental Science and Technology , 40 : 3572 – 3577 .
   PubMed Web of Science ®Google Scholar
• Arp , H. P. H. , Niederer , C. and Goss , K. 2006 . Predicting the partitioning behavior of various highly fluorinated compounds . Environmental Science and Technology , 40 : 7298 – 7304 .
   PubMed Web of Science ®Google Scholar
• Cobranchi , D. P. , Botelho , M. , Buxton , L. W. , Buck , R. C. and Kaiser , M. A. 2006 . Vapor pressure determinations of 8–2 fluorortelomer alcohol and 1-H perfluorooctane by capillary gas chromatography Relative retention time versus headspace methods . The Journal of Chromatography A , 1108 : 248 – 251 .
   PubMed Web of Science ®Google Scholar
• Moroi , Y. , Yano , H. , Shibata , O. and Yonemitsu , T. 2001 . Determination of acidity constants of perfluoroalkanoic acids . Bulletin of the Chemical Society of Japan , 74 : 667 – 672 .
   Web of Science ®Google Scholar
• Burns , D. C. , Ellis , D. A. , Li , H. , McMurdo , C. J. and Webster , E. 2008 . Experimental pKa determination for perfluorooctanoic acid (PFOA) and the potential impact of pKa concentration dependence on laboratory-measured partitioning phenomena and environmental modeling . Environmental Science and Technology , 42 : 9283 – 9288 .
   PubMed Web of Science ®Google Scholar
• McMurdo , C. J. , Ellis , D. A. , Webster , E. , Butler , J. , Christensen , R. D. and Reid , L. K. 2008 . Aerosol enrichment of the surfactant PFO and mediation of the water-air transport of gaseous PFOA . Environmental Science and Technology , 42 : 3969 – 3974 .
   PubMed Web of Science ®Google Scholar
• Goss , K. U. 2008 . The pKa values of PFOA and other highly fluorinated carboxylic acids . Environmental Science and Technology , 42 : 456 – 458 .
   PubMed Web of Science ®Google Scholar
• Goss , K. U. 2008 . The pKa values of PFOA and other highly fluorinated carboxylic acids—correction . Environmental Science and Technology , 42 : 5032 – 5032 .
   Web of Science ®Google Scholar
• Goss , K. U. and Arp , H. P. H. 2009 . Comment on “Experimental pKa determination for perfluorooctanoic acid (PFOA) and the potential impact of pKa concentration dependence on laboratory-measured partitioning phenomena and environmental modeling” . Environmental Science and Technology , 43 : 5150 – 5151 .
   PubMed Web of Science ®Google Scholar
• Ellis , D. A. and Webster , E. 2009 . Response to comment on “Aerosol enrichment of the surfactant PFO and mediation of the water-air transport of gaseous PFOA.” . Environmental Science and Technology , 43 : 1234 – 1235 .
   Web of Science ®Google Scholar
• Rayne , S. , Forest , K. and Friesen , K. J. 2009 . Computational approaches may underestimate pKa values of longer-chain perfluorinated carboxylic acids: Implications for assessing environmental and biological effects . Journal of Environmental Science and Health, Part A , 44 : 317 – 326 .
   PubMed Web of Science ®Google Scholar
• Rayne , S. , Forest , K. and Friesen , K. 2009 . Extending the semi-empirical PM6 method for carbon oxyacid pKa prediction to sulfonic acids: application toward congener-specific estimates for the environmentally and toxicologically relevant C1 through C8 perfluoroalkyl derivatives . Nature Precedings , Retrieved from http://hdl.handle.net/10101/npre.2009.2922.1
   Google Scholar
• Rayne , S. and Forest , K. 2009 . Theoretical studies on the pKa values of perfluoroalkyl carboxylic acids: chain helicity . Nature Precedings , Retrieved from http://hdl.handle.net/10101/npre.2009.3829.1
   Google Scholar
• Rayne , S. and Forest , K. 2009 . Theoretical studies on the pKa values of perfluoroalkyl carboxylic acids: Non-helical conformation acidity constants for n-perfluorooctanoic acid (n-PFOA) . Nature Precedings , Retrieved from http://hdl.handle.net/10101/npre.2009.3837.2
   Google Scholar
• Brace , N. O. 1962 . Long chain alkanoic and alkenoic acids with perfluoroalkyl terminal segments . The Journal of Organic Chemistry , 27 : 4491 – 4498 .
