Biodegradation of Fluorinated Alkyl Substances

Part of the Reviews of Environmental Contamination and Toxicology book series (RECT, volume 208)

Abstract

The interest in the fate of fluorinated chemicals in the environment emerged in the 1980s–1990s, when chlorofluorocarbons were banned due to their extreme potential for destroying the ozone layer (Molina and Rowland 1974; Rowland 2002). More recent concerns connected with fluorinated chemicals have arisen within the last decade when the perfluorinated carboxylic acids (PFCAs) and perfluorinated alkane sulfonates (PFASs) were found to be environmentally ubiquitous (Giesy and Kannan 2001; Hansen et al. 2001). Indeed, the presence of these chemicals in human blood serum had been surmised in the 1960s (Taves 1968), but at that time, analytical methods were not yet capable of identifying these compounds.

References

  1. 3 M (1999) Fluorochemical use, distribution and release overview, U.S. Public Docket AR-226-0550. http://www.chemicalindustryarchives.org/dirtysecrets/scotchgard/pdfs/226-0550.pdf. Last access 23 Sep 2009
  2. Begley TH, White K, Honigfort P, Twaroski ML, Neches R, Walker RA (2005) Perfluorochemicals: potential sources of and migration from food packaging. Food Addit Contam 22:1023–1031CrossRefGoogle Scholar
  3. Boulanger B, Vargo JD, Schnoor JL, Hornbuckle KC (2005) Evaluation of perfluorooctane surfactants in a wastewater treatment system and in a commercial surface protection product. Environ Sci Technol 39:5524–5530CrossRefGoogle Scholar
  4. Butt CM, Mabury SA, Muir DCG, Braune BM (2007) Prevalence of long-chained perfluorinated carboxylates in seabirds from the Canadian arctic between 1975 and 2004. Environ Sci Technol 41:3521–3528CrossRefGoogle Scholar
  5. Dinglasan MJA, Ye Y, Edwards EA, Mabury SA (2004) Fluorotelomer alcohol biodegradation yields poly- and perfluorinated acids. Environ Sci Technol 38:2857–2864CrossRefGoogle Scholar
  6. DuPont Company (2004) Hydrolytic stability study report. U.S. EPA Administrative Record OPPT2003-0012-2607. http://www.regulations.gov. Last access 23 Sep 2009
  7. Ellis DA, Martin JW, De Silva AO, Mabury SA, Hurley MD, Andersen MPS, Wallington TJ (2004) Degradation of fluorotelomer alcohols: a likely atmospheric source of perfluorinated carboxylic acids. Environ Sci Technol 38:3316–3321CrossRefGoogle Scholar
  8. Ellis DA, Martin JW, Mabury SA, Hurley MD, Andersen MPS, Wallington TJ (2003) Atmospheric lifetime of fluorotelomer alcohols. Environ Sci Technol 37:3816–3820CrossRefGoogle Scholar
  9. Eubeler JP, Zok S, Bernhard M, Knepper TP (2009) Environmental biodegradation of synthetic polymers I. Test methodologies and procedures. Trac – Trend Anal Chem 9:1057–1072Google Scholar
  10. Frömel T, Knepper TP (2008) Mass spectrometry as an indispensable tool for studies of biodegradation of surfactants. Trac – Trend Anal Chem 27:1091–1106CrossRefGoogle Scholar
  11. Frömel T, Peschka M, Fichtner N, Hierse W, Ignatiev NV, Bauer KH, Knepper TP (2008) ω-(Bis(trifluoromethyl)amino)alkane-1-sulfonates: synthesis and mass spectrometric study of the biotransformation products. Rapid Commun Mass Spectrom 22:3957–3967CrossRefGoogle Scholar
  12. Frömel T, Knepper TP (2010) Fluoroteomer ethoxylates: Sources of highly fluorinated environmental contaminants part I: Biotransformation. Chemosphere, in PressGoogle Scholar
  13. Furdui VI, Stock NL, Ellis DA, Butt CM, Whittle DM, Crozier PW, Reiner EJ, Muir DCG, Mabury SA (2007) Spatial distribution of perfluoroalkyl contaminants in lake trout from the Great Lakes. Environ Sci Technol 41:1554–1559CrossRefGoogle Scholar
  14. Giesy JP, Kannan K (2001) Global distribution of perfluorooctane sulfonate in wildlife. Environ Sci Technol 35:1339–1342CrossRefGoogle Scholar
  15. Goss KU, Bronner G, Harner T, Hertel M, Schmidt TC (2006) The partition behavior of fluorotelomer alcohols and olefins. Environ Sci Technol 40:3572–3577CrossRefGoogle Scholar
  16. Hansen KJ, Clemen LA, Ellefson ME, Johnson HO (2001) Compound-specific, quantitative characterization of organic fluorochemicals in biological matrices. Environ Sci Technol 35:766–770CrossRefGoogle Scholar
