Fast Fractionation of Technical Lignins by Organic Cosolvents
Abstract
A simple and fast fractionation method was developed to obtain carbohydrate-free lignin with well-defined characteristics, such as narrowly distributed molecular weights and a tunable chemical structure for specific applications. In this study, an industrial softwood kraft lignin and a hardwood CELF lignin (coproduct lignin obtained from cosolvent enhanced lignocellulosic fractionation pretreatment) were dissolved in acetone–methanol and tetrahydrofuran–methanol cosolvents, respectively. Hexane was applied as the antisolvent for sequential precipitation of both lignin preparations. A thorough characterization including various NMR techniques (31P, quantitative 13C, and 2D-HSQC), GPC, DSC and TGA was conducted to correlate the molecular weight of obtained lignin fractions with their structural features including distributions of aliphatic and phenolic hydroxyl groups and relative abundance of interunit linkages. It was found that approximately 10% of the softwood kraft lignin was lignin carbohydrate complexes, and the latter one could be removed efficiently by decreasing polarity of the cosolvent.
- Authors:
-
- Univ. of Tennessee, Knoxville, TN (United States)
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Univ. of California, Riverside, CA (United States)
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Univ. of Tennessee, Knoxville, TN (United States)
- Publication Date:
- Research Org.:
- Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Biological and Environmental Research (BER)
- OSTI Identifier:
- 1474537
- Grant/Contract Number:
- AC05-00OR22725
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ACS Sustainable Chemistry & Engineering
- Additional Journal Information:
- Journal Volume: 6; Journal Issue: 5; 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
Citation Formats
Wang, Yun-Yan, Li, Mi, Wyman, Charles E., Cai, Charles M., and Ragauskas, Arthur J. Fast Fractionation of Technical Lignins by Organic Cosolvents. United States: N. p., 2018.
Web. doi:10.1021/acssuschemeng.7b04546.
Wang, Yun-Yan, Li, Mi, Wyman, Charles E., Cai, Charles M., & Ragauskas, Arthur J. Fast Fractionation of Technical Lignins by Organic Cosolvents. United States. https://doi.org/10.1021/acssuschemeng.7b04546
Wang, Yun-Yan, Li, Mi, Wyman, Charles E., Cai, Charles M., and Ragauskas, Arthur J. Sun .
"Fast Fractionation of Technical Lignins by Organic Cosolvents". United States. https://doi.org/10.1021/acssuschemeng.7b04546. https://www.osti.gov/servlets/purl/1474537.
@article{osti_1474537,
title = {Fast Fractionation of Technical Lignins by Organic Cosolvents},
author = {Wang, Yun-Yan and Li, Mi and Wyman, Charles E. and Cai, Charles M. and Ragauskas, Arthur J.},
abstractNote = {A simple and fast fractionation method was developed to obtain carbohydrate-free lignin with well-defined characteristics, such as narrowly distributed molecular weights and a tunable chemical structure for specific applications. In this study, an industrial softwood kraft lignin and a hardwood CELF lignin (coproduct lignin obtained from cosolvent enhanced lignocellulosic fractionation pretreatment) were dissolved in acetone–methanol and tetrahydrofuran–methanol cosolvents, respectively. Hexane was applied as the antisolvent for sequential precipitation of both lignin preparations. A thorough characterization including various NMR techniques (31P, quantitative 13C, and 2D-HSQC), GPC, DSC and TGA was conducted to correlate the molecular weight of obtained lignin fractions with their structural features including distributions of aliphatic and phenolic hydroxyl groups and relative abundance of interunit linkages. It was found that approximately 10% of the softwood kraft lignin was lignin carbohydrate complexes, and the latter one could be removed efficiently by decreasing polarity of the cosolvent.},
doi = {10.1021/acssuschemeng.7b04546},
journal = {ACS Sustainable Chemistry & Engineering},
number = 5,
volume = 6,
place = {United States},
year = {Sun Mar 18 00:00:00 EDT 2018},
month = {Sun Mar 18 00:00:00 EDT 2018}
}
Web of Science
Works referenced in this record:
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
NMR Characterization of Pyrolysis Oils from Kraft Lignin
journal, May 2011
- Ben, Haoxi; Ragauskas, Arthur J.
