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Journal of Environmental Science and Health, Part A
Toxic/Hazardous Substances and Environmental Engineering
Volume 44, 2009 - Issue 12
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ARTICLES

Perfluoroalkyl sulfonic and carboxylic acids: A critical review of physicochemical properties, levels and patterns in waters and wastewaters, and treatment methods

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Pages 1145-1199 | Received 05 May 2009, Published online: 04 Sep 2009

References

  • Rayne , S. and Ikonomou , M. G. 2003 . Development of a multiple-class high-resolution gas chromatographic relative retention time model for halogenated environmental contaminants . Anal. Chem. , 75 : 1049 – 1057 .
  • Rayne , S. , Ikonomou , M. G. , Ross , P. S. , Ellis , G. M. and Barrett-Lennard , L. G. 2004 . PBDEs PBBs, and PCNs in three communities of free-ranging killer whales (Orcinus orca) from the northeastern Pacific Ocean . Environ. Sci. Technol. , 38 : 4293 – 4299 .
  • Ikonomou , M. G. , Rayne , S. and Addison , R. F. 2002 . Exponential increases of the brominated flame retardants, polybrominated diphenyl ethers, in the Canadian Arctic from 1981 to 2000 . Environ. Sci. Technol. , 36 : 1886 – 1892 .
  • Kissa , E. 2001 . Fluorinated Surfactants and Repellents , New York, USA : Marcel Dekker .
  • Giesy , J. , Mabury , S. , Martin , J. , Kannan , K. , Jones , P. , Newsted , J. and Coady , K. 2006 . “ Perfluorinated compounds in the Great Lakes ” . In Persistent Organic Pollutants in the Great Lakes , Edited by: Hites , R. 391 – 438 . New York, NY, , USA : Springer .
  • Martin , J. W. , Kannan , K. , Berger , U. , de Voogt , P. , Field , J. , Franklin , J. , Giesy , J. P. , Harner , T. , Muir , D. C. G. , Scott , B. , Kaiser , M. , Järnberg , U. , Jones , K. C. , Mabury , S. A. , Schroeder , H. , Simcik , M. , Sottani , C. , van Bavel , B. , Kärrman , A. , Lindström , G. and van Leeuwen , S. 2004 . Analytical challenges hamper perfluoroalkyl research . Environ. Sci. Technol. , 38 : 248A – 255A .
  • Lehmler , H. 2005 . Synthesis of environmentally relevant fluorinated surfactants: A review . Chemosphere , 58 : 1471 – 1496 .
  • Schultz , M. , Barofsky , D. and Field , J. 2004 . Fluorinated alkyl surfactants . Environ. Eng. Sci. , 20 : 487 – 501 .
  • Giesy , J. P. and Kannan , K. 2002 . Perfluorochemical surfactants in the environment . Environ. Sci. Technol. , 36 : 146A – 152A .
  • Rayne , S. , Forest , K. and Friesen , K. J. 2008 . 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 Pt. A , 43 : 1391 – 1401 .
  • Miyake , Y. , Yamashita , N. , Rostkowski , P. , So , M. K. , Taniyasu , S. , Lam , P. K. S. and Kannan , K. 2007 . 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 .
  • Arp , H. P. H. , Niederer , C. and Goss , K. 2006 . Predicting the partitioning behavior of various highly fluorinated compounds . Environ. Sci. Technol. , 40 : 7298 – 7304 .
  • Goss , K. and Bronner , G. 2006 . What is so special about the sorption behavior of highly fluorinated compounds? . J. Phys. Chem. A , 110 : 9518 – 9522 .
  • Goss , K. , Bronner , G. , Harner , T. , Hertel , M. and Schmidt , T. C. 2006 . The partition behavior of fluorotelomer alcohols and olefins . Environ. Sci. Technol. , 40 : 3572 – 3577 .
  • Fujii , S. , Tanaka , S. , Hong Lien , N. , Qiu , Y. and Polprasert , C. 2007 . New POPs in the water environment: Distribution, bioaccumulation and treatment of perfluorinated compounds—A review paper . J. Wat. Res. Supply Res. Technol.—AQUA , 56 : 313 – 326 .
  • Ellis , D. , Moody , C. and Mabury , S. 2002 . “ Trifluoroacetic acid and longer chain perfluoro acids: Sources and analysis ” . In Organofluorines , Edited by: Neilson , A. H. 103 – 120 . New York, NY, , USA : Springer .
  • Paul , A. G. , Jones , K. C. and Sweetman , A. J. 2009 . A first global production, emission, and environmental inventory for perfluorooctane sulfonate . Environ. Sci. Technol. , 43 : 386 – 392 .
  • Prevedouros , K. , Cousins , I. T. , Buck , R. C. and Korzeniowski , S. H. 2006 . Sources, fate and transport of perfluorocarboxylates . Environ. Sci. Technol. , 40 : 32 – 44 .
  • 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 . Crit. Rev. Toxicol. , 34 : 351 – 384 .
  • Lau , C. , Anitole , K. , Hodes , C. , Lai , D. , Pfahles-Hutchens , A. and Seed , J. 2007 . Perfluoroalkyl acids: A review of monitoring and toxicological findings . Toxicol. Sci. , 99 : 366 – 394 .
  • Andersen , M. E. , Butenhoff , J. L. , Chang , S. , Farrar , D. G. , Kennedy , G. L. J. , Lau , C. , Olsen , G. W. , Seed , J. and Wallace , K. B. 2008 . Perfluoroalkyl acids and related chemistries: Toxicokinetics and modes of action . Toxicol. Sci. , 102 : 3 – 14 .
  • 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 . Environ. Sci. Technol. , 42 : 995 – 1003 .
  • Beach , S. A. , Newsted , J. L. , Coady , K. and Giesy , J. P. 2006 . Ecotoxicological evaluation of perfluorooctanesulfonate (PFOS) . Rev. Environ. Contam. Toxicol. , 186 : 133 – 174 .
  • Boutonnet , J. C. , Bingham , P. , Calamari , D. , de Rooij , C. , Franklin , J. , Kawano , T. , Libre , J. , McCul-loch , A. , Malinverno , G. , Odom , J. M. , Rusch , G. M. , Smythe , K. , Sobolev , I. , Thompson , R. and Tiedje , J. M. 1999 . Environmental risk assessment of trifluoroacetic acid . Human Ecol. Risk Assess. , 5 : 59 – 124 .
  • DeWitt , J. C. , Shnyra , A. , Badr , M. Z. , Loveless , S. E. , Hoban , D. , Frame , S. R. , Cunard , R. , Anderson , S. E. , Meade , B. J. , Peden-Adams , M. M. , Luebke , R. W. and Luster , M. I. 2009 . Immunotoxicity of perfluorooctanoic acid and perfluorooctane sulfonate and the role of peroxisome proliferator-activated receptor alpha . Crit. Rev. Toxicol. , 39 : 76 – 94 .
  • Fromme , H. , Tittlemier , S. A. , Volkel , W. , Wilhelm , M. and Twardella , D. 2009 . Perfluorinated compounds–Exposure assessment for the general population in western countries . Int. J. Hyg. Environ. Health , 212 : 239 – 270 .
  • Kudo , N. and Kawashima , Y. 2003 . Toxicity and toxicokinetics of perfluorooctanoic acid in humans and animals . J. Toxicol. Sci. , 28 : 49 – 57 .
  • Natarajan , R. , Azerad , R. , Badet , B. and Copin , E. 2005 . Microbial cleavage of C─F bond . J. Fluor. Chem. , 126 : 424 – 435 .
  • Parsons , J. R. , Sáez , M. , Dolfing , J. and de Voogt , P. 2008 . Biodegradation of perfluorinated compounds . Rev. Environ. Contam. Toxicol. , 196 : 53 – 71 .
  • Trudel , D. , Horowitz , L. , Wormuth , M. , Scheringer , M. , Cousins , I. T. and Hungerbuhler , K. 2008 . Estimating consumer exposure to PFOS and PFOA . Environ. Sci. Technol. , 28 : 251 – 269 .
