Emerging Brominated Flame Retardants in the Environment

  • Cynthia A. de WitEmail author
  • Amelie Kierkegaard
  • Niklas Ricklund
  • Ulla Sellström
Part of the The Handbook of Environmental Chemistry book series (HEC, volume 16)


A number of new brominated flame retardants (BFRs) are being found in the environment but the amount of data is still very small. The best studied emerging BFRs are 1,2-bis(2,4,6-tribromophenoxy)ethane and decabromodiphenyl ethane, with some data for hexabromobenzene, pentabromoethylbenzene, pentabromotoluene, tetrabromobisphenol A derivatives, bis(2-ethylhexyl) tetrabromophthalate, 2-ethylhexyltetrabromobenzoate, 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane, and 2,4,6-tribromophenol. Very little data are available for 2,4,6-tribromophenyl allyl ether, 2,3-dibromopropyl-2,4,6-tribromophenyl ether, hexachlorocyclopentadienyldibromocyclooctane, tris(2,3-dibromopropyl) isocyanurate, tetrabromophthalic anhydride, 1,2,5,6-tetrabromocyclooctane, and octabromo-1,3,3-trimethyl-1-phenylindane. Indoor air concentrations are generally higher than outdoor air concentrations, indicating emissions from flame-retarded products. Their presence in indoor air and dust indicates possible human exposure from this pathway, but there are little human data available to determine this. The presence of several of these BFRs in fish, birds, and mammals indicates that they are bioavailable and can be absorbed and bioaccumulated. Their presence in outdoor air and in the Arctic indicates that several are capable of long range atmospheric transport. More data on these new BFRs are needed in order to determine if they pose unacceptable risks to the environment and to human health.

Graphical Abstract


1,2,5,6-Tetrabromocyclooctane 1,2-Bis(2,4,6-tribromophenoxy)ethane 1,2-Dibromo-4-(1,2-dibromoethyl)cyclohexane 2,3-Dibromopropyl-2,4,6-tribromophenyl ether 2,4,6-Tribromophenol 2,4,6-Tribromophenyl allyl ether 2-Ethylhexyltetrabromobenzoate Bis(2-ethylhexyl) tetrabromophthalate Decabromodiphenyl ethane Hexabromobenzene Hexachlorocyclopentadienyldibromocyclooctane Octabromo-1,3,3-trimethyl-1-phenylindane Pentabromoethylbenzene Pentabromotoluene Tetrabromobisphenol A derivatives Tetra bromophthalic anhydride Tris(2,3-dibromopropyl) isocyanurate 



2,4,6-Tribromophenyl allyl ether


Brominated flame retardant




Decabromodiphenyl ethane


2,3-Dibromopropyl-2,4,6-tribromophenyl ether










Polybrominated diphenyl ether








Tetrabromobisphenol A


Tetrabromobisphenol A bis(allyl ether)


Tetrabromobisphenol A (2,3-dibromopropyl ether)


