New catalytic strategies for α,ω-diols production from lignocellulosic biomass
Abstract
Catalytic strategies for the synthesis of 1,5-pentanediol (PDO) with 69% yield from hemicellulose and the synthesis of 1,6-hexanediol (HDO) with 28% yield from cellulose are presented. Fractionation of lignocellulosic biomass (white birch wood chips) in gamma-valerolactone (GVL)/H2O generates a pure cellulose solid and a liquid stream containing hemicellulose and lignin, which is further dehydrated to furfural with 85% yield. Furfural is converted to PDO with sequential dehydration, hydration, ring-opening tautomerization, and hydrogenation reactions. Acid-catalyzed cellulose dehydration in tetrahydrofuran (THF)/H2O produces a mixture of levoglucosenone (LGO) and 5-hydroxymethylfurfural (HMF), which are converted with hydrogen to tetrahydrofuran-dimethanol (THFDM). HDO is then obtained from hydrogenolysis of THFDM. Techno-economic analysis demonstrates that this approach can produce HDO and PDO at a minimum selling price of $4090 per ton.
- Authors:
-
- Department of Chemical and Biological Engineering; University of Wisconsin-Madison; Madison; USA
- Department of Chemical and Biological Engineering; University of Wisconsin-Madison; Madison; USA; Department of Chemistry
- Publication Date:
- Research Org.:
- Univ. of Wisconsin, Madison, WI (United States)
- Sponsoring Org.:
- USDOE Office of Energy Efficiency and Renewable Energy (EERE)
- OSTI Identifier:
- 1535229
- DOE Contract Number:
- EE0006878
- Resource Type:
- Journal Article
- Journal Name:
- Faraday Discussions
- Additional Journal Information:
- Journal Volume: 202; Journal ID: ISSN 1359-6640
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- Chemistry
Citation Formats
He, Jiayue, Huang, Kefeng, Barnett, Kevin J., Krishna, Siddarth H., Alonso, David M., Brentzel, Zachary J., Burt, Samuel P., Walker, Theodore, Banholzer, Williams F., Maravelias, Christos T., Hermans, Ive, Dumesic, James A., and Huber, George W. New catalytic strategies for α,ω-diols production from lignocellulosic biomass. United States: N. p., 2017.
Web. doi:10.1039/c7fd00036g.
He, Jiayue, Huang, Kefeng, Barnett, Kevin J., Krishna, Siddarth H., Alonso, David M., Brentzel, Zachary J., Burt, Samuel P., Walker, Theodore, Banholzer, Williams F., Maravelias, Christos T., Hermans, Ive, Dumesic, James A., & Huber, George W. New catalytic strategies for α,ω-diols production from lignocellulosic biomass. United States. https://doi.org/10.1039/c7fd00036g
He, Jiayue, Huang, Kefeng, Barnett, Kevin J., Krishna, Siddarth H., Alonso, David M., Brentzel, Zachary J., Burt, Samuel P., Walker, Theodore, Banholzer, Williams F., Maravelias, Christos T., Hermans, Ive, Dumesic, James A., and Huber, George W. 2017.
"New catalytic strategies for α,ω-diols production from lignocellulosic biomass". United States. https://doi.org/10.1039/c7fd00036g.