   Web of Science ®Google Scholar
• Igarashi , S. and Yotsuyanagi , T. 1992 . Homogeneous liquid-liquid extraction by pH dependent phase separation with a fluorocarbon ionic surfactant and its application to the preconcentration of porphyrin compounds . Microchimica Acta , 106 : 37 – 44 .
   Web of Science ®Google Scholar
• López-Fontán , J. L. , Sarmiento , F. and Schulz , P. C. 2005 . The aggregation of sodium perfluorooctanoate in water . Colloid and Polymer Science , 283 : 862 – 871 .
   Web of Science ®Google Scholar
• Barton , C. A. , Kaiser , M. A. and Russell , M. H. 2007 . Partitioning and removal of perfluorooctanoate during rain events: The importance of physical-chemical properties . Journal of Environmental Monitoring , 9 : 839 – 846 .
   PubMed Web of Science ®Google Scholar
• Bowden , D. J. , Clegg , S. L. and Brimblecombe , P. 1996 . The Henry's law constant of trifluoroacetic acid and its partitioning into liquid water in the atmosphere . Chemosphere , 32 : 405 – 420 .
   Web of Science ®Google Scholar
• Kutsuna , S. and Hori , H. 2008 . Experimental determination of Henry's law constants of trifluoroacetic acid at 278–298 K . Atmospheric Environment , 42 : 1399 – 1412 .
   Web of Science ®Google Scholar
• Li , H. , Ellis , D. and Mackay , D. 2007 . Measurement of low air-water partition coefficients of organic acids by evaporation from a water surface . Journal of Chemical and Engineering Data , 52 : 1580 – 1584 .
   Web of Science ®Google Scholar
• Kah , M. and Brown , C. D. 2008 . Log D: Lipophilicity for ionisable compounds . Chemosphere , 72 : 1401 – 1408 .
   PubMed Web of Science ®Google Scholar
• Schwarzenbach , R. P. , Gschwend , P. M. and Imboden , D. M. 2002 . Environmental organic chemistry (2nd ed.) , Hoboken , NJ : Wiley .
   Google Scholar
• Carmosini , N. and Lee , L. S. 2008 . Partitioning of fluorotelomer alcohols to octanol and different sources of dissolved organic carbon . Environmental Science and Technology , 42 : 6559 – 6565 .
   PubMed Web of Science ®Google Scholar
• Jing , P. , Rodgers , P. J. and Amemiya , S. 2009 . High lipophilicity of perfluoroalkyl carboxylate and sulfonate: Implications for their membrane permeability . Journal of the American Chemical Society , 131 : 2290 – 2296 .
   PubMed Web of Science ®Google Scholar
• Thuens , S. , Dreyer , A. , Sturm , R. , Temme , C. and Ebinghaus , R. 2008 . Determination of the octanol-air partition coefficient (K OA) of fluorotelomer alcohols . Journal of Chemical and Engineering Data , 53 : 223 – 227 .
   Web of Science ®Google Scholar
• Dreyer , A. , Langer , V. and Ebinghaus , R. 2009 . Determination of octanol-air partition coefficients (Koa) of fluorotelomer acrylates, perfluoroalkyl sulfonamids, and perfluoroalkylsulfonamido ethanols . Journal of Chemical and Engineering Data , 54 : 3022 – 3025 .
   Web of Science ®Google Scholar
• Higgins , C. P. and Luthy , R. G. 2006 . Sorption of perfluorinated surfactants on sediments . Environmental Science and Technology , 40 : 7251 – 7256 .
   PubMed Web of Science ®Google Scholar
• Mackay , D. and Fraser , A. 2000 . Bioaccumulation of persistent organic chemicals: mechanisms and models . Environmental Pollution , 110 : 375 – 391 .
