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Issue 6, 2016
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Intermediate oxiranes in the base-catalyzed depolymerisation of lignin

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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

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Publication details

The article was received on 14 Sep 2015, accepted on 27 Oct 2015 and first published on 27 Oct 2015


Article type: Paper
DOI: 10.1039/C5GC02192H
Green Chem., 2016,18, 1590-1596

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    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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