skip to main content
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Lignin extraction and upgrading using deep eutectic solvents

Abstract

Deep eutectic solvents (DESs) are a class of green solvents exhibiting low vapor pressure, high thermal stability,low toxicity, and biodegradability. These features make them attractive solvents for lignocellulosic biomassprocessing, especially for lignin valorization. DESs not only solubilize lignin from lignocellulose biomass, butalso confer extracted lignin with properties favorable to its further upgrading. This review summarizes recentadvances in biomass fractionation using DESs for lignin extraction. It also covers lignin upgrading in DESs interms of depolymerization and functionalization. The challenges of tailoring lignin properties by DESs for differentvalorization routes are also discussed.

Authors:
 [1]; ORCiD logo [2]; ORCiD logo [1]
  1. Univ. of Missouri, Columbia, MO (United States)
  2. Univ. of Tennessee, Knoxville, TN (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1649190
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
Industrial Crops and Products
Additional Journal Information:
Journal Volume: 147; Journal Issue: 112241; Journal ID: ISSN 0926-6690
Publisher:
Elsevier
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES

Citation Formats

Chen, Zhu, Ragauskas, Arthur, and Wan, Caixia. Lignin extraction and upgrading using deep eutectic solvents. United States: N. p., 2020. Web. https://doi.org/10.1016/j.indcrop.2020.112241.
Chen, Zhu, Ragauskas, Arthur, & Wan, Caixia. Lignin extraction and upgrading using deep eutectic solvents. United States. https://doi.org/10.1016/j.indcrop.2020.112241
Chen, Zhu, Ragauskas, Arthur, and Wan, Caixia. Fri . "Lignin extraction and upgrading using deep eutectic solvents". United States. https://doi.org/10.1016/j.indcrop.2020.112241. https://www.osti.gov/servlets/purl/1649190.
@article{osti_1649190,
title = {Lignin extraction and upgrading using deep eutectic solvents},
author = {Chen, Zhu and Ragauskas, Arthur and Wan, Caixia},
abstractNote = {Deep eutectic solvents (DESs) are a class of green solvents exhibiting low vapor pressure, high thermal stability,low toxicity, and biodegradability. These features make them attractive solvents for lignocellulosic biomassprocessing, especially for lignin valorization. DESs not only solubilize lignin from lignocellulose biomass, butalso confer extracted lignin with properties favorable to its further upgrading. This review summarizes recentadvances in biomass fractionation using DESs for lignin extraction. It also covers lignin upgrading in DESs interms of depolymerization and functionalization. The challenges of tailoring lignin properties by DESs for differentvalorization routes are also discussed.},
doi = {10.1016/j.indcrop.2020.112241},
journal = {Industrial Crops and Products},
number = 112241,
volume = 147,
place = {United States},
year = {2020},
month = {2}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 4 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Deep Eutectic Solvents Formed between Choline Chloride and Carboxylic Acids:  Versatile Alternatives to Ionic Liquids
journal, July 2004

  • Abbott, Andrew P.; Boothby, David; Capper, Glen
  • Journal of the American Chemical Society, Vol. 126, Issue 29
  • DOI: 10.1021/ja048266j

Glycerol eutectics as sustainable solvent systems
journal, January 2011

  • Abbott, Andrew P.; Harris, Robert C.; Ryder, Karl S.
  • Green Chem., Vol. 13, Issue 1
  • DOI: 10.1039/C0GC00395F

Brønsted acidity in deep eutectic solvents and ionic liquids
journal, January 2018

  • Abbott, Andrew P.; Alabdullah, Sahar S. M.; Al-Murshedi, Azhar Y. M.
  • Faraday Discussions, Vol. 206
  • DOI: 10.1039/C7FD00153C

Phenolic hydrogen bond donors in the formation of non-ionic deep eutectic solvents: the quest for type V DES
journal, January 2019

  • Abranches, Dinis O.; Martins, Mónia A. R.; Silva, Liliana P.
  • Chemical Communications, Vol. 55, Issue 69
  • DOI: 10.1039/C9CC04846D

Deep Eutectic Solvents: The Organic Reaction Medium of the Century
journal, January 2016

