(Georgia Institute of Technology, 2008)
Nolan, Michael R.
MeMBL (α-methylene-γ-methyl-γ-butyrolactone) is a biomass-derived compound known to be polymerizable to make an acrylic material with a high glass transition temperature. Presence of a lactone ring in the structure of MeMBL can be opened to create a pathway to modification of a MeMBL polymer. This would expand the range of uses for poly(MeMBL) as a plastic. A polymer composed of pure MeMBL and a polymer composed of MeMBL and styrene (the main component of Styrofoam) were prepared, and subjected to reactions with sodium hydroxide in alcohols, water, or dimethyl sulfoxide (DMSO). Evidence of ring-opening was determined either by observation of a change in the polymer’s solubility or by NMR analysis. Both the pure MeMBL polymer and MeMBL/styrene copolymer showed evidence of ring-opening when exposed to sodium hydroxide in water, while no reaction was observed with the same treatment in alcohols. The poly(MeMBL) ring was observed to close over time. Ring-opening was found to be achievable, but ring-opening with hydroxide was found to be an ineffective pathway to further work on the opened ring.