  • Vestergren , R. , Cousins , I. T. , Trudel , D. , Wormuth , M. and Scheringer , M. 2008 . Estimating the contribution of precursor compounds in consumer exposure to PFOS and PFOA . Chemosphere , 73 : 1617 – 1624 .
  • Houde , M. , Martin , J. W. , Letcher , R. J. , Solomon , K. R. and Muir , D. C. G. 2006 . Biological monitoring of polyfluoroalkyl substances: A review . Environ. Sci. Technol. , 40 : 3463 – 3473 .
  • Rayne , S. , Forest , K. and Friesen , K. J. 2008 . Predicting the congener-specific environmental behaviour of perfluorinated acid contaminants using semi-empirical computational methods . Nat. Prec. , http://dx.doi.org/10.1038/npre.2008.1956.1
  • Ochoa-Herrera , V. , Sierra-Alvarez , R. , Somogyi , A. , Jacobsen , N. E. , Wysocki , V. H. and Field , J. A. 2008 . Reductive defluorination of perfluorooctane sulfonate . Environ. Sci. Technol. , 42 : 3260 – 3264 .
  • Torres , F. J. , Ochoa-Herrera , V. , Blowers , P. and Sierra-Alvarez , R. 2009 . Ab initio study of the structural, electronic, and thermodynamic properties of linear perfluorooctane sulfonate (PFOS) and its branched isomers . Chemosphere , in press, DOI:10.1016/j.chemosphere.2009.04.009
  • Rayne , S. , Forest , K. and Friesen , K. J. 2008 . 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 – 82 .
  • Arsenault , G. , Chittim , B. , McAlees , A. , McCrindle , R. , Riddell , N. and Yeo , B. 2008 . Some issues relating to the use of perfluorooctanesulfonate (PFOS) samples as reference standards . Chemosphere , 70 : 616 – 625 .
  • Arsenault , G. , Chittim , B. , Gu , J. , McAlees , A. , McCrindle , R. and Robertson , V. 2008 . Separation and fluorine nuclear magnetic resonance spectroscopic (19F NMR) analysis of individual branched isomers present in technical perfluorooctanesulfonic acid (PFOS) . Chemosphere , 73 : S53 – S59 .
  • Chu , S. and Letcher , R. J. 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 – 4262 .
  • Houde , M. , Czub , G. , Small , J. M. , Backus , S. , Wang , X. , Alaee , M. and Muir , D. C. G. 2008 . Fractionation and bioaccumulation of perfluorooctane sulfonate (PFOS) isomers in a Lake Ontario food web . Environ. Sci. Technol. , 42 : 9397 – 9403 .
  • Langlois , I. , Berger , U. , Zencak , Z. and Oehme , M. 2007 . Mass spectral studies of perfluorooctane sulfonate derivatives separated by high-resolution gas chromatography . Rapid Commun. Mass Spectrom. , 21 : 3547 – 3553 .
  • Vyas , S. M. , Kania-Korwel , I. and Lehmler , H. 2007 . Differences in the isomer composition of perfluoroctanesulfonyl (PFOS) derivatives . J. Environ. Sci. Health Pt. A , 42 : 249 – 255 .
  • 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 . J. Environ. Sci. Health Pt. A , 44 : 317 – 326 .
  • Rayne , S. and Forest , K. 2009 . ADME/Tox WEB in silico predictions of longer chain perfluoroalkyl carboxylic acid pKa values are more accurate than other computational methods . Nat. Prec. , http://hdl.handle.net/10101/npre.2009.2936.1
  • Rayne , S. , Forest , K. and Friesen , K. J. 2009 . Estimated bioconcentration factors (BCFs) for the C4 through C8 perfluorinated alkylsulfonic acid (PFSA) and alkylcarboxylic acid (PFCA) congeners . J. Environ. Sci. Health Pt. A , 44 : 598 – 604 .
  • Rayne , S. , Forest , K. and Friesen , K. J. 2009 . Estimated congener specific gas phase atmospheric behavior and fractionation of perfluoroalkyl compounds: Rates of reaction with atmospheric oxidants, air-water partitioning, and wet/dry deposition lifetimes . J. Environ. Sci. Health Pt A , in press
  • Rayne , S. , Forest , K. and Friesen , K. 2009 . Extending the semi-empirical PM6 method for carbon oxyacid pKa prediction to sulfonic acids: Application towards congener-specific estimates for the environmentally and toxicologically relevant C1 through C8 perfluoroalkyl derivatives . Nat. Prec. , http://hdl.handle.net/10101/npre.2009.2922.1
  • Rayne , S. , Forest , K. and Friesen , K. 2009 . Linear free energy relationship based estimates for the congener specific relative reductive defluorination rates of perfluorinated alkyl compounds . J. Environ. Sci. Health Pt. A , 43 : 866 – 879 .
  • Rayne , S. and Forest , K. 2009 . Congener specific organic carbon normalized soil and sediment-water partitioning coefficients for the C1 through C8 perfluorinated alkylsulfonic and alkylcarboxylic acids . J. Environ. Sci. Health Pt. A , in press
  • Rayne , S. and Forest , K. 2009 . An assessment of organic solvent based equilibrium partitioning methods for predicting the bioconcentration behavior of perfluorinated sulfonic acids, carboxylic acids, and sulfonamides . Nat. Prec. , http://hdl.handle.net/10101/npre.2009.3256.1
  • Rayne , S. and Forest , K. 2009 . A comparative assessment of octanol-water partitioning and distribution constant estimation methods for perfluoroalkyl carboxylates and sulfonates . Nat. Prec. , http://hdl.handle.net/10101/npre.2009.3282.1
  • Jing , P. , Rodgers , P. J. and Amemiya , S. 2009 . High lipophilicity of perfluoroalkyl carboxylate and sulfonate: Implications for their membrane permeability . J. Am. Chem. Soc. , 131 : 2290 – 2296 .
  • López-Fontán , J. L. , Sarmiento , F. and Schulz , P. C. 2005 . The aggregation of sodium perfluorooctanoate in water . Coll. Polymer Sci. , 283 : 862 – 871 .
  • Shinoda , K. , Hato , M. and Hayashi , T. 1972 . Physicochemical properties of aqueous solutions of fluorinated surfactants . J. Phys. Chem. , 76 : 909 – 914 .
  • 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) . Environ. Toxicol. Chem. , 22 : 196 – 204 .
  • Kaiser , M. A. , Larsen , B. S. , Kao , C. C. and Buck , R. C. 2005 . Vapor pressures of perfluorooctanoic, -nonanoic, -decanoic, -undecanoic, and -dodecanoic acids . J. Chem. Engr. Data , 50 : 1841 – 1843 .
  • 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 .
  • Kutsuna , S. and Hori , H. 2008 . Experimental determination of Henry's law constants of trifluoroacetic acid at 278–298 K . Atmos. Environ. , 42 : 1399 – 1412 .
  • Li , H. , Ellis , D. and Mackay , D. 2007 . Measurement of low air-water partition coefficients of organic acids by evaporation from a water surface . J. Chem. Engr. Data , 52 : 1580 – 1584 .
  • 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 . J. Environ. Monit. , 9 : 839 – 846 .
  • Goss , K. 2008 . The pKa values of PFOA and other highly fluorinated carboxylic acids . Environ. Sci. Technol. , 42 : 456 – 458 .
  • Goss , K. 2008 . The pKa values of PFOA and other highly fluorinated carboxylic acids—Correction . Environ. Sci. Technol. , 42 : 5032 – 5032 .
  • Lide , D. R. 2008 . CRC Handbook of Chemistry and Physics , Boca Raton, FL, , USA : Taylor & Francis .
  • Howard , P. H. 1989 . Handbook of Environmental Fate and Exposure Data for Organic Chemicals , Chelsea, MI, , USA : Lewis Publishers .
  • Mackay , D. , Shiu , W. Y. and Ma , K. C. 2005 . Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals , Boca Raton, FL, , USA : Taylor & Francis .
  • Boethling , R. and Mackay , D. 2000 . Handbook of Property Estimation Methods for Environmental chemicals: Environmental and Health Sciences , Boca Raton, FL, , USA : Lewis Publishers .
