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Metal Triflates for the Production of Aromatics from Lignin
Author(s) -
Deuss Peter J.,
Lahive Ciaran W.,
Lancefield Christopher S.,
Westwood Nicholas J.,
Kamer Paul C. J.,
Barta Katalin,
de Vries Johannes G.
Publication year - 2016
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201600831
Subject(s) - lignin , depolymerization , chemistry , organic chemistry , reactivity (psychology) , ethylene glycol , catalysis , decarbonylation , monomer , yield (engineering) , aldehyde , acetal , materials science , polymer , medicine , alternative medicine , pathology , metallurgy
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 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.