Degradation of UV filters 2-ethylhexyl-4-methoxycinnamate and 4-tert-butyl-4′-methoxydibenzoylmethane in chlorinated water
A. Joel M. Santos A , Diana M. A. Crista A , Margarida S. Miranda B , Isabel F. Almeida C , José P. Sousa e Silva C , Paulo C. Costa C , Maria H. Amaral C , Paulo A. L. Lobão C , José M. Sousa Lobo C and Joaquim C. G. Esteves da Silva A D
+ Author Affiliations
- Author Affiliations
A Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre s/n, PT-4169-007 Porto, Portugal.
B Centro de Geologia da Universidade do Porto, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, s/n, PT-4169-007 Porto, Portugal.
C Centro de Investigação em Ciências Farmacêuticas, Laboratório de Tecnologia Farmacêutica, Departamento de Ciências do Medicamento, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, PT-4050-313 Porto, Portugal.
D Corresponding author. E-mail: jcsilva@fc.up.pt
Environmental Chemistry 10(2) 127-134 https://doi.org/10.1071/EN13012
Submitted: 22 January 2013 Accepted: 9 April 2013 Published: 9 May 2013
Environmental context. The increasing use of sun-creams containing UV-filtering chemicals has led to increased inputs of these compounds to the aquatic environment. Chlorinated waters can convert these chemicals into chlorinated products whose toxic effects are of primary concern. To better understand the environmental fate of sun-cream chemicals, we studied the stability of two UV-filtering compounds under varying conditions of pH, chlorine concentration, temperature, dissolved organic matter and solar irradiation.
Abstract. The stability of the UV filters 2-ethylhexyl-4-methoxycinnamate (EHMC) and 4-tert-butyl-4′-methoxydibenzoylmethane (BDM) in chlorinated water was studied. High-performance liquid chromatography (HPLC)-UV-diode array detection (DAD) was used to follow the reaction kinetics of both UV filters and HPLC-tandem mass spectrometry (MS/MS) was used to tentatively identify the major transformation by-products. Under the experimental conditions used in this work both UV filters reacted with chlorine following pseudo-first order kinetics: rate constant k = 0.0095 ± 0.0007 min–1 and half-life t1/2 = 73 ± 4 min for EHMC and rate constant k = 0.006 ± 0.001 min–1 and half-life t1/2 = 119 ± 14 min for BDM (mean ± standard deviation). The chemical transformation of the UV filters in chlorinated water led to the formation of chlorinated by-products that were tentatively identified as mono- and dichloro-substituted compounds that resulted from substitution of the hydrogen atoms in the benzene rings by one or two chlorine atoms. Experimental Box–Behnken designs were used to assess the effect of experimental factors: pH, temperature, chlorine concentration, dissolved organic matter and artificial sunlight irradiation on the transformation of the UV filters.
Additional keywords: chlorinated by-products, chlorination reactions.
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