Issue 6, 2015

Unprecedented catalyst-free lignin dearomatization with hydrogen peroxide and dimethyl carbonate

Abstract

Lignin can be efficiently dearomatized and oxidized under catalyst-free conditions in dimethyl carbonate as solvent and hydrogen peroxide as oxidant at 20–80 °C. Based on H2O2 loadings, modified fibres with different aromatic content and sizes can be achieved (from 100% to 0% aromatics). At loadings > 0.2 mol H2O2 g lignin−1 almost complete dearomatized lignin can be achieved, resulting in a pale oily gel. Analyses of the derivatives show increase in carbonylic bonds (FTIR) and oxygen (elemental analysis) and smaller size fibres (ESI-MS). Changes were also in-depth monitored by 2D 1H-13C HSQC NMR. Depending on a desired application (e.g. resins, additives, coatings, etc.), tailored dearomatized lignin fibres can be straightforwardly produced. Being a novel reaction with relatively high peroxide concentrations, experiments must be conducted under strong safety conditions to avoid possible explosions and other risks associated to peroxides and/or in situ formed derivatives.

Graphical abstract: Unprecedented catalyst-free lignin dearomatization with hydrogen peroxide and dimethyl carbonate

Article information

Article type
Paper
Submitted
24 Oct 2014
Accepted
04 Dec 2014
First published
04 Dec 2014

RSC Adv., 2015,5, 4009-4018

Unprecedented catalyst-free lignin dearomatization with hydrogen peroxide and dimethyl carbonate

L. Wiermans, H. Schumacher, C. Klaaßen and P. Domínguez de María, RSC Adv., 2015, 5, 4009 DOI: 10.1039/C4RA13113D

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