  17. Key BD, Howell RD, Criddle CS (1997) Fluorinated organics in the biosphere. Environ Sci Technol 31:2445–2454CrossRefGoogle Scholar
  18. Key BD, Howell RD, Criddle CS (1998) Defluorination of organofluorine sulfur compounds by Pseudomonas sp. strain D2. Environ Sci Technol 32:2283–2287CrossRefGoogle Scholar
  19. Lange CC (2000) The aerobic biodegradation of N-EtFOSE alcohol by the microbial activity present in municipal wastewater treatment sludge. http://www.nikwax.com/cmsdata/Downloads/pr/5-3 M_biodegradation_report.pdf. Last access 23 Sep 2009Google Scholar
  20. Lau C, Anitole K, Hodes C, Lai D, Pfahles-Hutchens A, Seed J (2007) Perfluoroalkyl acids: a review of monitoring and toxicological findings. Toxicol Sci 99:366–394CrossRefGoogle Scholar
  21. Lei YD, Wania F, Mathers D, Mabury SA (2004) Determination of vapor pressures, octanol–air, and water–air partition coefficients for polyfluorinated sulfonamide, sulfonamidoethanols, and telomer alcohols. J Phys Chem A 49:1013–1022Google Scholar
  22. Liao C, Wang T, Cui L, Zhou Q, Duan S, Jiang G (2009) Changes in synaptic transmission, calcium current, and neurite growth by perfluorinated compounds are dependent on the chain length and functional group. Environ Sci Technol 43:2099–2104CrossRefGoogle Scholar
  23. Liu J, Lee LS (2005) Solubility and sorption by soils of 8:2 fluorotelomer alcohol in water and cosolvent systems. Environ Sci Technol 39:7535–7540CrossRefGoogle Scholar
  24. Liu J, Lee LS, Nies LF, Nakatsu CH, Turcot RF (2007) Biotransformation of 8:2 fluorotelomer alcohol in soil and by soil bacteria isolates. Environ Sci Technol 41:8024–8030CrossRefGoogle Scholar
  25. Molina MJ, Rowland FS (1974) Stratospheric sink for chlorofluoromethanes: chlorine atom-catalysed destruction of ozone. Nature 249:810–812CrossRefGoogle Scholar
  26. Murphy CD, Schaffrath C, O’Hagan D (2003) Fluorinated natural products: the biosynthesis of fluoroacetate and 4-fluorothreonine in Streptomyces cattleya. Chemosphere 52:455–461CrossRefGoogle Scholar
  27. Natarajan R, Azerad R, Badet B, Copin E (2005) Microbial cleavage of CF bond. J Fluorine Chem 126:424–435CrossRefGoogle Scholar
  28. O’Hagan D, Harper B (1999) Fluorine-containing natural products. J Fluorine Chem 100:127–133CrossRefGoogle Scholar
  29. Organisation of Economic Co-operation and Development (1992) OECD guideline for the testing of chemicals 302 B – Zahn-Wellens/EMPA test. http://www.oecd.org/dataoecd/17/18/1948225.pdf. Last access 22 Sep 2009
  30. Organisation of Economic Co-operation and Development (2007) Lists of PFOS, PFAS, PFOA, PFCA, related compounds and chemicals that may degrade to PFCA. http://www.olis.oecd.org/olis/2006doc.nsf/LinkTo/NT00000F9A/$FILE/JT03231059.PDF. Last access 23 Sep 2009
  31. Parsons JR, Sáez M, Dolfing J, de Voogt P (2008) Biodegradation of perfluorinated compounds. Rev Environ Contam Toxicol 196:53–71CrossRefGoogle Scholar
  32. Paul AG, Jones KC, Sweetman AJ (2008) A first global production, emission, and environmental inventory for perfluorooctane sulfonate. Environ Sci Technol 43:386–392CrossRefGoogle Scholar
  33. Peden-Adams MM, Keller JM, Eudaly JG, Berger J, Gilkeson GS, Keil DE (2008) Suppression of humoral immunity in mice following exposure to perfluorooctane sulfonate. Toxicol Sci 104:144–154CrossRefGoogle Scholar
  34. Peschka M, Fichtner N, Hierse W, Kirsch P, Montenegro E, Seidel M, Wilken RD, Knepper TP (2008a) Synthesis and analytical follow-up of the mineralization of a new fluorosurfactant prototype. Chemosphere 72:1534–1540CrossRefGoogle Scholar
  35. Peschka M, Fromel T, Fichtner N, Hierse W, Kleineidam M, Montenegro E, Knepper TP (2008b) Mechanistic studies in biodegradation of the new synthesized fluorosurfactant 9-[4-(trifluoromethyl)phenoxy]nonane-1-sulfonate. J Chromatogr A 1187:79–86CrossRefGoogle Scholar
  36. Prevedouros K, Cousins IT, Buck RC, Korzeniowski SH (2006) Sources, fate and transport of perfluorocarboxylates. Environ Sci Technol 40:32–44CrossRefGoogle Scholar
