Effective biomass fractionation and lignin stabilization using a diol DES system

Cheng, Jinyuan; Huang, Chen; Zhan, Yunni; Han, Shanming; Wang, Jia; Meng, Xianzhi; Yoo, Chang Geun; Fang, Guigan; Ragauskas, Arthur J.

doi:10.1016/j.cej.2022.136395

Effective biomass fractionation and lignin stabilization using a diol DES system

Journal Article · Sat Apr 16 04:00:00 EDT 2022 · Chemical Engineering Journal

DOI:https://doi.org/10.1016/j.cej.2022.136395· OSTI ID:1867769

Cheng, Jinyuan ^[1]; Huang, Chen ^[2]; Zhan, Yunni ^[1]; Han, Shanming ^[1]; Wang, Jia ^[3]; Meng, Xianzhi ^[4]; Yoo, Chang Geun ^[5]; Fang, Guigan ^[6]; Ragauskas, Arthur J. ^[7]

Chinese Academy of Forestry, Nanjing (China)
Chinese Academy of Forestry, Nanjing (China); Nanjing Forestry Univ. (China); Univ. of Tennessee, Knoxville, TN (United States)
Nanjing Forestry Univ. (China)
Univ. of Tennessee, Knoxville, TN (United States)
State Univ. of New York (SUNY), Syracuse, NY (United States)
Chinese Academy of Forestry, Nanjing (China); Nanjing Forestry Univ. (China)
Univ. of Tennessee, Knoxville, TN (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

A sustainable and renewable biorefinery will increase the economic viability of lignocellulose-derived products. In this study, a diol-based deep eutectic solvent (DES) was developed to reduce the recalcitrance of bamboo, facilitate saccharification and valorize the lignin fraction. The DES pretreatment dramatically enhanced glucan digestibility by the effective removal of lignin (as high as 85.45%) and xylan (91.12%). Notably, the recovered lignin from DES pretreatment was protected during the fractionation, showing well-preserved β-O-4 structures (31.82%–59.06%). The mechanism of lignin protection was analyzed to be accomplished by incorporating the diol hydroxyl functional groups into the α position of the lignin β-O-4 structure via etherification. This work highlighted that diol DES is a promising pretreatment solvent to valorize both cellulose and lignin fractions with high enzymatic hydrolysis yield and high-quality lignin co-product.

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE; Jiangsu Province Key Laboratory of Biomass Energy and Materials; National Natural Science Foundation of China (NSFC)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1867769

Journal Information:: Chemical Engineering Journal, Journal Name: Chemical Engineering Journal Journal Issue: 1 Vol. 443; ISSN 1385-8947

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (46)

