Factors affecting photooxidation of oil constituents in the marine environment. I. Photochemical transformations of dimethylnaphthalenes in an aqueous environment in the presence and absence of oil

Photooxidation studies of 1,3-, 1,4-, 1,8- and 2,3-dimethylnaphthalene (DMN) suspended in and layered on seawater and distilled water have been performed in the presence and absence of crude Ekofisk oil, methylene blue and dibenzothiophene. With the exception of 2,3-DMN which was very insensitive to the reaction conditions, the course of reaction was, generally, influenced by the structure of the substrate, the salinity of the water, the oil and the presence of sulfur-containing compounds. In the absence of oil the photooxidation was fairly inefficient and took place exclusively in benzylic positions. In the presence of oil oxidation of the naphthalene moiety predominated due to abundant formation of singlet oxygen.