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^*

^*Corresponding author for this work

College of Engineering and Physical Sciences

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

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
Publication status	Published - 6 Sept 2018

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

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note = "This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.",

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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 - This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.

PY - 2018/9/6

Y1 - 2018/9/6

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

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