Domino Reaction Catalyzed by Zeolites with Brønsted and Lewis Acid Sites for the Production of γ-Valerolactone from Furfural Bui, Linh; Luo, Helen; Gunther, William R. Angewandte Chemie, Vol. 125, Issue 31 https://doi.org/10.1002/ange.201302575	journal	June 2013
Protection Group Effects During α,γ-Diol Lignin Stabilization Promote High-Selectivity Monomer Production Lan, Wu; Amiri, Masoud Talebi; Hunston, Christopher M. Angewandte Chemie International Edition, Vol. 57, Issue 5 https://doi.org/10.1002/anie.201710838	journal	January 2018
Product‐oriented Direct Cleavage of Chemical Linkages in Lignin Shen, Xiaojun; Xin, Yu; Liu, Huizhen ChemSusChem, Vol. 13, Issue 17 https://doi.org/10.1002/cssc.202001025	journal	June 2020
Effect of functional groups in acid constituent of deep eutectic solvent for extraction of reactive lignin Tan, Yee Tong; Ngoh, Gek Cheng; Chua, Adeline Seak May Bioresource Technology, Vol. 281 https://doi.org/10.1016/j.biortech.2019.02.010	journal	June 2019
Deconstruction of oriented crystalline cellulose by novel levulinic acid based deep eutectic solvents pretreatment for improved enzymatic accessibility Ling, Zhe; Guo, Zongwei; Huang, Caoxing Bioresource Technology, Vol. 305 https://doi.org/10.1016/j.biortech.2020.123025	journal	June 2020
Novel betaine-amino acid based natural deep eutectic solvents for enhancing the enzymatic hydrolysis of corncob Liang, Yuan; Duan, Wenjing; An, Xiaoxi Bioresource Technology, Vol. 310 https://doi.org/10.1016/j.biortech.2020.123389	journal	August 2020
Aqueous solutions of deep eutectic systems as reaction media for the saccharification and fermentation of hardwood xylan into xylitol Romaní, Aloia; Morais, Eduarda S.; Soares, Pedro O. Bioresource Technology, Vol. 311 https://doi.org/10.1016/j.biortech.2020.123524	journal	September 2020
Mild fractionation of sugarcane bagasse into fermentable sugars and β-O-4 linkage-rich lignin based on acid-catalysed crude glycerol pretreatment Hassanpour, Morteza; Abbasabadi, Mahsa; Moghaddam, Lalehvash Bioresource Technology, Vol. 318 https://doi.org/10.1016/j.biortech.2020.124059	journal	December 2020
Design of experiments driven optimization of alkaline pretreatment and saccharification for sugarcane bagasse Mota, Thatiane R.; Oliveira, Dyoni M.; Simister, Rachael Bioresource Technology, Vol. 321 https://doi.org/10.1016/j.biortech.2020.124499	journal	February 2021
Features correlated to improved enzymatic digestibility of corn stover subjected to alkaline hydrogen peroxide pretreatment Yang, Li; Ru, Yue; Xu, Shuai Bioresource Technology, Vol. 325 https://doi.org/10.1016/j.biortech.2021.124688	journal	April 2021
Facilitating enzymatic hydrolysis with a novel guaiacol-based deep eutectic solvent pretreatment Huang, Chen; Zhan, Yunni; Cheng, Jinyuan Bioresource Technology, Vol. 326 https://doi.org/10.1016/j.biortech.2021.124696	journal	April 2021
Novel dihydrogen-bonding deep eutectic solvents: Pretreatment of rice straw for butanol fermentation featuring enzyme recycling and high solvent yield Xing, Wanru; Xu, Guochao; Dong, Jinjun Chemical Engineering Journal, Vol. 333 https://doi.org/10.1016/j.cej.2017.09.176	journal	February 2018
Pretreatments for the continuous production of pyrolytic sugar from lignocellulosic biomass Rollag, Sean A.; Lindstrom, Jake K.; Brown, Robert C. Chemical Engineering Journal, Vol. 385 https://doi.org/10.1016/j.cej.2019.123889	journal	April 2020
Bifunctional porous polyethyleneimine-grafted lignin microspheres for efficient adsorption of 2,4-dichlorophenoxyacetic acid over a wide pH range and controlled release Wu, Hongye; Gong, Lang; Zhang, Xin Chemical Engineering Journal, Vol. 411 https://doi.org/10.1016/j.cej.2021.128539	journal	May 2021
High-solid ethylenediamine pretreatment to fractionate new lignin streams from lignocellulosic biomass Xu, Li; Zhang, Jiayin; Zong, Qiu-Jin Chemical Engineering Journal, Vol. 427 https://doi.org/10.1016/j.cej.2021.130962	journal	January 2022
Unmasking the structural features and property of lignin from bamboo Wen, Jia-Long; Xue, Bai-Liang; Xu, Feng Industrial Crops and Products, Vol. 42 https://doi.org/10.1016/j.indcrop.2012.05.041	journal	March 2013
