Metal triflates for the production of aromatics from lignin
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The depolymerization of lignin into valuable aromatic chemicals is one of the key goals towards establishing economically viable biorefineries. In this contribution we present a simple approach for converting lignin to aromatic monomers in high yields, under mild reaction conditions. The methodology relies on the use of catalytic amounts of easy to handle metal triflates (M(OTf)x). Initially, we evaluated the reactivity of a broad range of metal triflates using simple lignin model compounds. More advanced lignin model compounds were also used to study the reactivity of different lignin linkages. The product aromatic monomers were either phenolic C2-acetals obtained by stabilization of the aldehyde cleavage products by reaction with ethylene glycol, or methyl aromatics obtained by catalytic decarbonylation. Notably, when the former method was ultimately tested on lignin, especially Fe(OTf)3 proved very effective and the phenolic C2-acetal products were obtained in an excellent, 19.3±3.2 wt % yield.
Deuss , P J , Lahive , C , Lancefield , C S , Westwood , N J , Kamer , P C J , Barta , K & de Vries , J G 2016 , ' Metal triflates for the production of aromatics from lignin ' CHEMSUSCHEM , vol. 9 , no. 20 , pp. 2974-2981 . DOI: 10.1002/cssc.201600831
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 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/10.1002/cssc.201600831
DescriptionThis work was funded by the European Union (Marie Curie ITN ‘SuBiCat’ PITN-GA-2013-607044, PJD, CWL, NJW, PCKL, KB, JGdeV) as well as EP/J018139/1, EP/K00445X/1 grants (NJW and PCJK) and an EPSRC Doctoral Prize Fellowship (CSL).
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