  • 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 . Environ. Sci. Technol. , 42 : 9283 – 9288 .
  • 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.” . Environ. Sci. Technol. , 43 : 1234 – 1235 .
  • Mader , B. T. 2009 . Comment on “Aerosol enrichment of the surfactant PFO and mediation of the water-air transport of gaseous PFOA.” . Environ. Sci. Technol. , 43 : 1232 – 1233 .
  • Moroi , Y. , Yano , H. , Shibata , O. and Yonemitsu , T. 2001 . Determination of acidity constants of perfluoroalkanoic acids . Bull. Chem. Soc. Jpn. , 74 : 667 – 672 .
  • Guo , W. , Brown , T. A. and Fung , B. M. 1991 . Micelles and aggregates of fluorinated surfactants . J. Phys. Chem. A , 95 : 1829 – 1836 .
  • Ylinen , M. , Kojo , A. , Hanhijärvi , H. and Peura , P. 1990 . Disposition of perfluorooctanoic acid in the rat after single and subchronic administration . Bull. Environ. Contam. Toxicol. , 44 : 46 – 53 .
  • Brace , N. O. 1962 . Long chain alkanoic and alkenoic acids with perfluoroalkyl terminal segments . J. Org. Chem. , 27 : 4491 – 4498 .
  • Henne , A. L. and Fox , C. J. 1951 . Ionization constants of fluorinated acids . J. Am. Chem. Soc. , 73 : 2323 – 2325 .
  • Lampert , D. J. , Frisch , M. A. and Speitel , J. 2007 . Removal of perfluorooctanoic acid and perfluorooctane sulfonate from wastewater by ion exchange . Pract. Period. Haz. Toxic Radioactive Waste Mgmt. , 11 : 60 – 68 .
  • 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 . Microchim. Acta , 106 : 37 – 44 .
  • Dippy , J. F. J. , Hughes , S. R. C. and Rozanski , A. 1959 . The dissociation constants of some symmetrically disubstituted succinic acids . J. Chem. Soc. , : 2492 – 2498 .
  • Vanden Heuvel , J. P. , Kuslikis , B. I. and Peterson , R. E. 1992 . Covalent binding of perfluorinated fatty acids to proteins in the plasma, liver and testes of rats . Chem. Biol. Interact. , 82 : 317 – 328 .
  • Jones , P. D. , Hu , W. , De Coen , W. , Newsted , J. L. and Giesy , J. P. 2003 . Binding of perfluorinated fatty acids to serum proteins . Environ. Toxicol. Chem. , 22 : 2639 – 2649 .
  • OECD . 2002 . Hazard assessment of perfluorooctane sulfonate (PFOS) and its salts , Paris, , France : Organization for Economic Co-operation and Development .
  • Higgins , C. P. and Luthy , R. G. 2006 . Sorption of perfluorinated surfactants on sediments . Environ. Sci. Technol. , 40 : 7251 – 7256 .
  • Higgins , C. P. and Luthy , R. G. 2007 . Modeling sorption of anionic surfactants onto sediment materials: An a priori approach for perfluoroalkyl surfactants and linear alkylbenzene sulfonates . Environ. Sci. Technol. , 41 : 3254 – 3261 .
  • Barcelona , M. and Atwood , D. 1979 . Gypsum-organic interactions in the marine environment: Sorption of fatty acids and hydrocarbons . Geochim. Cosmochim. Acta , 43 : 47 – 53 .
  • Meyers , P. A. and Quinn , J. G. 1973 . Factors affecting the association of fatty acids with mineral particles in sea water . Geochim. Cosmochim. Acta , 37 : 1745 – 1759 .
  • McNamee , C. E. , Matsumoto , M. , Hartley , P. G. , Mulvaney , P. , Tsujii , Y. and Nakahara , M. 2001 . Interaction forces and zeta potentials of cationic polyelectrolyte coated silica surfaces in water and in ethanol: Effects of chain length and concentration of perfluorinated anionic surfactants on their binding to the surface . Langmuir , 17 : 6220 – 6227 .
  • Johnson , R. L. , Anschutz , A. J. , Smolen , J. M. , Simcik , M. F. and Penn , R. L. 2007 . The adsorption of perfluorooctane sulfonate onto sand, clay, and iron oxide surfaces . J. Chem. Engr. Data , 52 : 1165 – 1170 .
  • Hilal , S. , Karickhoff , S. and Carreira , L. 2004 . Prediction of the solubility, activity coefficient and liquid/liquid partition coefficient of organic compounds . QSAR Comb. Sci. , 23 : 709 – 720 .
  • Tetko , I. V. 2005 . Computing chemistry on the web . Drug Discov. Today , 10 : 1497 – 1500 .
  • Tetko , I. V. , Gasteiger , J. , Todeschini , R. , Mauri , A. , Livingstone , D. , Ertl , P. , Palyulin , V. A. , Radchenko , E. V. , Zefirov , N. S. , Makarenko , A. S. , Tanchuk , V. Y. and Prokopenko , V. V. 2005 . Virtual computational chemistry laboratory: Design and description . J. Comput. Aided Mol. Des. , 19 : 453 – 463 .
  • Tetko , I. V. and Tanchuk , V. Y. 2002 . Application of associative neural networks for prediction of lipophilicity in ALOGPS 2.1 program . J. Chem. Inf. Comput. Sci. , 42 : 1136 – 1145 .
  • Tetko , I. V. , Tanchuk , V. Y. and Villa , A. E. 2001 . Prediction of n-octanol/water partition coefficients from PHYSPROP database using artificial neural networks and E-state indices . J. Chem. Inf. Comput. Sci. , 41 : 1407 – 1421 .
  • Tetko , I. V. and Poda , G. I. 2004 . Application of ALOGPS 2.1 to predict log D distribution coefficient for Pfizer proprietary compounds . J. Med. Chem. , 47 : 5601 – 5604 .
  • Tetko , I. V. and Bruneau , P. 2004 . Application of ALOGPS to predict 1-octanol/water distribution coefficients, logP, and logD, of AstraZeneca in-house database . J. Pharm. Sci. , 93 : 3103 – 3110 .
  • Weininger , D. 1988 . SMILES: A chemical language and information system. 1. Introduction to methodology and encoding rules . J. Chem. Inf. Comp. Sci. , 28 : 31 – 36 .
  • Weininger , D. , Weininger , A. and Weininger , J. L. 1989 . SMILES. 2. Algorithm for generation of unique SMILES notation . J. Chem. Inf. Comp. Sci. , 29 : 97 – 101 .
  • Kah , M. and Brown , C. D. 2008 . Log D: Lipophilicity for ionisable compounds . Chemosphere , 72 : 1401 – 1408 .
  • Kelly , B. C. , Ikonomou , M. G. , Blair , J. D. , Surridge , B. , Hoover , D. , Grace , R. and Gobas , F. A. P. C. 2009 . Perfluoroalkyl contaminants in an arctic marine food web: Trophic magnification and wildlife exposure . Environ. Sci. Technol. , 43 : 4037 – 4043 .
  • Schwarzenbach , R. P. , Gschwend , P. M. and Imboden , D. M. 2003 . Environmental Organic Chemistry , New York, USA : John Wiley and Sons .
  • Rayne , S. , Forest , K. and Friesen , K. J. 2009 . Examining the PM6 semiempirical method for pKa prediction across a wide range of oxyacids . Nat. Prec. , http://hdl.handle.net/10101/npre.2009.2981.1
  • Martin , J. W. , Mabury , S. A. , Solomon , K. R. and Muir , D. C. G. 2003 . Dietary accumulation of perfluorinated acids in juvenile rainbow trout (Oncorhynchus mykiss) . Environ. Toxicol. Chem. , 22 : 189 – 195 .
  • Rayne , S. and Forest , K. 2009 . An assessment of organic solvent based equilibrium partitioning methods for predicting the bioconcentration behavior of perfluorinated sulfonic acids, carboxylic acids, and sulfonamides . Nat. Prec. , http://hdl.handle.net/10101/npre.2009.3256.1
  • Tromp , T. K. , Ko , M. K. W. , Rodriguez , J. M. and Sze , N. D. 1995 . Potential accumulation of a CFC-replacement degradation product in seasonal wetlands . Nature , 376 : 327 – 330 .