   PubMed Web of Science ®Google Scholar
• Conder , J. M. , Hoke , R. A. , De Wolf , W. , Russell , M. H. and Buck , R. C. 2008 . Are PFCAs bioaccumulative? A critical review and comparison with regulatory criteria and persistent lipophilic compounds . Environmental Science and Technology , 42 : 995 – 1003 .
   PubMed Web of Science ®Google Scholar
• Han , X. , Snow , T. A. , Kemper , R. A. and Jepson , G. W. 2003 . Binding of perfluorooctanoic acid to rat and human plasma proteins . Chemical Research in Toxicology , 16 : 775 – 781 .
   PubMed Web of Science ®Google Scholar
• Biffinger , J. C. , Kim , H. W. and DiMagno , S. G. 2004 . The polar hydrophobicity of fluorinated compounds . ChemBioChem , 5 : 622 – 627 .
   PubMed Web of Science ®Google Scholar
• Van de Vijver , K. I. , Hoff , P. , Das , K. , Brasseur , S. , Van Dongen , W. , Esmans , E. , Reijnders , P. , Blust , R. and De Coen , W. 2005 . Tissuedistribution of perfluorinated chemicals in harbor seals (Phoca vitulina) from the Dutch Wadden Sea . Environmental Science and Technology , 39 : 6978 – 6984 .
   PubMed Web of Science ®Google Scholar
• Taniyasu , S. , Kannan , K. , Horii , Y. , Hanari , N. and Yamashita , N. 2003 . A survey of perfluorooctane sulfonate and related perfluorinated organic compounds in water, fish, birds and humans in Japan . Environmental Science and Technology , 37 : 2634 – 2639 .
   PubMed Web of Science ®Google Scholar
• Ankley , G. T. , Kuehl , D. W. , Kahl , M. D. , Jensen , K. M. , Butterworth , B. C. and Nichols , J. W. 2004 . Partial life-cycle toxicity and bioconcentration modeling of perfluorooctanesulfonate in the northern leopard frog (rana pipiens) . Environmental Toxicology and Chemistry , 23 : 2745 – 2755 .
   PubMed Web of Science ®Google Scholar
• Kannan , K. , Tao , L. , Sinclair , E. , Pastva , S. D. , Jude , D. J. and Giesy , J. P. 2005 . Perfluorinated compounds in aquatic organisms at various trophic levels in a Great Lakes food chain . Archives of Environmental Contamination and Toxicology , 48 : 559 – 566 .
   PubMed Web of Science ®Google Scholar
• Sinclair , E. , Mayack , D. T. , Roblee , K. , Yamashita , N. and Kannan , K. 2006 . Occurrence of perfluoroalkyl surfactants in water, fish, and birds from New York State . Archives of Environmental Contamination and Toxicology , 50 : 398 – 410 .
   PubMed Web of Science ®Google Scholar
• Morikawa , A. , Kamei , N. , Harada , K. , Inoue , K. , Yoshinaga , T. , Saito , N. and Koizumi , A. 2006 . The bioconcentration factor of perfluorooctane sulfonate is significantly larger than that of perfluorooctanoate in wild turtles (Trachemys scripta elegans and Chinemys reevessii): An Ai River ecological study in Japan . Ecotoxicology and Environmental Safety , 65 : 14 – 21 .
   PubMed Web of Science ®Google Scholar
• Houde , M. , Bujas , T. A. D. , Small , J. , Wells , R. S. , Fair , P. A. , Bossart , G. D. , Solomon , K. R. and Muir , D. C. G. 2006 . Biomagnification of perfluoroalkyl compounds in the bottlenose dolphin (Tursiops truncatus) food web . Environmental Science and Technology , 40 : 4138 – 4144 .
   PubMed Web of Science ®Google Scholar
• Furdui , V. , Stock , N. , Ellis , D. A. , Butt , C. M. , Whittle , M. , Crozier , P. W. , Reiner , E. J. , Muir , D. C. G. and Mabury , S. 2007 . Spatial distribution of perfluoroalkyl contaminants in lake trout from the Great Lakes . Environmental Science and Technology , 41 : 1554 – 1559 .
