Jacob Votava

Polyurethanes are versatile materials with industrially relevant mechanical and physical properties. Their applications range from everyday wood-coatings to insulation foams, to the paints on commercial airliners. Currently, industrial polyurethanes are synthesized from the polyaddition of isocyanates and polyols. Isocyanates are not only toxic by nature, but are also derivatives of phosgene, which is significantly more deadly. For this reason, a green synthesis of non-isocyanate polyurethanes (NIPUs) is of interest to chemists. One recent advance in the NIPU field is the anionic ring opening polymerization of bicyclic oxazolidinones, but the vinyl-cyclohexene-based monomers are sourced from fossil fuels and phosgene derivatives. This work aims to synthesize oxazolidinone monomers with the goal of making a NIPU from biologically sourced feedstocks and using carbon dioxide as an abundant, cheap, non-toxic reagent. Our proposed synthetic route involves epoxidizing common monoterpenes (e.g., limonene), ring opening the epoxide with ammonia to form a trans-amino alcohol, and finally ring closing the resulting amino alcohol with carbon dioxide to form the oxazolidinone. Optimization of the synthetic route, challenges, and future directions will be discussed in this presentation. Continued work will need to be done in order to further optimize the synthesis of the oxazolidinone monomer, as well as to characterize it rigorously. However, the results of this project represent an encouraging first step towards the synthesis of the proposed bio-based NIPU-monomers.