Synthesis and polymerization of bio-cyclic monomers in pursuit of viable alternatives to commodity plastics

Haley M. Donow, Gabriel N. Short, and Stephen A. Miller

University of Florida

As commodity plastics continue depletion of the earth’s finite reserves of fossil fuels, it becomes increasingly important to find sustainable alternatives. Bio-cyclic monomers were synthesized in large yields from various biorenewable sources, including vanillin, urea, citric acid, and a variety of amino acids. Cyclization during monomer synthesis serves to increase the glass transition temperature and subsequently the application range of nascent polymers. One particularly useful mechanism for monomer cyclization is the Biginelli one-pot, multicomponent synthesis of aryl aldehydes such as vanillin with β-ketoesters and urea. The 3,4-dihydropyrimidin-2(1H)-one (DHMP) product can be polymerized with expectations of high thermal properties. Initial optimization parameters for the polymerization of this and certain other bio-cyclic monomers will be explored. To address the intractability of such polymers, alkyl chains will be incorporated during post-polymerization modification.