  • Alonso, Diego A.; Baeza, Alejandro; Chinchilla, Rafael
  • European Journal of Organic Chemistry, Vol. 2016, Issue 4
  • DOI: 10.1002/ejoc.201501197

Unique low-molecular-weight lignin with high purity extracted from wood by deep eutectic solvents (DES): a source of lignin for valorization
journal, January 2016

  • Alvarez-Vasco, Carlos; Ma, Ruoshui; Quintero, Melissa
  • Green Chemistry, Vol. 18, Issue 19
  • DOI: 10.1039/C6GC01007E

Fungal degradation of lignin-based rigid polyurethane foams
journal, October 2012


The use of lipases as biocatalysts for the epoxidation of fatty acids and phenolic compounds
journal, January 2014

  • Aouf, Chahinez; Durand, Erwann; Lecomte, Jérôme
  • Green Chem., Vol. 16, Issue 4
  • DOI: 10.1039/C3GC42143K

An economically viable ionic liquid for the fractionation of lignocellulosic biomass
journal, January 2017

  • Brandt-Talbot, Agnieszka; Gschwend, Florence J. V.; Fennell, Paul S.
  • Green Chemistry, Vol. 19, Issue 13
  • DOI: 10.1039/C7GC00705A

Deep eutectic solvent pretreatment enabling full utilization of switchgrass
journal, September 2018


High-purity lignin isolated from poplar wood meal through dissolving treatment with deep eutectic solvents
journal, January 2019

  • Chen, Yujie; Zhang, Lili; Yu, Juan
  • Royal Society Open Science, Vol. 6, Issue 1
  • DOI: 10.1098/rsos.181757

Ternary deep eutectic solvents for effective biomass deconstruction at high solids and low enzyme loadings
journal, May 2019


Chemicals from lignocellulosic biomass: opportunities, perspectives, and potential of biorefinery systems
journal, May 2011

  • Cherubini, Francesco; Strømman, Anders H.
  • Biofuels, Bioproducts and Biorefining, Vol. 5, Issue 5
  • DOI: 10.1002/bbb.297

Improved Lignin Polyurethane Properties with Lewis Acid Treatment
journal, May 2012

  • Chung, Hoyong; Washburn, Newell R.
  • ACS Applied Materials & Interfaces, Vol. 4, Issue 6
  • DOI: 10.1021/am300425x

Tailoring properties of natural deep eutectic solvents with water to facilitate their applications
journal, November 2015


Electrochemical depolymerisation of lignin in a deep eutectic solvent
journal, January 2016

  • Di Marino, Davide; Stöckmann, David; Kriescher, Stefanie
  • Green Chemistry, Vol. 18, Issue 22
  • DOI: 10.1039/C6GC01353H

Emulsion electro-oxidation of kraft lignin
journal, January 2017

  • Di Marino, Davide; Aniko, Vadim; Stocco, Antonio
  • Green Chemistry, Vol. 19, Issue 20
  • DOI: 10.1039/C7GC02115A

Evaluation of deep eutectic solvent–water binary mixtures for lipase-catalyzed lipophilization of phenolic acids
journal, January 2013

  • Durand, Erwann; Lecomte, Jérôme; Baréa, Bruno
  • Green Chemistry, Vol. 15, Issue 8
  • DOI: 10.1039/c3gc40899j

Carbohydrates-based deep eutectic solvents: Thermophysical properties and rice straw dissolution
journal, December 2017


New natural and renewable low transition temperature mixtures (LTTMs): screening as solvents for lignocellulosic biomass processing
journal, January 2012

  • Francisco, María; van den Bruinhorst, Adriaan; Kroon, Maaike C.
  • Green Chemistry, Vol. 14, Issue 8
  • DOI: 10.1039/c2gc35660k

Short-time deep eutectic solvent pretreatment for enhanced enzymatic saccharification and lignin valorization
journal, January 2019

  • Guo, Zongwei; Zhang, Qilin; You, Tingting
  • Green Chemistry, Vol. 21, Issue 11
  • DOI: 10.1039/C9GC00704K

Zinc-based deep eutectic solvent-mediated hydroxylation and demethoxylation of lignin for the production of wood adhesive
journal, January 2016

