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Analysis and Characterization of Halogenated Transformation Products of Pharmaceuticals and Personal Care Products in Wastewater Effluent


Wastewater is a complex mixture of natural and anthropogenic pollutants including inorganic and organic species. The use of disinfection treatments such as chlorine is necessary to attenuate pollutants encountered in wastewater prior to its discharge into the environment. In recent years, the presence of pharmaceuticals and personal care products (PPCPs) in wastewater has received increasing attention due to the concern that these compounds may disrupt the normal endocrine function of aquatic biota. Less attention has been paid to the potential for PPCP transformation into new, chemically unique compounds via disinfection treatments. This dissertation focuses on the identification and quantification of halogenated pharmaceutical analogs in wastewater effluent generated by disinfection treatment with chlorine. The goal of this research is twofold: 1. Identify chlorination transformation products (TPs) of selected PPCPs, synthesize and purify standards (with and without deuterium labeling) for each unique TP and characterize the structure and purity of the TP standards; 2. Use these TP standards to develop targeted high performance liquid chromatography hyphenated to mass spectrometry (HPLC-MS) methods for the analysis of the selected PPCPs and their TPs and accurately quantify each analyte in solid phase extracts (SPE) of several wastewater effluents from Southern California.

This dissertation initially focuses on the chlorination TPs of the lipid regulator gemfibrozil and their occurrence in advanced primary wastewater effluent. Standards of gemfibrozil's TPs were synthesized, purified by HPLC and characterized by nuclear magnetic resonance (NMR) spectroscopy and accurate mass MS. This research is extended to identify and quantify the chlorination TPs of the analgesic salicylic acid, the non-steroidal anti-inflammatory (NSAID) diclofenac and the plasticizer bisphenol A in secondary wastewater effluent. Standards for TPs of the additional compounds were synthesized, isolated and characterized by the same methods as used for the gemfibrozil TPs. The dissertation culminates by expanding the selected PPCPs for secondary and tertiary wastewater analysis to include the surfactants octylphenol and nonylphenol, the NSAID naproxen, in addition to the synthesis of deuterated analogs of each PPCP and TP. Several of the identified TPs were quantified for the first time at ng/L levels in several of the analyzed wastewaters.

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