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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)8127-8133
Number of pages7
JournalChemical Science
Volume9
Issue number42
DOIs
Publication statusPublished - 6 Sep 2018

Fingerprint

Lignin
Gold
Molecular weight
Monomers
Nanoparticles
Oxidation
Depolymerization
Catalysts
Molecular oxygen
Dimers
Atmospheric pressure
Hydrolysis
Alcohols
hydroxide ion

Bibliographical note

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

Cite this

Song, Y., Mobley, J. K., Motagamwala, A. H., Isaacs, M., Dumesic, J. A., Ralph, J., ... Crocker, M. (2018). Gold-catalyzed conversion of lignin to low molecular weight aromatics. Chemical Science, 9(42), 8127-8133. https://doi.org/10.1039/c8sc03208d
Song, Yang ; Mobley, Justin K. ; Motagamwala, Ali Hussain ; Isaacs, Mark ; Dumesic, James A. ; Ralph, John ; Lee, Adam F. ; Wilson, Karen ; Crocker, Mark. / Gold-catalyzed conversion of lignin to low molecular weight aromatics. In: Chemical Science. 2018 ; Vol. 9, No. 42. pp. 8127-8133.
@article{99b940dd18864fd6bebe4614939cbed8,
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 = "This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.",
year = "2018",
month = "9",
day = "6",
doi = "10.1039/c8sc03208d",
language = "English",
volume = "9",
pages = "8127--8133",
journal = "Chemical Science",
issn = "2041-6520",
publisher = "Royal Society of Chemistry",
number = "42",

}

Song, Y, Mobley, JK, Motagamwala, AH, Isaacs, M, Dumesic, JA, Ralph, J, Lee, AF, Wilson, K & Crocker, M 2018, 'Gold-catalyzed conversion of lignin to low molecular weight aromatics', Chemical Science, vol. 9, no. 42, pp. 8127-8133. https://doi.org/10.1039/c8sc03208d

Gold-catalyzed conversion of lignin to low molecular weight aromatics. / Song, Yang; Mobley, Justin K.; Motagamwala, Ali Hussain; Isaacs, Mark; Dumesic, James A.; Ralph, John; Lee, Adam F.; Wilson, Karen; Crocker, Mark.

In: Chemical Science, Vol. 9, No. 42, 06.09.2018, p. 8127-8133.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Gold-catalyzed conversion of lignin to low molecular weight aromatics

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.

UR - http://www.scopus.com/inward/record.url?scp=85056112884&partnerID=8YFLogxK

UR - https://pubs.rsc.org/en/Content/ArticleLanding/2018/SC/C8SC03208D#!divAbstract

U2 - 10.1039/c8sc03208d

DO - 10.1039/c8sc03208d

M3 - Article

AN - SCOPUS:85056112884

VL - 9

SP - 8127

EP - 8133

JO - Chemical Science

JF - Chemical Science

SN - 2041-6520

IS - 42

ER -

Song Y, Mobley JK, Motagamwala AH, Isaacs M, Dumesic JA, Ralph J et al. Gold-catalyzed conversion of lignin to low molecular weight aromatics. Chemical Science. 2018 Sep 6;9(42):8127-8133. https://doi.org/10.1039/c8sc03208d