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Issue 11, 2020
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Mechanochemical cleavage of lignin models and lignin via oxidation and a subsequent base-catalyzed strategy

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Abstract

Mechanochemical cleavage of lignin dimer model compounds to phenolic monomers has been developed via a two-step strategy under milling conditions. In the first step of this process, the secondary benzylic alcohol of lignin β-O-4 linkages was selectively oxidized to the corresponding ketones over a 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)/NaNO2 catalytic system under milling conditions. In the subsequent step, mechanochemical selective cleavage of the Cβ–O bonds and Cα–Cβ bonds of lignin β-O-4 ketones to acids and phenols was promoted by NaOH-catalyzed depolymerization. In addition, this two-step strategy was performed to depolymerize organosolv birch lignin, giving aromatic monomers with good selectivity for syringate. This approach provides an efficient method to convert the β-O-4 linkages of lignin to valuable aromatic monomers under mild reaction conditions.

Graphical abstract: Mechanochemical cleavage of lignin models and lignin via oxidation and a subsequent base-catalyzed strategy

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Supplementary files

Article information


Submitted
30 Jan 2020
Accepted
28 Apr 2020
First published
29 Apr 2020

Green Chem., 2020,22, 3489-3494
Article type
Paper

Mechanochemical cleavage of lignin models and lignin via oxidation and a subsequent base-catalyzed strategy

C. Sun, L. Zheng, W. Xu, A. V. Dushkin and W. Su, Green Chem., 2020, 22, 3489
DOI: 10.1039/D0GC00372G

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