Collaborative Industrial/Academic Research on Alternate Phosgene Chemistry for Environmentally Benign Chemical Synthesis and Processing

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Under the Grant Opportunities for Academic Liaisons with Industry (GOALI) initiative, the Organic Synthesis Program and the Office of Multidisciplinary Activities of the Directorate for Mathematical and Physical Sciences support the studies of Professor William Jones of the Department of Chemistry at the University of Rochester. Professor Jones, in collaboration with Eastman Kodak Company, develops environmentally more benign synthesis and processing chemistry for photographic chemicals production through the replacement of phosgene as an acyl source in the synthesis of thiocarbamate, urea, and isocyanate intermediates and through the replacement of acyl chlorides in amide syntheses. Replacement of phosgene with carbon monoxide is permitted by newly-discovered transition-metal based catalysts which activate carbon monoxide toward the sequential addition of nucleophiles, allowing the formation of thiocarbamates and related functional groups from simple and comparatively safe precursors. Mechanistic studies of the catalytic systems offer insights into improved catalyst design and will lead to the extension of the scope of the catalysis to permit the coupling of other hetero- and carbon-based nucleophiles. Phosgene is an essential reagent in the synthetic chemicals industry, but the hazards of this highly toxic gas to both human life and to the environment are significant. With support under the Grant Opportunities for Academic Liaisons with Industry (GOALI) initiative, Professor Jones explores the use of carbon monoxide as a comparatively safe substitute for phosgene. Although rather unreactive by itself, carbon monoxide may be enticed through the use of metal-containing catalysts to form the same products as are otherwise prepared from phosgene. These studies may lead to significant reductions in the use of phosgene in the large-scale production of photographic chemicals at Eastman Kodak Company, a coparticipant in this collaborative GOALI research program, and the long-range implications of the studies go well beyond the photographic chemicals arena. Students and postdoctoral scholars involved in the project will spend significant periods of time learning about and working on process development chemistry in Kodak's laboratories, thereby bringing this breadth of experience, not ordinarily encountered in the academic environment, back to the University of Rochester.