Tetrabromobisphenol A dihydroxyethyl ether


Tris(2,3-dibromopropyl) isocyanurate








Tetrabromophthalic anhydride


Bis(2-ethylhexyl) tetrabromophthalate


  1. 1.
    Alaee M, Arias P, Sjodin A, Bergman A (2003) An overview of commercially used brominated flame retardants, their applications, their use patterns in different countries/regions and possible modes of release. Environ Int 29:683–689Google Scholar
  2. 2.
    Hess G (2009) Industry to phase out decaBDE. Chem Eng News. Accessed March 2010
  3. 3.
    Albemarle (2009) Albemarle announces phase-out of Decabrom. Press release 17 December 2009. Accessed March 2010
  4. 4.
    Chemtura (2009) Chemtura corporation announces phase-out of DecaBDE. Press release 17 December 2009. Accessed March 2010
  5. 5.
    de Wit CA, Herzke D, Vorkamp K (2010) Brominated flame retardants in the Arctic environment – trends and new candidates. Sci Total Environ 408:2885–2918Google Scholar
  6. 6.
    Hoh E, Zhu LY, Hites RA (2005) Novel flame retardants, 1,2-bis(2,4,6-tribromophenoxy)ethane and 2, 3, 4, 5, 6-pentabromoethylbenzene, in United States’ environmental samples. Environ Sci Technol 39:2472–2477Google Scholar
  7. 7.
    Shi T, Chen SJ, Luo XJ et al (2009) Occurrence of brominated flame retardants other than polybrominated diphenyl ethers in environmental and biota samples from southern China. Chemosphere 74:910–916Google Scholar
  8. 8.
    ESIS (2010) European chemical substance information system. European Commission Joint Research Centre European Chemicals Bureau.
  9. 9.
    Verreault J, Gebbink WA, Gauthier LT, Gabrielsen GW, Letcher RJ (2007) Brominated flame retardants in glaucous gulls from the Norwegian Arctic: more than just an issue of polybrominated diphenyl ethers. Environ Sci Technol 41:4925–4931Google Scholar
  10. 10.
    Zweidinger RA, Cooper SD, Pellizzari ED (1979) Identification and quantitation of brominated fire retardants. In: Van Hall CE (ed) Measurement of organic pollutants in water and wastewater. ASTM STP 686. American Society for Testing and Materials, p 365Google Scholar
  11. 11.
    Zweidinger RA, Cooper SD, Erickson MD, Michael LC, Pellizzari ED (1979) Sampling and analysis for semivolatile brominated organics in ambient air. ACS Symp Ser 94:217–231Google Scholar
  12. 12.
    DeCarlo VJ (1979) Studies on brominated chemicals in the environment. Ann N Y Acad Sci 320:678–681Google Scholar
  13. 13.
    Hoh E, Hites RA (2005) Brominated flame retardants in the atmosphere of the east-central United States. Environ Sci Technol 39:7794–7802Google Scholar
  14. 14.
    Venier M, Hites RA (2008) Flame retardants in the atmosphere near the Great Lakes. Environ Sci Technol 42:4745–4751Google Scholar
  15. 15.
    Sjödin A, Carlsson H, Thuresson K, Sjölin S, Bergman Å, Östman C (2001) Flame retardants in indoor air at an electronics recycling plant and at other work environments. Environ Sci Technol 35:448–454Google Scholar
  16. 16.
    Chen LG, Mai BX, Bi XH et al (2006) Concentration levels, compositional profiles, and gas-particle partitioning of polybrominated diphenyl ethers in the atmosphere of an urban city in South China. Environ Sci Technol 40:1190–1196Google Scholar
  17. 17.
    Zhu LY, Hites RA (2006) Brominated flame retardants in tree bark from North America. Environ Sci Technol 40:3711–3716Google Scholar
  18. 18.
    Qiu XH, Hites RA (2008) Dechlorane plus and other flame retardants in tree bark from the northeastern United States. Environ Sci Technol 42:31–36Google Scholar
  19. 19.
    Pettersson-Julander A, van Bavel B, Engwall M, Westberg H (2004) Personal air sampling and analysis of polybrominated diphenyl ethers and other bromine containing compounds at an electronic recycling facility in Sweden. J Environ Monit 6:874–880Google Scholar
  20. 20.
    Julander A, Westberg H, Engwall M, van Bavel B (2005) Distribution of brominated flame retardants in different dust fractions in air from an electronics recycling facility. Sci Total Environ 350:151–160Google Scholar
  21. 21.
    Karlsson M, Julander A, van Bavel B, Hardell L (2007) Levels of brominated flame retardants in blood in relation to levels in household air and dust. Environ Int 33:62–69Google Scholar
  22. 22.
    Stapleton HM, Allen JG, Kelly SM et al (2008) Alternate and new brominated flame retardants detected in US house dust. Environ Sci Technol 42:6910–6916Google Scholar
  23. 23.
