Oxidative Transformation of Antimicrobial Compounds by Ferric-Modified Montmorillonite

Abstract

The presence of wide spectrum antimicrobial agents triclosan (TCS) and triclocarban (TCC) in the environment has become a concern due to the adverse impact on the environment. Montmorillonite, a widely distributed clay mineral in the natural environment, has been used as an obstacle in landfills to avoid contamination of soil and water by contaminants in leachates due to its high surface area, cation exchange capacity, and abundance. The research reported here focuses on understanding the abiotic oxidative transformation of TCS and TCC by Fe(III)-modified montmorillonite. The overall objectives of this work were: 1) to investigate TCS and TCC oxidative transformation kinetics and transformation products in different environmental conditions, and 2) to elucidate their reaction pathways. TCS was reacted with Fe(III)-modified montmorillonite under the following experimental conditions: 1) at 40% relative humidity and room temperature for up to 100 d with and without UV light exposure; and 2) in aqueous environment with different initial TCS concentrations, light exposure, pH levels, and in the presence of natural organic matters. Reaction in the presence of Na- montmorillonite was conducted for comparison with results from TCS reaction in the presence of Fe(III)-modified montmorillonite. In addition, transformation of TCS in the presence of other types of minerals was also investigated. Transformation of TCC on Fe(III) and Na-montmorillonite in an aqueous environment with and without exposure to light was also studied at different initial TCC concentrations. TCS and TCC transformation products were a) characterized using LC/MS, GC/MS, and computational modeling, and b) quantified using HPLC/UV and GC/MS. The main TCS transformation products were 2,4-dichlorophenol, 2,4-dichlorophenol dimer, chlorophenoxy phenols and, TCS dimers and trimers. 2,8-dichlorodibenzo-p-dioxin was identified under UV light and the sun simulator experiments. Formation of 4-chloroaniline and 3,4-dichloroaniline were confirmed as transformation products of TCC. To the best of our knowledge, this is the first time that 4-chloroaniline and 3,4-dichloroaniline were confirmed as abiotic transformation of TCC. This research has generated a better understanding of the abiotic environmental fate of TCS and TCC and demonstrates the feasibility of utilizing Fe(III)-modified montmorillonite as remediation material for TCS, TCC and other related pharmaceutical and personal care products (PPCPs)

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