   PubMed Web of Science ®Google Scholar
• Haukås , M. , Berger , U. , Hop , H. , Gulliksen , B. and Gabrielsen , G. W. 2007 . Bioaccumulation of polyfluorinated alkyl substances (PFAS) in selected species from the Barents Sea food web . Environmental Pollution , 148 : 360 – 371 .
   PubMed Web of Science ®Google Scholar
• Higgins , C. P. , McLeod , P. B. , MacManus-Spencer , L. A. and Luthy , R. G. 2007 . Bioaccumulation of perfluorochemicals in sediments by the aquatic oligochaete Lumbriculus variegatus . Environmental Science and Technology , 41 : 4600 – 4606 .
   PubMed Web of Science ®Google Scholar
• Houde , M. , Czub , G. , Small , J. M. , Backus , S. , Wang , X. W. , Alaee , M. and Muir , D. C. G. 2008 . Fractionation and bioaccumulation of perfluorooctane sulfonate (PFOS) isomers in a Lake Ontario food web . Environmental Science and Technology , 42 : 9397 – 9403 .
   PubMed Web of Science ®Google Scholar
• Boudreau , T. M. , Sibley , P. K. , Mabury , S. A. , Muir , D. C. G. and Solomon , K. R. 2003 . Laboratory evaluation of the toxicity of perfluorooctane sulfonate (PFOS) on Selenastrum capricornutum, Chlorella vulgaris, Lemna gibba, Daphnia magna, and Daphnia pulicaria . Archives of Environmental Contamination and Toxicology , 44 : 307 – 313 .
   PubMed Web of Science ®Google Scholar
• Hanson , M. L. , Sibley , P. K. , Brain , R. A. , Mabury , S. A. and Solomon , K. R. 2005 . Microcosm evaluation of the toxicity and risk to aquatic macrophytes from perfluorooctane sulfonic acid . Archives of Environmental Contamination and Toxicology , 48 : 329 – 337 .
   PubMed Web of Science ®Google Scholar
• Hanson , M. L. , Small , J. , Sibley , P. K. , Boudreau , T. , Brain , R. A. , Mabury , S. A. and Solomon , K. R. 2005 . Microcosm evaluation of the fate, toxicity and risk to aquatic macrophytes from perfluorooctanoic acid (PFOA) . Archives of Environmental Contamination and Toxicology , 49 : 307 – 316 .
   PubMed Web of Science ®Google Scholar
• Phillips , M. M. , Dinglasan-Panlilio , M. J. , Mabury , S. A. , Solomon , K. R. and Sibley , P. K. 2007 . Fluorotelomer acids are more toxic than perfluorinated acids . Environmental Science and Technology , 41 : 7159 – 7163 .
   PubMed Web of Science ®Google Scholar
• Li , M. H. 2009 . Toxicity of perfluorooctane sulfonate and perfluorooctanoic acid to plants and aquatic invertebrates . Environmental Toxicology , 24 : 95 – 101 .
   PubMed Web of Science ®Google Scholar
• Colombo , I. , de Wolf , W. , Thompson , R. S. , Farray , D. G. , Hoke , R. A. and L’Haridon , J. L. 2008 . Acute and chronic aquatic toxicity of ammonium perfluorooctanoate (APFO) to freshwater organisms . Ecotoxicology and Environmental Safety , 71 : 749 – 756 .
   PubMed Web of Science ®Google Scholar
• Liu , W. , Chen , S. , Quan , X. and Jin , Y. H. 2008 . Toxic effect of serial perfluorosulfonic and perfluorocarboxylic acids on the membrane system of a freshwater alga measured by flow cytometry . Environmental Toxicology and Chemistry , 27 : 1597 – 1604 .
   PubMed Web of Science ®Google Scholar
• Liu , W. , Zhang , Y. B. , Quan , X. , Jin , Y. H. and Chen , S. 2009 . Effect of perfluorooctane sulfonate on toxicity and cell uptake of other compounds with different hydrophobicity in green alga . Chemosphere , 75 : 405 – 409 .
