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

61 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

Funding Information:
This research was funded by the National Science Foundation under Cooperative Agreement No. 1355438 and by the Global Bioenergy, Biofuels, and Biorening 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.

Publisher Copyright:
© 2018 The Royal Society of Chemistry.

ASJC Scopus subject areas

Chemistry (all)

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10.1039/c8sc03208d

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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",

note = "Funding Information: This research was funded by the National Science Foundation under Cooperative Agreement No. 1355438 and by the Global Bioenergy, Biofuels, and Biorening 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. Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c8sc03208d",

language = "English",

volume = "9",

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

N1 - Funding Information: This research was funded by the National Science Foundation under Cooperative Agreement No. 1355438 and by the Global Bioenergy, Biofuels, and Biorening 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. Publisher Copyright: © 2018 The Royal Society of Chemistry.

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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JO - Chemical Science

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ER -

Gold-catalyzed conversion of lignin to low molecular weight aromatics

Abstract

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