Sustainable Synthesis of BTX-Derived Chemicals

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In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor John W. Frost of the Department of Chemistry at Michigan State University will interface microbial catalysis with chemical catalysis to convert renewable, nontoxic sugar starting materials into chemicals currently derived from the benzene-toluene-xylene (BTX) stream of petroleum and gas refining. Dienes will be microbe synthesized and chemically reacted with dienophiles to yield cycloaddition products designed to provide access to a new generation of monomers and plasticizers where all carbon atoms are derived from renewable sugars. Catalytic dehydrogenation of the cycloaddition products is to afford substituted terephthalates. Other cycloaddition products will provide access to substituted cyclohexene tricarboxylates and cyclohexane tricarboxylates. Substituted terephthalic acids can impart unique properties when employed as additives or monomers in liquid crystalline polymers used in electronic and medical applications as well as in polyethyleneterephthalate used in clothing fiber and bottle resin. The novel properties that substituted terephthalates impart to engineering and consumer polymers could open new applications and new markets thereby providing an important economic multiplier along with job creation. Similarly, the wide array of ring-substituted cyclohexene and cyclohexane tricarboxylates are targeted towards nonaromatic plasticizer markets. By interfacing microbial synthesis with chemical synthesis, a level of structural diversity is accessed that may ultimately enable the identification of new high-performance plasticizers that do not bind to estrogen receptors. The attendant health safety and environmental benefits would be considerable. Finally, this research program will provide a unique training opportunity for pre-undergraduate, undergraduate, graduate and post-doctoral students, including those from groups historically underrepresented in the sciences.