   PubMed Web of Science ®Google Scholar
• Latała , A. , Nędzi , M. and Stepnowski , P. 2009 . Acute toxicity assessment of perfluorinated carboxylic acids toward the Baltic microalgae . Environmental Toxicology and Pharmacology , 28 : 167 – 171 .
   PubMed Web of Science ®Google Scholar
• Li , M. H. 2010 . Chronic effects of perfluorooctane sulfonate and ammonium perfluorooctanoate on biochemical parameters, survival and reproduction of Daphnia magna . Journal of Health Science , 56 : 104 – 111 .
   Web of Science ®Google Scholar
• Ji , K. , Kim , Y. , Oh , S. , Ahn , B. , Jo , H. and Choi , K. 2008 . Toxicity of perfluorooctane sulfonic acid and perfluorooctanoic acid on freshwater macroinvertebrates (Daphnia magna and Moina macrocopa) and fish (Oryzias latipes) . Environmental Toxicology and Chemistry , 27 : 2159 – 2168 .
   PubMed Web of Science ®Google Scholar
• Phillips , M. M. , Dinglasan-Panlilio , M. J. , Mabury , S. A. , Solomon , K. R. and Sibley , P. K. 2010 . Chronic toxicity of fluorotelomer acids to Daphnia magna and Chironomus dilutus . Environmental Toxicology and Chemistry , 29 : 1123 – 1131 .
   PubMed Web of Science ®Google Scholar
• MacDonald , M. M. , Warne , A. L. , Stock , N. L. , Mabury , S. A. , Solomon , K. R. and Sibley , P. K. 2004 . Toxicity of perfluorooctane sulfonic acid and perfluorooctanoic acid to Chironomus tentans . Environmental Toxicology and Chemistry , 23 : 2116 – 2123 .
   PubMed Web of Science ®Google Scholar
• Wang , Z. Y. , Ud-Daula , A , Fiedler , S. and Schramm , K. W. 2010 . Impact of fluorotelomer alcohols (FTOH) on the molecular and macroscopic phenotype of Tetrahymena thermophila . Environmental Science and Pollution Research International , 17 : 154 – 164 .
   PubMed Web of Science ®Google Scholar
• Sanderson , H. , Boudreau , T. M. , Mabury , S. A. , Cheong , W. J. and Solomon , K. R. 2002 . Ecological impact and environmental fate of perfluorooctane sulfonate on the zooplankton community in indoor microcosms . Environmental Toxicology and Chemistry , 21 : 1490 – 1496 .
   PubMed Web of Science ®Google Scholar
• Sanderson , H. , Boudreau , T. M. , Mabury , S. A. and Solomon , K. R. 2003 . Impact of perfluorooctanoic acid on the structure of the zooplankton community in indoor microcosms . Aquatic Toxicology , 62 : 227 – 234 .
   PubMed Web of Science ®Google Scholar
• Sanderson , H. , Boudreau , T. M. , Mabury , S. A. and Solomon , K. R. 2004 . Effects of perfluorooctane sulfonate and perfluorooctanoic acid on the zooplanktonic community . Ecotoxicology and Environmental Safety , 58 : 68 – 76 .
   PubMed Web of Science ®Google Scholar
• Mulkiewicz , E. , Jastorff , B. , Skałdanowski , A. C. , Kleszczyński , K. and Stepnowski , P. 2007 . Evaluation of the acute toxicity of perfluorinated carboxylic acids using eukaryotic cell lines, bacteria and enzymatic assays . Environ Toxicol Pharmacol , 23 : 279 – 285 .
   PubMed Web of Science ®Google Scholar
• Ankley , G. T. , Kuehl , D. W. , Kahl , M. D. , Jensen , K. M. , Linnum , A. , Leino , R. L. and Villeneuvet , D. A. 2005 . Reproductive and developmental toxicity and bioconcentration of perfluorooctanesulfonate in a partial life-cycle test with the fathead minnow (Pimephales promelas) . Environmental Toxicology and Chemistry , 24 : 2316 – 2324 .