  • Frank , H. , Christoph , E. H. , Holm-Hansen , O. and Bullister , J. L. 2002 . Trifluoroacetate in ocean waters . Environ. Sci. Technol. , 36 : 12 – 15 .
  • Lehr , J. K. 2000 . Standard Handbook of Environmental Science, Health, and Technology , New York, NY, , USA : McGraw-Hill Professional .
  • Emptage , M. , Tabinowski , J. and Odom , J. M. 1997 . Effect of fluoroacetates on methanogenesis in samples from selected methanogenic environments . Environ. Sci. Technol. , 31 : 732 – 734 .
  • Jordan , A. and Frank , H. 1999 . Trifluoroacetate in the environment. Evidence for sources other than HFC/HCFCs . Environ. Sci. Technol. , 33 : 522 – 527 .
  • Nielsen , O. J. , Scott , B. F. , Spencer , C. , Wallington , T. J. and Ball , J. C. 2001 . Trifluoroacetic acid in ancient freshwater . Atmos. Environ. , 35 : 2799 – 2801 .
  • Scott , B. F. , Macdonald , R. W. , Kannan , K. , Fisk , A. , Witter , A. , Yamashita , N. , Durham , L. , Spencer , C. and Muir , D. C. G. 2005 . Trifluoroacetate profiles in the Arctic, Atlantic, and Pacific Oceans . Environ. Sci. Technol. , 39 : 6555 – 6560 .
  • Tang , C. Y. , Fu , Q. S. , Robertson , A. P. , Criddle , C. S. and Leckie , J. O. 2006 . Use of reverse osmosis membranes to remove perfluorooctane sulfonate (PFOS) from semiconductor wastewater . Environ. Sci. Technol. , 40 : 7343 – 7349 .
  • Lin , A. Y. , Ch , S. , Panchangam , A. and Lo , C. 2009 . The impact of semiconductor, electronics and optoelectronic industries on downstream perfluorinated chemical contamination in Taiwanese rivers . Environ. Poll. , 157 : 1365 – 1372 .
  • Ju , X. , Jin , Y. , Sasaki , K. and Saito , N. 2008 . Perfluorinated surfactants in surface, subsurface water and microlayer from Dalian Coastal waters in China . Environ. Sci. Technol. , 42 : 3538 – 3542 .
  • Hebert , G. N. , Odom , M. A. , Craig , P. S. , Dick , D. L. and Strauss , S. H. 2002 . Method for the determination of sub-ppm concentrations of perfluoroalkylsulfonate anions in water . J. Environ. Monitor. , 4 : 90 – 95 .
  • Moody , C. A. , Hebert , G. N. , Strauss , S. H. and Field , J. A. 2003 . Occurrence and persistence of perfluorooctanesulfonate and other perfluorinated surfactants in groundwater at a fire-training area at Wurtsmith Air Force Base, Michigan, USA . J. Environ. Monit. , 5 : 341 – 345 .
  • Schultz , M. M. , Barofsky , D. F. and Field , J. A. 2004 . Quantitative determination of fluorotelomer sulfonates in groundwater by LC MS/MS . Environ. Sci. Technol. , 38 : 1828 – 1835 .
  • Moody , C. A. , Kwan , W. C. , Martin , J. W. , Muir , D. C. and Mabury , S. A. 2001 . Determination of perfluorinated surfactants in surface water samples by two independent analytical techniques: Liquid chromatography/tandem mass spectrometry and 19F NMR . Anal. Chem. , 73 : 2200 – 2206 .
  • Moody , C. A. , Martin , J. W. , Kwan , W. C. , Muir , D. C. G. and Mabury , S. A. 2002 . Monitoring perfluorinated surfactants in biota and surface water samples following an accidental release of fire-fighting foam into Etobicoke Creek . Environ. Sci. Technol. , 36 : 545 – 551 .
  • Skutlarek , D. , Exner , M. and Färber , H. 2006 . Perfluorinated surfactants in surface and drinking waters . Environ. Sci. Pollut. Res. Int. , 13 : 299 – 307 .
  • Holzer , J. , Midasch , O. , Rauchfuss , K. , Kraft , M. , Reupert , R. , Angerer , J. , Kleeschulte , P. , Marschall , N. and Wilhelm , M. 2008 . Biomonitoring of perfluorinated compounds in children and adults exposed to perfluorooctanoate-contaminated drinking water . Environ. Health Perspect. , 116 : 651 – 657 .
  • Wilhelm , M. , Hölzer , J. , Dobler , L. , Rauchfuss , K. , Midasch , O. , Kraft , M. , Angerer , J. and Wiesmüller , G. 2009 . Preliminary observations on perfluorinated compounds in plasma samples (1977–2004) of young German adults from an area with perfluorooctanoate-contaminated drinking water . Int. J. Hyg. Environ. Health , 212 : 142 – 145 .
  • Wilhelm , M. , Kraft , M. , Rauchfuss , K. and Hölzer , J. 2008 . Assessment and management of the first German case of a contamination with perfluorinated compounds (PFC) in the Region Sauerland, North Rhine-Westphalia . J. Toxicol. Environ. Health Part A , 71 : 725 – 733 .
  • Paustenbach , D. J. , Panko , J. M. , Scott , P. K. and Unice , K. M. 2007 . A methodology for estimating human exposure to perfluorooctanoic acid (PFOA): A retrospective exposure assessment of a community (1951–2003) . J. Toxicol. Environ. Health Part A , 70 : 28 – 57 .
  • Emmett , E. A. , Shofer , F. S. , Zhang , H. , Freeman , D. , Desai , C. and Shaw , L. M. 2006 . Community exposure to perfluorooctanoate: Relationships between serum concentrations and exposure sources . J. Occup. Environ. Med. , 48 : 759 – 770 .
  • Emmett , E. A. , Zhang , H. , Shofer , F. S. , Freeman , D. , Rodway , N. V. , Desai , C. and Shaw , L. M. 2006 . Community exposure to perfluorooctanoate: Relationships between serum levels and certain health parameters . J. Occup. Environ. Med. , 48 : 771 – 779 .
  • Loos , R. , Wollgast , J. , Huber , T. and Hanke , G. 2007 . Polar herbicides, pharmaceutical products, perfluorooctanesulfonate (PFOS), perfluorooctanoate (PFOA), and nonylphenol and its carboxylates and ethoxylates in surface and tap waters around Lake Maggiore in Northern Italy . Anal. Bioanal. Chem. , 387 : 1469 – 1478 .
  • Takagi , S. , Adachi , F. , Miyano , K. , Koizumi , Y. , Tanaka , H. , Mimura , M. , Watanabe , I. , Tanabe , S. and Kannan , K. 2008 . Perfluorooctanesulfonate and perfluorooctanoate in raw and treated tap water from Osaka, Japan . Chemosphere , 72 : 1409 – 1412 .
  • Higgins , C. P. , Field , J. A. , Criddle , C. S. and Luthy , R. G. 2005 . Quantitative determination of perfluorochemicals in sediments and domestic sludge . Environ. Sci. Technol. , 39 : 3946 – 3956 .
  • Sinclair , E. and Kannan , K. 2006 . Mass loading and fate of perfluoroalkyl surfactants in wastewater treatment plants . Environ. Sci. Technol. , 40 : 1408 – 1414 .
  • Schultz , M. M. , Higgins , C. P. , Huset , C. A. , Luthy , R. G. , Barofsky , D. F. and Field , J. A. 2006 . Fluorochemical mass flows in a municipal wastewater treatment facility . Environ. Sci. Technol. , 40 : 7350 – 7357 .
  • Loganathan , B. G. , Sajwan , K. S. , Sinclair , E. , Senthil Kumar , K. and Kannan , K. 2007 . Perfluoroalkyl sulfonates and perfluorocarboxylates in two wastewater treatment facilities in Kentucky and Georgia . Water Res. , 41 : 4611 – 4620 .
