Advanced model compounds for understanding acid catalyzed lignin depolymerization: identification of renewable aromatics and a lignin-derived solvent
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The development of fundamentally new approaches for lignin depolymerization is challenged by the complexity of this aromatic biopolymer. While overly simplified model compounds often lack relevance to the chemistry of lignin, the direct use of lignin streams poses significant analytical challenges to methodology development. Ideally, new methods should be tested on model compounds that are complex enough to mirror the structural diversity in lignin but still of sufficiently low molecular weight to enable facile analysis. In this contribution, we present a new class of advanced (β-O-4)-(β-5) dilinkage models that are highly realistic representations of a lignin fragment. Together with selected β-O-4, β-5, and β–β structures, these compounds provide a detailed understanding of the reactivity of various types of lignin linkages in acid catalysis in conjunction with stabilization of reactive intermediates using ethylene glycol. The use of these new models has allowed for identification of novel reaction pathways and intermediates and led to the characterization of new dimeric products in subsequent lignin depolymerization studies. The excellent correlation between model and lignin experiments highlights the relevance of this new class of model compounds for broader use in catalysis studies. Only by understanding the reactivity of the linkages in lignin at this level of detail can fully optimized lignin depolymerization strategies be developed.
Lahive , C , Deuss , P J , Lancefield , C S , Sun , Z , Cordes , D B , Young , C M , Tran , F , Slawin , A M Z , de Vries , J G , Kamer , P C J , Westwood , N J & Barta , K 2016 , ' Advanced model compounds for understanding acid catalyzed lignin depolymerization: identification of renewable aromatics and a lignin-derived solvent ' Journal of the American Chemical Society , vol 138 , no. 28 , pp. 8900-8911 . DOI: 10.1021/jacs.6b04144
Journal of the American Chemical Society
Copyright © 2016 American Chemical Society. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1021/jacs.6b04144
This work was funded by the EP/J018139/1, EP/K00445X/1 grants (NJW and PCJK), an EPSRC Doctoral Prize Fellowship (CSL), and the European Union (Marie Curie ITN ‘SuBiCat’ PITN-GA-2013-607044, CWL, NJW, PCJK, PJD, KB, JdeV).
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