The need to produce chemicals and materials from renewable sources in an environmentally responsible manner motivates my research into the use of alternatives to petrochemical feedstocks. I want to extend my thesis work by synthesizing a large realistic model lignin oligomer. Use of dimeric model compounds such as benyl phenyl ether (α-O-4 model) or 2-phenoxy-1-phenylethanol (β-O-4 model) provides insight on the cleavage of particular linkages but does not properly account for the robustness or the complexity of lignin. My objective is to prepare a realistic lignin octamer that contains common types of ether linkages (α-O-4, β-O-4, β-5, and 5-5). I will test the hypothesis that due to the large, robust size of natural lignin (modeled by the synthesized lignin octamer) the ability to reach the active site in the pores of a catalyst is affected and thus the ability to depolymerize the lignin is hindered. Synthesis of this model oligomer will provide insight into the catalysis occurring at the ether linkage level and will be useful in determining the sequence of events occurring during depolymerization.
Advisor: Susannah Scott