Hydrothermal Liquefaction of α‐O‐4 Aryl Ether Linkages in Lignin

Matthew Y. Lui; Bun Chan; Alexander K. L. Yuen; Anthony F. Masters; Thomas Maschmeyer

doi:10.1002/cssc.201903263

journal article Feb 27, 2020

Hydrothermal Liquefaction of α‐O‐4 Aryl Ether Linkages in Lignin

Matthew Y. Lui

ChemSusChem Vol. 13 No. 8 pp. 2002-2006 · Wiley

View at Publisher Save 10.1002/cssc.201903263

Abstract

AbstractBy using lignin model compounds with relevant key characteristic structural features, the reaction pathways of α‐O‐4 aryl ether linkages under hydrothermal conditions are elucidated. Experimental results and computational modeling suggest that the α‐O‐4 linkages in lignin undergo catalyzed hydrolysis and elimination to give phenolic and alkenylbenzene derivatives as major products in subcritical water. The decreased relative permittivity of water at these high temperatures and pressures facilitates the elimination reactions. The alkyl group on the α‐carbon and the methoxy groups on the phenyl rings both have positive effects on the rate of conversion of α‐O‐4 linkages in native lignin.

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References

42

[1]

10.1016/j.biortech.2014.09.132

[2]

10.1021/ef201373m

[3]

10.1002/ceat.200800073

[4]

10.1021/acs.chemrev.7b00395

[5]

The Catalytic Valorization of Lignin for the Production of Renewable Chemicals

Joseph Zakzeski, Pieter C. A. Bruijnincx, Anna L. Jongerius et al.

Chemical Reviews 10.1021/cr900354u

[6]

10.1002/anie.201510351

[7]

10.1002/ange.201510351

[8]

Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading

W. Schutyser, T. Renders, S. Van den Bosch et al.

Chemical Society Reviews 10.1039/c7cs00566k

[9]

Bright Side of Lignin Depolymerization: Toward New Platform Chemicals

Zhuohua Sun, Bálint Fridrich, Alessandra de Santi et al.

Chemical Reviews 10.1021/acs.chemrev.7b00588

[10]

Non‐Oxidative Vanadium‐Catalyzed CO Bond Cleavage: Application to Degradation of Lignin Model Compounds

Sunghee Son, F. Dean Toste

Angewandte Chemie International Edition 10.1002/anie.201001293

[11]

10.1002/ange.201001293

[12]

10.1039/b209686b

[13]

Lignin Biosynthesis

Wout Boerjan, John Ralph, Marie Baucher

Annual Review of Plant Biology 10.1146/annurev.arplant.54.031902.134938

[14]

10.1002/chem.201002438

[15]

10.1007/s12649-014-9307-6

[16]

10.1016/j.jaap.2014.01.008

[17]

10.1016/j.supflu.2016.12.015

[18]

10.1021/jo00125a044

[19]

10.1021/jo991479k

[20]

10.1021/jp3104694

[21]

10.1039/c5gc02268a

[22]

10.1021/acssuschemeng.5b00070

[23]

10.1002/cssc.201000112

[24]

10.1002/cssc.201700528

[25]

10.1021/ef050192p

[26]

10.1016/j.energy.2011.03.013

[27]

10.1016/j.rser.2014.07.216

[28]

10.1016/j.jcat.2013.10.024

[29]

10.1016/j.apcatb.2009.12.010

[30]

10.1016/j.cclet.2010.12.026

[31]

10.1627/jpi1958.40.465

[32]

10.1016/j.biombioe.2012.07.011

[33]

10.1021/ef00023a014

[34]

10.1021/acssuschemeng.7b03218

[35]

The Ionization Constant of Water over Wide Ranges of Temperature and Density

Andrei V. Bandura, Serguei N. Lvov

Journal of Physical and Chemical Reference Data 10.1063/1.1928231

[36]

10.1063/1.555632

[37]

10.1016/j.biortech.2013.12.083

[38]

M. J. Frisch G. W. Trucks H. B. Schlegel G. E. Scuseria M. A. Robb J. R. Cheeseman G. Scalmani V. Barone B. Mennucci G. A. Petersson H. Nakatsuji M. Caricato X. Li H. P. Hratchian A. F. Izmaylov J. Bloino G. Zheng J. L. Sonnenberg M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven J. A. Montgomery Jr. J. E. Peralta F. Ogliaro M. Bearpark J. J. Heyd E. Brothers K. N. Kudin V. N. Staroverov R. Kobayashi J. Normand K. Raghavachari A. Rendell J. C. Burant S. S. Iyengar J. Tomasi M. Cossi N. Rega N. J. Millam M. Klene J. E. Knox J. B. Cross V. Bakken C. Adamo J. Jaramillo R. Gomperts R. E. Stratmann O. Yazyev A. J. Austin R. Cammi C. Pomelli J. W. Ochterski R. L. Martin K. Morokuma V. G. Zakrzewski G. A. Voth P. Salvador J. J. Dannenberg S. Dapprich A. D. Daniels O. Farkas J. B. Foresman J. V. Ortiz J. Cioslowski D. J. Fox Gaussian 16 Revision A.03 Gaussian Inc. Wallingford CT 2016.

[39]

Design of Density Functionals by Combining the Method of Constraint Satisfaction with Parametrization for Thermochemistry, Thermochemical Kinetics, and Noncovalent Interactions

Yan Zhao, Nathan E. Schultz, Donald G. Truhlar

Journal of Chemical Theory and Computation 10.1021/ct0502763

[40]

Universal Solvation Model Based on Solute Electron Density and on a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions

Aleksandr V. Marenich, Christopher J. Cramer, Donald G. Truhlar

The Journal of Physical Chemistry B 10.1021/jp810292n

[41]

An Evaluation of Harmonic Vibrational Frequency Scale Factors

Jeffrey P. Merrick, Damian Moran, Leo Radom

The Journal of Physical Chemistry A 10.1021/jp073974n

[42]

The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals

Yan Zhao, Donald G. Truhlar

Theoretical Chemistry Accounts 10.1007/s00214-007-0310-x

Metrics

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Citations

42

References

Details

Published: Feb 27, 2020
Vol/Issue: 13(8)
Pages: 2002-2006
License: View

Authors

M

Matthew Y. Lui

Department of Chemistry Hong Kong Baptist University Kowloon Tong Hong Kong China

B

Bun Chan

Graduate School of Engineering Nagasaki University Bunkyo 1-14 Nagasaki 852-8521 Japan

A

Alexander K. L. Yuen

Laboratory of Advanced Catalysis for Sustainability School of Chemistry The University of Sydney Sydney 2006 Australia

A

Anthony F. Masters

Laboratory of Advanced Catalysis for Sustainability School of Chemistry The University of Sydney Sydney 2006 Australia

T

Thomas Maschmeyer

Laboratory of Advanced Catalysis for Sustainability School of Chemistry The University of Sydney Sydney 2006 Australia

Funding

Science and Industry Endowment Fund Award: RP03-028

Cite This Article

Matthew Y. Lui, Bun Chan, Alexander K. L. Yuen, et al. (2020). Hydrothermal Liquefaction of α‐O‐4 Aryl Ether Linkages in Lignin. ChemSusChem, 13(8), 2002-2006. https://doi.org/10.1002/cssc.201903263

Hydrothermal Liquefaction of α‐O‐4 Aryl Ether Linkages in Lignin

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