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Photochemical transformations of tetrabromobisphenol A and related phenols in water
Stockholm University, Faculty of Science, Department of Environmental Chemistry.
Stockholm University, Stockholm Resilience Centre, Interdisciplinary Environmental Research (CTM). Stockholm University, Faculty of Science, Department of Environmental Chemistry.
Stockholm University, Faculty of Science, Department of Environmental Chemistry.
Stockholm University, Faculty of Science, Department of Environmental Chemistry.
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2004 (English)In: Chemosphere, ISSN 0045-6535, Vol. 54, no 1, 117-126 p.Article in journal (Refereed) Published
Abstract [en]

romobisphenolA (TBBPA), tribromobisphenol A (TriBBPA), tetrachlorobisphenol A (TCBPA), 2,4-dichlorophenolat various pHs as well as 2-chlorophenol, 2-bromophenol, 3,4-dichlorophenol and bisphenol A at pH 11. The absorbancespectra of the compounds and the emission spectra of the light-source were determined and used to calculatedisappearance quantum yields of the photochemical reactions that were taking place. No major differences between thedisappearance quantum yields of TBBPA and TCBPA were observed at pH 10, while the disappearance quantum yieldof TriBBPA was approximately two times higher. The rate of decomposition of TBBPA was six times higher at pH 8than at pH 6. Identification of the degradation products of TBBPA and TriBBPA, by GC–MS analysis and bycomparison to synthesised reference compounds, indicated that TBBPA and TriBBPA decompose via differentmechanisms. Three isopropylphenol derivatives; 4-isopropyl-2,6-dibromophenol, 4-isopropylene-2,6-dibromophenoland 4-(2-hydroxyisopropyl)-2,6-dibromophenol, were identified as major degradation products of TBBPA while themajor degradation product of TriBBPA was tentatively identified as 2-(2,4-cyclopentadienyl)-2-(3,5-dibromo-4-hydroxyphenyl)propane.

Place, publisher, year, edition, pages
Elsevier , 2004. Vol. 54, no 1, 117-126 p.
Keyword [en]
Tetrabromobisphenol A; Brominated flame retardants; Reactivity; Photodegradation
National Category
Environmental Sciences
Identifiers
URN: urn:nbn:se:su:diva-23144DOI: 10.1016/S0045-6535(03)00704-5OAI: oai:DiVA.org:su-23144DiVA: diva2:190395
Note
Part of urn:nbn:se:su:diva-167Available from: 2004-05-13 Created: 2004-05-13 Last updated: 2009-12-21Bibliographically approved
In thesis
1. Polybrominated diphenyl ethers and Tetrabromobisphenol A: Chemical synthesis, X-ray crystallography and Photochemical degradation
Open this publication in new window or tab >>Polybrominated diphenyl ethers and Tetrabromobisphenol A: Chemical synthesis, X-ray crystallography and Photochemical degradation
2004 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

In the 1960s’ several manmade chemicals were detected in the environment, far from their sources. The most well known, and most likely those with the largest impact on the society, were DDT and its related compounds, and PCBs. These anthropogenic compounds were characterised as persistent organic pollutants (POPs). Following these POPs, several other chemicals have found their way to the environment. Over the last two decades, brominated flame retardants (BFRs) have become a matter of concern. Among all BFRs being commercially produced, tetrabromobisphenol A (TBBPA) and polybrominated diphenyl ethers (PBDEs) are the ones with the largest annual production. TBBPA is a very well defined compound while PBDEs consist of a large number of isomers and homologues (congeners). TBBPA does not seem to accumulate in biota as the PBDEs do, but is still of concern since it is found in e.g. sediments. The PBDEs can reach accumulation levels up in the ppm range. Still there is a lack of basic data for both TBBPA and PBDEs. Hence the present thesis is aimed to fill some of the data gaps by pursuing work on 1) photochemical degradation of TBBPA, some related compounds, and PBDEs; 2) synthesis of PBDE congeners and of TBBPA degradation products and 3) structural identifications of a selected set of BFRs by X-ray crystallography.

An apparatus was designed for carrying out photochemical degradation test of chemicals in general but in particular for BFRs. Quantum yield, rate of degradation and to some extent, identification of degradation products were performed on TBBPA, the corresponding chlorinated compound and a number of TBBPA degradation products and on 15 single PBDE congeners. In order to make this work possible all three nonaBDE isomers were synthesised via a reductive pathway applying sodium borohydride as a reducing agent. The three nona-BDEs were all characterised by X-ray crystallography.

The results of the photochemical degradation of TBBPA in water show a rapidly degradable compound also at pH’s that are environmentally relevant. Hence it is likely that TBBPA is not transported long distances, when exposed to sunlight, without undergoing photochemical degradation. It is notable that the TBBPA is degraded through cleavage between the two phenol rings. When the method was applied to study quantum yields and rate constants for the reaction of PBDE congeners it is evident that the decabromodiphenyl ether (BDE-209) is rapidly transformed. The reaction rate differ drastically from PBDEs with four or five bromine substituents that have very long half-lives when subjected to UV-light under the same conditions as for BDE-209. Lower brominated diphenyl ethers and polybrominated dibenzofurans were identified as PBDE degradation products. The synthesis of PBDEs and of TBBPA degradation products expanded the study as did the X-ray structure identifications.

Place, publisher, year, edition, pages
Stockholm: Institutionen för miljökemi, 2004. 96 p.
National Category
Environmental Sciences
Identifiers
urn:nbn:se:su:diva-167 (URN)91-7265-878-9 (ISBN)
Public defence
2004-06-04, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00
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Available from: 2004-05-13 Created: 2004-05-13Bibliographically approved

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