Senior Project Advisor

Gregory O’Neil

Document Type

Project

Publication Date

Spring 2024

Keywords

DDT, TCPM, TCPM-OH, Environmental Persistence, tris(4-chlorophenyl) methane, tris(4-chlorophenyl)-methanol

Abstract

This study focuses on the synthesis of radiolabeled tris(4-chlorophenyl) methane (TCPM) and tris(4-chlorophenyl)-methanol (TCPM-OH), compounds identified as environmental contaminants linked to DDT production. Given their persistence and bioaccumulation in marine and terrestrial ecosystems, understanding their environmental fate is critical. This research aims to provide a detailed methodology for the synthesis of carbon-14 labeled TCPM and TCPM-OH to facilitate further studies on their degradation and impact. TCPM-OH was synthesized via two distinct routes. The first method involved esterification of 4-chlorobenzoic acid followed by a double Grignard addition. The second method started with chlorobenzene, which was brominated using gold-catalyzed N-bromosuccinimide (NBS), followed by a lithium-halogen exchange and addition to a ketone. Purification was achieved through silica gel flash column chromatography, and product purity was confirmed using Thin Layer Chromatography (TLC) and Nuclear Magnetic Resonance (NMR) spectroscopy. TCPM was synthesized by reducing TCPM-OH using triethyl silane and trifluoroacetic acid. The reduction process was optimized to achieve high yields and purity, verified through TLC and NMR. The synthesized compounds were characterized, showing distinct Rf values and NMR spectra consistent with the desired products. The results demonstrate effective synthesis pathways for radiolabeled TCPM and TCPM-OH, setting the stage for environmental fate studies. These compounds will be utilized in future research to investigate their degradation in marine sediments, particularly in the San Pedro Basin, where significant contamination has been reported. The synthesized radiolabeled compounds will enable precise tracking and analysis using advanced mass spectrometry techniques, contributing to a deeper understanding of their persistence and ecological impact. This work provides a foundation for subsequent studies on TCPM and TCPM-OH, aiding in the development of strategies to mitigate their environmental and health risks.

Department

Chemistry

Type

Text

Rights

Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this document for commercial purposes, or for financial gain, shall not be allowed without the author’s written permission.

Language

English

Format

application/pdf

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