Wood delignification with aqueous solutions of deep eutectic solvents Soares, Belinda; da Costa Lopes, André M.; Silvestre, Armando J. D. Industrial Crops and Products, Vol. 160 https://doi.org/10.1016/j.indcrop.2020.113128	journal	February 2021
Study on the pyrolysis mechanism of three guaiacyl-type lignin monomeric model compounds Liu, Chao; Deng, Yubin; Wu, Shubin Journal of Analytical and Applied Pyrolysis, Vol. 118 https://doi.org/10.1016/j.jaap.2016.01.007	journal	March 2016
Dehydration of d-glucose in high temperature water at pressures up to 80MPa Aida, Taku Michael; Sato, Yukiko; Watanabe, Masaru The Journal of Supercritical Fluids, Vol. 40, Issue 3 https://doi.org/10.1016/j.supflu.2006.07.027	journal	April 2007
Alkali-Based Pretreatment-Facilitated Lignin Valorization: A Review Xu, Li; Zhang, Sen-Jia; Zhong, Cheng Industrial & Engineering Chemistry Research, Vol. 59, Issue 39 https://doi.org/10.1021/acs.iecr.0c01456	journal	May 2020
Increasing the Carbohydrate Output of Bamboo Using a Combinatorial Pretreatment Huang, Chen; Fang, Guigan; Zhou, Yang ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 19 https://doi.org/10.1021/acssuschemeng.0c01126	journal	May 2020
Insights into Structural Changes of Lignin toward Tailored Properties during Deep Eutectic Solvent Pretreatment Chen, Zhu; Bai, Xianglan; A., Lusi ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 26 https://doi.org/10.1021/acssuschemeng.0c01361	journal	June 2020
On-Demand Regulation of Lignocellulosic Nanofibrils Based on Rapid Fractionation Using Acid Hydrotrope: Kinetic Study and Characterization Bian, Huiyang; Dong, Maolin; Chen, Lidong ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 25 https://doi.org/10.1021/acssuschemeng.0c02968	journal	June 2020
Investigation of a Lignin-Based Deep Eutectic Solvent Using p -Hydroxybenzoic Acid for Efficient Woody Biomass Conversion Wang, Yunxuan; Meng, Xianzhi; Jeong, Keunhong ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 33 https://doi.org/10.1021/acssuschemeng.0c03533	journal	August 2020
Improving Enzymatic Saccharification and Ethanol Production from Hardwood by Deacetylation and Steam Pretreatment: Insight into Mitigating Lignin Inhibition Chu, Qiulu; Wang, Rui; Tong, Wenyao ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 49 https://doi.org/10.1021/acssuschemeng.0c05583	journal	December 2020
Kraft Lignin Solubility and Its Chemical Modification in Deep Eutectic Solvents Sosa, Filipe H. B.; Abranches, Dinis O.; da Costa Lopes, André M. ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 50 https://doi.org/10.1021/acssuschemeng.0c06655	journal	December 2020
Lignin: A Review on Structure, Properties, and Applications as a Light-Colored UV Absorber Zhang, Yi; Naebe, Maryam ACS Sustainable Chemistry & Engineering, Vol. 9, Issue 4 https://doi.org/10.1021/acssuschemeng.0c06998	journal	January 2021
Alkaline Peroxide Delignification of Corn Stover Mittal, Ashutosh; Katahira, Rui; Donohoe, Bryon S. ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 7 https://doi.org/10.1021/acssuschemeng.7b01424	journal	June 2017
Aqueous Choline Chloride: A Novel Solvent for Switchgrass Fractionation and Subsequent Hemicellulose Conversion into Furfural Chen, Zhu; Reznicek, Wesley D.; Wan, Caixia ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 5 https://doi.org/10.1021/acssuschemeng.8b00728	journal	April 2018
Structural and Morphological Transformations of Lignin Macromolecules during Bio-Based Deep Eutectic Solvent (DES) Pretreatment Shen, Xiao-Jun; Chen, Tianying; Wang, Han-Min ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 5 https://doi.org/10.1021/acssuschemeng.9b05106	journal	December 2019
Lewis Acid-Facilitated Deep Eutectic Solvent (DES) Pretreatment for Producing High-Purity and Antioxidative Lignin Wang, Zhi-Kun; Hong, Si; Wen, Jia-long ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 2 https://doi.org/10.1021/acssuschemeng.9b05846	journal	December 2019
Structural Elucidation of Lignin Polymers of Eucalyptus Chips during Organosolv Pretreatment and Extended Delignification Wen, Jia-Long; Sun, Shao-Long; Yuan, Tong-Qi Journal of Agricultural and Food Chemistry, Vol. 61, Issue 46 https://doi.org/10.1021/jf403717q	journal	November 2013
Structural elucidation of whole lignin from Eucalyptus based on preswelling and enzymatic hydrolysis Wen, Jia-Long; Sun, Shao-Long; Yuan, Tong-Qi Green Chemistry, Vol. 17, Issue 3 https://doi.org/10.1039/C4GC01889C	journal	January 2015