    Stapleton HM, Klosterhaus S, Eagle S, Fuh J, Meeker JD, Blum A, Webster TF (2009) Detection of organophosphate flame retardants in furniture foam and US house dust. Environ Sci Technol 43:7490–7495Google Scholar
  24. 24.
    Harrad S, Ibarra C, Abdallah MAE, Boon R, Neels H, Covaci A (2008) Concentrations of brominated flame retardants in dust from United Kingdom cars, homes, and offices: causes of variability and implications for human exposure. Environ Int 34:1170–1175Google Scholar
  25. 25.
    Kalachová K, Pulkrabová J, Hrádková P, Poustka J, Hajšlová J (2009) Polybrominated diphenyl ethers (PBDEs) in dust samples from Czech households. Organohalogen Compd 71:2320–2324Google Scholar
  26. 26.
    Chen SJ, Ma YJ, Wang J, Chen D, Luo XJ, Mai BX (2009) Brominated flame retardants in children’s toys: concentration, composition, and children’s exposure and risk assessment. Environ Sci Technol 43:4200–4206Google Scholar
  27. 27.
    Law K, Halldorson T, Danell R et al (2006) Bioaccumulation and trophic transfer of some brominated flame retardants in a Lake Winnipeg (Canada) food web. Environ Toxicol Chem 25:2177–2186Google Scholar
  28. 28.
    Qiu X, Marvin CH, Hites RA (2007) Dechlorane plus and other flame retardants in a sediment core from Lake Ontario. Environ Sci Technol 41:6014–6019Google Scholar
  29. 29.
    Lopez P, Leonards P, Brandsma S, De Boer J (2008) New brominated flame retardants in Dutch sediments and suspended particulate matter. Organohalogen Compd 70:224–227Google Scholar
  30. 30.
    Law K, Halldorson T, Danell R et al (2007) Bioaccumulation and trophic transfer of some brominated flame retardants in a Lake Winnipeg (Canada) food web. [Erratum to document cited in CA145:277560]. Environ Toxicol Chem 26:190–190Google Scholar
  31. 31.
    Tomy GT, Palace VP, Pleskach K et al (2007) Dietary exposure of juvenile rainbow trout (Oncorhynchus mykiss) to 1, 2-bis(2, 4, 6-tribromo- phenoxy)ethane: bioaccumulation parameters, biochemical effects, and metabolism. Environ Sci Technol 41:4913–4918Google Scholar
  32. 32.
    Ismail N, Gewurtz SB, Pleskach K, Whittle DM, Helm PA, Marvin CH, Tomy GT (2009) Brominated and chlorinated flame retardants in Lake Ontario, Canada, lake trout (Salvelinus Namaycush) between 1979 and 2004 and possible influences of food-web changes. Environ Toxicol Chem 28:910–920Google Scholar
  33. 33.
    Munschy C, Heas-Moisan K, Loizeau V, Tixier C, Tronczynski J, Alaee M, Pacepavicius G (2007) Identification of past and novel brominated flame retardants in common sole (Solea solea L.) from coastal areas in France. Organohalogen Compd 69:2681–2685Google Scholar
  34. 34.
    Park J-S, Holden A, Chu V et al (2009) Exposure of California peregrine falcon (Falco Peregrinus) to brominated flame retardants (PBDEs and new alternative BFRs) and PCBs: different profiles of PBDEs, prey, and isotope patterns between coastal and big city nesting birds. Organohalogen Compd 71:820–823Google Scholar
  35. 35.
    Gauthier LT, Hebert CE, Weseloh DVC, Letcher RJ (2007) Current-use flame retardants in the eggs of herring gulls (Larus argentatus) from the Laurentian Great Lakes. Environ Sci Technol 41:4561–4567Google Scholar
  36. 36.
    Gauthier LT, Potter D, Hebert CE, Letcher RJ (2009) Temporal trends and spatial distribution of non-polybrominated diphenyl ether flame retardants in the eggs of colonial populations of Great Lakes herring gulls. Environ Sci Technol 43:312–317Google Scholar
  37. 37.
    Karlsson M, Ericson I, van Bavel B, Jensen JK, Dam M (2006) Levels of brominated flame retardants in Northern Fulmar (Fulmarus glacialis) eggs from the Faroe Islands. Sci Total Environ 367:840–846Google Scholar
  38. 38.
    Tomy GT, Ismail N, Pleskach K et al (2007) Temporal and spatial trends of brominated and chlorinated flame retardants in beluga (Delphinapterus leucas) from the Canadian Arctic. In: Fourth international workshop on brominated flame retardants (BFR 2007), Toronto, Canada, 6-9 June, Extended abstractGoogle Scholar
  39. 39.
    Muir D, Kwan M, Evans M (2007) Temporal trends of persistent organic pollutants and metals in ringed seals from the Canadian Arctic. In: Smith S, Stow J (eds) Synopsis of research conducted under the 2006–2007 Northern Contaminants Program, Indian Affairs and Northern Development, Ottawa, ON, CanadaGoogle Scholar
  40. 40.
    Sjödin A, Patterson DG, Bergman Å (2003) A review on human exposure to brominated flame retardants – particularly polybrominated diphenyl ethers. Environ Int 29:829–839Google Scholar
  41. 41.