- Energy & Fuels, Vol. 25, Issue 5
Engineering Plastics from Lignin. IX. Phenolic Resin Synthesis and Characterization
journal, September 1984
- Muller, Peter C.; Kelley, Stephen S.; Glasser, Wolfgang G.
- The Journal of Adhesion, Vol. 17, Issue 3
Engineering Plastics from Lignin. 22. Cure of Lignin Based Epoxy Resins
journal, May 1993
- Hofmann, Klaus; Glasser, Wolfgang G.
- The Journal of Adhesion, Vol. 40, Issue 2-4
Synthesis of Renewable Thermoset Polymers through Successive Lignin Modification Using Lignin-Derived Phenols
journal, April 2017
- Zhao, Shou; Abu-Omar, Mahdi M.
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 6
Green synthesis of flexible polyurethane foams from liquefied lignin
journal, June 2013
- Cinelli, Patrizia; Anguillesi, Irene; Lazzeri, Andrea
- European Polymer Journal, Vol. 49, Issue 6
Lignin-Based Rigid Polyurethane Foam Reinforced with Pulp Fiber: Synthesis and Characterization
journal, May 2014
- Xue, Bai-Liang; Wen, Jia-Long; Sun, Run-Cang
- ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 6
Production and properties of adhesives formulated from laccase modified Kraft lignin
journal, February 2013
- Ibrahim, Victor; Mamo, Gashaw; Gustafsson, Per-Johan
- Industrial Crops and Products, Vol. 45
Characterization and Optimization of the Glyoxalation of a Methanol-Fractionated Alkali Lignin using Response Surface Methodology
journal, May 2015
- Ang, Aikfei; Ashaari, Zaidon; Bakar, Edi Suhaimi
- BioResources, Vol. 10, Issue 3
Heat Treatment of Industrial Alkaline Lignin and its Potential Application as an Adhesive for Green Wood–Lignin Composites
journal, July 2017
- Zhang, Yun; Wu, Jian-Quan; Li, Hui
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 8
Effects of NCO:OH ratio on the mechanical properties and chemical structure of Kraft lignin–based polyurethane adhesive
journal, April 2016
- Nacas, A. M.; Ito, N. M.; Sousa, R. R. De
- The Journal of Adhesion, Vol. 93, Issue 1-2
Polyurethane Coatings Based on Chemically Unmodified Fractionated Lignin
journal, April 2015
- Griffini, Gianmarco; Passoni, Valeria; Suriano, Raffaella
- ACS Sustainable Chemistry & Engineering, Vol. 3, Issue 6
Path to plastics composed of ligninsulphonates (lignosulfonates)
journal, January 2015
- Wang, Yun-Yan; Chen, Yi-ru; Sarkanen, Simo
- Green Chemistry, Vol. 17, Issue 11
Blend configuration in functional polymeric materials with a high lignin content
journal, January 2017
- Wang, Yun-Yan; Chen, Yi-ru; Sarkanen, Simo
- Faraday Discussions, Vol. 202
Polyurethanes from Alcell® lignin fractions obtained by sequential solvent extraction
journal, May 1998
- Vanderlaan, M. N.; Thring, R. W.
- Biomass and Bioenergy, Vol. 14, Issue 5-6
Recent Industrial Applications of Lignin: A Sustainable Alternative to Nonrenewable Materials
journal, April 2002
- Lora, Jairo H.; Glasser, Wolfgang G.