  • Becker , A. M. , Gerstmann , S. and Frank , H. 2008 . Perfluorooctane surfactants in waste waters, the major source of river pollution . Chemosphere , 72 : 115 – 121 .
  • Boulanger , B. , Vargo , J. D. , Schnoor , J. L. and Hornbuckle , K. C. 2005 . Evaluation of perfluorooctane surfactants in a wastewater treatment system and in a commercial surface protection product . Environ. Sci. Technol. , 39 : 5524 – 5530 .
  • Dinglasan , M. J. A. , Ye , Y. , Edwards , E. A. and Mabury , S. A. 2004 . Fluorotelomer alcohol biodegradation yields poly- and perfluorinated acids . Environ. Sci. Technol. , 38 : 2857 – 2864 .
  • Schultz , M. M. , Barofsky , D. F. and Field , J. A. 2006 . Quantitative determination of fluorinated alkyl substances by large-volume-injection liquid chromatography tandem mass spectrometry-characterization of municipal wastewaters . Environ. Sci. Technol. , 40 : 289 – 295 .
  • Renner , R. 2001 . Growing concern over perfluorinated chemicals . Environ. Sci. Technol. , 35 : 154A – 160A .
  • Simons , J. H. , Bond , R. L. and McArthur , R. E. 1940 . The preparation and properties of certain trifluoromethyl compounds . J. Am. Chem. Soc. , 62 : 3477 – 3480 .
  • LaZerte , J. D. , Hals , L. J. , Reid , T. S. and Smith , G. H. 1953 . Pyrolyses of the salts of the perfluoro carboxylic acids . J. Am. Chem. Soc. , 75 : 4525 – 4528 .
  • Dallenbach , R. and Tissot , P. 1981 . Properties of molten alkali metal trifluoracetates . J. Therm. Anal. Calorim. , 20 : 409 – 417 .
  • Haszeldine , R. N. 1951 . The reactions of metallic salts of acids with halogens. Part I. The reaction of metal trifluoroacetates with iodine, bromine, and chlorine . J. Chem. Soc. , : 584
  • Baillic , M. J. , Brown , D. H. , Moss , K. C. and Sharp , D. W. A. 1968 . Anhydrous metal trifluoroacetates . J. Chem. Soc. , : 3110 – 3114 .
  • Golic , L. and Speakman , J. 1965 . The crystal structures of the acid salts of some trifluoroacetates . J. Chem. Soc. , : 2530 – 2542 .
  • Rillings , K. W. and Roberts , J. E. 1974 . A thermal study of the trifluoroacetates and pentafluoropropionates of praseodymium, samarium, and erbium . Thermochim. Acta , 10 : 285 – 298 .
  • Roberts , J. E. 1983 . Lanthanum and neodymium salts of trifluoroacetic acid . J. Am. Chem. Soc. , 1961 : 1087 – 1088 .
  • Auerbach , I. , Verhoek , F. H. and Henne , A. L. 1950 . Kinetic studies on the decarboxylation of sodium trifluoroacetate in ethylene glycol . J. Am. Chem. Soc. , 72 : 299 – 300 .
  • Lines , D. and Sutcliffe , H. 1984 . Preparation and properties of some salts of perfluorooctanoic acid . J. Fluor. Chem. , 25 : 505 – 512 .
  • Krusic , P. J. , Roe , D. C. and Gas-phase , N MR . 2004 . technique for studying the thermolysis of materials: Thermal decomposition of ammonium perfluorooctanoate . Anal. Chem. , 76 : 3800 – 3803 .
  • Krusic , P. J. , Alex Marchione , E. A. , Roe , D. C. and Gas-phase , N MR . 2005 . studies of the thermolysis of perfluorooctanoic acid . J. Fluor. Chem. , 126 : 1510 – 1516 .
  • Blake , P. G. and Pritchard , H. 1967 . The thermal decomposition of trifluoroacetic acid . J. Chem. Soc. B , : 282 – 286 .
  • Pola , J. , Bastl , Z. and Tlaskal , J. 1990 . Infrared-laser induced production of silicon coating via reaction of silane with trifluoroacetic acid . Infrared Phys. , 30 : 355 – 357 .
  • Ashworth , A. and Harrison , P. G. 1993 . Fourier-transform infrared study of the gas-phase thermolysis of trifluoroacetic acid . Faraday Trans. , 89 : 2409 – 2412 .
  • Jollie , D. M. and Harrison , P. G. 1997 . An in situ IR study of the thermal decomposition of trifluoroacetic acid . J. Chem. Soc. Perkin Trans. 2 , : 1571 – 1576 .
  • Ellis , D. A. , Mabury , S. A. , Martin , J. W. and Muir , D. C. G. 2001 . Thermolysis of fluoropolymers as a potential source of halogenated organic acids in the environment . Nature , 412 : 321 – 324 .
  • Ellis , D. A. , Martin , J. W. , Muir , D. C. G. and Mabury , S. A. 2003 . 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 – 764 .
  • Yamada , T. , Taylor , P. H. , Buck , R. C. , Kaiser , M. A. and Giraud , R. J. 2005 . Thermal degradation of fluorotelomer treated articles and related materials . Chemosphere , 61 : 974 – 984 .
  • Hori , H. , Takano , Y. , Koike , K. , Takeuchi , K. and Einaga , H. 2003 . Decomposition of environmentally persistent trifluoroacetic acid to fluoride ions by a homogeneous photocatalyst in water . Environ. Sci. Technol. , 37 : 418 – 422 .
  • Chen , J. , Zhang , P. and Liu , J. 2007 . Photodegradation of perfluorooctanoic acid by 185 nm vacuum ultraviolet light . J. Environ. Sci. , 19 : 387 – 390 .
  • Yamamoto , T. , Noma , Y. , Sakai , S. and Shibata , Y. 2007 . Photodegradation of perfluorooctane sulfonate by UV irradiation in water and alkaline 2-propanol . Environ. Sci. Technol. , 41 : 5660 – 5665 .
  • Pehkonen , S. O. , Siefert , R. L. and Hoffmann , M. R. 1995 . Photoreduction of iron oxyhydroxides and the photooxidation of halogenated acetic acids . Environ. Sci. Technol. , 29 : 1215 – 1222 .
  • Hori , H. , Yamamoto , A. , Koike , K. , Kutsuna , S. , Osaka , I. and Arakawa , R. 2007 . Photochemical decomposition of environmentally persistent short-chain perfluorocarboxylic acids in water mediated by iron(II)/(III) redox reactions . Chemosphere , 68 : 572 – 578 .
  • Maruthamuthu , P. and Huie , R. E. 1995 . Ferric ion assisted photooxidation of haloacetates . Chemosphere , 30 : 2199 – 2207 .
  • Wang , Y. , Zhang , P. , Pan , G. and Chen , H. 2008 . Ferric ion mediated photochemical decomposition of perfluorooctanoic acid (PFOA) by 254 nm UV light . J. Hazard. Mater. , 160 : 181 – 186 .
  • Hori , H. , Hayakawa , E. , Einaga , H. , Kutsuna , S. , Koike , K. , Ibusuki , T. , Kiatagawa , H. and Arakawa , R. 2004 . Decomposition of environmentally persistent perfluorooctanoic acid in water by photochemical approaches . Environ. Sci. Technol. , 38 : 6118 – 6124 .
  • Maruthamuthu , P. , Padmaja , S. and Huie , R. E. 1995 . Rate constants for some reactions of free radicals with haloacetates in aqueous solution . Int. J. Chem. Kinet. , 27 : 605 – 612 .
  • Hori , H. , Takano , Y. , Koike , K. , Kutsuna , S. , Einaga , H. and Ibusuki , T. 2003 . Photochemical decomposition of pentafluoropropionic acid to fluoride ions with a water-soluble heteropolyacid photocatalyst . Appl. Catal. B , 46 : 333 – 340 .
  • Zhao , B. and Zhang , P. 2009 . Photocatalytic decomposition of perfluorooctanoic acid with β-Ga2O3 wide bandgap photocatalyst . Catal. Comm. , 10 : 1184 – 1187 .