    Zhu L, Ma B, Hites RA (2009) Brominated flame retardants in serum from the general population in northern China. Environ Sci Technol 43:6963–6968Google Scholar
  42. 42.
    Hakk H, Larsen G, Bowers J (2004) Metabolism, tissue disposition, and excretion of 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE) in male Sprague-Dawley rats. Chemosphere 54:1367–1374Google Scholar
  43. 43.
    Nomeir AA, Markham PM, Ghanayem BI, Chadwick M (1993) Disposition of the flame-retardant 1,2-bis(2,4,6-tribromophenoxy)ethane in rats following administration in the diet. Drug Metab Dispos 21:209–214Google Scholar
  44. 44.
    UBA (2001) Erarbeitung von Bewertungsgrundlagen zur Substitution umweltrelevanter Flammschutzmittel. Umweltbundesamt, Germany. Accessed October 2005
  45. 45.
    Arias PA (2001) Brominated flame retardants – an overview. In: The second international workshop on brominated flame retardants (BFR 2001), Stockholm, Sweden, 14–16 May 2001, Extended abstractGoogle Scholar
  46. 46.
    Kierkegaard A, Björklund J, Friden U (2004) Identification of the flame retardant decabromodiphenyl ethane in the environment. Environ Sci Technol 38:3247–3253Google Scholar
  47. 47.
    Albemarle (2007) Albemarle to expand production of popular Saytex 8010 flame retardant. Newsletter September 17, 2007. Accessed September 2009
  48. 48.
    Zhang XL, Luo XJ, Chen SJ, Wu JP, Mai BX (2009) Spatial distribution and vertical profile of polybrominated diphenyl ethers, tetrabromobisphenol A, and decabromodiphenylethane in river sediment from an industrialized region of south China. Environ Pollut 157:1917–1923Google Scholar
  49. 49.
    Watanabe I, Sakai SI (2003) Environmental release and behavior of brominated flame retardants. Environ Int 29:665–682Google Scholar
  50. 50.
    Takigami H, Suzuki G, Hirai Y, Ishikawa Y, Sunami M, Sakai S (2009) Flame retardants in indoor dust and air of a hotel in Japan. Environ Int 35:688–693Google Scholar
  51. 51.
    Leonards P, Lopez P, De Boer J (2008) Analysis and occurrence of new brominated flame retardants in the environment. Organohalogen Compd 70:926–929Google Scholar
  52. 52.
    Eljarrat E, Labandeira A, Martinez A, Fabrellas B, Barceló D (2005) Occurrence of the “new” brominated flame retardant, decabromodiphenyl ethane, in sewage sludge from Spain. Organohalogen Compd 67:459–461Google Scholar
  53. 53.
    de la Torre A, Concejero MA, Sanz P, Martinez MA (2007) Optimisation of a MS/MS method for DBDPE: applications to Spanish sewage sludges. Organohalogen Compd 69:2702–2705Google Scholar
  54. 54.
    Konstantinov A, Arsenault G, Chittim B et al (2006) Characterization of mass-labeled [13C14]-decabromodiphenylethane and its use as a surrogate standard in the analysis of sewage sludge samples. Chemosphere 64:245–249Google Scholar
  55. 55.
    Ricklund N, Kierkegaard A, McLachlan MS (2008) An international survey of decabromodiphenyl ethane (deBDethane) and decabromodiphenyl ether (decaBDE) in sewage sludge samples. Chemosphere 73:1799–1804Google Scholar
  56. 56.
    Law RJ, Allchin CR, De Boer J et al (2006) Levels and trends of brominated flame retardants in the European environment. Chemosphere 64:187–208Google Scholar
  57. 57.
    Ricklund N, Kierkegaard A, McLachlan MS, Wahlberg C (2009) Mass balance of decabromodiphenyl ethane and decabromodiphenyl ether in a WWTP. Chemosphere 74:389–394Google Scholar
  58. 58.
    de la Torre A, Sanz P, Martinez MA (2008) Presence of PBDEs and DBDPE in leachate and compost from different Spanish landfills. Organohalogen Compd 70:1958–1960Google Scholar
  59. 59.
    Ricklund N, Kierkegaard A, McLachlan MS (2010) Levels and potential sources of decabromodiphenyl ethane (DBDPE) and decabromodiphenyl ether (DecaBDE) in lake and marine sediments in Sweden. Environ Sci Technol 44:1987–1991Google Scholar
  60. 60.
    Ismail N, Pleskach K, Marvin C, Whittle M, Keir M, Helm P, Tomy GT (2006) Temporal trends of flame retardants in Lake Ontario lake trout (1979–2004). Organohalogen Compd 68:1808–1811Google Scholar
  61. 61.
    Gao F, Luo XJ, Yang ZF, Wang XM, Mai BX (2009) Brominated flame retardants, polychlorinated biphenyls, and organochlorine pesticides in bird eggs from the Yellow River delta, north China. Environ Sci Technol 43:6956–6962Google Scholar
  62. 62.
    Luo XJ, Zhang XL, Liu J et al (2009) Persistent halogenated compounds in waterbirds from an e-waste recycling region in south China. Environ Sci Technol 43:306–311Google Scholar
