Polybrominated dibenzo-p-dioxins

M. Freiberg, D.L. McAllister, C.J. Mazac, P. Ranken Analysis of Trace Levels of Polybrominated Dibenzo-p-dioxins and Dibenzofurans in Brominated Flame Retardants Presented on June 30, 1993 at Orgabrom 93 in Jerusalem. 

In addition, the concern about e-waste not only focuses on its vast quantity generated daily, but also more on the need to handle the toxic chemicals embedded in it. It is well known that e-waste contains lead, beryllium, mercury, cadmium (Cd), and brominated flame retardants (BFRs) among other chemical materials [3]. Furthermore, highly toxic chemicals such as polychlorinated dibenzo-p-dioxins and dibenzofurans (PCDD/Fs) and polybrominated dibenzo-p-dioxins and dibenzo-furans (PBDD/Fs) can be formed during the recycling process [4]. 

Table 1 Concentrations of chlorinated polycyclic aromatic hydrocarbons (CIPAHs), polybrominated diphenyl ethers (PBDEs), polychlorinated biphenyls (PCBs), polybrominated biphenyls (PBBs), polychlorinated dibenzo-p-dioxins and dibenzofurans (PCDD/Fs), and polybrominated dibenzo-p-dioxins and dibenzofurans (PBDD/Fs) in ambient air, soil, and human samples collected from e-waste recycling and reference sites in China... 

Fig. 7 Generic chemical structures of polyhalogenated compounds. X=C1, Br. (I) Polychlorinated biphenyls (PCBs), polybrominated biphenyls (PBBs) (II) chlorophenols (CPs), bromophenols (BPs) (III) polychlorinated diphenyl ethers (PCDE), polybrominated diphenyl ethers (PBDE) (IV) polychlorinated dibenzo-p-dioxin (PCDD), polybrominated dibenzo-p-dioxin (PBDD) (V) polychlorinated dibenzofuran (PCDF), polybrominated dibenzofuran (PBDF) (VI) tetrabromobisphenol A (TBBPA)...

WHO/ICPS (1998) Environmental Health Criteria 205 polybrominated dibenzo-p-dioxins and dibenzofurans. World Health Organization, Geneva... 

Polybrominated biphenyls (No. 152,1994) Polybrominated dibenzo-p-dioxins and dibenzofurans (No. 205,1998) Polychlorinated biphenyls and terphenyls (No. 2,1976,1st edition) ... 

It would be helpful to develop data determining the accuracy of PBDE determinations (e.g., percent recovery) in environmental samples. Methods for determining degradation products and metabolites of PBDE are needed. There is no information in the literature of detectable biodegradation of PBDEs in the environment under aerobic or anaerobic conditions. The analysis of PBDE pyrolysis degradation products, such as polybrominated dibenzo-p-dioxins and dibenzofurans (PBDD/Fs), is often disturbed by the presence of PBDEs. Ebert et al. (1999) demonstrated that by using a Florisil column ina sample clean-up process, almost complete separation of PBDEs and PBDD/Fs is achieved before analysis by GC-MS. 

Cramer PH, Ayling RE, Thornburg KR, et al. 1990. Evaluation of an analytical method for the determination of polybrominated dibenzo-p-dioxins/dibenzofurans (PBDD/PBDF) in human adipose. Chemosphere 20(7-9) 821-827. 

Ebert J, Lorenze W, Bahadir M. 1999. Optimization of the analytical performance of polybrominated dibenzo-p-dioxins and dibenzofiirans (PBDD-F). Chemosphere 39(6) 977-986. 

Luijk R, Covers HAJ. 1992. The formation of polybrominated dibenzo-p-dioxins (PBDDs) and dibenzofurans (PBDFs) during pyrolysis of polymer blends containing brominated flame retardants. Chemosphere 25(3) 361-374. 

Lutes CC, Charles MJ, Odum JR, et al. 1992. Chamber aging studies on the atmospheric stability of polybrominated dibenzo-p-dioxins and dibenzofurans. Environ Sci Technol 26(5) 991-998. 

Mennear JH, Lee C-C. 1994. Polybrominated dibenzo-p-dioxins and dibenzofurans literature review and health assessment. Environ Health Perspect Suppl 102 265-274. 

Utkina NK, Denisenko VA, Virovaya MV, Scholokova OV, Prokofeva NG (2002) Two New Minor Polybrominated Dibenzo-p-dioxins from the Marine Sponge Dysidea dendyi. J Nat Prod 65 1213... 

Mason G, Zacharewiski T, Denomme MA, Safe L, Safe S (1987) Polybrominated Dibenzo-p-dioxins and Related Compounds Quantitative In Vivo and In Vitro Structure Activity Relationships. Toxicology 44 245... 

Malmvam A, Zebiihr Y, Jensen S, Kautsky L, Greyerz E, Nakano T, Asplund L (2005) Identification of Polybrominated Dibenzo-p-dioxins in Blue Mussels (Mytilus edulis) from the Baltic Sea. Environ Sci Technol 39 8235... 

Choi, J.W., Fujimaki, S., Kitamura, K., Hashimoto, S., Ito, H., Suzuki, N., Sakai, S., Morita, M., 2003. Polybrominated dibenzo-p-dioxins, dibenzofurans, and diphenyl ethers in Japanese human adipose tissue. Environ. Sci. Technol. 37, 817-821. 

Neupert M, Grape A, Weis H. 1988. Stability of polybrominated dibenzo-p-dioxins and dibenzofurans under laboratory handling conditions. Chemosphere 17 1089-1097. 