   PubMed Web of Science ®Google Scholar
• Huang , H. H. , Huang , C. J. , Wang , L. J. , Ye , X. W. , Bai , C. L. , Simonich , M. T. , Tanguay , R. L. and Dong , Q. X. 2010 . Toxicity, uptake kinetics and behavior assessment in zebrafish embryos following exposure to perfluorooctanesulphonicacid (PFOS) . Aquatic Toxicology , 98 : 139 – 147 .
   PubMed Web of Science ®Google Scholar
• Hoff , P. T. , Van Dongen , W. , Esmans , E. L. , Blust , R. and De Coen , W. M. 2003 . Evaluation of the toxicological effects of perfluorooctane sulfonic acid in the common carp (Cyprinus carpio) . Aquatic Toxicology , 62 : 349 – 359 .
   PubMed Web of Science ®Google Scholar
• Oakes , K. , Sibley , P. K. , Martin , J. M. , Maclean , D. D. , Solomon , K. R. , Mabury , S. A. and Van der Kraak , G. 2005 . Short-term exposures of fish to perfluorooctane sulfonate: acute effects on fatty acyl-CoA oxidase activity, oxidative stress, and circulating sex steroids . Environmental Toxicology and Chemistry , 24 : 1172 – 1181 .
   PubMed Web of Science ®Google Scholar
• Hagenaars , A. , Knapen , D. , Meyer , I. J. , van der Ven , K. , Hoff , P. and De Coen , W. 2008 . Toxicity evaluation of perfluorooctane sulfonate (PFOS) in the liver of common carp (Cyprinus carpio) . Aquatic Toxicology , 88 : 155 – 163 .
   PubMed Web of Science ®Google Scholar
• Wei , Y. H. , Dai , J. Y. , Liu , M. , Wang , J. S. , Xu , M. Q. , Zha , J. M. and Wang , Z. J. 2007 . Estrogenlike properties of perfluorooctanoic acid as revealed by expressing hepatic estrogen-responsive genes in rare minnows (Gobiocypris rarus) . Environmental Toxicology and Chemistry , 26 : 2440 – 2447 .
   PubMed Web of Science ®Google Scholar
• Liu , Y. , Wang , J. S. , Wei , Y. H. , Zhang , H. X. , Liu , Y. and Dai , J. Y. 2008 . Molecular characterization of cytochrome P450 1A and 3A and the effects of perfluorooctanoic acid on their mRNA levels in rare minnow (Gobiocypris rarus) gills . Aquatic Toxicology , 88 : 183 – 190 .
   PubMed Web of Science ®Google Scholar
• Liu , Y. , Wang , J. S. , Liu , Y. , Zhang , H. X. , Xu , M. Q. and Dai , J. Y. 2009 . Expression of a novel cytochrome P450 4T gene in rare minnow (Gobiocypris rarus) following perfluorooctanoic acid exposure . Comparative Biochemistry and Physiology, Part C , 150 : 57 – 64 .
   PubMed Web of Science ®Google Scholar
• Liu , Y. , Wang , J. S. , Wei , Y. H. , Zhang , H. X. , Xu , M. Q. and Dai , J. Y. 2008 . Induction of time-dependent oxidative stress and related transcriptional effects of perfluorododecanoic acid in zebrafish liver . Aquatic Toxicology , 89 : 242 – 250 .
   PubMed Web of Science ®Google Scholar
• Wei , Y. H. , Chan , L. L. , Wang , D. Z. , Zhang , H. X. , Wang , J. S. and Dai , J. Y. 2008 . Proteomic analysis of hepatic protein profiles in rare minnow (Gobiocypris rarus) exposed to perfluorooctanoic acid . Journal of Proteome Research , 7 : 1729 – 1739 .
