Lignin is an aromatic biopolymer that represents a major component of non-edible biomass and could be a valuable feedstock for the production of organic chemicals. A current challenge is the selective, high-yielding conversion of lignin into useful small aromatics. We are pursuing oxidative methods toward this end. Our initial efforts have focused on dimeric model compounds with a �-O-4 linkage that features secondary benzylic and primary aliphatic alcohols resembling authentic samples of lignin. We have investigated diverse alcohol oxidation methods to establish whether selective oxidation of the primary aliphatic or the secondary benzylic alcohol in the model compoundcould be achieved. Oxidation reactions with traditional chemical oxidants show that TEMPO-based methods enable highly selective oxidation of this substrate. These results have led to the development of an efficient aerobic organocatalytic method, which has been demonstrated to oxidize selectively the secondary benzylic alcohol in up to 96% isolated yield. Efforts associated with the development of these methods and their application to selective lignin conversion will be presented.

Chemoselective aerobic oxidation methods for conversion of lignin to value-added aromatics

246th National Meeting (2013)

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