@article{osti_1535229,
title = {New catalytic strategies for α,ω-diols production from lignocellulosic biomass},
author = {He, Jiayue and Huang, Kefeng and Barnett, Kevin J. and Krishna, Siddarth H. and Alonso, David M. and Brentzel, Zachary J. and Burt, Samuel P. and Walker, Theodore and Banholzer, Williams F. and Maravelias, Christos T. and Hermans, Ive and Dumesic, James A. and Huber, George W.},
abstractNote = {Catalytic strategies for the synthesis of 1,5-pentanediol (PDO) with 69% yield from hemicellulose and the synthesis of 1,6-hexanediol (HDO) with 28% yield from cellulose are presented. Fractionation of lignocellulosic biomass (white birch wood chips) in gamma-valerolactone (GVL)/H2O generates a pure cellulose solid and a liquid stream containing hemicellulose and lignin, which is further dehydrated to furfural with 85% yield. Furfural is converted to PDO with sequential dehydration, hydration, ring-opening tautomerization, and hydrogenation reactions. Acid-catalyzed cellulose dehydration in tetrahydrofuran (THF)/H2O produces a mixture of levoglucosenone (LGO) and 5-hydroxymethylfurfural (HMF), which are converted with hydrogen to tetrahydrofuran-dimethanol (THFDM). HDO is then obtained from hydrogenolysis of THFDM. Techno-economic analysis demonstrates that this approach can produce HDO and PDO at a minimum selling price of $4090 per ton.},
doi = {10.1039/c7fd00036g},
url = {https://www.osti.gov/biblio/1535229},
journal = {Faraday Discussions},
issn = {1359-6640},
number = ,
volume = 202,
place = {United States},
year = {Sun Jan 01 00:00:00 EST 2017},
month = {Sun Jan 01 00:00:00 EST 2017}
}
Works referenced in this record:
Central effects of 1,4-butanediol are mediated by GABAB receptors via its conversion into γ-hydroxybutyric acid
journal, April 2002
- Carai, Mauro A. M.; Colombo, Giancarlo; Reali, Roberta
- European Journal of Pharmacology, Vol. 441, Issue 3
In vivo conversion of γ-aminobutyric acid and 1,4-butanediol to γ-hydroxybutyric acid in rat brain
journal, December 1989
- Snead, O. Carter; Furner, Raymond
- Biochemical Pharmacology, Vol. 38, Issue 24
Review: The involvement of gamma-hydroxybutyrate in reported sexual assaults: a systematic review
journal, May 2010
- Németh, Zsófia; Kun, Bernadette; Demetrovics, Zsolt
- Journal of Psychopharmacology, Vol. 24, Issue 9
Emerging catalytic processes for the production of adipic acid
journal, January 2013
- Van de Vyver, Stijn; Román-Leshkov, Yuriy
- Catalysis Science & Technology, Vol. 3, Issue 6, p. 1465-1479
Potential Analysis of Smart Flow Processing and Micro Process Technology for Fastening Process Development: Use of Chemistry and Process Design as Intensification Fields
journal, June 2012
- Hessel, V.; Vural Gürsel, I.; Wang, Q.
- Chemical Engineering & Technology, Vol. 35, Issue 7
Aerobic Alcohol Oxidations Mediated by Nitric Acid
journal, October 2011
- Aellig, Christof; Girard, Christophe; Hermans, Ive
- Angewandte Chemie International Edition, Vol. 50, Issue 51
Acid-Catalyzed Decomposition of the Benzyl Nitrite Intermediate in HNO3-Mediated Aerobic Oxidation of Benzyl Alcohol
journal, February 2012
- Aellig, Christof; Neuenschwander, Ulrich; Hermans, Ive
- ChemCatChem, Vol. 4, Issue 4, p. 525-529
Continuous D-Fructose Dehydration to 5- Hydroxymethylfurfural Under Mild Conditions
journal, July 2012
- Aellig, Christof; Hermans, Ive
- ChemSusChem, Vol. 5, Issue 9
Kinetics and mechanism of hydrogenation of furfural on Cu/SiO2 catalysts
journal, January 2011
- Sitthisa, Surapas; Sooknoi, Tawan; Ma, Yuguang
- Journal of Catalysis, Vol. 277, Issue 1
Total Hydrogenation of Furfural over a Silica‐Supported Nickel Catalyst Prepared by the Reduction of a Nickel Nitrate Precursor
journal, July 2012
- Nakagawa, Yoshinao; Nakazawa, Hiroya; Watanabe, Hideo
- ChemCatChem, Vol. 4, Issue 11