  • Theron , P. , Pichat , P. , Guillard , C. , Petrier , C. and Chopin , T. 1999 . Degradation of phenyltrifluoromethylketone in water by separate or simultaneous use of TiO2 photocatalysis and 30 or 515 kHz ultrasound . Phys. Chem. Chem. Phys. , 1 : 4663 – 4668 .
  • Panchangam , S. , Lin , A. Y. , Tsai , J. and Lin , C. 2009 . Sonication-assisted photocatalytic decomposition of perfluorooctanoic acid . Chemosphere , 75 : 654 – 660 .
  • Hori , H. , Yamamoto , A. , Hayakawa , E. , Taniyasu , S. , Yamashita , N. , Kutsuna , S. , Kiatagawa , H. and Arakawa , R. 2005 . Efficient decomposition of environmentally persistent perfluorocarboxylic acids by use of persulfate as a photochemical oxidant . Environ. Sci. Technol. , 39 : 2383 – 2388 .
  • Hori , H. , Yamamoto , A. and Kutsuna , S. 2005 . Efficient photochemical decomposition of long-chain perfluorocarboxylic acids by means of an aqueous/liquid CO2 biphasic system . Environ. Sci. Technol. , 39 : 7692 – 7697 .
  • Chen , J. and Zhang , P. 2006 . Photodegradation of perfluorooctanoic acid in water under irradiation of 254 nm and 185 nm light by use of persulfate . Water Sci. Technol. , 54 : 317 – 325 .
  • Moriwaki , H. , Takagi , Y. , Tanaka , M. , Tsuruho , K. , Okitsu , K. and Maeda , Y. 2005 . Sonochemical decomposition of perfluorooctane sulfonate and perfluorooctanoic acid . Environ. Sci. Technol. , 39 : 3388 – 3392 .
  • Cheng , J. , Vecitis , C. D. , Park , H. , Mader , B. T. and Hoffmann , M. R. 2008 . Sonochemical degradation of perfluorooctane sulfonate (PFOS) and perfluorooctanoate (PFOA) in landfill groundwater: Environmental matrix effects . Environ. Sci. Technol. , 42 : 8057 – 8063 .
  • Vecitis , C. D. , Park , H. , Cheng , J. , Mader , B. T. and Hoffmann , M. R. 2008 . Kinetics and mechanism of the sonolytic conversion of the aqueous perfluorinated surfactants, perfluorooctanoate (PFOA), and perfluorooctane sulfonate (PFOS) into inorganic products . J. Phys. Chem. A , 112 : 4261 – 4270 .
  • Szajdzinska-Pietek , E. and Gebicki , J. 2000 . Pulse radiolytic investigation of perfluorinated surfactants in aqueous solutions . Res. Chem. Intermed. , 26 : 897 – 912 .
  • Buxton , G. , Greenstock , C. , Helman , W. and Ross , A. 1988 . Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (OH/O−) in aqueous solution . J. Phys. Chem. Ref. Data , 17 : 513 – 886 .
  • Hori , H. , Nagaoka , Y. , Yamamoto , A. , Sano , T. , Yamashita , N. , Taniyasu , S. , Kutsuna , S. , Osaka , I. and Arakawa , R. 2006 . Efficient decomposition of environmentally persistent perfluorooctanesulfonate and related fluorochemicals using zerovalent iron in subcritical water . Environ. Sci. Technol. , 40 : 1049 – 1054 .
  • Hori , H. , Nagaoka , Y. , Sano , T. and Kutsuna , S. 2008 . Iron-induced decomposition of perfluorohexanesulfonate in sub- and supercritical water . Chemosphere , 70 : 800 – 806 .
  • Park , H. , Vecitis , C. D. , Cheng , J. , Choi , W. , Mader , B. T. and Hoffmann , M. R. 2009 . Reductive defluorination of aqueous perfluorinated alkyl surfactants: Effects of ionic headgroup and chain length . J. Phys. Chem. A , 113 : 690 – 696 .
  • Paul , A. , Wannere , C. S. and Schaefer , H. F. 2004 . Do linear-chain perfluoroalkanes bind an electron? . J. Phys. Chem. A , 108 : 9428 – 9434 .
  • Schroder , H. F. and Meesters , R. 2005 . Stability of fluorinated surfactants in advanced oxidation processes: A follow up of degradation products using flow injection-mass spectrometry, liquid chromatography-mass spectrometry and liquid chromatography-multiple stage mass spectrometry . J. Chromatogr. A , 1082 : 110 – 119 .
  • Carter , K. E. and Farrell , J. 2008 . Oxidative destruction of perfluorooctane sulfonate using boron-doped diamond film electrodes . Environ. Sci. Technol. , 42 : 6111 – 6115 .
  • Hori , H. , Nagaoka , Y. , Murayama , M. and Kutsuna , S. 2008 . Efficient decomposition of perfluorocarboxylic acids and alternative fluorochemical surfactants in hot water . Environ. Sci. Technol. , 42 : 7438 – 7443 .
  • 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 .
  • Tang , C. Y. , Fu , Q. S. , Criddle , C. S. and Leckie , J. O. 2007 . Effect of flux (transmembrane pressure) and membrane properties on fouling and rejection of reverse osmosis and nanofiltration membranes treating perfluorooctane sulfonate containing wastewater . Environ. Sci. Technol. , 41 : 2008 – 2014 .
  • Steinle-Darling , E. and Reinhard , M. 2008 . Nanofiltration for trace organic contaminant removal: Structure, solution, and membrane fouling effects on the rejection of perfluorochemicals . Environ. Sci. Technol. , 42 : 5292 – 5297 .
  • Ochoa-Herrera , V. and Sierra-Alvarez , R. 2008 . Removal of perfluorinated surfactants by sorption onto granular activated carbon, zeolite and sludge . Chemosphere , 72 : 1588 – 1593 .
  • Yu , Q. , Zhang , R. , Deng , S. , Huang , J. and Yu , G. 2009 . Sorption of perfluorooctane sulfonate and perfluorooctanoate on activated carbons and resin: Kinetic and isotherm study . Water Res. , 43 : 1150 – 1158 .
  • Yu , Q. , Deng , S. and Yu , G. 2008 . Selective removal of perfluorooctane sulfonate from aqueous solution using chitosan-based molecularly imprinted polymer adsorbents . Water Res. , 42 : 3089 – 3097 .
  • Nordby , G. L. and Luck , J. M. 1956 . Perfluorooctanoic acid interactions with human serum albumin . J. Biol. Chem. , 219 : 399 – 404 .
  • 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 . Environ. Sci. Technol. , 42 : 3969 – 3974 .
  • Key , B. D. , Howell , R. D. and Criddle , C. S. 1998 . Defluorination of organofluorine sulfur compounds by Pseudomonas sp. strain D2 . Environ. Sci. Technol. , 32 : 2283 – 2287 .
  • Visscher , P. T. , Culbertson , C. W. and Oremland , R. S. 1994 . Degradation of trifluoroacetate in oxic and anoxic sediments . Nature , 369 : 729 – 731 .
  • Kim , B. , Suidan , M. , Wallington , T. and Du , X. 2000 . Biodegradability of trifluoroacetic acid . Environ. Eng. Sci. , 17 : 337 – 342 .
  • Schroder , H. F. 2003 . Determination of fluorinated surfactants and their metabolites in sewage sludge samples by liquid chromatography with mass spectrometry and tandem mass spectrometry after pressurised liquid extraction and separation on fluorine-modified reversed-phase sorbents . J. Chromatogr. A , 1020 : 131 – 151 .
  • Meesters , R. J. W. and Schröder , H. F. 2004 . Perfluorooctane sulfonate: A quite mobile anionic anthropogenic surfactant, ubiquitously found in the environment . Water Sci. Technol. , 50 : 235 – 242 .
  • Dimitrov , S. , Kamenska , V. , Walker , J. D. , Windle , W. , Purdy , R. , Lewis , M. and Mekenyan , O. 2004 . Predicting the biodegradation products of perfluorinated chemicals using CATABOL . SAR QSAR Environ. Res. , 15 : 69 – 82 .
