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Title: Antimicrobial Properties of Corn Stover Lignin Fractions Derived from Catalytic Transfer Hydrogenolysis in Supercritical Ethanol with a Ru/C Catalyst

Abstract

Converting lignin to value-added products at high yields provides an avenue for making ethanol biorefineries more profitable while reducing the carbon footprint of products generally derived from petroleum. In this study, corn stover lignin was depolymerized by catalytic transfer hydrogenolysis (CTH) in supercritical ethanol with a Ru/C catalyst. The lignin-derived bio-oil was then sequentially extracted utilizing hexane, petroleum ether, chloroform, and ethyl acetate as solvents in order of less polar to polar, and the subsequent bio-oils were characterized using GPC, GC/MS, and HSQC NMR. In this work, results show that the monomers in the bio-oil fractions contained primarily alkylated phenols, hydrogenated hydroxycinnamic acid derivatives, syringol and guaiacol-type lignins created from reductive cleavages of ether linkages, which were sequentially extracted into groups depending on the solvent polarity. The antimicrobial properties of the bio-oils were screened against Gram-positive (Bacillus subtilis, Lactobacillus amylovorus, and Staphylococcus epidermidis) and Gram-negative (Escherichia coli) bacteria and yeast (Saccharomyces cerevisiae) by examining microbial growth inhibition. Results show that CTH-derived bio-oils inhibited all tested organisms at concentrations less than 3 mg/mL. Total monomer concentration and the presence of specific monomers (i.e., syringyl propane) showed correlations to antimicrobial activity, likely due to cell death or membrane damage. This study providesmore » insights into using sequential extraction to fractionate lignin-derived compounds and correlations between the properties of the extracted compounds and their antimicrobial activity.« less

Authors:
 [1]; ORCiD logo [1]; ORCiD logo [1];  [1];  [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]
  1. Univ. of Kentucky, Lexington, KY (United States)
  2. National Renewable Energy Lab. (NREL), Golden, CO (United States)
Publication Date:
Research Org.:
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Transportation Office. Bioenergy Technologies Office; National Science Foundation (NSF); National Institute of Food and Agriculture (NIFA); USDA
OSTI Identifier:
1760677
Report Number(s):
NREL/JA-5100-77631
Journal ID: ISSN 2168-0485; MainId:29557;UUID:615063a0-44c3-4c5d-94d5-6fd725b201af;MainAdminID:19142
Grant/Contract Number:  
AC36-08GO28308
Resource Type:
Accepted Manuscript
Journal Name:
ACS Sustainable Chemistry & Engineering
Additional Journal Information:
Journal Volume: 8; Journal Issue: 50; Journal ID: ISSN 2168-0485
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Ru/C catalyst; DMR; jet fuel; lignin upgrading; hydrogenolysis; catalysis, antimicrobial; liquid−liquid extraction; depolymerization

Citation Formats

Kalinoski, Ryan M., Li, Wenqi, Mobley, Justin K., Asare, Shardrack O., Dorrani, Masoumeh, Lynn, Bert C., Chen, Xiaowen, and Shi, Jian. Antimicrobial Properties of Corn Stover Lignin Fractions Derived from Catalytic Transfer Hydrogenolysis in Supercritical Ethanol with a Ru/C Catalyst. United States: N. p., 2020. Web. doi:10.1021/acssuschemeng.0c05812.
Kalinoski, Ryan M., Li, Wenqi, Mobley, Justin K., Asare, Shardrack O., Dorrani, Masoumeh, Lynn, Bert C., Chen, Xiaowen, & Shi, Jian. Antimicrobial Properties of Corn Stover Lignin Fractions Derived from Catalytic Transfer Hydrogenolysis in Supercritical Ethanol with a Ru/C Catalyst. United States. https://doi.org/10.1021/acssuschemeng.0c05812
Kalinoski, Ryan M., Li, Wenqi, Mobley, Justin K., Asare, Shardrack O., Dorrani, Masoumeh, Lynn, Bert C., Chen, Xiaowen, and Shi, Jian. Fri . "Antimicrobial Properties of Corn Stover Lignin Fractions Derived from Catalytic Transfer Hydrogenolysis in Supercritical Ethanol with a Ru/C Catalyst". United States. https://doi.org/10.1021/acssuschemeng.0c05812. https://www.osti.gov/servlets/purl/1760677.
@article{osti_1760677,
title = {Antimicrobial Properties of Corn Stover Lignin Fractions Derived from Catalytic Transfer Hydrogenolysis in Supercritical Ethanol with a Ru/C Catalyst},
author = {Kalinoski, Ryan M. and Li, Wenqi and Mobley, Justin K. and Asare, Shardrack O. and Dorrani, Masoumeh and Lynn, Bert C. and Chen, Xiaowen and Shi, Jian},
abstractNote = {Converting lignin to value-added products at high yields provides an avenue for making ethanol biorefineries more profitable while reducing the carbon footprint of products generally derived from petroleum. In this study, corn stover lignin was depolymerized by catalytic transfer hydrogenolysis (CTH) in supercritical ethanol with a Ru/C catalyst. The lignin-derived bio-oil was then sequentially extracted utilizing hexane, petroleum ether, chloroform, and ethyl acetate as solvents in order of less polar to polar, and the subsequent bio-oils were characterized using GPC, GC/MS, and HSQC NMR. In this work, results show that the monomers in the bio-oil fractions contained primarily alkylated phenols, hydrogenated hydroxycinnamic acid derivatives, syringol and guaiacol-type lignins created from reductive cleavages of ether linkages, which were sequentially extracted into groups depending on the solvent polarity. The antimicrobial properties of the bio-oils were screened against Gram-positive (Bacillus subtilis, Lactobacillus amylovorus, and Staphylococcus epidermidis) and Gram-negative (Escherichia coli) bacteria and yeast (Saccharomyces cerevisiae) by examining microbial growth inhibition. Results show that CTH-derived bio-oils inhibited all tested organisms at concentrations less than 3 mg/mL. Total monomer concentration and the presence of specific monomers (i.e., syringyl propane) showed correlations to antimicrobial activity, likely due to cell death or membrane damage. This study provides insights into using sequential extraction to fractionate lignin-derived compounds and correlations between the properties of the extracted compounds and their antimicrobial activity.},
doi = {10.1021/acssuschemeng.0c05812},
journal = {ACS Sustainable Chemistry & Engineering},
number = 50,
volume = 8,
place = {United States},
year = {Fri Dec 04 00:00:00 EST 2020},
month = {Fri Dec 04 00:00:00 EST 2020}
}

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