  • Hong, Shu; Lian, Hailan; Sun, Xiang
  • RSC Advances, Vol. 6, Issue 92
  • DOI: 10.1039/C6RA18290A

Insight into the structure-function relationships of deep eutectic solvents during rice straw pretreatment
journal, February 2018


Effect of constituents molar ratios of deep eutectic solvents on rice straw fractionation efficiency and the micro-mechanism investigation
journal, September 2018


Pseudo-lignin formation and its impact on enzymatic hydrolysis
journal, August 2012


Low-melting sugar–urea–salt mixtures as solvents for Diels–Alder reactions
journal, January 2005

  • Imperato, Giovanni; Eibler, Ernst; Niedermaier, Julia
  • Chem. Commun., Issue 9
  • DOI: 10.1039/B414515A

Low melting sugar–urea–salt mixtures as solvents for organic reactions—estimation of polarity and use in catalysis
journal, January 2006

  • Imperato, Giovanni; Höger, Silke; Lenoir, Dieter
  • Green Chem., Vol. 8, Issue 12
  • DOI: 10.1039/B603660K

Replacing 100% of phenol in phenolic adhesive formulations with lignin: ARTICLE
journal, April 2017

  • Kalami, Somayyeh; Arefmanesh, Maryam; Master, Emma
  • Journal of Applied Polymer Science, Vol. 134, Issue 30
  • DOI: 10.1002/app.45124

Bioprocessing of bio-based chemicals produced from lignocellulosic feedstocks
journal, December 2016


Biomass pretreatment using deep eutectic solvents from lignin derived phenols
journal, January 2018

  • Kim, Kwang Ho; Dutta, Tanmoy; Sun, Jian
  • Green Chemistry, Vol. 20, Issue 4
  • DOI: 10.1039/C7GC03029K

Natural deep eutectic solvent mediated pretreatment of rice straw: bioanalytical characterization of lignin extract and enzymatic hydrolysis of pretreated biomass residue
journal, June 2015

  • Kumar, Adepu K.; Parikh, Bhumika S.; Pravakar, Mohanty
  • Environmental Science and Pollution Research, Vol. 23, Issue 10
  • DOI: 10.1007/s11356-015-4780-4

Technical assessment of natural deep eutectic solvent (NADES) mediated biorefinery process: A case study
journal, June 2018


Protection Group Effects During α,γ-Diol Lignin Stabilization Promote High-Selectivity Monomer Production
journal, January 2018

  • Lan, Wu; Amiri, Masoud Talebi; Hunston, Christopher M.
  • Angewandte Chemie International Edition, Vol. 57, Issue 5
  • DOI: 10.1002/anie.201710838

Furfural: A Promising Platform Compound for Sustainable Production of C 4 and C 5 Chemicals
journal, October 2016


Fractionation and characterization of lignin streams from unique high-lignin content endocarp feedstocks
journal, November 2018


Processing of lignin in urea–zinc chloride deep-eutectic solvent and its use as a filler in a phenol-formaldehyde resin
journal, January 2015


A simple process for lignin nanoparticle preparation
journal, January 2016

  • Lievonen, Miikka; Valle-Delgado, Juan José; Mattinen, Maija-Liisa
  • Green Chemistry, Vol. 18, Issue 5
  • DOI: 10.1039/C5GC01436K

Deep eutectic solvents’ ability to solubilize lignin, cellulose, and hemicellulose; thermal stability; and density
journal, August 2017


Characterization of Lignin Extracted from Willow by Deep Eutectic Solvent Treatments
journal, August 2018


Physicochemical transformation of rice straw after pretreatment with a deep eutectic solvent of choline chloride/urea
journal, November 2017


Structure-property relationships for technical lignins for the production of lignin-phenol-formaldehyde resins
journal, December 2017


Predicting lignin depolymerization yields from quantifiable properties using fractionated biorefinery lignins
journal, January 2017

  • Phongpreecha, Thanaphong; Hool, Nicholas C.; Stoklosa, Ryan J.
  • Green Chem., Vol. 19, Issue 21
  • DOI: 10.1039/C7GC02023F

Deep eutectic solvent pretreatment and subsequent saccharification of corncob
journal, September 2015


