Isolation of functionalized phenolic monomers through selective oxidation and C-O bond cleavage of the β-O-4 linkages in lignin.
Functionalized phenolic monomers have been generated and isolated from an organosolv lignin through a two-step depolymerization process. Chemoselective catalytic oxidation of β-O-4 linkages promoted by the DDQ/tBuONO/O2 system was achieved in model compounds, including polymeric models and in real lignin. The oxidized β-O-4 linkages were then cleaved on reaction with zinc. Compared to many existing methods, this protocol, which can be achieved in one pot, is highly selective, giving rise to a simple mixture of products that can be readily purified to give pure compounds. The functionality present in these products makes them potentially valuable building blocks.
School of Chemistry and Biomedical Sciences Research Complex, University of St Andrews and EaStCHEM, North Haugh, St Andrews, Fife (UK).
Christopher S
CS
Lancefield
O Stephen
OS
Ojo
Fanny
F
Tran
Nicholas J
NJ
Westwood
D016227:Benzoquinones / Q000737:chemistry; D008031:Lignin / Q000737:chemistry*; D016877:Oxidants / Q000737:chemistry; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry* / Q000302:isolation & purification; D058105:Polymerization
D016227:Benzoquinones; D016877:Oxidants; D010636:Phenols; C000928:dichlorodicyanobenzoquinone; D008031:Lignin
biomass; depolymerization; lignin; oxidation; renewable chemicals