  • Wang , N. , Szostek , B. , Buck , R. C. , Folsom , P. W. , Sulecki , L. M. , Capka , V. , Berti , W. R. and Gannon , J. T. 2005 . Fluorotelomer alcohol biodegradation: Direct evidence that perfluorinated carbon chains breakdown . Environ. Sci. Technol. , 39 : 7516 – 7528 .
  • Wang , N. , Szostek , B. , Folsom , P. W. , Sulecki , L. M. , Capka , V. , Buck , R. C. , Berti , W. R. and Gannon , J. T. 2005 . Aerobic biotransformation of 14C-labeled 8–2 telomer B alcohol by activated sludge from a domestic sewage treatment plant . Environ. Sci. Technol. , 39 : 531 – 538 .
  • Wang , N. , Szostek , B. , Buck , R. C. , Folsom , P. W. , Sulecki , L. M. and Gannon , J. T. 2009 . 8–2 Fluorotelomer alcohol aerobic soil biodegradation: Pathways, metabolites, and metabolite yields . Chemosphere , 75 : 1089 – 1096 .
  • Remde , A. and Debus , R. 1996 . Biodegradability of fluorinated surfactants under aerobic and anaerobic conditions . Chemosphere , 32 : 1563 – 1574 .
  • Barton , C. A. , Botelho , M. A. and Kaiser , M. A. 2008 . Solid vapor pressure and enthalpy of sublimation for perfluorooctanoic acid . J. Chem. Engr. Data , 53 : 939 – 941 .
  • Dewar , M. J. S. , Zoebisch , E. G. , Healy , E. F. and Stewart , J. J. P. 1985 . Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model . J. Am. Chem. Soc. , 107 : 3902 – 3909 .
  • Stewart , J. J. P. 1989 . Optimization of parameters for semiempirical methods I . Method. J. Comput. Chem. , 10 : 209 – 220 .
  • Allinger , N. L. 1977 . Conformational analysis. 130. MM2. A hydrocarbon force field utilizing V1 and V2 torsional terms . J. Am. Chem. Soc. , 99 : 8127 – 8134 .
  • Hilal , S. , Karickhoff , S. and Carreira , L. 2003 . Prediction of the vapor pressure boiling point, heat of vaporization and diffusion coefficient of organic compounds . QSAR Comb. Sci. , 22 : 565 – 574 .
  • Hilal , S. H. , Karickhoff , S. W. and Carreira , L. A. 1995 . A rigorous test for SPARC's chemical reactivity models: Estimation of more than 4300 ionization pKas . Quant. Struc. Act. Relat. , 14 : 348 – 355 .
  • 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 . Environ. Sci. Technol. , 38 : 1313 – 1320 .
  • Ellis , D. A. , Martin , J. W. , Mabury , S. A. , Hurley , M. D. , Sulbaek Andersen , M. P. and Wallington , T. J. 2003 . Atmospheric lifetime of fluorotelomer alcohols . Environ. Sci. Technol. , 37 : 3816 – 3820 .
  • 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 . J. Phys. Chem. A , 109 : 6232 – 6241 .
  • 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 . Environ. Sci. Technol. , 38 : 1693 – 1699 .
  • Cobranchi , D. P. , Botelho , M. , Buxton , L. W. , Buck , R. C. and Kaiser , M. A. 2006 . 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 .
  • 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 . J. Chem. Engr. Data , 49 : 1013 – 1022 .
  • Mannhold , R. , Poda , G. I. , Ostermann , C. and Tetko , I. V. 2009 . Calculation of molecular lipophilicity: State-of-the-art and comparison of log P methods on more than 96,000 compounds . J. Pharm. Sci. , 98 : 861 – 893 .
  • 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 reevesii): An Ai river ecological study in Japan . Ecotoxicol. Environ. Safety , 65 : 14 – 21 .
  • Berg , M. , Muller , S. R. , Muhlemann , J. , Wiedmer , A. and Schwarzenbach , R. P. 2000 . Concentrations and mass fluxes of chloroacetic acids and trifluoroacetic acid in rain and natural waters in Switzerland . Environ. Sci. Technol. , 34 : 2675 – 2683 .
  • Likens , G. E. , Tartowski , S. L. , Berger , T. W. , Richey , D. G. , Driscoll , C. T. , Frank , H. G. and Klein , A. 1997 . Transport and fate of trifluoroacetate in upland forest and wetland ecosystems . Proc. Natl. Acad. Sci. USA , 94 : 4499 – 4503 .
  • Wujcik , C. E. , Cahill , T. M. and Seiber , J. N. 1999 . Determination of trifluoroacetic acid in 1996–1997 precipitation and surface waters in California and Nevada . Environ. Sci. Technol. , 33 : 1747 – 1751 .
  • Hoehn , E. , Plumlee , M. H. and Reinhard , M. 2007 . Natural attenuation potential of downwelling streams for perfluorochemicals and other emerging contaminants . Water Sci. Technol. , 56 : 59 – 64 .
  • Frank , H. , Klein , A. and Renschen , D. 1996 . Environmental trifluoroacetate . Nature , 382 : 34 – 34 .
  • 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 . Arch. Environ. Contam. Toxicol. , 50 : 398 – 410 .
  • Boulanger , B. , Vargo , J. , Schnoor , J. L. and Hornbuckle , K. C. 2004 . Detection of perfluorooctane surfactants in Great Lakes water . Environ. Sci. Technol. , 38 : 4064 – 4070 .
  • Simcik , M. F. and Dorweiler , K. J. 2005 . Ratio of perfluorochemical concentrations as a tracer of atmospheric deposition to surface waters . Environ. Sci. Technol. , 39 : 8678 – 8683 .
  • Davis , K. L. , Aucoin , M. D. , Larsen , B. S. , Kaiser , M. A. and Hartten , A. S. 2007 . Transport of ammonium perfluorooctanoate in environmental media near a fluoropolymer manufacturing facility . Chemosphere , 67 : 2011 – 2019 .
  • So , M. K. , Miyake , Y. , Yeung , W. Y. , Ho , Y. M. , Taniyasu , S. , Rostkowski , P. , Yamashita , N. , Zhou , B. S. , Shi , X. J. , Wang , J. X. , Giesy , J. P. , Yu , H. and Lam , P. K. S. 2007 . Perfluorinated compounds in the Pearl River and Yangtze River of China . Chemosphere , 68 : 2085 – 2095 .
  • 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 . Arch. Environ. Contam. Toxicol. , 48 : 559 – 566 .
  • Becker , A. M. , Gerstmann , S. and Frank , H. 2008 . Perfluorooctanoic acid and perfluorooctane sulfonate in the sediment of the Roter Main river, Bayreuth, Germany . Environ. Poll. , 156 : 818 – 820 .
  • Weremiuk , A. M. , Gerstmann , S. and Frank , H. 2006 . Quantitative determination of perfluorinated surfactants in water by LC-ESI-MS/MS . J. Sep. Sci. , 29 : 2251 – 2255 .
  • Hansen , K. J. , Johnson , H. O. , Eldridge , J. S. , Butenhoff , J. L. and Dick , L. A. 2002 . Quantitative characterization of trace levels of PFOS and PFOA in the Tennessee River . Environ. Sci. Technol. , 36 : 1681 – 1685 .
  • Zushi , Y. , Takeda , T. and Masunaga , S. 2008 . Existence of nonpoint source of perfluorinated compounds and their loads in the Tsurumi River basin, Japan . Chemosphere , 71 : 1566 – 1573 .
  • Plumlee , M. H. , Larabee , J. and Reinhard , M. 2008 . Perfluorochemicals in water reuse . Chemosphere , 72 : 1541 – 1547 .
  • Cahill , T. M. and Seiber , J. N. 2000 . Regional distribution of trifluoroacetate in surface waters downwind of urban areas in northern California . Environ U. S. A. Sci. Technol. , 34 : 2909 – 2912 .
  • Wujcik , C. E. , Zehavi , D. and Seiber , J. N. 1988 . Trifluoroacetic acid levels in 1994–1996 fog, rain, snow and surface waters from California and Nevada . Chemosphere , 36 : 1233 – 1245 .