- Journal of Polymers and the Environment, Vol. 10, Issue 1/2, p. 39-48
A new method for stabilizing softwood kraft lignin fibers for carbon fiber production
journal, October 2012
- Norberg, Ida; Nordström, Ylva; Drougge, Rickard
- Journal of Applied Polymer Science, Vol. 128, Issue 6
The behavior of kraft lignin during thermal treatment
journal, January 2010
- Brodin, Ida; Sjöholm, Elisabeth; Gellerstedt, Göran
- Journal of Analytical and Applied Pyrolysis, Vol. 87, Issue 1
Manufacture and application of lignin-based carbon fibers (LCFs) and lignin-based carbon nanofibers (LCNFs)
journal, January 2017
- Fang, Wei; Yang, Sheng; Wang, Xi-Luan
- Green Chemistry, Vol. 19, Issue 8
Fractionation of Industrial Softwood Kraft Lignin: Solvent Selection as a Tool for Tailored Material Properties
journal, February 2016
- Passoni, Valeria; Scarica, Carmela; Levi, Marinella
- ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 4
Fractionation of wheat straw Dioxane lignin reveals molar mass dependent structural differences
journal, November 2016
- Zikeli, Florian; Ters, Thomas; Fackler, Karin
- Industrial Crops and Products, Vol. 91
Purification of Biorefinery Lignin with Alcohols
journal, March 2016
- Cabrera, Yohanna; Cabrera, Andrés; Jensen, Anders
- Journal of Wood Chemistry and Technology, Vol. 36, Issue 5
Solvent screening for the fractionation of industrial kraft lignin
journal, January 2016
- Duval, Antoine; Vilaplana, Francisco; Crestini, Claudia
- Holzforschung, Vol. 70, Issue 1
Aqueous acetone fractionation of kraft, organosolv and soda lignins
journal, January 2018
- Domínguez-Robles, Juan; Tamminen, Tarja; Liitiä, Tiina
- International Journal of Biological Macromolecules, Vol. 106
Aqueous organic solvent fractionation as means to improve lignin homogeneity and purity
journal, September 2017
- Jääskeläinen, A. -S.; Liitiä, T.; Mikkelson, A.
- Industrial Crops and Products, Vol. 103
Fractionation and Characterization of Kraft Lignin by Sequential Precipitation with Various Organic Solvents
journal, December 2016
- Jiang, Xiao; Savithri, Dhanalekshmi; Du, Xueyu
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 1
Fractionation of Organosolv Lignin Using Acetone:Water and Properties of the Obtained Fractions
journal, November 2016
- Sadeghifar, Hasan; Wells, Tyrone; Le, Rosemary Khuu
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 1
Fractionation of Kraft Lignin by Successive Extraction with Organic Solvents. III. Fractionation of Kraft Lignin from Birch
journal, January 1988
- Mörck, Roland; Reimann, Anders; Kringstad, Knut P.
- Holzforschung, Vol. 42, Issue 2
Cosolvent pretreatment in cellulosic biofuel production: effect of tetrahydrofuran-water on lignin structure and dynamics
journal, January 2016
- Smith, Micholas Dean; Mostofian, Barmak; Cheng, Xiaolin
- Green Chemistry, Vol. 18, Issue 5
Application of quantitative 31P NMR in biomass lignin and biofuel precursors characterization
journal, January 2011
- Pu, Yunqiao; Cao, Shilin; Ragauskas, Arthur J.
- Energy & Environmental Science, Vol. 4, Issue 9
Effect of autohydrolysis pretreatment on biomass structure and the resulting bio-oil from a pyrolysis process
journal, October 2017
- Hao, Naijia; Bezerra, Tais Lacerda; Wu, Qiong
- Fuel, Vol. 206
Fractionation of bamboo culms by autohydrolysis, organosolv delignification and extended delignification: Understanding the fundamental chemistry of the lignin during the integrated process
journal, December 2013
- Wen, Jia-Long; Sun, Shao-Ni; Yuan, Tong-Qi
- Bioresource Technology, Vol. 150
Characterization and analysis of the molecular weight of lignin for biorefining studies
journal, June 2014
- Tolbert, Allison; Akinosho, Hannah; Khunsupat, Ratayakorn
- Biofuels, Bioproducts and Biorefining, Vol. 8, Issue 6
Alcell® lignin solubility in ethanol–water mixtures
journal, September 1995
- Ni, Y.; Hu, Q.
- Journal of Applied Polymer Science, Vol. 57, Issue 12
The Solvent Properties of Liquids and Their Relation to the Solubility, Swelling, Isolation and Fractionation of Lignin
journal, October 1952
- Schuerch, Conrad
- Journal of the American Chemical Society, Vol. 74, Issue 20
The Ultrastructure of Wood from a Solubility Parameter Point of View
journal, January 1998
- Hansen, C. M.; Björkman, A.
- Holzforschung, Vol. 52, Issue 4
Chemical aspects of kraft pulping
journal, January 1980
- Gierer, J.
