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Novel Octabrominated Phenolic Diphenyl Ether Identified in Blue Mussels from the Swedish West Coast
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
Stockholm University, Faculty of Science, Department of Applied Environmental Science (ITM).
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
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2014 (English)In: Environmental Science and Technology, ISSN 0013-936X, E-ISSN 1520-5851, Vol. 48, no 6, 3319-3326 p.Article in journal (Refereed) Published
Abstract [en]

Hydroxylated (OH−) and methoxylated (MeO−) polybrominated diphenyl ethers (PBDEs) are compounds present in the marine environment and OH–PBDEs are of toxicological concern and are therefore of interest to monitor in the environment. A phenolic octaBDE was tentatively identified in the phenolic fraction of previously analyzed mussel samples after methylation of the halogenated phenolic compounds (HPCs). The aim of the present study was to confirm the identity of this compound in blue mussels and investigate whether the analyte is diOH– and/or OH–MeO–octaBDE. Two reference standards, 6,6′-dimethoxy-2,2′,3,3′,4,4′,5,5′-octabromodiphenyl ether (6,6′-diMeO–BDE194) and 6-ethoxy-6′-methoxy-2,2′,3,3′,4,4′,5,5′-octabromodiphenyl ether (6-EtO-6′-MeO–BDE194) were prepared via O-arylation of 2,3,4,5-tetrabromo-6-methoxyphenol and 2,3,4,5-tetrabromo-6-ethoxyphenol, respectively, with a novel unsymmetrical diaryliodonium salt, 2,3,4,5-tetrabromo-6-methoxydiphenyliodonium triflate. The GC retention time and GC/MS spectrum of the synthesized 6,6′-diMeO–BDE194 correspond well with the analyte in the methylated phenolic fraction of a mussel extract from a previous study. Structural analysis performed in this study indicate that the synthesized 6,6′-diMeO–BDE194 and 6-EtO-6′-MeO–BDE194 correspond well with 6-hydroxy-6′-methoxy-2,2′,3,3′,4,4′,5,5′-octabromodiphenyl ether (6-OH–6′-MeO–BDE194) after methylation and ethylation, respectively, of the HPCs in the mussel extracts. The compound 6-OH–6′-MeO–BDE194 was identified and quantified in new mussels, sampled in 2012 from two locations on the Swedish west coast, with geometric mean concentrations of 3700 and 410 ng/g fat, respectively.

Place, publisher, year, edition, pages
2014. Vol. 48, no 6, 3319-3326 p.
National Category
Analytical Chemistry Organic Chemistry Environmental Sciences
Research subject
Environmental Chemistry
Identifiers
URN: urn:nbn:se:su:diva-95828DOI: 10.1021/es404969eISI: 000333776000029OAI: oai:DiVA.org:su-95828DiVA: diva2:662617
Funder
Swedish Research Council Formas, 2009-1309Swedish Research Council Formas, 2009-2116Swedish Research Council Formas, 2012-2116
Available from: 2013-11-07 Created: 2013-11-04 Last updated: 2017-12-06Bibliographically approved
In thesis
1. Synthesis of organobromines as a tool for their characterisation and environmental occurrence assessment
Open this publication in new window or tab >>Synthesis of organobromines as a tool for their characterisation and environmental occurrence assessment
2013 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Polybrominated diphenyl ethers (PBDEs) have been intensively used as flame retardants (FRs) and have become ubiquitous environmental pollutants. PBDEs form hydroxylated PBDEs (OH-PBDEs) as metabolites. Further, some OH-PBDEs and methoxy-PBDEs (MeO-PBDEs) are natural products. These are all compounds of environmental and health concern and it is therefore important to confirm their identity and to assess their environmental levels and toxicities. Hence, it is vital to obtain authentic reference standards of individual PBDEs and OH/MeO-PBDEs. The thesis main aim was to develop synthesis methods of congener specific PBDEs, OH- and MeO-PBDEs. The second aim was to identify and quantify PBDEs, OH- and MeO-PBDEs in environmental samples. The third was to propose an abbreviation system for FRs.

O-Arylation of brominated phenols, using either symmetrical or unsymmetrical brominated diphenyliodonium salts, was selected for synthesis of PBDEs and OH-/MeO-PBDEs. A total of 16 MeO-PBDEs, 11 OH-PBDEs, 1 diMeO-PBDE and 1 EtO-MeO-PBDE were synthesised. Three novel unsymmetrical diaryliodonium triflates were synthesised and used in synthesis. Optimisations were made to construct a reliable general method for congener specific PBDE synthesis, which was used in the synthesis of 8 representative PBDE congeners. The products were generally characterised by electron ionisation mass spectrometry (EIMS) and nuclear magnetic resonance (NMR) spectroscopy.

Identification of PBDEs and OH-PBDEs in various matrixes was based on gas chromatographic and mass spectrometric analyses. Fourteen OH-PBDE congeners were identified in a pooled human blood sample. One previously uncharacterised natural PBDE analogue was identified as 6-OH-6’-MeO-BDE-194, and quantified in Swedish blue mussels. PBDE congeners and other BFRs were identified and quantified in workers and dust from a smelter in Sweden.

A structured and practical abbreviation system was developed for halogen- and phosphorus containing FRs.

Place, publisher, year, edition, pages
Stockholm: Department of Materials and Environmental Chemistry (MMK), Stockholm University, 2013. 85 p.
Keyword
Polybrominated diphenyl ethers, Brominated diphenyliodoniums salts, PBDEs, OH-PBDEs, MeO-PBDEs, Synthesis, Analysis, Abbreviations, Metabolites, Marine natural products, E-waste, Brominated flameretardants
National Category
Other Chemistry Topics
Research subject
Environmental Chemistry
Identifiers
urn:nbn:se:su:diva-95649 (URN)978-91-7447-800-6 (ISBN)
Public defence
2013-12-12, Stora hörsalen, Naturhistoriska riksmuseet, Frescativägen 40, Stockholm, 10:00 (English)
Opponent
Supervisors
Funder
Formas, 2009-1297Formas, 2009-1309Formas, 2009-1303
Note

At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 2: Manuscript. Paper 3: Submitted. Paper 4: Manuscript.

Available from: 2013-11-20 Created: 2013-10-31 Last updated: 2013-11-08Bibliographically approved

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Winnberg, UlrikaRydén, AndreasLöfstrand, KarinAsplund, Lillemor
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