  • Huset , C. A. , Chiaia , A. C. , Barofsky , D. F. , Jonkers , N. , Kohler , H. E. , Ort , C. , Giger , D. W. and Field , J. A. 2008 . Occurrence and mass flows of fluorochemicals in the Glatt Valley watershed, Switzerland . Environ. Sci. Technol. , 42 : 6369 – 6377 .
  • Ericson , I. , Nadal , M. , van Bavel , B. , Lindström , G. and Domingo , J. 2008 . Levels of perfluorochemicals in water samples from Catalonia, Spain: Is drinking water a significant contribution to human exposure? . Env. Sci. Pollut. Res. , 15 : 614 – 619 .
  • Murakami , M. , Imamura , E. , Shinohara , H. , Kiri , K. , Muramatsu , Y. , Harada , A. and Takada , H. 2008 . Occurrence and sources of perfluorinated surfactants in rivers in Japan . Environ. Sci. Technol. , 42 : 6566 – 6572 .
  • Senthilkumar , K. , Ohi , E. , Sajwan , K. , Takasuga , T. and Kannan , K. 2007 . Perfluorinated compounds in river water, river sediment, market fish, and wildlife samples from Japan . Bull. Environ. Contam. Toxicol. , 79 : 427 – 431 .
  • Ryosuke , O. and Shigeki , M. 2006 . Environmental behavior of perfluorinated surfactants in Tokyo Bay . J. Japan Soc. Wat. Environ. , 29 : 221 – 228 .
  • Saito , N. , Harada , K. , Inoue , K. , Sasaki , K. , Yoshinaga , T. and Koizumi , A. 2004 . Perfluorooctanoate and perfluorooctane sulfonate concentrations in surface water in Japan . J. Occup. Health , 46 : 49 – 59 .
  • Harada , K. , Saito , N. , Sasaki , K. , Inoue , K. and Koizumi , A. 2003 . Perfluorooctane sulfonate contamination of drinking water in the Tama River, Japan: Estimated effects on resident serum levels . Bull. Environ. Contam. Toxicol. , 71 : 31 – 36 .
  • Rostkowski , P. , Yamashita , N. , So , I. M. K. , Taniyasu , S. , Lam , P. K. S. , Falandysz , J. , Lee , K. T. , Kim , S. K. , Khim , J. S. , Im , S. H. , Newsted , J. L. , Jones , P. D. , Kannan , K. and Giesy , J. P. 2006 . Perfluorinated compounds in streams of the Shihwa Industrial Zone and Lake Shihwa, South Korea . Environ. Toxicol. Chem. , 25 : 2374 – 2380 .
  • Tseng , C. , Liu , L. , Chen , C. and Ding , W. 2006 . 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 .
  • McLachlan , M. S. , Holmstrom , K. E. , Reth , M. and Berger , U. 2007 . Riverine discharge of perfluorinated carboxylates from the European continent . Environ. Sci. Technol. , 41 : 7260 – 7265 .
  • Takazawa , Y. , Nishino , T. , Sasaki , Y. , Yamashita , H. , Suzuki , N. , Tanabe , K. and Shibata , Y. 2009 . Occurrence and distribution of perfluorooctane sulfonate and perfluorooctanoic acid in the rivers of Tokyo . Wat. Air Soil Poll. , in press, DOI:10.1007/s11270–008-9958–7
  • Zhao , X. , Li , J. , Shi , Y. , Cai , Y. , Mou , S. and Jiang , G. 2007 . Determination of perfluorinated compounds in wastewater and river water samples by mixed hemimicelle-based solid-phase extraction before liquid chromatography-electrospray tandem mass spectrometry detection . J. Chromatogr. A , 1154 : 52 – 59 .
  • 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 from Japan . Environ. Sci. Technol. , 37 : 2634 – 2639 .
  • Kim , S. and Kannan , K. 2007 . Perfluorinated acids in air, rain, snow, surface runoff, and lakes: Relative importance of pathways to contamination of urban lakes . Environ. Sci. Technol. , 41 : 8328 – 8334 .
  • Cahill , T. M. , Thomas , C. M. , Schwarzbach , S. E. and Seiber , J. N. 2001 . Accumulation of trifluoroacetate in seasonal wetlands in California . Environ. Sci. Technol. , 35 : 820 – 825 .
  • Moody , C. A. and Field , J. A. 1999 . Determination of perfluorocarboxylates in groundwater impacted by fire-fighting activity . Environ. Sci. Technol. , 33 : 2800 – 2806 .
  • Yu , J. , Hu , J. , Tanaka , S. and Fujii , S. 2009 . Perfluorooctane sulfonate (PFOS) and perfluorooctanoic acid (PFOA) in sewage treatment plants . Water Res. , 43 : 2399 – 2408 .
  • González-Barreiro , C. , Martínez-Carballo , E. , Sitka , A. , Scharf , S. and Gans , O. 2006 . Method optimization for determination of selected perfluorinated alkylated substances in water samples . Anal. Bioanal. Chem. , 386 : 2123 – 2132 .
  • Alzaga , R. and Bayona , J. M. 2004 . Determination of perfluorocarboxylic acids in aqueous matrices by ion-pair solid-phase microextraction-in-port derivatization-gas chromatography-negative ion chemical ionization mass spectrometry . J. Chromatogr. A , 1042 : 155 – 162 .
  • Nozoe , M. , Fujii , S. , Hu , J. and Tanaka , S. 2008 . Behavior of perfluorinated organic compounds in several wastewater treatment plants . Adv. Asian Environ. Eng. , 7 : 33 – 40 .
  • Murakami , M. , Shinohara , H. and Takada , H. 2009 . Evaluation of wastewater and street runoff as sources of perfluorinated surfactants (PFSs) . Chemosphere , 74 : 487 – 493 .
  • Yamashita , N. , Kannan , K. , Taniyasu , S. , Horii , Y. , Petrick , G. and Gamo , T. 2005 . A global survey of perfluorinated acids in oceans . Mar. Pollut. Bull. , 51 : 658 – 668 .
  • Yamashita , N. , Kannan , K. , Taniyasu , S. , Horii , Y. , Okazawa , T. , Petrick , G. and Gamo , T. 2004 . Analysis of perfluorinated acids at parts-per-quadrillion levels in seawater using liquid chromatography-tandem mass spectrometry . Environ. Sci. Technol. , 38 : 5522 – 5528 .
  • Yamashita , N. , Taniyasu , S. , Petrick , G. , Wei , S. , Gamo , T. , Lam , P. K. S. and Kannan , K. 2008 . Perfluorinated acids as novel chemical tracers of global circulation of ocean waters . Chemosphere , 70 : 1247 – 1255 .
  • Ahrens , L. , Felizeter , S. and Ebinghaus , R. 2009 . Spatial distribution of polyfluoroalkyl compounds in seawater of the German Bight . Chemosphere , 76 : 179 – 184 .
  • Wei , S. , Chen , L. Q. , Taniyasu , S. , So , M. K. , Murphy , M. B. , Yamashita , N. , Yeung , L. W. Y. and Lam , P. K. S. 2007 . Distribution of perfluorinated compounds in surface seawaters between Asia and Antarctica . Mar. Pollut. Bull. , 54 : 1813 – 1818 .
  • Ahrens , L. , Barber , J. L. , Xie , Z. and Ebinghaus , R. 2009 . Longitudinal and latitudinal distribution of perfluoroalkyl compounds in the surface water of the Atlantic Ocean . Environ. Sci. Technol , 43 : 3122 – 3127 .
  • So , M. K. , Taniyasu , S. , Yamashita , N. , Giesy , J. P. , Zheng , J. , Fang , Z. , Im , S. H. and Lam , P. K. S. 2004 . Perfluorinated compounds in coastal waters of Hong Kong, South China, and Korea . Environ. Sci. Technol. , 38 : 4056 – 4063 .
  • Taniyasu , S. , Kannan , K. , So , M. K. , Gulkowska , A. , Sinclair , E. , Okazawa , T. and Yamashita , N. 2005 . Analysis of fluorotelomer alcohols, fluorotelomer acids, and short- and long-chain perfluorinated acids in water and biota . J. Chromatogr. A , 1093 : 89 – 97 .

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