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Center for Direct Catalytic Conversion of Biomass to Biofuels

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Center for Direct Catalytic Conversion of Biomass to Biofuels

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  1. Lignin comprises as much as 25% of terrestrial biomass, but remains one of the most underused carbon sources in the biosphere.1 The main obstacle in utilizing lignin is its irregular, heterogeneous structure, and thus, developing processes that convert it into a single material in high yield would greatly increase its value and utility within the biorefinery. Models of G subunits: Proposed mechanism UV/Vis reveals that the sterically hindered base does not coordinate to the catalyst. We envision deprotonation of the phenol substrate: Common monolignols in lignin When using these oxidizing conditions on lignin itself we observe formation ofquinones among other unidentified products.2 We seek to convert lignin into a high-value material, p-quinones, which are: • Essential structural blocks for dyes and antibiotics and many have shown biological, pharmacological and antitumor activity. • Molecules that can be functionalized in order to synthesize complex natural products. • Due to their unique proton and electron transfer abilities, they form part of the respiration process of almost all living organisms. Our approach is to focus on the single unifying structural feature of lignin - its network of aromatic rings - and examine a processes that can cause selective oxidation of this aromatic network in models of S and G subunits and in lignin itself. Impact: We have successfully oxidized models of the S and G subunits in lignin in the presence a variety of axial ligands and hindered bases. In addition, we used these oxidizing conditions in lignin itself. This is a starting point for the conversion of lignin into a single material. Current work is expanding the range of metal catalysts and investigating the mechanism through EPR studies. Models of S subunits Oxidized in the presence of a pyridine or imidazole coordinating base. Models of G subunits More difficult to oxidize1 but yields are improved in the presence of a non-coordinating base. Metal Catalyzed Oxidation of Biorefinery Lignin Diana Cedeno, Joseph J. Bozell University of Tennessee Center for Direct Catalytic Conversion of Biomass to Biofuels • References and Notes • Bozell, J. J.; Hames, B. R. J. Org. Chem.1995, 60, 2398. • 2. Superimposed 2D HMQC spectra before (red) and after (gray) oxidation. Isolated lignin was reacted in the presence of methanol, 10% cobalt catalyst, O2 (60psi), 24 hrs. The Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio) is an Energy Frontier Research Center funded by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award Number DE-SC0000997.

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