Vapor phase hydrogenation of furfural over nickel mixed metal oxide catalysts derived from layered double hydroxides
journal, May 2016
- Sulmonetti, Taylor P.; Pang, Simon H.; Claure, Micaela Taborga
- Applied Catalysis A: General, Vol. 517
Promoting effect of Mo on the hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol over Rh/SiO2
journal, October 2009
- Koso, Shuichi; Ueda, Naoyuki; Shinmi, Yasunori
- Journal of Catalysis, Vol. 267, Issue 1
Catalytic Conversions of Furfural to Pentanediols
journal, August 2015
- Nakagawa, Yoshinao; Tamura, Masazumi; Tomishige, Keiichi
- Catalysis Surveys from Asia, Vol. 19, Issue 4
Chemoselective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol
journal, January 2009
- Koso, Shuichi; Furikado, Ippei; Shimao, Akira
- Chemical Communications, Issue 15
Bimetallic RhRe/C catalysts for the production of biomass-derived chemicals
journal, December 2013
- Chia, Mei; O’Neill, Brandon J.; Alamillo, Ricardo
- Journal of Catalysis, Vol. 308
Production of 1,5-pentanediol from biomass via furfural and tetrahydrofurfuryl alcohol
journal, November 2012
- Nakagawa, Yoshinao; Tomishige, Keiichi
- Catalysis Today, Vol. 195, Issue 1
C–O bond hydrogenolysis of cyclic ethers with OH groups over rhenium-modified supported iridium catalysts
journal, October 2012
- Chen, Kaiyou; Mori, Kazuma; Watanabe, Hideo
- Journal of Catalysis, Vol. 294
Selective Hydrogenolysis of Polyols and Cyclic Ethers over Bifunctional Surface Sites on Rhodium–Rhenium Catalysts
journal, August 2011
- Chia, Mei; Pagán-Torres, Yomaira J.; Hibbitts, David
- Journal of the American Chemical Society, Vol. 133, Issue 32
Mechanism of the hydrogenolysis of ethers over silica-supported rhodium catalyst modified with rhenium oxide
journal, June 2011
- Koso, Shuichi; Nakagawa, Yoshinao; Tomishige, Keiichi
- Journal of Catalysis, Vol. 280, Issue 2
Caprolactam from Renewable Resources: Catalytic Conversion of 5-Hydroxymethylfurfural into Caprolactone
journal, June 2011
- Buntara, Teddy; Noel, Sebastien; Phua, Pim Huat
- Angewandte Chemie International Edition, Vol. 50, Issue 31
From 5-Hydroxymethylfurfural (HMF) to Polymer Precursors: Catalyst Screening Studies on the Conversion of 1,2,6-hexanetriol to 1,6-hexanediol
journal, July 2012
- Buntara, Teddy; Noel, Sebastien; Phua, Pim Huat
- Topics in Catalysis, Vol. 55, Issue 7-10
Amorphous silica solubility and the thermodynamic properties of H4SiO°4 in the range of 0° to 350°C at Psat
journal, July 2000
- Gunnarsson, Ingvi; Arnórsson, Stefán
- Geochimica et Cosmochimica Acta, Vol. 64, Issue 13
Silica Solubility, 0°-200° C., and the Diagenesis of Siliceous Sediments
journal, March 1962
- Siever, Raymond
- The Journal of Geology, Vol. 70, Issue 2
Synthesis of 1,6-hexanediol from HMF over double-layered catalysts of Pd/SiO 2 + Ir–ReO x /SiO 2 in a fixed-bed reactor
journal, January 2016
- Xiao, Bin; Zheng, Mingyuan; Li, Xinsheng
- Green Chemistry, Vol. 18, Issue 7
Chemoselective Hydrogenolysis of Tetrahydropyran-2-methanol to 1,6-Hexanediol over Rhenium-Modified Carbon-Supported Rhodium Catalysts
journal, April 2010
- Chen, Kaiyou; Koso, Shuichi; Kubota, Takeshi
- ChemCatChem, Vol. 2, Issue 5
A new perspective in bio-refining: levoglucosenone and cleaner lignin from waste biorefinery hydrolysis lignin by selective conversion of residual saccharides
journal, January 2016
- De bruyn, M.; Fan, J.; Budarin, V. L.
- Energy & Environmental Science, Vol. 9, Issue 8
Chemicals from Biomass: Combining Ring-Opening Tautomerization and Hydrogenation Reactions to Produce 1,5-Pentanediol from Furfural
journal, March 2017
- Brentzel, Zachary J.; Barnett, Kevin J.; Huang, Kefeng
- ChemSusChem, Vol. 10, Issue 7
Hydrogenation of levoglucosenone to renewable chemicals
journal, January 2017
- Krishna, Siddarth H.; McClelland, Daniel J.; Rashke, Quinn A.