- Wood Science and Technology, Vol. 14, Issue 4
Fractional Precipitation of Softwood Kraft Lignin: Isolation of Narrow Fractions Common to a Variety of Lignins
journal, February 2014
- Cui, Chengzhong; Sun, Runkun; Argyropoulos, Dimitris S.
- ACS Sustainable Chemistry & Engineering, Vol. 2, Issue 4
Universal fractionation of lignin-carbohydrate complexes (LCCs) from lignocellulosic biomass: an example using spruce wood
journal, March 2013
- Du, Xueyu; Gellerstedt, Goran; Li, Jiebing
- The Plant Journal, Vol. 74, Issue 2
Effects of delignification on residual lignin-carbohydrate complexes in normal pine wood and pine wood enriched in compression wood. 1. Kraft pulping
journal, August 2001
- Hortling, Bo; Tamminen, Tarja; Pekkala, Osmo
- Nordic Pulp & Paper Research Journal, Vol. 16, Issue 3
Lignin depolymerization/repolymerization and its critical role for delignification of aspen wood by steam explosion
journal, November 2007
- Li, Jiebing; Henriksson, Gunnar; Gellerstedt, Göran
- Bioresource Technology, Vol. 98, Issue 16
Quantitative Structures and Thermal Properties of Birch Lignins after Ionic Liquid Pretreatment
journal, January 2013
- Wen, Jia-Long; Sun, Shao-Long; Xue, Bai-Liang
- Journal of Agricultural and Food Chemistry, Vol. 61, Issue 3
Structural transformation of hemicelluloses and lignin from triploid poplar during acid-pretreatment based biorefinery process
journal, July 2012
- Wang, Kun; Yang, Haiyan; Yao, Xi
- Bioresource Technology, Vol. 116
Thermal degradation of polyurethanes containing lignin studied by TG-FTIR
journal, November 1998
- Hirose, Shigeo; Kobashigawa, Ken; Izuta, Yoshinobu
- Polymer International, Vol. 47, Issue 3
Synthesis and characterization of birch wood xylan succinoylated in 1-n-butyl-3-methylimidazolium chloride
journal, January 2011
- Hansen, Natanya M. L.; Plackett, David
- Polymer Chemistry, Vol. 2, Issue 9
Works referencing / citing this record:
A simple fractionation method and GPC analysis of organosolv extracts obtained from lignocellulosic materials
journal, January 2020
- Andreo-Martínez, Pedro; Ortiz-Martínez, Víctor Manuel; García-Martínez, Nuria
- Biomass Conversion and Biorefinery
Characterization of Lignin Extracted from Willow by Deep Eutectic Solvent Treatments
journal, August 2018
- Lyu, Gaojin; Li, Tengfei; Ji, Xingxiang
- Polymers, Vol. 10, Issue 8
Effect of Solvent, Role of Formic Acid and Rh/C Catalyst for the Efficient Liquefaction of Lignin
journal, August 2019
- Matsagar, Babasaheb M.; Wang, Zheng‐Yen; Sakdaronnarong, Chularat
- ChemCatChem, Vol. 11, Issue 18
Morphology of yellow passion fruit seedlings submitted to triazole induced growth inhibition
journal, January 2019
- Teixeira, Ednilson Carvalho; Matsumoto, Sylvana Naomi; Silva, Delmira da Costa
- Ciência e Agrotecnologia, Vol. 43
Using Fractionation and Diffusion Ordered Spectroscopy to Study Lignin Molecular Weight.
journal, April 2019
- Montgomery, James R. D.; Bazley, Priory; Lebl, Tomas
- ChemistryOpen, Vol. 8, Issue 5
Synthesis, Characterization, and Utilization of a Lignin-Based Adsorbent for Effective Removal of Azo Dye from Aqueous Solution
journal, February 2020
- Meng, Xianzhi; Scheidemantle, Brent; Li, Mi
- ACS Omega, Vol. 5, Issue 6
The Roles of H2O/Tetrahydrofuran System in Lignocellulose Valorization
journal, February 2020
- Li, Jianmei; Zhang, Wenyu; Xu, Shuguang
- Frontiers in Chemistry, Vol. 8
Characterization of Lignin Extracted from Willow by Deep Eutectic Solvent Treatments
journal, August 2018
- Lyu, Gaojin; Li, Tengfei; Ji, Xingxiang
- Polymers, Vol. 10, Issue 8