IPCS Environmental Health Criteria 205 Polybrominated Dibenzo-p-dioxins and Dibenzofurans, Geneva World Health Organization, International Programme on Chemical Safety, 1996. 

Luijk R, Dorland K, Smit P, Govers HAJ (1993), in Polycyclic aromatic compounds", prediction of the gas chromatographic retention behaviour of polybrominated dibenzo-p-dioxins , p. 565-572, Garrigues Ph, Lamotte M (Eds.), Gordon and Breach, Yverdon Weber R, Hagenmaier H (1994), Organohalogen Compounds 19 7-11. Polyfluorinated diben-zodioxins/furans - Synthesis, analysis and formation", Eds. University of Kyoto, Japan... 

Thies J, Neupert M, Pump W (1990), Chemosphere 20 1921-1928. Tetrabromobisphenol A (TBBA), its derivatives and their flame retarded (FR) polymers -content of polybrominated dibenzo-p-dioxins (PBDD) and dibenzofurans (PBDF) - PBDD/F formation under processing and smouldering (worst case) conditions"... 

Hamm S, Theisen J (1992), Posterbeitrag auf dem Kongress DIOXIN 92.. .Formation of polybrominated dibenzofurans and polybrominated dibenzo-p-dioxins at fires of electrical appliances" Marklund S, Kjeller LO, Hansson M, Tysklind M, Rappe C, Ryan C, Collazo H, Dougherty R (1986), in Chlorinated Dioxins and Dibenzofurans in Perspective Determination of PCDDs and PCDFs in incineration samples and pyrolytic products", p. 79-92, Lewis Publishers, London... 

Loganathan BG, Kannan K, Watanabe I, Kawano M, Irvine K, Kumar S, Sikka HC (1995) Isomer-specific determination and toxic evaluation of polychlorinated biphenyls, polychlorinated/polybrominated dibenzo-p-dioxins and furans, polybrominated biphenylethers and extractable organic halogen in Carp from the Buffalo river, New York. Environ Sci Technol 29, 1832-1838. 

Analytes. DBF, decabromobiphenyl HBCD, Hexabromocyclododecane PBCDE, polybrominated or chlorinated diphenyl ether PBDE, polybrominated diphenyl ether PCB, polychlorinated biphenyl PBDD, polybrominated dibenzo-p-dioxins PBB, polybrominated biphenyl PeBDE, pentabromodiphenyl ether. 

Polybrominated dibenzo-p-dioxins (PB-DDs) are highly toxic however, less toxic than the chloro compounds. The effects and symptoms are comparable to those of chlorinated dioxins. In rats, 2,3,7,8-bromo isomer was 3 to 10 times less toxic than 2,3,7,8-TCDD (Loeser and Ivens 1988). Mason et al. (1987b) have investigated the biological and toxic effects and structure-activity relationships of brominated and chlorinated... 

Hayakawa K, Takatsuki H, Watanabe I et al (2004) Polybrominated diphenyl ethers (PBDEs), polybrominated dibenzo-p-dioxins/dibenzofurans (PBDD/Fs) and monobromo-polychlori-nated dibenzo-p-dioxins/dibenzofurans (MoBPXDD/Fs) in the atmosphere and bulk deposition in Kyoto, Jrqian. Chemosphere 57 343-356 Hildemarm LM, Markowski GR, Jones MC et al (1991) Submicrometer aerosol mass distributions of emissions from boilers, fireplaces, automobiles, diesel trucks, and meatcooking operations. Aerosol Sci Technol 14 138-152 HlUery BR, Basu I, Sweet CW et al (1997) Temporal and spatial trends in a long-term study of gas-phase PCB eoncentrations near the Great Lakes. Environ Sci Technol 31 1811-1816 Hites RA (2004) Polybrominated diphenyl ethers in the environment and in people a metaanalysis of eoneentrations. Environ Sci Technol 38 945-956... 

Polybrominated Dibenzo-p-dioxins (PBDDs) and Dibenzofurans (PBDFs)... 

Polychlorinated and polybrominated dibenzo-p-dioxins and dibenzo-p-furans, which are byproducts of combustion, can also be sampled in air nsing the high-volume air sampler and the quartz filter and PUF cartridges depicted in Figure 15.27. The dioxins and furans are determined by high-resolntion GCMS. Detection limits of 10-20 fg/m are possible for these compounds in air when 300-400 m of air is sampled (121). 

The HO -initiated oxidation of 2,4,4 -tribromodiphenyl ether (BDE-28) in the atmosphere and in water solution has been studied and found to occur more readily in the former, especially at the less-brominated Ph ring. The hydrox-ylated dibrominated diphenyl ethers (HO -PBDEs, PBDE = polybrominated diphenyl ethers) are formed through direct bromine-substitution reactions or secondary reactions of HO adducts. Polybrominated dibenzo-p-dioxins resulting from o-HO -PBDEs are favoured products compared with polybrominated dibenzofurans generated by bromophenols and their radicals. The complete degradation of HO adducts in the presence of O2/NO, which generates unsaturated ketones and aldehydes, is less feasible compared with the H-abstraction pathways by 03." ... 

DOP, dioctylphthalate IPPD, A -isopropyl-W-phenyl-p-phenylene diamine NBR, acrylonitrile-butadiene rubber NR, natural rubber PA, polyamide PAAE, polyamide amine epichlorohydrin PBDD, polybrominated dibenzo-p-dioxins PBDF, polybrominated dibenzofu-rans PBT, polybutylene terephthalate PDBS, polydibromostyrene. 

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