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Quantitative structure-Photodegradation relationships of polybrominated diphenyl ethers, phenoxyphenols and selected organochlorines
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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2009 (English)In: Chemosphere, ISSN 0045-6535, E-ISSN 1879-1298, Vol. 77, no 7, 914-921 p.Article in journal (Refereed) Published
Abstract [en]

Among other developments, the technological revolution has lead to introduction of new chemicals to better serve in instruments and materials. The consequences of the extensive increase in use of new chemicals can be detected in the environment world wide, i.e. in wildlife and humans. To ensure this problem to be minimised in the future, new chemicals need to be subjected to predictive assessments before commercialised. To facilitate screening, qualitative structure-activity relationships, quantitative structure-activity relationships may be applied to describe reactivity of chemicals. Physico-chemical properties of chemicals such as partition coefficients and half-lives for the various environmental compartments are essential input data in multimedia environmental fate models. In this study we examine how structural characteristics can quantitatively describe laboratory determined photolytic half-lives of halogenated compounds of different classes, such as polybrominated diphenyl ethers (PBDEs), hydroxylated brominated diphenyl ethers (OH-PBDEs), and other organohalogens. A total of 30 chemicals with experimentally measured half-lives are used. Results reveal that the most important descriptors for describing the half-lives of the brominated compounds are the energy gap (GAP-1) between HOMO-1 and LUMO, the lowest partial charge on a halogen atom (Qhal-), topological polar surface area (TPSA), the atom with highest radical superdelocalizability (Rad-super+) and LUMO density (LUMO+).

Place, publisher, year, edition, pages
2009. Vol. 77, no 7, 914-921 p.
Keyword [en]
QSAR, QSPR, OH-PBDEs, PBDEs, Photodegradation, Water-methanol
National Category
Chemical Sciences
Research subject
Environmental Chemistry
Identifiers
URN: urn:nbn:se:su:diva-26058DOI: 10.1016/j.chemosphere.2009.08.037ISI: 000271992200006OAI: oai:DiVA.org:su-26058DiVA: diva2:202282
Available from: 2009-03-09 Created: 2009-03-09 Last updated: 2017-12-13Bibliographically approved
In thesis
1. Comparison of experimentally and theoretically determined oxidation and photochemical transformation rates of some organohalogens to promote prediction of persistence
Open this publication in new window or tab >>Comparison of experimentally and theoretically determined oxidation and photochemical transformation rates of some organohalogens to promote prediction of persistence
2009 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The diversity of choices we have to make everyday influence our environment and ourselves in more ways than most of us realise. Anthropogenic substances, such as flame retardants, date back as early as 450 BC when the Egyptians used alum to reduce flammability. The increasing demand for new articles has led to an increased production of chemical substances, for which many are commercially produced without complete knowledge on properties such as persistence, bioaccumulation and toxicology (PBT). Commercial compounds may be properly tested and denominated as “safe” regarding PBT properties, but their degradation products and/or metabolites may cause environmental impact.

The availability of uniform and accurate data for prediction of persistence is of key importance for the understanding of chemical fate. A method to determine the susceptibility of chemicals to undergo oxidation in water has been developed and applied on several organohalogens, including PBDEs and OH-PBDEs. The method was used to determine reaction rates and the group of OH-PBDEs were subsequently subjected to photolysis by use of UV-light. Hence, susceptibility to undergo both oxidation and photolysis for the OH-PBDEs were investigated and compared to previously reported degradation rates on PBDEs.

As a final step in promoting the prediction of persistence, Quantitative structure-property relationship (QSPR) models were performed on a set of compounds which had undergone photolytic degradation under similar conditions. The QSPRs were used as a preliminary step in predicting photolysis half-lives for chemical substances and to determine which physicochemical descriptors are of greatest importance thereof.

This thesis presents the possibility of performing and assessing oxidation transformations on compounds of low and high water solubility, photolysis transformations in various media and using obtained data to predict behaviour via QSPR models, to promote predictions of persistence.

Place, publisher, year, edition, pages
Stockholm: Department of Environmental Chemistry, Stockholm University, 2009. 68 p.
Keyword
Oxidation, Persistence, Photolysis, QSPR, BFRs, PBDEs, OH-PBDEs
National Category
Other Basic Medicine
Research subject
Environmental Chemistry
Identifiers
urn:nbn:se:su:diva-26040 (URN)978-91-7155-753-7 (ISBN)
Public defence
2009-04-17, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00 (English)
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Available from: 2009-03-26 Created: 2009-03-06 Last updated: 2009-05-07Bibliographically approved

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