  63. 63.
    Hu GC, Luo XJ, Dai JY et al (2008) Brominated flame retardants, polychlorinated biphenyls, and organochlorine pesticides in captive giant panda (Ailuropoda melanoleuca) and red panda (Ailurus fulgens) from China. Environ Sci Technol 42:4704–4709Google Scholar
  64. 64.
    Yamaguchi Y, Kawano M, Tatsukawa R, Moriwaki S (1988) Hexabromobenzene and its debrominated compounds in human adipose tissues of Japan. Chemosphere 17:703–707Google Scholar
  65. 65.
    Watanabe I, Kashimoto T, Tatsukawa R (1986) Hexabromobenzene and its debrominated compounds in river and estuary sediments in Japan. Bull Environ Contam Toxicol 36:778–784Google Scholar
  66. 66.
    Buser H-R (1986) Polybrominated dibenzofurans and dibenzo-p-dioxins: thermal reaction products of polybrominated diphenyl ether flame retardants. Environ Sci Technol 20:404–408Google Scholar
  67. 67.
    Gouteux B, Alaee M, Mabury SA, Pacepavicius G, Muir DCG (2008) Polymeric brominated flame retardants: are they a relevant source of emerging brominated aromatic compounds in the environment? Environ Sci Technol 42:9039–9044Google Scholar
  68. 68.
    Sawal G, Feibicke M, Meinecke S, Warmbrunn-Suckrow E, Lepom P (2008) Identification of a novel brominated flame retardant in dust. Organohalogen Compd 70:2029–2032Google Scholar
  69. 69.
    Saito I, Onuki A, Seto H (2007) Indoor organophosphate and polybrominated flame retardants in Tokyo. Indoor Air 17:28–36Google Scholar
  70. 70.
    Sinkkonen S, Paasivirta J, Lahtiperä M, Vattulainen A (2004) Screening of halogenated aromatic compounds in some raw material lots for an aluminium recycling plant. Environ Int 30:363–366Google Scholar
  71. 71.
    Nyholm JR, Norman A, Norrgren L, Haglund P, Andersson PL (2008) Maternal transfer of brominated flame retardants in zebrafish (Danio rerio). Chemosphere 73:203–208Google Scholar
  72. 72.
    Nyholm JR, Norman A, Norrgren L, Haglund P, Andersson PL (2009) Uptake and biotransformation of structurally diverse brominated flame retardants in zebrafish (Danio rerio) after dietary exposure. Environ Toxicol Chem 28:1035–1042Google Scholar
  73. 73.
    Letcher RJ (2007) Temporal and spatial trends of organic and metal contaminants in Canadian polar bears: 2006–2007 project summary report. In: Smith S, Stow J (eds) Synopsis of research conducted under the 2006–2007 Northern Contaminants Program, Indian Affairs and Northern Development, Ottawa, ON, CanadaGoogle Scholar
  74. 74.
    Smeds A, Saukko P (2003) Brominated flame retardants and phenolic endocrine disrupters in Finnish human adipose tissue. Chemosphere 53:1123–1130Google Scholar
  75. 75.
    Shen H, Main KM, Andersson AM et al (2008) Concentrations of persistent organochlorine compounds in human milk and placenta are higher in Denmark than in Finland. Hum Reprod 23:201–210Google Scholar
  76. 76.
    WHO (1997) Environmental health criteria 192. Flame retardants: a general introduction. World Health Organization, Geneva, Switzerland.
  77. 77.
    OSPAR (2001) OSPAR list of chemicals for priority action (Update 2007). Accessed March 2010
  78. 78.
    Lee RGM, Thomas GO, Jones KC (2002) Atmospheric concentrations of PBDEs in western Europe. Organohalogen Compd 58:193–196Google Scholar
  79. 79.
    Niimi AJ, Oliver BG (1988) Influence of molecular weight and molecular volume on dietary absorption efficiency of chemicals by fishes. Can J Fish Aquat Sci 45:222–227Google Scholar
  80. 80.
    Mattsson PE, Norström Å, Rappe C (1975) Identification of the flame retardant pentabromotoluene in sewage sludge. J Chromatogr 111:209–213Google Scholar
  81. 81.
    Jakab E, MdA U, Bhaskar T, Sakata Y (2003) Thermal decomposition of flame-retarded high-impact polystyrene. J Anal Appl Pyrolysis 68–69:83–99Google Scholar
  82. 82.
    Lopez P, Brandsma SA, Leonards PEG, De Boer J (2009) Methods for the determination of phenolic brominated flame retardants, and by-products, formulation intermediates and decomposition products of brominated flame retardants in water. J Chromatogr A 1216:334–345Google Scholar
  83. 83.
    Schwarzbauer J, Ricking M, Franke S, Francke W (2001) Organic compounds as contaminants of the Elbe River and its tributaries. Part 5. Halogenated organic contaminants in sediments of the Havel and Spree Rivers (Germany). Environ Sci Technol 35:4015–4025Google Scholar
  84. 84.
    Zitko V, Carson WG (1977) Uptake and excretion of chlorinated diphenyl ethers and brominated toluenes by fish. Chemosphere 6:293–301Google Scholar
