Author： McConkey B.J. Hewitt L.M. Dixon D.G. Greenberg B.M.
Publisher： Springer Publishing Company
ISSN： 0049-6979
Source： Water, Air, and Soil Pollution, Vol.136, Iss.1-4, 2002-05, pp. : 347-359
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Abstract
There is surprisingly little data on the photooxidation of polycyclic aromatic hydrocarbons (PAHs) under environmentally relevant lighting conditions. The aqueous photooxidation reactions of naphthalene (the simplest and most water soluble PAH) were investigated using natural sunlight as a light source. Six of the major reaction products were identified, including 1-naphthol, coumarin, and two hydroxyquinones. The reaction products were consistent with initial [2,2] or [2,4] photocycloaddition reactions, with subsequent oxidations and/or rearrangements. The oxidation reactions in aqueous phase favored products different from those observed in atmospheric oxidation reactions. However, similar photoproducts were observed with titanium catalysts or in the presence of hydrogen peroxide. The products from aqueous photooxidation were also similar to the products resulting from naphthalene metabolism. The observed photooxidation products were generated by mechanisms that are expected to occur with other PAHs as well, and thus naphthalene oxidation provides a model for possible photoreactions of larger PAHs.
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