Woodham, Wesley H ; Liotta, Charles Chemical and Biomolecular Engineering Meredith, Carson Sievers, Carsten Walton, Krista Fisk, Jason ; Liotta, Charles
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.
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Introducing Sustainability into Industrial Homogeneous Catalysis