Monofluorinated analogues of polybrominated diphenyl ethers as analytical standards: Synthesis, NMR, and GC-MS characterization and molecular orbital studies

G. luthe, P.E.G. Leonards, G.S. Reijerink, H.L. Liu, J.E. Johansen, L.W. Robertson

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Abstract

Polybrominated diphenyl ethers (PBDEs), a group of 209 individual congeners distinguishable by the number and position of bromines, are produced for use as flame retardants in consumer goods. PBDEs have become ubiquitous environmental contaminants, present in increasing levels in the environment and humans. In the present study, 10 individual monofluorinated analogues of PBDEs (F-PBDEs) and one difluorinated PBDE (FF-PBDE) were synthesized and characterized, and their gas chromatographic (GC) and mass spectrometric (MS) characteristics determined. The synthesis method utilized a nucleophilic reaction of bromophenols with diphenyliodonium salts and the perbromination of fluorosubstituted diphenyl ethers. Reaction yields were between 10% and 59% with ≥98% purity. Apart from the aromatic ring carrying the fluorine atom, only minor chemical nuclear magnetic resonance (NMR) shift changes were observed in comparison to the corresponding parent PBDEs, with the exception that the J
Original languageEnglish
Pages (from-to)3023-3029
Number of pages7
JournalEnvironmental Science and Technology
Volume40
Issue number9
DOIs
Publication statusPublished - 2006

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