Early work by Lessard et al. and from our own labs demonstrated electrocatalytic cleavage of aryl-O bonds in alkoxyphenols. Electrocatalytic hydrogenation over Raney® Nickel electrodes converts G type and S type lignin monomers to cyclohexanol under mild, aqueous conditions within 6 hrs. However, to effectively depolymerize lignin, an efficient general tool to cleave its various linkages is needed. In this work, fragmentation of β-O-4 and 4-O-5 type dimers will be shown, along with observations of the various cleavage patterns. During the mapping of the lignin dimer substrate scope, novel ether bond cleavage paths were uncovered, prompting a study to explore C-O cleavage of several simple ethers over this heterogenous metal surface. This talk will present the ether bond cleavage results of various lignin-related aromatic ethers, analyzing the sometimes paradoxical breakdown patterns of ether C-O bonds and the effects of substituents on their selectivity.

Electrocatalytic hydrogenation of lignin dimers & derivatives: Towards selectivity of C-O cleavage over Raney® nickel surface

2019 Spring National Meeting

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