Journal
CHEMSUSCHEM
Volume 9, Issue 16, Pages 2074-2079Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cssc.201600683
Keywords
biomass; decarbonylation; lewis acid; lignin; tandem catalysis
Funding
- Netherlands Organization for Scientific Research (NWO)
- CatchBio program
- EPSRC [EP/J018139/1, EP/K00445X/1]
- SuBiCat Initial Training Network [607044]
- EPSRC [EP/J018139/1, EP/K00445X/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K00445X/1, EP/J018139/1] Funding Source: researchfish
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Lignin is an attractive renewable feedstock for aromatic bulk and fine chemicals production, provided that suitable depolymerization procedures are developed. Here, we describe a tandem catalysis strategy for ether linkage cleavage within lignin, involving ether hydrolysis by water-tolerant Lewis acids followed by aldehyde decarbonylation by a Rh complex. Insitu decarbonylation of the reactive aldehydes limits loss of monomers by recondensation, a major issue in acid-catalyzed lignin depolymerization. Rate of hydrolysis and decarbonylation were matched using lignin model compounds, allowing the method to be successfully applied to softwood, hardwood, and herbaceous dioxasolv lignins, as well as poplar sawdust, to give the anticipated decarbonylation products and, rather surprisingly, 4-(1-propenyl)phenols. Promisingly, product selectivity can be tuned by variation of the Lewis-acid strength and lignin source.
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