  37. Remde A, Debus R (1996) Biodegradability of fluorinated surfactants under aerobic and anaerobic conditions. Chemosphere 32:1563–1574CrossRefGoogle Scholar
  38. Renner R (2008) Do perfluoropolymers biodegrade into PFOA? Environ Sci Technol 42:648–650CrossRefGoogle Scholar
  39. Rhoads KR, Janssen EML, Luthy RG, Criddle CS (2008) Aerobic biotransformation and fate of N-ethyl perfluorooctane sulfonamidoethanol (N-EtFOSE) in activated sludge. Environ Sci Technol 42:2873–2878CrossRefGoogle Scholar
  40. Rowland FS (2002) Stratospheric ozone in the 21st century: the chlorofluorocarbon problem. Environ Sci Technol 25:622–628CrossRefGoogle Scholar
  41. Russell MH, Berti WR, Szostek B, Buck RC (2008) Investigation of the biodegradation potential of a fluoroacrylate polymer product in aerobic soils. Environ Sci Technol 42:800–807CrossRefGoogle Scholar
  42. Sáez M, de Voogt P, Parsons JR (2008) Persistence of perfluoroalkylated substances in closed bottle tests with municipal sewage sludge. Environ Sci Pollut Res 15:472–477CrossRefGoogle Scholar
  43. Schröder HF (2001) Tracing of surfactants in the biological wastewater treatment process and the identification of their metabolites by flow injection-mass spectrometry and liquid chromatography–mass spectrometry and -tandem mass spectrometry. J Chromatogr A 926:127–150CrossRefGoogle Scholar
  44. Schröder HF (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 1020:131–151CrossRefGoogle Scholar
  45. Schultz MM, Barofsky DF, Field JA (2004) Quantitative determination of fluorotelomer sulfonates in groundwater by LC MS/MS. Environ Sci Technol 38:1828–1835CrossRefGoogle Scholar
  46. Shoeib M, Harner T, Vlahos P (2006) Perfluorinated chemicals in the arctic atmosphere. Environ Sci Technol 40:7577–7583CrossRefGoogle Scholar
  47. Stock NL, Lau FK, Ellis DA, Martin JW, Muir DCG, Mabury SA (2004) Polyfluorinated telomer alcohols and sulfonamides in the North American troposphere. Environ Sci Technol 38:991–996CrossRefGoogle Scholar
  48. Taves DR (1968) Evidence that there are two forms of fluoride in human serum. Nature 217:1050–1051CrossRefGoogle Scholar
  49. Tittlemier SA, Pepper K, Edwards L (2006) Concentrations of perfluorooctanesulfonamides in Canadian total diet study composite food samples collected between 1992 and 2004. J Agric Food Chem 54:8385–8389CrossRefGoogle Scholar
  50. United States Environmental Protection Agency (2008) Fate, transport and transformation test guidelines – OPPTS 835.3215 – Inherent biodegradability – Conclawe test. http://www.epa.gov/opptsfrs/publications/835_3215.pdf. Last access 23 Sep 2009
  51. Wallington TJ, Hurley MD, Xia J, Wuebbles DJ, Sillman S, Ito A, Penner JE, Ellis DA, Martin J, Mabury SA, Nielsen OJ, Andersen MPS (2006) Formation of C7F15COOH (PFOA) and other perfluorocarboxylic acids during the atmospheric oxidation of 8:2 fluorotelomer alcohol. Environ Sci Technol 40:924–930CrossRefGoogle Scholar
  52. Wang N, Szostek B, Buck RC, Folsom PW, Sulecki LM, Capka V, Berti WR, Gannon JT (2005a) Fluorotelomer alcohol biodegradation – direct evidence that perfluorinated carbon chains breakdown. Environ Sci Technol 39:7516–7528CrossRefGoogle Scholar
  53. Wang N, Szostek B, Buck RC, Folsom PW, Sulecki LM, Gannon JT (2009) 8-2 Fluorotelomer alcohol aerobic soil biodegradation: pathways, metabolites, and metabolite yields. Chemosphere 75:1089–1096CrossRefGoogle Scholar
  54. Wang N, Szostek B, Folsom PW, Sulecki LM, Capka V, Buck RC, Berti WR, Gannon JT (2005b) Aerobic biotransformation of 14C-labeled 8-2 telomer B alcohol by activated sludge from a domestic sewage treatment plant. Environ Sci Technol 39:531–538CrossRefGoogle Scholar
  55. Washington JW, Ellington JJ, Jenkins TM, Evans JJ, Yoo H, Hafner SC (2009) Degradability of an acrylate-linked, fluorotelomer polymer in soil. Environ Sci Technol 43:6617–6623CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  1. 1.Institute for Analytic Research, Hochschule FreseniusIdsteinGermany

Personalised recommendations