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Environ Int 32, 2006, 575 585.pdf


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Environment International 32 (2006) 575 – 585
www.elsevier.com/locate/envint

Photochemistry of a major commercial polybrominated diphenyl ether flame
retardant congener: 2,2′,4,4′,5,5′-Hexabromodiphenyl ether (BDE153)
Sierra Rayne a,⁎, Peter Wan a , Michael Ikonomou b
a

b

Department of Chemistry, University of Victoria, PO Box 3065, Victoria, British Columbia, Canada V8W 3V6
Institute of Ocean Sciences, Fisheries and Oceans Canada, 9860 West Saanich Road, Sidney, British Columbia, Canada V8L 4B2
Received 5 September 2005; accepted 6 January 2006
Available online 6 March 2006

Abstract
The photochemistry of a major commercial polybrominated diphenyl ether (PBDE) flame retardant congener, 2,2′,4,4′,5,5′hexabromodiphenyl ether (BDE153), was investigated in acetonitrile, distilled water, and seawater. After a short irradiation period in acetonitrile
at 302nm, the major photoproducts of BDE153 included 2,2′,4,4′,5-(BDE99), 2,2′,4,5,5′-(BDE101), and 2,4,4′,5,5′-(BDE118) substituted pentaBDEs as primary photohydrodebromination products, 2,2′,4,4′-(BDE47), 3,3′,4,4′-(BDE77), 2,3′,4,4′-(BDE66), and 2,2′,4,5′-(BDE49)
substituted tetra-BDEs as secondary photohydrodebromination products, a suite of non-2,3,7,8-substituted mono- through penta-brominated
dibenzofurans, and three tetrabrominated 2-hydroxybiphenyl congeners. By comparison, irradiation in distilled water and seawater gave increased
relative photohydrodebromination contributions and no evidence for the formation of brominated dibenzofurans or 2-hydroxybiphenyls. In all
solvent systems, subsequent degradation of primary and secondary photoproducts under continuing irradiation led to a steadily decreasing reaction
mass balance. The results suggest a short photochemical half-life for BDE153 in aquatic systems, with rapid photohydrodebromination to some of
the most prevalent penta- and tetra-brominated diphenyl ether congeners typically observed in environmental matrices.
© 2006 Elsevier Ltd. All rights reserved.
Keywords: Polybrominated diphenyl ethers (PBDEs); Photochemistry; Environmental fate; Brominated dibenzofurans; Brominated 2-hydroxybiphenyls

1. Introduction
Since the 1970s, polybrominated diphenyl ethers (PBDEs) have come into widespread industrial use as flame retardants in a
variety of technical mixtures (tetra-, penta-, octa-, and deca-brominated) applied to plastics, textiles, and foams used in both
commercial and residential settings, at concentrations up to 30% by weight (Darnerud et al., 2001; de Boer, 2000; Rahman et al.,
2001). Subsequent use and disposal of products containing these compounds has resulted in widespread environmental
contamination (Darnerud et al., 2001; de Boer, 2000; Rahman et al., 2001; Hites, 2004). Mounting bioaccumulatory and
toxicological concerns over these compounds have led to several recent usage bans and voluntary production stoppages in Europe
and North America (Renner, 2000; Pelley et al., 2003; Betts, 2001; Renner and Cooney, 2004; Christen and Petkewich, 2003).

O
Br

Br
∑Br=1–10

⁎ Corresponding author. Department of Civil Engineering Technology, Okanagan College, 1000 K.L.O. Road, Kelowna, British Columbia, Canada. Tel.: +1 250
7625445; fax: +1 250 8625430.
E-mail address: srayne@okanagan.bc.ca (S. Rayne).
0160-4120/$ - see front matter © 2006 Elsevier Ltd. All rights reserved.
doi:10.1016/j.envint.2006.01.009