  85. 85.
    US EPA (2006) Non-confidential 2006 IUR records by chemical. Inventory update reporting (IUR), US Environmental Protection Agency.
  86. 86.
    Andersson PL, Öberg K, Örn U (2006) Chemical characterization of brominated flame retardants and identification of structurally representative compounds. Environ Toxicol Chem 25:1275–1282Google Scholar
  87. 87.
    WHO (1995) Environmental health criteria 172. Tetrabromobisphenol A and derivatives. World Health Organization, Geneva, Switzerland.
  88. 88.
    Rahm S, Green N, Norrgran J, Bergman Å (2005) Hydrolysis of environmental contaminants as an experimental tool for indication of their persistency. Environ Sci Technol 39:3128–3133Google Scholar
  89. 89.
    Jonsson S, Hörsing M (2009) Investigation of sorption phenomena by solid phase extraction and liquid chromatography for the determination of some ether derivatives of tetrabromobisphenol A. J Phys Org Chem 22:1120–1126Google Scholar
  90. 90.
    Harju M, Heimstad ES, Herzke D et al (2009) Emerging “new” brominated flame retardants in flame retarded products and the environment. SFT report 2462, Norwegian Pollution Control Authority, Oslo, Norway, p 113Google Scholar
  91. 91.
    Breivik K, Wania F, Muir DCG, Alaee M, Backus S, Pacepavicius G (2006) Empirical and modeling evidence of the long-range atmospheric transport of decabromodiphenyl ether. Environ Sci Technol 40:4612–4618Google Scholar
  92. 92.
    Karlsson M (2006) Levels of brominated flame retardants in humans and their environment – occupational and home exposure. PhD Thesis, Örebro University, Örebro, Sweden. ISBN:91-7668-499-7Google Scholar
  93. 93.
    Köppen R, Becker R, Jung C, Piechotta C, Nehls I (2006) Investigation of extraction procedures and HPLC-DAD/MS for the determination of the brominated flame retardant tetrabromobisphenol A bis(2,3-dibromopropylether) in environmental samples. Anal Bioanal Chem 384:1485–1492Google Scholar
  94. 94.
    Knudsen GA, Jacobs LM, Kuester RK, Sipes IG (2007) Absorption, distribution, metabolism and excretion of intravenously and orally administered tetrabromobisphenol A [2,3-dibromopropyl ether] in male Fischer-344 rats. Toxicology 237:158–167Google Scholar
  95. 95.
    Davis EF, Stapleton HM (2009) Photodegradation pathways of nonabrominated diphenyl ethers, 2-ethylhexyltetrabromobenzoate and di(2-ethylhexyl)tetrabromophthalate: identifying potential markers of photodegradation. Environ Sci Technol 43:5739–5746Google Scholar
  96. 96.
    US EPA (2010) Non-confidential production volume information submitted by companies under the 1986, 1990, 1994, 1998, and 2002 IUR. Inventory update reporting (IUR), US Environmental Protection Agency.
  97. 97.
    Betts K (2008) New flame retardants detected in indoor and outdoor environments. Environ Sci Technol 42:6778Google Scholar
  98. 98.
    Klosterhaus S, Konstantinov A, Stapleton HM (2008) Characterization of the brominated chemicals in PentaBDE replacement mixture and their detection in biosolids collected from two San Francisco Bay Area wastewater treatment plants. Accessed March 2010
  99. 99.
    Klosterhaus S, Stapleton HM, La Guardia M, Davis E, Eagle S, Blum A (2010) Recent studies on the identification and occurrence of PentaBDE replacement chemicals in indoor and outdoor environments. In: Fifth international symposium on brominated flame retardants (BFR 2010), Kyoto, Japan, 7–9 April 2010, Extended abstractGoogle Scholar
  100. 100.
    Hoh E, Lehotay SJ, Mastovska K, Ngo HL, Vetter W, Pangallo KC, Reddy CM (2009) Capabilities of direct sample introduction-comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry to analyze organic chemicals of interest in fish oils. Environ Sci Technol 43:3240–3247Google Scholar
  101. 101.
    Lam JCW, Lau RKF, Murphy MB, Lam PKS (2009) Temporal trends of hexabromocyclododecanes (HBCDs) and polybrominated diphenyl ethers (PBDEs) and detection of two novel flame retardants in marine mammals from Hong Kong, south China. Environ Sci Technol 43:6949Google Scholar
  102. 102.
    Arsenault G, Lough A, Marvin C et al (2008) Structure characterization and thermal stabilities of the isomers of the brominated flame retardant 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane. Chemosphere 72:1163–1170Google Scholar
  103. 103.
    Tomy GT, Pleskach K, Arsenault G et al (2008) Identification of the novel cycloaliphatic brominated flame retardant 1,2-dihromo-4-(1,2-dibromoethyl)cyclo-hexane in Canadian arctic beluga (Delphinapterus leucas). Environ Sci Technol 42:543–549Google Scholar
