Gold-catalyzed conversion of lignin to low molecular weight aromatics

Yang Song; Justin K. Mobley; Ali Hussain Motagamwala; Mark Isaacs; James A. Dumesic; John Ralph; Adam F. Lee; Karen Wilson; Mark Crocker

doi:10.1039/c8sc03208d

Gold-catalyzed conversion of lignin to low molecular weight aromatics

Yang Song, Justin K. Mobley, Ali Hussain Motagamwala, Mark Isaacs, James A. Dumesic, John Ralph, Adam F. Lee, Karen Wilson, Mark Crocker

Chemistry

Research output: Contribution to journal › Article › peer-review

74 Scopus citations

Abstract

A heterogeneous catalyst system, employing Au nanoparticles (NPs) and Li-Al (1:2) layered double hydroxide (LDH) as support, showed excellent activity in aerobic oxidation of the benzylic alcohol group in β-O-4 linked lignin model dimers to the corresponding carbonyl products using molecular oxygen under atmospheric pressure. The synergistic effect between Au NPs and the basic Li-Al LDH support induces further reaction of the oxidized model compounds, facilitating facile cleavage of the β-O-4 linkage. Extension to oxidation of γ-valerolactone (GVL) extracted lignin and kraft lignin using Au/Li-Al LDH under similar conditions produced a range of aromatic monomers in high yield. Hydrolysis of the Au/Li-Al LDH oxidized lignin was found to increase the degree of lignin depolymerization, with monomer yields reaching 40% for GVL extracted lignin. Based on these results, the Au/Li-Al LDH + O₂ catalyst system shows potential to be an environmentally friendly means of depolymerizing lignin to low molecular weight aromatics under mild conditions.

Original language	English
Pages (from-to)	8127-8133
Number of pages	7
Journal	Chemical Science
Volume	9
Issue number	42
DOIs	https://doi.org/10.1039/c8sc03208d
State	Published - 2018

Bibliographical note

Publisher Copyright:
© 2018 The Royal Society of Chemistry.

Funding

This research was funded by the National Science Foundation under Cooperative Agreement No. 1355438 and by the Global Bioenergy, Biofuels, and Biore\uE103ning network (GB3-Net) supported by the British Council and the Department for Business, Innovation and Skills (BIS). This work was also funded in part by the DOE Great Lakes Bioenergy Research Center (DOE Office of Science BER DE-FC02-07ER64494 and DE-SC0018409). The authors thank Shelley Hopps for performing the XRD measurements and Dr Mark Meier for helpful discussions.

Funders	Funder number
British Interplanetary Society
British Council
Biorening network
Great Lakes Bioenergy Research Center
Department for Business, Innovation and Skills
U.S. Department of Energy Chinese Academy of Sciences Guangzhou Municipal Science and Technology Project Oak Ridge National Laboratory Extreme Science and Engineering Discovery Environment National Science Foundation National Energy Research Scientific Computing Center National Natural Science Foundation of China	1355438
UK Industrial Decarbonization Research and Innovation Centre	53706
National Science Foundation Office of International Science and Engineering	DE-SC0018409, BER DE-FC02-07ER64494

ASJC Scopus subject areas

General Chemistry

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title = "Gold-catalyzed conversion of lignin to low molecular weight aromatics",

abstract = "A heterogeneous catalyst system, employing Au nanoparticles (NPs) and Li-Al (1:2) layered double hydroxide (LDH) as support, showed excellent activity in aerobic oxidation of the benzylic alcohol group in β-O-4 linked lignin model dimers to the corresponding carbonyl products using molecular oxygen under atmospheric pressure. The synergistic effect between Au NPs and the basic Li-Al LDH support induces further reaction of the oxidized model compounds, facilitating facile cleavage of the β-O-4 linkage. Extension to oxidation of γ-valerolactone (GVL) extracted lignin and kraft lignin using Au/Li-Al LDH under similar conditions produced a range of aromatic monomers in high yield. Hydrolysis of the Au/Li-Al LDH oxidized lignin was found to increase the degree of lignin depolymerization, with monomer yields reaching 40\% for GVL extracted lignin. Based on these results, the Au/Li-Al LDH + O2 catalyst system shows potential to be an environmentally friendly means of depolymerizing lignin to low molecular weight aromatics under mild conditions.",

author = "Yang Song and Mobley, \{Justin K.\} and Motagamwala, \{Ali Hussain\} and Mark Isaacs and Dumesic, \{James A.\} and John Ralph and Lee, \{Adam F.\} and Karen Wilson and Mark Crocker",

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doi = "10.1039/c8sc03208d",

language = "English",

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pages = "8127--8133",

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AU - Song, Yang

AU - Mobley, Justin K.

AU - Motagamwala, Ali Hussain

AU - Isaacs, Mark

AU - Dumesic, James A.

AU - Ralph, John

AU - Lee, Adam F.

AU - Wilson, Karen

AU - Crocker, Mark

PY - 2018

Y1 - 2018

N2 - A heterogeneous catalyst system, employing Au nanoparticles (NPs) and Li-Al (1:2) layered double hydroxide (LDH) as support, showed excellent activity in aerobic oxidation of the benzylic alcohol group in β-O-4 linked lignin model dimers to the corresponding carbonyl products using molecular oxygen under atmospheric pressure. The synergistic effect between Au NPs and the basic Li-Al LDH support induces further reaction of the oxidized model compounds, facilitating facile cleavage of the β-O-4 linkage. Extension to oxidation of γ-valerolactone (GVL) extracted lignin and kraft lignin using Au/Li-Al LDH under similar conditions produced a range of aromatic monomers in high yield. Hydrolysis of the Au/Li-Al LDH oxidized lignin was found to increase the degree of lignin depolymerization, with monomer yields reaching 40% for GVL extracted lignin. Based on these results, the Au/Li-Al LDH + O2 catalyst system shows potential to be an environmentally friendly means of depolymerizing lignin to low molecular weight aromatics under mild conditions.

AB - A heterogeneous catalyst system, employing Au nanoparticles (NPs) and Li-Al (1:2) layered double hydroxide (LDH) as support, showed excellent activity in aerobic oxidation of the benzylic alcohol group in β-O-4 linked lignin model dimers to the corresponding carbonyl products using molecular oxygen under atmospheric pressure. The synergistic effect between Au NPs and the basic Li-Al LDH support induces further reaction of the oxidized model compounds, facilitating facile cleavage of the β-O-4 linkage. Extension to oxidation of γ-valerolactone (GVL) extracted lignin and kraft lignin using Au/Li-Al LDH under similar conditions produced a range of aromatic monomers in high yield. Hydrolysis of the Au/Li-Al LDH oxidized lignin was found to increase the degree of lignin depolymerization, with monomer yields reaching 40% for GVL extracted lignin. Based on these results, the Au/Li-Al LDH + O2 catalyst system shows potential to be an environmentally friendly means of depolymerizing lignin to low molecular weight aromatics under mild conditions.

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Gold-catalyzed conversion of lignin to low molecular weight aromatics

Abstract

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