Issue 6, 2016

Intermediate oxiranes in the base-catalyzed depolymerisation of lignin

Abstract

Monomer yields from the base catalysed depolymerisation (BCD), which has recently evolved as a promising first step in the valorisation of lignin, are severely limited by the repolymerisation of the monomers. DFT calculations with β-phenoxy-α-phenylethanol as a model for the βO4′ link in lignin are used to explore various routes for the BCD process and the repolymerisation of its monomers. The depolymerisation proceeds via a resonance-stabilised carbanion, while intermediate oxiranes and formaldehyde, which originates from a second reaction path, are the key compounds in the repolymerisation. It is concluded that controlling the reactive intermediates such as the oxirane in the BCD process will increase monomer yields.

Graphical abstract: Intermediate oxiranes in the base-catalyzed depolymerisation of lignin

Supplementary files

Article information

Article type
Paper
Submitted
14 Sep 2015
Accepted
27 Oct 2015
First published
27 Oct 2015

Green Chem., 2016,18, 1590-1596

Intermediate oxiranes in the base-catalyzed depolymerisation of lignin

T. Lankau and C. Yu, Green Chem., 2016, 18, 1590 DOI: 10.1039/C5GC02192H

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