Environmental photochemistry of organic UV filter butyl methoxydibenzoylmethane: Implications for photochemical fate in surface waters.

ABSTRACT

With the widespread use of sunscreen and other personal care products, organic ultraviolet filters (OUVFs) have become widely detected in the aquatic environment. Direct and indirect photolysis are important transformation pathways of OUVFs in aquatic environments, so their transformation products (TPs) are also chemicals of concern. Butyl methoxydibenzoylmethane (BMDBM) is one of the most commonly used OUVFs worldwide due to its ability to absorb ultraviolet light across a wide range of wavelengths, and it is ubiquitously detected in aquatic environments. In this study, we investigated the photodegradation of BMDBM through direct photolysis and hydroxyl radical (•OH) photooxidation. TPs were identified using ultrahigh performance liquid chromatography-high resolution mass spectrometry, and reaction mechanisms were proposed. Our results showed that the photodegradation rates for both enol and keto tautomer forms of BMDBM during direct photolysis and •OH photooxidation were similar. The formation of TPs resulted from α-cleavage and decarbonylation reactions involving the keto form of BMDBM. Comparisons of the kinetic data and TPs revealed that the direct photolysis mechanism was a significant sink for BMDBM even during •OH photooxidation. Evaluations of environmental properties based on the predicted physicochemical properties of BMDBM and TPs suggests that some of the TPs will have higher mobility than BMDBM. The quantitative structure-activity relationship (QSAR) approach was used to evaluate the ecotoxicity of BMDBM and the identified TPs. Most TPs were found to be less ecotoxic than BMDBM; however, TPs that had a diphenyl ring structure could be more ecotoxic than BMDBM. Overall, this study provides new insights into the photochemical behavior and ecotoxicity of BMDBM and its TPs, which are important for assessing the fate, persistence, accumulation, and adverse impacts of these compounds in aquatic environments.