   PubMed Web of Science ®Google Scholar
• Wei , Y. H. , Liu , Y. , Wang , J. S. , Tao , Y. and Dai , J. Y. 2008 . Toxicogenomic analysis of the hepatic effects of perfluorooctanoic acid on rare minnows (Gobiocypris rarus) . Toxicology and Applied Pharmacology , 226 : 285 – 297 .
   PubMed Web of Science ®Google Scholar
• Wei , Y. H. , Shi , X. J. , Zhang , H. X. , Wang , J. S. , Zhou , B. S. and Dai , J. Y. 2009 . Combined effects of polyfluorinated and perfluorinated compounds on primary cultured hepatocytes from rare minnow (Gobiocypris rarus) using toxicogenomic analysis . Aquatic Toxicology , 95 : 27 – 36 .
   PubMed Web of Science ®Google Scholar
• Liu , C. S. , Yu , K. , Shi , X. J. , Wang , J. X. , Lam , P. K.mS. , Wu , R. S. S. and Zhou , B. S. 2007 . Induction of oxidative stress and apoptosis by PFOS and PFOA in primary cultured hepatocytes of freshwater tilapia (Oreochromis niloticus) . Aquatic Toxicology , 82 : 135 – 143 .
   PubMed Web of Science ®Google Scholar
• Liu , C. S. , Du , Y. B. and Zhou , B. S. 2007 . Evaluation of estrogenic activities and mechanism of action of perfluorinated chemicals determined by vitellogenin induction in primary cultured tilapia hepatocytes . Aquatic Toxicology , 85 : 267 – 277 .
   PubMed Web of Science ®Google Scholar
• Liu , C. S. , Yu , L. Q. , Deng , J. , Lam , P. K. S. , Wu , R. S. S. and Zhou , B. S. 2009 . Waterborne exposure to fluorotelomer alcohol 6:2 FTOH alters plasma sex hormone and gene transcription in the hypothalamic–pituitary–gonadal (HPG) axis of zebrafish . Aquatic Toxicology , 93 : 131 – 137 .
   PubMed Web of Science ®Google Scholar
• Liu , C. S. , Deng , J. , Yu , L. Q. , Ramesh , M. and Zhou , B. S. 2010 . Endocrine disruption and reproductive impairment in zebrafish by exposure to 8:2 fluorotelomer alcohol . Aquatic Toxicology , 96 : 70 – 76 .
   PubMed Web of Science ®Google Scholar
• Shi , X. J. , Du , Y. B. , Lam , P. K. S. , Wu , R. S. S. and Zhou , B. S. 2008 . Developmental toxicity and alteration of gene expression in zebrafish embryos exposed to PFOS . Toxicology and Applied Pharmacology , 230 : 23 – 32 .
   PubMed Web of Science ®Google Scholar
• Shi , X. J. , Yeung , L. W. Y. , Lam , P. K. S. , Wu , R. S. S. and Zhou , B. S. 2009 . Protein profiles in zebrafish (Danio rerio) embryos exposed to perfluorooctane sulfonate . Toxicological Sciences , 110 : 334 – 340 .
   PubMed Web of Science ®Google Scholar
• Shi , X. J. , Liu , C. S. , Wu , G. Q. and Zhou , B. S. 2009 . Waterborne exposure to PFOS causes disruption of the hypothalamus–pituitary–thyroid axis in zebrafish larvae . Chemosphere , 77 : 1010 – 1018 .
   PubMed Web of Science ®Google Scholar
• Du , Y. B. , Shi , X. J. , Liu , C. S. , Yu , K. and Zhou , B. S. 2009 . Chronic effects of water-borne PFOS exposure on growth, survival and hepatotoxicity in zebrafish: A partial life-cycle test . Chemosphere , 74 : 723 – 729 .
   PubMed Web of Science ®Google Scholar
• Fang , X. M. , Wei , Y. H. , Liu , Y. , Wang , J. S. and Dai , J. Y. 2010 . The identification of apolipoprotein genes in rare minnow (Gobiocypris rarus) and their expression following perfluorooctanoic acid exposure . Comparative Biochemistry and Physiology, Part C , 151 : 152 – 159 .
   PubMed Web of Science ®Google Scholar