Introducing Sustainability into Industrial Homogeneous Catalysis
Woodham, Wesley H
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This thesis describes four projects focused on the implementation of green chemistry and engineering in an industrial context. The first project describes efforts to transition Meerwein-Ponndorf-Verley reduction technology from a batch-wise production framework to a continuous-flow framework. This work was done in the context of improving the synthesis of HIV-protease inhibitor intermediates. The second project describes a similar transfer of hydropyridoindole synthesis technology from batch processing to continuous-flow processing. In particular, a tandem synthetic pathway was developed for conducting cyclopropanation and ring-opening cyclization reactions in series. The third project describes the development of a novel catalyst separation process incorporating the use of sulfur-containing additives and Organic-Aqueous Tunable Solvents. Specifically, this process is demonstrated on palladium catalysts that have been employed in Suzuki coupling reaction mixtures. The fourth project describes the development of a recyclable catalytic system for use in Suzuki coupling reaction processes. The technology described incorporates the use of water-soluble ligands to generate hydrophilic palladium species that can be recovered via Organic-Aqueous Tunable Solvents and reintroduced as an active catalyst species.