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

Calvaruso, G., Clough, M. T., & Rinaldi, R. (2017). Biphasic extraction of mechanocatalytically-depolymerized lignin from water-soluble wood and its catalytic downstream processing. Green Chemistry, 19(12), 2803-2811. doi:10.1039/C6GC03191A.

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 Creators:
Calvaruso, Gaetano1, Author           
Clough, Matthew T.2, Author           
Rinaldi, Roberto3, Author
Affiliations:
1Service Department Theyssen (Technical Labs), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445632              
2Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445589              
3Department of Chemical Engineering, Imperial College London, South Kensington Campus, SW7 2AZ London, UK , ou_persistent22              

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 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.

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 Dates: 2016-11-182017-02-102017-02-102017-06-21
 Publication Status: Issued
 Pages: 9
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1039/C6GC03191A
 Degree: -

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Title: Green Chemistry
  Other : Green Chem.
Source Genre: Journal
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Publ. Info: Royal Society of Chemistry
Pages: - Volume / Issue: 19 (12) Sequence Number: - Start / End Page: 2803 - 2811 Identifier: ISSN: 1463-9262
CoNE: https://pure.mpg.de/cone/journals/resource/954925625301