  104. 104.
    Muir DCG, Howard PH (2006) Are there other persistent organic pollutants? A challenge for environmental chemists. Environ Sci Technol 40:7157–7166Google Scholar
  105. 105.
    Santillo D, Labounskaia I, Stringer R, Johnston P (1997) Report on the analysis of industrial wastewaters from the Frutarom VCM/PVC plant, near Haifa, Israel, and adjacent shoreline sediments for organic contaminants. Greenpeace Research Laboratories Technical Note 03/97 1-25Google Scholar
  106. 106.
    Whitfield FB, Drew M, Helidoniotis F, Svoronos D (1999) Distribution of bromophenols in species of marine polychaetes and bryozoans from eastern Australia and the role of such animals in the flavor of edible ocean fish and prawns (shrimp). J Agric Food Chem 47:4756–4762Google Scholar
  107. 107.
    Flodin C, Whitfield FB (2000) Brominated anisoles and cresols in the red alga Polysiphonia sphaerocarpa. Phytochemistry 53:77–80Google Scholar
  108. 108.
    Chung HY, Ma WCJ, Ang PO Jr, Kim JS, Chen F (2003) Seasonal variations of bromophenols in brown algae (Padina arborescens, Sargassum siliquastrum, and Lobophora variegata) collected in Hong Kong. J Agric Food Chem 51:2619–2624Google Scholar
  109. 109.
    Fielman KT, Woodin SA, Lincoln DE (2001) Polychaete indicator species as a source of natural halogenated organic compounds in marine sediments. Environ Toxicol Chem 20:738–747Google Scholar
  110. 110.
    Qiu X, Bigsby RM, Hites RA (2009) Hydroxylated metabolites of polybrominated diphenyl ethers in human blood samples from the United States. Environ Health Perspect 117:93–98Google Scholar
  111. 111.
    Suzuki G, Takigami H, Watanabe M, Takahashi S, Nose K, Asari M, Sakai S (2008) Identification of brominated and chlorinated phenols as potential thyroid-disrupting compounds in indoor dusts. Environ Sci Technol 42:1794–1800Google Scholar
  112. 112.
    Vetter W, Haase-Aschoff P, Rosenfelder N, Komarova T, Mueller JF (2009) Determination of halogenated natural products in passive samplers deployed along the Great Barrier Reef, Queensland/Australia. Environ Sci Technol 43:6131–6137Google Scholar
  113. 113.
    Sim WJ, Lee IS, Lee SH, Oh JE, Lee TS (2007) Distribution of chlorinated and brominated phenols in marine, riverine, and estuarine sediments in southeastern Korea. Organohalogen Compd 69:1697–1700Google Scholar
  114. 114.
    Löfstrand K, Malmvärn A, Haglund P, Bignert A, Bergman Å, Asplund L (2007) PBDD, MeO-PBDE, OH-PBDE and brominated phenols in blue mussels from the Swedish coast line. Organohalogen Compd 69:287–290Google Scholar
  115. 115.
    Chung HY, Ma WCJ, Kim JS (2003) Seasonal distribution of bromophenols in selected Hong Kong seafood. J Agric Food Chem 51:6752–6760Google Scholar
  116. 116.
    Wan Y, Wiseman S, Chang H et al (2009) Origin of hydroxylated brominated diphenyl ethers: natural compounds or man-made flame retardants? Environ Sci Technol 43:7536–7542Google Scholar
  117. 117.
    Mardones C, Palma J, Sepulveda C, Berg A, von Baer D (2003) Determination of tribromophenol and pentachlorophenol and its metabolite pentachloroanisole in Asparagus officinalis by gas chromatography/mass spectrometry. J Sep Sci 26:923–926Google Scholar
  118. 118.
    Unson MD, Holland ND, Faulkner DJ (1994) A brominated secondary metabolite synthesized by the cyanobacterial symbiont of a marine sponge and accumulation of the crystalline metabolite in the sponge tissue. Mar Biol 119:1–11Google Scholar
  119. 119.
    Teuten EL, Xu L, Reddy CM (2005) Two abundant bioaccumulated halogenated compounds are natural products. Science 307:917–920Google Scholar
  120. 120.
    Malmvärn A, Marsh G, Kautsky L, Athanasiadou M, Bergman Å, Asplund L (2005) Hydroxylated and methoxylated brominated diphenyl ethers in the red algae Ceramium tenuicorne and blue mussels from the Baltic Sea. Environ Sci Technol 39:2990–2997Google Scholar
  121. 121.
    Takigami H, Suzuki G, Hirai Y, Sakai S (2009) Brominated flame retardants and other polyhalogenated compounds in indoor air and dust from two houses in Japan. Chemosphere 76:270–277Google Scholar
  122. 122.
    Öberg K, Warman K, Öberg T (2002) Distribution and levels of brominated flame retardants in sewage sludge. Chemosphere 48:805–809Google Scholar
  123. 123.
    Kurata Y, Ono Y, Ono Y (2008) Occurrence of phenols in leachates from municipal solid waste landfill sites in Japan. J Mater Cycles Waste Manage 10:144–152Google Scholar
  124. 124.
    Hovander L, Malmberg T, Athanasiadou M, Athanassiadis I, Rahm S, Bergman A, Wehler EK (2002) Identification of hydroxylated PCB metabolites and other phenolic halogenated pollutants in human blood plasma. Arch Environ Contam Toxicol 42:105–117Google Scholar
  125. 125.
    Thomsen C, Lundanes E, Becher G (2001) Brominated flame retardants in plasma samples from three different occupational groups in Norway. J Environ Monit 3:366–370Google Scholar
  126. 126.
    Thomsen C, Lundanes E, Becher G (2002) Brominated flame retardants in archived serum samples from Norway: a study on temporal trends and the role of age. Environ Sci Technol 36:1414–1418Google Scholar
  127. 127.
    Dallaire R, Ayotte P, Pereg D, Dery S, Dumas P, Langlois E, Dewailly E (2009) Determinants of plasma concentrations of perfluorooctanesulfonate and brominated organic compounds in Nunavik inuit adults (Canada). Environ Sci Technol 43:5130–5136Google Scholar
  128. 128.
    Ohta S, Okumura T, Nishimura H et al (2010) Levels of PBDEs, TBBPA, TBPs, PCDDs/DFs, PXDDs/DFs and PBDDs/DFs in human milk of nursing women and dairy milk products in Japan. Organohalogen Compd 66:2857–2862Google Scholar
  129. 129.
    Fisk PR, Girling AE, Wildey RJ (2003) Prioritisation of flame retardants for environmental risk assessment. UK Environment Science Agency. Accessed 2010-03-10
  130. 130.
    von der Recke R, Vetter W (2007) Synthesis and characterization of 2, 3-dibromopropyl-2,4,6-tribromophenyl ether (DPTE) and structurally related compounds evidenced in seal blubber and brain. Environ Sci Technol 41:1590–1595Google Scholar
  131. 131.
    Brown TN, Wania F (2008) Screening chemicals for the potential to be persistent organic pollutants: a case study of Arctic contaminants. Environ Sci Technol 42:5202–5209Google Scholar
  132. 132.
    Vetter W, von der Recke R, Ostrowicz P, Rosenfelder N (2010) Liquid chromatographic enantioseparation of the brominated flame retardant 2,3-dibromopropyl-2, 4, 6-tribromophenyl ether (DPTE) and enantiomer fractions in seal blubber. Chemosphere 78:134–138Google Scholar
  133. 133.
    Riddell N, Arsenault G, Lough A, McAlees A, Mccrindle R, Meissner J, Robertson V (2008) The three-dimensional structural characterization of hexachlorocyclopentenyldibromocyclooctane (HCDBCO). Chemosphere 73:479–483Google Scholar
  134. 134.
    Zhu J, Hou Y, Feng Y-L, Shoeib M, Harner T (2008) Identification and determination of hexachlorocyclopentadienyl-dibromocyclooctane (HCDBCO) in residential indoor air and dust: a previously unreported halogenated flame retardant in the environment. Environ Sci Technol 42:386–391Google Scholar
  135. 135.
    Zhou SN, Reiner EJ, Marvin C et al (2010) Liquid chromatography–atmospheric pressure photoionization tandem mass spectrometry for analysis of 36 halogenated flame retardants in fish. J Chromatogr A 1217:633–641Google Scholar
  136. 136.
    Ruan T, Wang YW, Wang C et al (2009) Identification and evaluation of a novel heterocyclic brominated flame retardant tris(2,3-dibromopropyl) isocyanurate in environmental matrices near a manufacturing plant in southern China. Environ Sci Technol 43:3080–3086Google Scholar
  137. 137.
    Riddell N, Arsenault G, Klein J et al (2009) Structural characterization and thermal stabilities of the isomers of the brominated flame retardant 1,2,5,6-tetrabromocyclooctane (TBCO). Chemosphere 74:1538–1543Google Scholar
  138. 138.
    Traag W, Kotz A, van der Weg G, Malisch R, Hoogenboom R (2009) Bioassay directed detection of brominated dioxins in the feed additive cholin chloride. Organohalogen Compd 71:2210–2213Google Scholar
  139. 139.
    Kuramochi H, Maeda K, Kawamoto K (2004) Measurements of water solubilities and 1-octanol/water partition coefficients and estimations of Henry’s law constants for brominated benzenes. J Chem Eng Data 49:720–724Google Scholar
  140. 140.
    Tittlemier SA, Halldorson T, Stern GA, Tomy GT (2002) Vapor pressures, aqueous solubilities, and Henry’s law constants of some brominated flame retardants. Environ Toxicol Chem 21:1804–1810Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  • Cynthia A. de Wit
    • 1
    Email author
  • Amelie Kierkegaard
    • 1
  • Niklas Ricklund
    • 1
  • Ulla Sellström
    • 1
  1. 1.Department of Applied Environmental Science (ITM)Stockholm UniversityStockholmSweden

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