Acid-functionalized mesoporous carbons for the continuous production of 5-hydroxymethylfurfural
Abstract
The stability of solid acid catalysts is essential in the development of sustainable biomass conversion processes. In this report we study the activity and stability of acid-functionalized periodic mesoporous carbons (CMK-3 and CMK-5) for the continuous production of 5-hydroxymethylfurfural from fructose. The acid-functionalized mesoporous carbon catalysts show comparable selectivities and turnover frequency (TOF) to that of propylsulfonic acid functionalized SBA-15. However, the first-order deactivation rate coefficient of the carbon-based materials are up to 60 times more stable than that for the acid-functionalized SBA-15 catalyst and up to 3 times more stable than commercial Nafion SAC-13. Of the catalysts studied, phenylsulfonic acid CMK-5 showed both the highest TOF for HMF production and lowest deactivation rate coefficient.
- Authors:
-
[1];
- University of Wisconsin, Madison, WI (United States); Federal University of São Carlos, Sao Paulo (Brazil)
- University of Wisconsin, Madison, WI (United States)
- Publication Date:
- Research Org.:
- Univ. of Wisconsin, Madison, WI (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC); National Science Foundation (NSF)
- OSTI Identifier:
- 1534116
- Alternate Identifier(s):
- OSTI ID: 1359570
- Grant/Contract Number:
- FG02-84ER13183; CHE-1205189; DGE-0718123
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of Molecular Catalysis A: Chemical
- Additional Journal Information:
- Journal Volume: 422; Journal Issue: C; Journal ID: ISSN 1381-1169
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; mesoporous carbon5-hydroxymethylfurfural; biomass conversion; heterogeneous catalysis; deactivation
Citation Formats
Gallo, Jean R., Alamillo, Ricardo, and Dumesic, James A. Acid-functionalized mesoporous carbons for the continuous production of 5-hydroxymethylfurfural. United States: N. p., 2016.
Web. doi:10.1016/j.molcata.2016.01.005.
Gallo, Jean R., Alamillo, Ricardo, & Dumesic, James A. Acid-functionalized mesoporous carbons for the continuous production of 5-hydroxymethylfurfural. United States. https://doi.org/10.1016/j.molcata.2016.01.005
Gallo, Jean R., Alamillo, Ricardo, and Dumesic, James A. Mon .
"Acid-functionalized mesoporous carbons for the continuous production of 5-hydroxymethylfurfural". United States. https://doi.org/10.1016/j.molcata.2016.01.005. https://www.osti.gov/servlets/purl/1534116.
@article{osti_1534116,
title = {Acid-functionalized mesoporous carbons for the continuous production of 5-hydroxymethylfurfural},
author = {Gallo, Jean R. and Alamillo, Ricardo and Dumesic, James A.},
abstractNote = {The stability of solid acid catalysts is essential in the development of sustainable biomass conversion processes. In this report we study the activity and stability of acid-functionalized periodic mesoporous carbons (CMK-3 and CMK-5) for the continuous production of 5-hydroxymethylfurfural from fructose. The acid-functionalized mesoporous carbon catalysts show comparable selectivities and turnover frequency (TOF) to that of propylsulfonic acid functionalized SBA-15. However, the first-order deactivation rate coefficient of the carbon-based materials are up to 60 times more stable than that for the acid-functionalized SBA-15 catalyst and up to 3 times more stable than commercial Nafion SAC-13. Of the catalysts studied, phenylsulfonic acid CMK-5 showed both the highest TOF for HMF production and lowest deactivation rate coefficient.},
doi = {10.1016/j.molcata.2016.01.005},
journal = {Journal of Molecular Catalysis A: Chemical},
number = C,
volume = 422,
place = {United States},
year = {Mon Jan 11 00:00:00 EST 2016},
month = {Mon Jan 11 00:00:00 EST 2016}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Cited by: 46 works
Citation information provided by
Web of Science
Web of Science
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Acid-Functionalized SBA-15-Type Silica Catalysts for Carbohydrate Dehydration
journal, May 2011
- Crisci, Anthony J.; Tucker, Mark H.; Lee, Ming-Yung
- ACS Catalysis, Vol. 1, Issue 7, p. 719-728
Solid state NMR study of chemical structure and hydrothermal deactivation of moderate-temperature carbon materials with acidic SO3H sites
journal, August 2014
- Anderson, Jason M.; Johnson, Robert L.; Schmidt-Rohr, Klaus
- Carbon, Vol. 74
Functionalization of SBA-15 mesoporous silica with thiol or sulfonic acid groups under the crystallization conditions
journal, September 2005
- Yang, L. M.; Wang, Y. J.; Luo, G. S.
- Microporous and Mesoporous Materials, Vol. 84, Issue 1-3
Active solid acid catalysts prepared by sulfonation of carbonization-controlled mesoporous carbon materials
journal, September 2007
- Xing, Rong; Liu, Yueming; Wang, Yong
- Microporous and Mesoporous Materials, Vol. 105, Issue 1-2
Synthesis and Characterization of Hexagonally Ordered Carbon Nanopipes
journal, June 2003
- Kruk, Michal; Jaroniec, Mietek; Kim, Tae-Wan
- Chemistry of Materials, Vol. 15, Issue 14
Self-Condensation of Cyclohexanone Catalyzed by Amberlyst-15. Study of Diffusional Resistances and Deactivation of the Catalyst
journal, March 1994
- Aragon, Jose M.; Vegas, Jesus M. R.; Jodra, Luis G.
