Investigation of a lignin-based deep eutectic solvent using p-hydroxybenzoic acid for efficient woody biomass conversion

Yunxuan Wang; Xianzhi Meng; Keunhong Jeong; Shuya Li; Gyu Leem; Kwang Ho Kim; Yunqiao Pu; Arthur J. Ragauskas; Chang Geun Yoo

doi:10.1021/acssuschemeng.0c03533

Investigation of a lignin-based deep eutectic solvent using p-hydroxybenzoic acid for efficient woody biomass conversion

Yunxuan Wang, Xianzhi Meng, Keunhong Jeong, Shuya Li, Gyu Leem, Kwang Ho Kim, Yunqiao Pu, Arthur J. Ragauskas, Chang Geun Yoo

Biomaterials and Biomass Characterizatio

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

100 Scopus citations

Abstract

Deep eutectic solvents (DESs) are effective solvents for biomass conversion and have been proposed as alternatives to ionic liquids (ILs). Herein, we first report an effective pretreatment of woody biomass using a novel hardwood lignin-based DES prepared from p-hydroxybenzoic acid (PB) and choline chloride (ChCl), which are used as the hydrogen bond donor and acceptor, respectively. The impacts of the ChCl-PB DES on structural properties and enzymatic hydrolysis of poplar wood were comprehensively evaluated. The performance of ChCl-PB DES was also compared with two other DESs with pcoumaric acid (PCA) and 4-hydroxybenzaldehyde (PHA) as the hydrogen bond donors, which have been successfully applied to herbaceous biomass conversion in previous studies. The results showed that hemicellulose and lignin were effectively fractionated during the proposed ChCl-PB DES pretreatment under a relatively mild temperature. The ChCl-PB DES pretreatment resulted in up to 69% of delignification, and the pretreated poplar residues had over 90% of glucose yield by a 72 h-enzymatic hydrolysis. Transformation of poplar biomass during the DES pretreatment was evaluated by gel permeation chromatography (GPC), two-dimensional heteronuclear single quantum coherence (2D-HSQC), and ³¹P nuclear magnetic resonance (NMR) spectroscopies. The recovered lignin showed relatively high purity, narrow molecular weight distribution (PDI < 1.6), and relatively low molecular weight (∼1400 g/mol for M_w). A sustainable process was achieved by recycling DES as well as the utilization of PB, which is a producible aromatic compound from hardwood lignin, for the proposed DES formation in the system. This study indicates that the proposed novel DES with a hardwood lignin-based PB compound is a promising pretreatment solvent to achieve an economically feasible biomass conversion process.

Original language	English
Pages (from-to)	12542-12553
Number of pages	12
Journal	ACS Sustainable Chemistry and Engineering
Volume	8
Issue number	33
DOIs	https://doi.org/10.1021/acssuschemeng.0c03533
State	Published - Aug 24 2020

Funding

Financial support from State University of New York College of Environmental Science and Forestry (SUNY ESF), is gratefully acknowledged. NMR analysis is supported by SUNY ESF and NIH Shared Instrumentation Grant 1S10OD012254. This work is supported, in part, by the Korea Institute of Science and Technology-The University of British Columbia Biorefinery on-site laboratory project. In addition, this work is partly supported by the Hwarangdae institute in the Korea Military Academy. Oak Ridge National Laboratory is managed by UT-Battelle, LLC, under Contract DE-AC05-00OR22725 with the U.S. Department of Energy (DOE). This study was partially supported by the Center for Bioenergy Innovation (CBI), a U.S. DOE Bioenergy Research Center supported by the Office of Biological and Environmental Research in the DOE Office of Science. The publisher, by accepting the article for publication, acknowledges that the U.S. Government retains a nonexclusive, paid-up, irrevocable, worldwide license to reproduce the published form of this manuscript, or allow others to do so, for U.S. Government purposes. The DOE will provide public access to these results of federally sponsored research in accord with the DOE Public Access Plan (https://www.energy.gov/downloads/doe-public-access-plan). The views and opinions of the authors expressed herein do not necessarily state or reflect those of the U.S. Government or any agency thereof. Neither the U.S. Government nor any agency thereof, nor any of their employees, makes any warranty, expressed or implied, or assumes any legal liability or responsibility for the accuracy, completeness, or usefulness of any information, apparatus, product, or process disclosed, or represents that its use would not infringe privately owned rights. Financial support from State University of New York College of Environmental Science and Forestry (SUNY ESF), is gratefully acknowledged. NMR analysis is supported by SUNY ESF and NIH Shared Instrumentation Grant 1S10OD012254. This work is supported, in part, by the Korea Institute of Science and Technology—The University of British Columbia Biorefinery on-site laboratory project. In addition, this work is partly supported by the Hwarangdae institute in the Korea Military Academy. Oak Ridge National Laboratory is managed by UT-Battelle, LLC, under Contract DE-AC05-00OR22725 with the U.S. Department of Energy (DOE). This study was partially supported by the Center for Bioenergy Innovation (CBI), a U.S. DOE Bioenergy Research Center supported by the Office of Biological and Environmental Research in the DOE Office of Science. The publisher, by accepting the article for publication, acknowledges that the U.S. Government retains a nonexclusive, paid-up, irrevocable, worldwide license to reproduce the published form of this manuscript, or allow others to do so, for U.S. Government purposes. The DOE will provide public access to these results of federally sponsored research in accord with the DOE Public Access Plan ( https://www.energy.gov/downloads/doe-public-access-plan ). The views and opinions of the authors expressed herein do not necessarily state or reflect those of the U.S. Government or any agency thereof. Neither the U.S. Government nor any agency thereof, nor any of their employees, makes any warranty, expressed or implied, or assumes any legal liability or responsibility for the accuracy, completeness, or usefulness of any information, apparatus, product, or process disclosed, or represents that its use would not infringe privately owned rights.

