482 brominated diphenyl ethers

Polybrominated diphenyl ethers have a large number of congeners, depending on the number and position of the bromine atoms on the two phenyl rings. Commercial brominated diphenyl ethers are produced by the bromination of diphenyl oxide. Brominated diphenyl ethers are used as flame retardants. 

Since brominated diphenyl ethers are used by blending, they are referred to as additive flame retardants. These additive flame retardants are much more prone to leaching or escape from the finished polymer product than the reactive flame retardants. 

Examples of polymer t5rpes, principal applications, and final products have been compiled (22). Studies upon potential risks have been conducted by industry. These studies do not reveal severe risks of the use of polybrominated diphenyl ethers. 

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It should, however, be noted that good flame retardancy is only achieved with the use of flame retardant additives and that some of the best of these, such as the brominated diphenyls and brominated diphenyl ethers, are restricted in their use in some countries. 

The reaction of brominated diphenyl ethers with methoxide in dimethyl formamide has been examined, and suggested as a ranking of their susceptibility to hydrolytic reactions under natural conditions (Rahm et al. 2005). The nature of the products was not apparently systematically examined. 

Sakai S-i, Hirai Y, Aizawa H, Ota S, Muroishi Y (2006) Emission inventory of deca-brominated diphenyl ether (DBDE) in Japan. J Mater Cycles Waste Manag 8(1 ) 56—62... 

EPA (1984) Health and environmental effects profile for brominated diphenyl ethers. Environ criteria and assessment office, Cincinnati. US Environmental Protection Agency, (see also... 

EPA (2000c) Environmental Protection Agency. Integrated risk information system (IRIS) data for brominated diphenyl ethers. Available at http //www.epa.gov/iris EPA (2005a) http //www.epa.gov/OGWDW/dwh/t-ioc/cadmium.html... 

White sponge, Dysidea sp. (Fig. 10.5), has been observed to overgrow members of the family Poritidae at Okinawa Island. Extracts from this sponge have been shown to contain brominated diphenyl ethers, which show potent cytotoxicity against P388 cells. Two known compounds, S -dibromo -p /l -dibromophenoxy) and 3,6-dibromo-2-(4 -dibromo-phenoxy)phenol (Fu and Schmitz, 1996 Fu et al., 1995 Fig. 10.6), were... 

FIGURE 10.6 Brominated diphenyl ether from Dysidea sp. 

Fu, X. and Schmitz, F. J. (1996). New brominated diphenyl ether from an unidentified species of Dysidea sponge. 13C NMR data for some brominated diphenyl ethers. J. Nat. Prod. 59, 1102-1103. 

Marsh et al. [36] examined analogous p-hydroxybromodiphenyl ethers and their binding to TR. The diphenyl ethers (brominated or not) bind much less avidly than T3 or T4, probably owing to the absence of the 4-carboxyl group. 4-Hydroxydiphenyl ether had the lowest affinity for THR. Within the brominated diphenyl ethers, the lowest binding was observed with the unsubstituted 4-hydroxydiphenyl ether, followed by bromine substitution in the 3 - and 5-positions, and followed by substitution by iodine. 

Compound/ IIUIUPACIUPAOdktRACIhto." Brominated biphenyls (BB) " Brominated diphenyl ethers (BDE) ... 

Table 4-7. Composition of Commercial Brominated Diphenyl Ethers...

Carlson GP. 1980a. Induction of xenobiotic metabolism in rats by brominated diphenyl ethers administered for 90 days. Toxicol Lett 6 207-212. 

Hale R, La Guardia M, Harvey E, et al. 2001. Brominated diphenyl ethers in land-spoiled sewage sludges in the US. BFR 149-152. 

Hale RC, La Guardia MJ, Harvey EP, et al. 2000. Comparison of brominated diphenyl ether fire retardant and organochlorine burdens in fish from Virginia (USA). Organohalogen Compounds 47 65-68. 

Ryan JJ, Patry B. 2000. Determination of brominated diphenyl ethers (BDE s) and levels in Canadian human milks. Organohalogen Compounds 47 57-60. 

Stanley JS, Cramer PH, Thornburg KR, et al. 1991. Mass spectral confirmation of chlorinated and brominated diphenyl ethers in human adipose tissues. Chemosphere 23(8-10) 1185-1186. 

Tittlemier SA, Tomy GT. 2000. Vapor pressure of six brominated diphenyl ether congeners. Organohalogen Compoimds 47 206-209. 

WH0. 1994a. Brominated diphenyl ethers. International programme on chemical safety. 

Zhou T, Taylor MM, De Vito MJ, et al. 2000. Thyroid hormone disruptive effects of brominated diphenyl ethers following developmental exposure. Toxicologist 54(l) 260-261. 

Zhou T, Taylor MM, DeVito MJ, et al. 2002. Developmental exposure to brominated diphenyl ethers results in thyroid hormone disruption. Toxicol Sci 66 105-116. 

Fu X, Schmitz FJ (1996) New Brominated Diphenyl Ether from an Unidentified Species of Dysidea Sponge. 13C NMR Data for Some Brominated Diphenyl Ethers. J Nat Prod 59 1102... 

Bowden BF, Towerzey L, Junk PC (2000) A New Brominated Diphenyl Ether from the Marine Sponge Dysidea herbacea. Aust J Chem 53 299... 

Agrawal MS, Bowden BF (2005) Marine Sponge Dysidea herbacea Revisited Another Brominated Diphenyl Ether. Mar Drugs 3 9... 

Malmvam A, Marsh G, Kautsky L, Athanasiadou M, Bergman A, 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... 

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