- Industrial & Engineering Chemistry Research, Vol. 33, Issue 3
Dehydration of fructose to 5-hydroxymethylfurfural over H-mordenites
journal, October 1996
- Moreau, C.; Durand, R.; Razigade, S.
- Applied Catalysis A: General, Vol. 145, Issue 1-2
Design of solid catalysts for the conversion of biomass
journal, January 2009
- Rinaldi, Roberto; Schüth, Ferdi
- Energy & Environmental Science, Vol. 2, Issue 6
Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited
journal, January 2010
- Bozell, Joseph J.; Petersen, Gene R.
- Green Chemistry, Vol. 12, Issue 4, p. 539-554
Catalytic dehydration of fructose into 5-hydroxymethylfurfural by ion-exchange resin in mixed-aqueous system by microwave heating
journal, January 2008
- Qi, Xinhua; Watanabe, Masaru; Aida, Taku M.
- Green Chemistry, Vol. 10, Issue 7
Acid-Functionalized SBA-15-Type Periodic Mesoporous Organosilicas and Their Use in the Continuous Production of 5-Hydroxymethylfurfural
journal, July 2012
- Tucker, Mark H.; Crisci, Anthony J.; Wigington, Bethany N.
- ACS Catalysis, Vol. 2, Issue 9
Sulfonated Ordered Mesoporous Carbon as a Stable and Highly Active Protonic Acid Catalyst
journal, May 2007
- Wang, Xiqing; Liu, Rui; Waje, Mahesh M.
- Chemistry of Materials, Vol. 19, Issue 10
Surface and Pore Structures of CMK-5 Ordered Mesoporous Carbons by Adsorption and Surface Spectroscopy
journal, August 2003
- Darmstadt, Hans; Roy, Christian; Kaliaguine, Serge
- Chemistry of Materials, Vol. 15, Issue 17
Nafion® SAC-13: heterogeneous and reusable catalyst for the activation of HMDS for efficient and selective O-silylation reactions under solvent-free condition
journal, June 2009
- Rajagopal, Gurusamy; Lee, Hanbin; Kim, Sung Soo
- Tetrahedron, Vol. 65, Issue 24, p. 4735-4741
Dehydration of fructose to 5-hydroxymethylfurfural in sub-critical water over heterogeneous zirconium phosphate catalysts
journal, October 2006
- Asghari, Feridoun Salak; Yoshida, Hiroyuki
- Carbohydrate Research, Vol. 341, Issue 14
Ordered nanoporous arrays of carbon supporting high dispersions of platinum nanoparticles
journal, July 2001
- Joo, Sang Hoon; Choi, Seong Jae; Oh, Ilwhan
- Nature, Vol. 412, Issue 6843
The effect of solvent addition on fructose dehydration to 5-hydroxymethylfurfural in biphasic system over zeolites
journal, March 2012
- Ordomsky, V. V.; van der Schaaf, J.; Schouten, J. C.
- Journal of Catalysis, Vol. 287
Thermal deactivation of strong-acid ion-exchange resins in water
journal, June 1981
- Petrus, Leonardus; Stamhuis, Eize J.; Joosten, Geert E. H.
- Industrial & Engineering Chemistry Product Research and Development, Vol. 20, Issue 2
From Microporous to Mesoporous Molecular Sieve Materials and Their Use in Catalysis
journal, October 1997
- Corma, Avelino
- Chemical Reviews, Vol. 97, Issue 6, p. 2373-2420
Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural
journal, June 2007
- Zhao, H.; Holladay, J. E.; Brown, H.
- Science, Vol. 316, Issue 5831, p. 1597-1600
Phase Modifiers Promote Efficient Production of Hydroxymethylfurfural from Fructose
journal, June 2006
- Roman-Leshkov, Yuriy; Chheda, Juben N.; Dumesic, James A.
- Science, Vol. 312, Issue 5782, p. 1933-1937
Synthesis of New, Nanoporous Carbon with Hexagonally Ordered Mesostructure
journal, November 2000
- Jun, Shinae; Joo, Sang Hoon; Ryoo, Ryong
- Journal of the American Chemical Society, Vol. 122, Issue 43
Sustainable Solvent Systems for Use in Tandem Carbohydrate Dehydration Hydrogenation
journal, March 2013
- Tucker, Mark H.; Alamillo, Ricardo; Crisci, Anthony J.
- ACS Sustainable Chemistry & Engineering, Vol. 1, Issue 5
Stability of sulfated zirconia and the nature of the catalytically active species in the transesterification of triglycerides
journal, April 2008
- Suwannakarn, K.; Lotero, E.; Goodwinjr, J.
- Journal of Catalysis, Vol. 255, Issue 2
Production and upgrading of 5-hydroxymethylfurfural using heterogeneous catalysts and biomass-derived solvents
journal, January 2013
- Gallo, Jean Marcel R.; Alonso, David Martin; Mellmer, Max A.
- Green Chem., Vol. 15, Issue 1
Bifunctional Solid Catalysts for the Selective Conversion of Fructose to 5-Hydroxymethylfurfural
journal, May 2010
- Crisci, Anthony J.; Tucker, Mark H.; Dumesic, James A.
- Topics in Catalysis, Vol. 53, Issue 15-18
Solvent Effects on Fructose Dehydration to 5-Hydroxymethylfurfural in Biphasic Systems Saturated with Inorganic Salts
journal, January 2009
- Román-Leshkov, Yuriy; Dumesic, James A.
- Topics in Catalysis, Vol. 52, Issue 3, p. 297-303