Funders	Funder number
DOE Office of Science
DOE Public Access Plan
Hwarangdae institute in the Korea Military Academy
Korea Institute of Science and Technology-The University of British Columbia Biorefinery
Office of Biological and Environmental Research
U.S. Government
UT-Battelle
University of British Columbia Biorefinery
National Institutes of Health	1S10OD012254
U.S. Department of Energy
Office of Science
Biological and Environmental Research
Oak Ridge National Laboratory
College of Environmental Science and Forestry, State University of New York
Center for Bioenergy Innovation
UT-Battelle	DE-AC05-00OR22725
Korea Institute of Science and Technology

Keywords

Biorefinery
Characterization
Density functional theory
Pretreatment
Renewable deep eutectic solvent

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10.1021/acssuschemeng.0c03533

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@article{a0ec7be104504ed383d4897b26b97e9d,

title = "Investigation of a lignin-based deep eutectic solvent using p-hydroxybenzoic acid for efficient woody biomass conversion",

abstract = "Deep eutectic solvents (DESs) are effective solvents for biomass conversion and have been proposed as alternatives to ionic liquids (ILs). Herein, we first report an effective pretreatment of woody biomass using a novel hardwood lignin-based DES prepared from p-hydroxybenzoic acid (PB) and choline chloride (ChCl), which are used as the hydrogen bond donor and acceptor, respectively. The impacts of the ChCl-PB DES on structural properties and enzymatic hydrolysis of poplar wood were comprehensively evaluated. The performance of ChCl-PB DES was also compared with two other DESs with pcoumaric acid (PCA) and 4-hydroxybenzaldehyde (PHA) as the hydrogen bond donors, which have been successfully applied to herbaceous biomass conversion in previous studies. The results showed that hemicellulose and lignin were effectively fractionated during the proposed ChCl-PB DES pretreatment under a relatively mild temperature. The ChCl-PB DES pretreatment resulted in up to 69% of delignification, and the pretreated poplar residues had over 90% of glucose yield by a 72 h-enzymatic hydrolysis. Transformation of poplar biomass during the DES pretreatment was evaluated by gel permeation chromatography (GPC), two-dimensional heteronuclear single quantum coherence (2D-HSQC), and 31P nuclear magnetic resonance (NMR) spectroscopies. The recovered lignin showed relatively high purity, narrow molecular weight distribution (PDI < 1.6), and relatively low molecular weight (∼1400 g/mol for Mw). A sustainable process was achieved by recycling DES as well as the utilization of PB, which is a producible aromatic compound from hardwood lignin, for the proposed DES formation in the system. This study indicates that the proposed novel DES with a hardwood lignin-based PB compound is a promising pretreatment solvent to achieve an economically feasible biomass conversion process.",

keywords = "Biorefinery, Characterization, Density functional theory, Pretreatment, Renewable deep eutectic solvent",

author = "Yunxuan Wang and Xianzhi Meng and Keunhong Jeong and Shuya Li and Gyu Leem and Kim, {Kwang Ho} and Yunqiao Pu and Ragauskas, {Arthur J.} and Yoo, {Chang Geun}",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

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doi = "10.1021/acssuschemeng.0c03533",

language = "English",

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journal = "ACS Sustainable Chemistry and Engineering",

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TY - JOUR

T1 - Investigation of a lignin-based deep eutectic solvent using p-hydroxybenzoic acid for efficient woody biomass conversion

AU - Wang, Yunxuan

AU - Meng, Xianzhi

AU - Jeong, Keunhong

AU - Li, Shuya

AU - Leem, Gyu

AU - Kim, Kwang Ho

AU - Pu, Yunqiao

AU - Ragauskas, Arthur J.

