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Title: From Lignin to Valuable Aromatic Chemicals: Lignin Depolymerization and Monomer Separation via Centrifugal Partition Chromatography

Abstract

Lignin has long been recognized as a potential feedstock for aromatic molecules; however, most lignin depolymerization methods create a complex mixture of products. The present study describes an alkaline aerobic oxidation method that converts lignin extracted from poplar into a collection of oxygenated aromatics, including valuable commercial compounds such as vanillin and p-hydroxybenzoic acid. Centrifugal partition chromatography (CPC) is shown to be an effective method to isolate the individual compounds from the complex product mixture. The liquid–liquid extraction method proceeds in two stages. The crude depolymerization mixture is first subjected to ascending-mode extraction with the Arizona solvent system L (pentane/ethyl acetate/methanol/water 2:3:2:3), enabling isolation of vanillin, syringic acid, and oligomers. The remaining components, syringaldehyde, vanillic acid, and p-hydroxybenzoic acid (pHBA), were resolved by using ascending-mode extraction with solvent mixture comprising dichloromethane/methanol/water (10:6:4) separation. These results showcase CPC as an effective technology that could provide scalable access to valuable chemicals from lignin and other biomass-derived feedstocks.

Authors:
 [1];  [1];  [2];  [3]; ORCiD logo [3]; ORCiD logo [2]
  1. Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States
  2. Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States, Wisconsin Energy Institute, University of Wisconsin-Madison, Madison, Wisconsin 53726, United States
  3. Department of Biochemistry & Molecular Biology, Michigan State University, 603 Wilson Road, East Lansing, Michigan 48824, United States
Publication Date:
Research Org.:
Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)
OSTI Identifier:
1827762
Alternate Identifier(s):
OSTI ID: 1832851
Grant/Contract Number:  
SC0018409
Resource Type:
Published Article
Journal Name:
ACS Central Science
Additional Journal Information:
Journal Name: ACS Central Science Journal Volume: 7 Journal Issue: 11; Journal ID: ISSN 2374-7943
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Alherech, Manar, Omolabake, Surajudeen, Holland, Christopher M., Klinger, Gracielou E., Hegg, Eric L., and Stahl, Shannon S. From Lignin to Valuable Aromatic Chemicals: Lignin Depolymerization and Monomer Separation via Centrifugal Partition Chromatography. United States: N. p., 2021. Web. doi:10.1021/acscentsci.1c00729.
Alherech, Manar, Omolabake, Surajudeen, Holland, Christopher M., Klinger, Gracielou E., Hegg, Eric L., & Stahl, Shannon S. From Lignin to Valuable Aromatic Chemicals: Lignin Depolymerization and Monomer Separation via Centrifugal Partition Chromatography. United States. https://doi.org/10.1021/acscentsci.1c00729
Alherech, Manar, Omolabake, Surajudeen, Holland, Christopher M., Klinger, Gracielou E., Hegg, Eric L., and Stahl, Shannon S. Wed . "From Lignin to Valuable Aromatic Chemicals: Lignin Depolymerization and Monomer Separation via Centrifugal Partition Chromatography". United States. https://doi.org/10.1021/acscentsci.1c00729.
@article{osti_1827762,
title = {From Lignin to Valuable Aromatic Chemicals: Lignin Depolymerization and Monomer Separation via Centrifugal Partition Chromatography},
author = {Alherech, Manar and Omolabake, Surajudeen and Holland, Christopher M. and Klinger, Gracielou E. and Hegg, Eric L. and Stahl, Shannon S.},
abstractNote = {Lignin has long been recognized as a potential feedstock for aromatic molecules; however, most lignin depolymerization methods create a complex mixture of products. The present study describes an alkaline aerobic oxidation method that converts lignin extracted from poplar into a collection of oxygenated aromatics, including valuable commercial compounds such as vanillin and p-hydroxybenzoic acid. Centrifugal partition chromatography (CPC) is shown to be an effective method to isolate the individual compounds from the complex product mixture. The liquid–liquid extraction method proceeds in two stages. The crude depolymerization mixture is first subjected to ascending-mode extraction with the Arizona solvent system L (pentane/ethyl acetate/methanol/water 2:3:2:3), enabling isolation of vanillin, syringic acid, and oligomers. The remaining components, syringaldehyde, vanillic acid, and p-hydroxybenzoic acid (pHBA), were resolved by using ascending-mode extraction with solvent mixture comprising dichloromethane/methanol/water (10:6:4) separation. These results showcase CPC as an effective technology that could provide scalable access to valuable chemicals from lignin and other biomass-derived feedstocks.},
doi = {10.1021/acscentsci.1c00729},
journal = {ACS Central Science},
number = 11,
volume = 7,
place = {United States},
year = {2021},
month = {10}
}

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