- Green Chemistry, Vol. 19, Issue 5
Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents
journal, January 2014
- Sherwood, James; De bruyn, Mario; Constantinou, Andri
- Chem. Commun., Vol. 50, Issue 68
Kinetics of Levoglucosenone Isomerization
journal, December 2016
- Krishna, Siddarth H.; Walker, Theodore W.; Dumesic, James A.
- ChemSusChem, Vol. 10, Issue 1
Furfural: a renewable and versatile platform molecule for the synthesis of chemicals and fuels
journal, January 2016
- Mariscal, R.; Maireles-Torres, P.; Ojeda, M.
- Energy & Environmental Science, Vol. 9, Issue 4
Increasing the revenue from lignocellulosic biomass: Maximizing feedstock utilization
journal, May 2017
- Alonso, David Martin; Hakim, Sikander H.; Zhou, Shengfei
- Science Advances, Vol. 3, Issue 5
Integrated conversion of hemicellulose and cellulose from lignocellulosic biomass
journal, January 2013
- Alonso, David Martin; Wettstein, Stephanie G.; Mellmer, Max A.
- Energy Environ. Sci., Vol. 6, Issue 1
Gamma-valerolactone, a sustainable platform molecule derived from lignocellulosic biomass
journal, January 2013
- Alonso, David Martin; Wettstein, Stephanie G.; Dumesic, James A.
- Green Chemistry, Vol. 15, Issue 3
Advanced Biorefinery based on the Fractionation of Biomass in γ-Valerolactone and Water
journal, November 2014
- Fang, Wenwen; Sixta, Herbert
- ChemSusChem, Vol. 8, Issue 1
Effects of γ-valerolactone in hydrolysis of lignocellulosic biomass to monosaccharides
journal, January 2014
- Mellmer, Max A.; Martin Alonso, David; Luterbacher, Jeremy S.
- Green Chem., Vol. 16, Issue 11
Lignin monomer production integrated into the γ-valerolactone sugar platform
journal, January 2015
- Luterbacher, Jeremy S.; Azarpira, Ali; Motagamwala, Ali H.
- Energy & Environmental Science, Vol. 8, Issue 9
Preparation of Dihydropyran, δ-Hydroxyvaleraldehyde and 1,5-Pentanediol from Tetrahydrofurfuryl Alcohol
journal, August 1946
- Schniepp, L. E.; Geller, H. H.
- Journal of the American Chemical Society, Vol. 68, Issue 8
Ring-Chain Tautomerism of Hydroxy Aldehydes
journal, November 1952
- Hurd, Charles D.; Saunders, William H.
- Journal of the American Chemical Society, Vol. 74, Issue 21
High resolution NMR studies of ring-chain tautomerism in ω-hydroxy aldehydes [高分解能核磁気共鳴法によるω-ハイドロキシアルデヒドのring-chain互変異性の分析]
journal, January 1971
- Shono, Toshiyuki; Godo, Masayuki; Shinra, Koichiro
- Bunseki kagaku, Vol. 20, Issue 9
Dehydration of cellulose to levoglucosenone using polar aprotic solvents
journal, January 2015
- Cao, Fei; Schwartz, Thomas J.; McClelland, Daniel J.
- Energy & Environmental Science, Vol. 8, Issue 6
The selective hydrogenation of biomass-derived 5-hydroxymethylfurfural using heterogeneous catalysts
journal, January 2012
- Alamillo, Ricardo; Tucker, Mark; Chia, Mei
- Green Chemistry, Vol. 14, Issue 5, p. 1413-1419
Upgrading biomass-derived furans via acid-catalysis/hydrogenation: the remarkable difference between water and methanol as the solvent
journal, January 2015
- Hu, Xun; Westerhof, Roel J. M.; Wu, Liping
- Green Chemistry, Vol. 17, Issue 1
Process Design and Economics for the Conversion of Lignocellulosic Biomass to Hydrocarbons: Dilute-Acid and Enzymatic Deconstruction of Biomass to Sugars and Biological Conversion of Sugars to Hydrocarbons
report, October 2013
- Davis, R.; Tao, L.; Tan, E. C. D.
- NREL/TP-5100-60223