Issue 12, 2017

Biphasic extraction of mechanocatalytically-depolymerized lignin from water-soluble wood and its catalytic downstream processing

Abstract

Mechanocatalysis is an efficient method for deep depolymerization of lignocellulosic materials. It renders full conversion of lignocellulose into water-soluble products, a mixture of oligosaccharides and lignin oligomers. In an aqueous monophasic system, it is known that further saccharification of these products affords high yields of fermentable sugars in addition to a lignin precipitate. Although much attention has been devoted to upgrading of the carbohydrate fraction, the reactivity of mechanocatalytically-isolated lignin has hitherto been overlooked. In this report, we demonstrate the saccharification of water-soluble lignocellulose in a biphasic mixture of water and 2-methyltetrahydrofuran, to prevent lignin fragments from recondensation, not only with other lignin fragments but also with oligosaccharides and their degradation products. The lignin stream extracted in the biphasic system exhibits a molecular weight much lower than that of the lignin precipitate obtained from monophasic aqueous saccharification, and that of lignin isolated by an Organosolv process with no added acid catalyst. Surprisingly, β-O-4 and phenylcoumaran (β-5 + α-O-4) linkages are quantitatively hydrolyzed during saccharification in the biphasic system. However, the extracted lignin still incorporates resinol bonding motifs (β-β + γ-O-α). Because of the lower molecular weight, low carbohydrate content, and high solubility in organic solvents, the catalytic downstream processing of the extracted lignin leads to higher yields of liquid products (e.g. 2-methoxyphenols and 2,6-dimethoxyphenols) by RANEY® Ni-catalyzed hydrogenolysis (200 °C, 7 MPa H2), compared to reactions performed on the lignin precipitate or Organosolv lignin.

Graphical abstract: Biphasic extraction of mechanocatalytically-depolymerized lignin from water-soluble wood and its catalytic downstream processing

Supplementary files

Article information

Article type
Paper
Submitted
18 nov. 2016
Accepted
10 févr. 2017
First published
10 févr. 2017

Green Chem., 2017,19, 2803-2811

Biphasic extraction of mechanocatalytically-depolymerized lignin from water-soluble wood and its catalytic downstream processing

G. Calvaruso, M. T. Clough and R. Rinaldi, Green Chem., 2017, 19, 2803 DOI: 10.1039/C6GC03191A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements