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

Title: 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:
ORCiD logo [1]; ORCiD logo [1];  [1];  [1];  [1];  [1];  [2];  [1];  [1]; ORCiD logo [1]; ORCiD logo [2];  [1]; ORCiD logo [1]
  1. Department of Chemical and Biological Engineering; University of Wisconsin-Madison; Madison; USA
  2. 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


In vivo conversion of γ-aminobutyric acid and 1,4-butanediol to γ-hydroxybutyric acid in rat brain
journal, December 1989


Review: The involvement of gamma-hydroxybutyrate in reported sexual assaults: a systematic review
journal, May 2010


Emerging catalytic processes for the production of adipic acid
journal, January 2013


Aerobic Alcohol Oxidations Mediated by Nitric Acid
journal, October 2011


Acid-Catalyzed Decomposition of the Benzyl Nitrite Intermediate in HNO3-Mediated Aerobic Oxidation of Benzyl Alcohol
journal, February 2012


Continuous D-Fructose Dehydration to 5- Hydroxymethylfurfural Under Mild Conditions
journal, July 2012


Kinetics and mechanism of hydrogenation of furfural on Cu/SiO2 catalysts
journal, January 2011


Vapor phase hydrogenation of furfural over nickel mixed metal oxide catalysts derived from layered double hydroxides
journal, May 2016


Promoting effect of Mo on the hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol over Rh/SiO2
journal, October 2009


Catalytic Conversions of Furfural to Pentanediols
journal, August 2015


Chemoselective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol
journal, January 2009


Bimetallic RhRe/C catalysts for the production of biomass-derived chemicals
journal, December 2013


Production of 1,5-pentanediol from biomass via furfural and tetrahydrofurfuryl alcohol
journal, November 2012


C–O bond hydrogenolysis of cyclic ethers with OH groups over rhenium-modified supported iridium catalysts
journal, October 2012


Selective Hydrogenolysis of Polyols and Cyclic Ethers over Bifunctional Surface Sites on Rhodium–Rhenium Catalysts
journal, August 2011


Mechanism of the hydrogenolysis of ethers over silica-supported rhodium catalyst modified with rhenium oxide
journal, June 2011


Caprolactam from Renewable Resources: Catalytic Conversion of 5-Hydroxymethylfurfural into Caprolactone
journal, June 2011


Amorphous silica solubility and the thermodynamic properties of H4SiO°4 in the range of 0° to 350°C at Psat
journal, July 2000


Silica Solubility, 0°-200° C., and the Diagenesis of Siliceous Sediments
journal, March 1962


Hydrogenation of levoglucosenone to renewable chemicals
journal, January 2017


Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents
journal, January 2014


Kinetics of Levoglucosenone Isomerization
journal, December 2016


Furfural: a renewable and versatile platform molecule for the synthesis of chemicals and fuels
journal, January 2016


Increasing the revenue from lignocellulosic biomass: Maximizing feedstock utilization
journal, May 2017


Integrated conversion of hemicellulose and cellulose from lignocellulosic biomass
journal, January 2013


Gamma-valerolactone, a sustainable platform molecule derived from lignocellulosic biomass
journal, January 2013


Advanced Biorefinery based on the Fractionation of Biomass in γ-Valerolactone and Water
journal, November 2014


Effects of γ-valerolactone in hydrolysis of lignocellulosic biomass to monosaccharides
journal, January 2014


Lignin monomer production integrated into the γ-valerolactone sugar platform
journal, January 2015


Preparation of Dihydropyran, δ-Hydroxyvaleraldehyde and 1,5-Pentanediol from Tetrahydrofurfuryl Alcohol
journal, August 1946


Ring-Chain Tautomerism of Hydroxy Aldehydes
journal, November 1952


Dehydration of cellulose to levoglucosenone using polar aprotic solvents
journal, January 2015


The selective hydrogenation of biomass-derived 5-hydroxymethylfurfural using heterogeneous catalysts
journal, January 2012