AU - Yoo, Chang Geun

PY - 2020/8/24

Y1 - 2020/8/24

N2 - Deep eutectic solvents (DESs) are effective solvents for biomass conversion and have been proposed as alternatives to ionic liquids (ILs). Herein, we first report an effective pretreatment of woody biomass using a novel hardwood lignin-based DES prepared from p-hydroxybenzoic acid (PB) and choline chloride (ChCl), which are used as the hydrogen bond donor and acceptor, respectively. The impacts of the ChCl-PB DES on structural properties and enzymatic hydrolysis of poplar wood were comprehensively evaluated. The performance of ChCl-PB DES was also compared with two other DESs with pcoumaric acid (PCA) and 4-hydroxybenzaldehyde (PHA) as the hydrogen bond donors, which have been successfully applied to herbaceous biomass conversion in previous studies. The results showed that hemicellulose and lignin were effectively fractionated during the proposed ChCl-PB DES pretreatment under a relatively mild temperature. The ChCl-PB DES pretreatment resulted in up to 69% of delignification, and the pretreated poplar residues had over 90% of glucose yield by a 72 h-enzymatic hydrolysis. Transformation of poplar biomass during the DES pretreatment was evaluated by gel permeation chromatography (GPC), two-dimensional heteronuclear single quantum coherence (2D-HSQC), and 31P nuclear magnetic resonance (NMR) spectroscopies. The recovered lignin showed relatively high purity, narrow molecular weight distribution (PDI < 1.6), and relatively low molecular weight (∼1400 g/mol for Mw). A sustainable process was achieved by recycling DES as well as the utilization of PB, which is a producible aromatic compound from hardwood lignin, for the proposed DES formation in the system. This study indicates that the proposed novel DES with a hardwood lignin-based PB compound is a promising pretreatment solvent to achieve an economically feasible biomass conversion process.

AB - Deep eutectic solvents (DESs) are effective solvents for biomass conversion and have been proposed as alternatives to ionic liquids (ILs). Herein, we first report an effective pretreatment of woody biomass using a novel hardwood lignin-based DES prepared from p-hydroxybenzoic acid (PB) and choline chloride (ChCl), which are used as the hydrogen bond donor and acceptor, respectively. The impacts of the ChCl-PB DES on structural properties and enzymatic hydrolysis of poplar wood were comprehensively evaluated. The performance of ChCl-PB DES was also compared with two other DESs with pcoumaric acid (PCA) and 4-hydroxybenzaldehyde (PHA) as the hydrogen bond donors, which have been successfully applied to herbaceous biomass conversion in previous studies. The results showed that hemicellulose and lignin were effectively fractionated during the proposed ChCl-PB DES pretreatment under a relatively mild temperature. The ChCl-PB DES pretreatment resulted in up to 69% of delignification, and the pretreated poplar residues had over 90% of glucose yield by a 72 h-enzymatic hydrolysis. Transformation of poplar biomass during the DES pretreatment was evaluated by gel permeation chromatography (GPC), two-dimensional heteronuclear single quantum coherence (2D-HSQC), and 31P nuclear magnetic resonance (NMR) spectroscopies. The recovered lignin showed relatively high purity, narrow molecular weight distribution (PDI < 1.6), and relatively low molecular weight (∼1400 g/mol for Mw). A sustainable process was achieved by recycling DES as well as the utilization of PB, which is a producible aromatic compound from hardwood lignin, for the proposed DES formation in the system. This study indicates that the proposed novel DES with a hardwood lignin-based PB compound is a promising pretreatment solvent to achieve an economically feasible biomass conversion process.

KW - Biorefinery

KW - Characterization

KW - Density functional theory

KW - Pretreatment

KW - Renewable deep eutectic solvent

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DO - 10.1021/acssuschemeng.0c03533

M3 - Article

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SN - 2168-0485

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SP - 12542

EP - 12553

JO - ACS Sustainable Chemistry and Engineering

JF - ACS Sustainable Chemistry and Engineering

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ER -

Investigation of a lignin-based deep eutectic solvent using p-hydroxybenzoic acid for efficient woody biomass conversion

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