title: Study of the transformation of two salicylates used in personal care products in chlorinated water.
abstract: Disinfection of swimming pool water is essential to inactivate pathogenic microorganisms. However chlorine based disinfectants, the most commonly used, are known to lead to the formation of disinfection by-products (DBPs), some of which have been associated with adverse health effects. Precursors of DBPs include the organic matter present in the water used to fill the swimming pool, human body fluids and personal care products (PCPs) used by swimmers and bathers. The increased use, in the last years, of PCPs lead to an increased concern about the fate of PCPs in swimming pool waters and potential health risks of formed DBPs. In this study, the chemical transformations of two salicylates, benzyl salicylate (BzS) and phenyl salicylate (PS), incorporated in several PCPs, in chlorinated water were investigated. High-performance liquid chromatography (HPLC) with UV-diode-array detection (HPLC-UV-DAD) was used to follow the reaction kinetics and HPLC with mass spectrometry (HPLC-MS) was used to tentatively identify the major transformation by-products. Under the experimental conditions used in this work both salicylates reacted with chlorine following pseudo-first order kinetics: rate constant k = (0.0038 ± 0.0002) min(-1) and half-life t1/2 = (182 ± 10) min for BzS and rate constant k = (0.0088 ± 0.0005) min(-1) and half-life t1/2 = (79 ± 4) min for PS (mean ± standard deviation). The reactions of the two salicylates in chlorinated water led to the formation of DBPs that were tentatively identified as mono- and dichloro- substituted compounds. Most probably they result from an electrophilic substitution of one or two hydrogen atoms in the phenolic ring of both salicylates by one or two chlorine atoms.
authors.affiliation: Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre s/n, P-4169-007 Porto, Portugal.
authors.forename: Mariana M
authors.initials: MM
authors.lastname: de Oliveira e Sá
authors.affiliation: Centro de Geologia da Universidade do Porto, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, s/n, P-4169-007 Porto, Portugal.
authors.forename: Margarida S
authors.initials: MS
authors.lastname: Miranda
authors.affiliation: Centro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre s/n, P-4169-007 Porto, Portugal. Electronic address: jcsilva@fc.up.pt.
authors.forename: Joaquim C G Esteves
authors.initials: JC
authors.lastname: da Silva
mesh_terms: D002713:Chlorine / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004202:Disinfectants / Q000737:chemistry*; D004203:Disinfection; D013058:Mass Spectrometry; D012459:Salicylates / Q000737:chemistry*; D013551:Swimming Pools; D014874:Water Pollutants, Chemical / Q000737:chemistry*; D014877:Water Pollution, Chemical
chemical_list: D004202:Disinfectants; D012459:Salicylates; D014874:Water Pollutants, Chemical; C026041:phenyl salicylate; D002713:Chlorine; C039672:benzyl salicylate
keywords: Benzyl salicylate; Disinfection by-products; Personal care products; Phenyl salicylate; Swimming pool