Pre-treatment of lignocellulosic feedstocks using biorenewable alcohols: towards complete biomass valorisation Lancefield, Christopher S.; Panovic, Isabella; Deuss, Peter J. Green Chemistry, Vol. 19, Issue 1 https://doi.org/10.1039/C6GC02739C	journal	January 2017
Biomass pretreatment using deep eutectic solvents from lignin derived phenols Kim, Kwang Ho; Dutta, Tanmoy; Sun, Jian Green Chemistry, Vol. 20, Issue 4 https://doi.org/10.1039/C7GC03029K	journal	January 2018
Multiple hydrogen bond coordination in three-constituent deep eutectic solvents enhances lignin fractionation from biomass Xia, Qinqin; Liu, Yongzhuang; Meng, Juan Green Chemistry, Vol. 20, Issue 12 https://doi.org/10.1039/C8GC00900G	journal	January 2018
Facile fractionation of lignocelluloses by biomass-derived deep eutectic solvent (DES) pretreatment for cellulose enzymatic hydrolysis and lignin valorization Shen, Xiao-Jun; Wen, Jia-Long; Mei, Qing-Qing Green Chemistry, Vol. 21, Issue 2 https://doi.org/10.1039/C8GC03064B	journal	January 2019
Diol pretreatment to fractionate a reactive lignin in lignocellulosic biomass biorefineries Dong, Chengyu; Meng, Xianzhi; Yeung, Chi Shun Green Chemistry, Vol. 21, Issue 10 https://doi.org/10.1039/C9GC00596J	journal	January 2019
High-strength cellulose nanofibers produced via swelling pretreatment based on a choline chloride–imidazole deep eutectic solvent Sirviö, Juho Antti; Hyypiö, Kalle; Asaadi, Shirin Green Chemistry, Vol. 22, Issue 5 https://doi.org/10.1039/C9GC04119B	journal	January 2020
Maleic acid as a dicarboxylic acid hydrotrope for sustainable fractionation of wood at atmospheric pressure and ≤100 °C: mode and utility of lignin esterification Cai, Cheng; Hirth, Kolby; Gleisner, Rolland Green Chemistry, Vol. 22, Issue 5 https://doi.org/10.1039/C9GC04267A	journal	January 2020
The fractionation of woody biomass under mild conditions using bifunctional phenol-4-sulfonic acid as a catalyst and lignin solvent He, Duo; Wang, Yunxuan; Yoo, Chang Geun Green Chemistry, Vol. 22, Issue 16 https://doi.org/10.1039/D0GC01722A	journal	January 2020
Structure–function relationships of deep eutectic solvents for lignin extraction and chemical transformation Hong, Si; Shen, Xiao-Jun; Xue, Zhimin Green Chemistry, Vol. 22, Issue 21 https://doi.org/10.1039/D0GC02439B	journal	January 2020
Understanding lignin micro- and nanoparticle nucleation and growth in aqueous suspensions by solvent fractionation Zwilling, Jacob D.; Jiang, Xiao; Zambrano, Franklin Green Chemistry, Vol. 23, Issue 2 https://doi.org/10.1039/D0GC03632C	journal	January 2021
Elucidating the mechanisms of enhanced lignin bioconversion by an alkali sterilization strategy Zhao, Zhi-Min; Zhang, Shuyang; Meng, Xianzhi Green Chemistry, Vol. 23, Issue 13 https://doi.org/10.1039/D1GC00911G	journal	January 2021
Conversion of Sugars to Lactic Acid Derivatives Using Heterogeneous Zeotype Catalysts Holm, Martin Spangsberg; Saravanamurugan, Shunmugavel; Taarning, Esben Science, Vol. 328, Issue 5978, p. 602-605 https://doi.org/10.1126/science.1183990	journal	April 2010
Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization Shuai, Li; Amiri, Masoud Talebi; Questell-Santiago, Ydna M. Science, Vol. 354, Issue 6310 https://doi.org/10.1126/science.aaf7810	journal	October 2016

Similar Records

Efficient Fast Fractionation of Biomass Using a Diol-Based Deep Eutectic Solvent for Facilitating Enzymatic Hydrolysis and Obtaining High-Quality Lignin

Journal Article · Tue Dec 19 23:00:00 EST 2023 · ChemSusChem · OSTI ID:2376315

Investigation of the alkaline hydrogen peroxide pretreatment: From cellulose saccharification to lignin isolation

Journal Article · Thu Apr 18 00:00:00 EDT 2024 · Industrial Crops and Products · OSTI ID:2406724

A high-solid DES pretreatment using never-dried biomass as the starting material: towards high-quality lignin fractionation

Journal Article · Mon Jan 09 23:00:00 EST 2023 · Green Chemistry · OSTI ID:1928910

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
delignification
diol DES
lignin protection
lignin valorization

Effective biomass fractionation and lignin stabilization using a diol DES system

Citation Formats

References (46)

Similar Records

Related Subjects