Lignin Valorization: Improving Lignin Processing in the Biorefinery
journal, May 2014

  • Ragauskas, A. J.; Beckham, G. T.; Biddy, M. J.
  • Science, Vol. 344, Issue 6185, p. 1246843-1246843
  • DOI: 10.1126/science.1246843

Pseudo-lignin and pretreatment chemistry
journal, January 2011

  • Sannigrahi, Poulomi; Kim, Dong Ho; Jung, Seokwon
  • Energy Environ. Sci., Vol. 4, Issue 4
  • DOI: 10.1039/C0EE00378F

Lignin fate and characterization during ionic liquid biomass pretreatment for renewable chemicals and fuels production
journal, January 2014

  • Sathitsuksanoh, Noppadon; Holtman, Kevin M.; Yelle, Daniel J.
  • Green Chem., Vol. 16, Issue 3
  • DOI: 10.1039/C3GC42295J

Assessing the Facile Pretreatments of Bagasse for Efficient Enzymatic Conversion and Their Impacts on Structural and Chemical Properties
journal, November 2018


Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading
journal, January 2018

  • Schutyser, W.; Renders, T.; Van den Bosch, S.
  • Chemical Society Reviews, Vol. 47, Issue 3
  • DOI: 10.1039/C7CS00566K

Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization
journal, October 2016

  • Shuai, Li; Amiri, Masoud Talebi; Questell-Santiago, Ydna M.
  • Science, Vol. 354, Issue 6310
  • DOI: 10.1126/science.aaf7810

Enhanced Solubility of Lignin Monomeric Model Compounds and Technical Lignins in Aqueous Solutions of Deep Eutectic Solvents
journal, March 2017

  • Soares, Belinda; Tavares, Daniel J. P.; Amaral, José Luis
  • ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 5
  • DOI: 10.1021/acssuschemeng.7b00053

Controlled depolymerization of lignin in an electrochemical membrane reactor
journal, December 2015


Bright Side of Lignin Depolymerization: Toward New Platform Chemicals
journal, January 2018


Evaluation of fractionation and delignification efficiencies of deep eutectic solvents on oil palm empty fruit bunch
journal, November 2018


Green Processing of Lignocellulosic Biomass and Its Derivatives in Deep Eutectic Solvents
journal, May 2017


Solvatochromic parameters of deep eutectic solvents formed by ammonium-based salts and carboxylic acids
journal, September 2017


Contribution of Deep Eutectic Solvents for Biomass Processing: Opportunities, Challenges, and Limitations
journal, March 2015

  • Vigier, Karine De Oliveira; Chatel, Gregory; Jérôme, François
  • ChemCatChem, Vol. 7, Issue 8
  • DOI: 10.1002/cctc.201500134

Multiple hydrogen bond coordination in three-constituent deep eutectic solvents enhances lignin fractionation from biomass
journal, January 2018

  • Xia, Qinqin; Liu, Yongzhuang; Meng, Juan
  • Green Chemistry, Vol. 20, Issue 12
  • DOI: 10.1039/C8GC00900G

Enhancing cellulose accessibility of corn stover by deep eutectic solvent pretreatment for butanol fermentation
journal, March 2016


Biocompatible Choline-Based Deep Eutectic Solvents Enable One-Pot Production of Cellulosic Ethanol
journal, May 2018


Deep eutectic solvents from hemicellulose-derived acids for the cellulosic ethanol refining of Akebia’ herbal residues
journal, January 2018


Deep eutectic solvents for polysaccharides processing. A review
journal, November 2018


Facile pretreatment of lignocellulosic biomass using deep eutectic solvents
journal, November 2016


Organosolv fractionating pre‐treatment of lignocellulosic biomass for efficient enzymatic saccharification: chemistry, kinetics, and substrate structures
journal, February 2017

  • Zhao, Xuebing; Li, Siming; Wu, Ruchun
  • Biofuels, Bioproducts and Biorefining, Vol. 11, Issue 3
  • DOI: 10.1002/bbb.1768

Pretreatment of wheat straw using basic ethanolamine-based deep eutectic solvents for improving enzymatic hydrolysis
journal, September 2018