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Isolation of Functionalized Phenolic Monomers through Selective Oxidation and CO Bond Cleavage of the β‐O‐4 Linkages in Lignin

Abstract

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.

Lignin nutzbar gemacht: Eine zweistufige Methode bestehend aus der selektiven aeroben Oxidation benzylischer Ligninalkohole mit DDQ/tBuONO/O2 und der anschließenden Spaltung der β‐O‐4‐Bindungen mit metallischem Zink liefert funktionalisierte kleine Moleküle. Die Produkte sind nützliche Bausteine für die Produktion von Feinchemikalien und Materialien aus Biomasse.

Authors:   Christopher S. Lancefield, O. Stephen Ojo, Fanny Tran, Nicholas J. Westwood
Journal:   Angewandte Chemie
Year:   2014
Pages:   n/a
DOI:   10.1002/ange.201409408
Publication date:   05-Nov-2014
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