Comparison of HMF hydrodeoxygenation over different metal catalysts in a continuous flow reactor
Abstract
The three-phase hydrodeoxygenation (HDO) of 5-hydroxymethylfurfural (HMF) and hydrogenation of 2,5-dimethylfuran (DMF) were studied over six carbon-supported metal catalysts (Pt, Pd, Ir, Ru, Ni, and Co) using a tubular flow reactor with 1-propanol solvent, at 180 °C and 33 bar. By varying the space time in the reactor, the reaction of HMF is shown to be sequential, with HMF reacting first to furfuryl ethers and other partially hydrogenated products, which then form 2,5-dimethylfuran (DMF). Ring-opened products and 2,5-dimethyltetrahydrofuran (DMTHF) were produced only from reaction of DMF. Rate constants for the pseudo-first-order sequential reactions were obtained for each of the metals. The selectivities for the reaction of DMF varied with the metal catalyst, with Pd forming primarily DMTHF, Ir forming a mixture of DMTHF and open-ring products, and the other metals forming primarily open-ring products. Catalyst stabilities followed the order Pt ~ Ir > Pd > Ni > Co > Ru. Since the stability order correlated with carbon balances in the product (>93% for Pt; <75% for Ru), deactivation appears to be caused by deposition of humins on the catalyst.
- Authors:
-
- Univ. of Pennsylvania, Philadelphia, PA (United States). Dept. of Chemical and Biomolecular Engineering
- Univ. of Pennsylvania, Philadelphia, PA (United States)
- Publication Date:
- Research Org.:
- Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1387337
- Alternate Identifier(s):
- OSTI ID: 1250114
- Grant/Contract Number:
- SC0001004
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Applied Catalysis. A, General
- Additional Journal Information:
- Journal Volume: 508; Journal Issue: C; Related Information: CCEI partners with the University of Delaware (lead); Brookhaven National Laboratory; California Institute of Technology; Columbia University; University of Delaware; Lehigh University; University of Massachusetts, Amherst; Massachusetts Institute of Technology; University of Minnesota; Pacific Northwest National Laboratory; University of Pennsylvania; Princeton University; Rutgers University; Journal ID: ISSN 0926-860X
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; catalysis (homogeneous); catalysis (heterogeneous); biofuels (including algae and biomass); bio-inspired; hydrogen and fuel cells; materials and chemistry by design; synthesis (novel materials); synthesis (self-assembly); synthesis (scalable processing)
Citation Formats
Luo, Jing, Arroyo-Ramírez, Lisandra, Wei, Jifeng, Yun, Hongseok, Murray, Christopher B., and Gorte, Raymond J. Comparison of HMF hydrodeoxygenation over different metal catalysts in a continuous flow reactor. United States: N. p., 2015.
Web. doi:10.1016/j.apcata.2015.10.009.
Luo, Jing, Arroyo-Ramírez, Lisandra, Wei, Jifeng, Yun, Hongseok, Murray, Christopher B., & Gorte, Raymond J. Comparison of HMF hydrodeoxygenation over different metal catalysts in a continuous flow reactor. United States. https://doi.org/10.1016/j.apcata.2015.10.009
Luo, Jing, Arroyo-Ramírez, Lisandra, Wei, Jifeng, Yun, Hongseok, Murray, Christopher B., and Gorte, Raymond J. Thu .
"Comparison of HMF hydrodeoxygenation over different metal catalysts in a continuous flow reactor". United States. https://doi.org/10.1016/j.apcata.2015.10.009. https://www.osti.gov/servlets/purl/1387337.
@article{osti_1387337,
title = {Comparison of HMF hydrodeoxygenation over different metal catalysts in a continuous flow reactor},
author = {Luo, Jing and Arroyo-Ramírez, Lisandra and Wei, Jifeng and Yun, Hongseok and Murray, Christopher B. and Gorte, Raymond J.},
abstractNote = {The three-phase hydrodeoxygenation (HDO) of 5-hydroxymethylfurfural (HMF) and hydrogenation of 2,5-dimethylfuran (DMF) were studied over six carbon-supported metal catalysts (Pt, Pd, Ir, Ru, Ni, and Co) using a tubular flow reactor with 1-propanol solvent, at 180 °C and 33 bar. By varying the space time in the reactor, the reaction of HMF is shown to be sequential, with HMF reacting first to furfuryl ethers and other partially hydrogenated products, which then form 2,5-dimethylfuran (DMF). Ring-opened products and 2,5-dimethyltetrahydrofuran (DMTHF) were produced only from reaction of DMF. Rate constants for the pseudo-first-order sequential reactions were obtained for each of the metals. The selectivities for the reaction of DMF varied with the metal catalyst, with Pd forming primarily DMTHF, Ir forming a mixture of DMTHF and open-ring products, and the other metals forming primarily open-ring products. Catalyst stabilities followed the order Pt ~ Ir > Pd > Ni > Co > Ru. Since the stability order correlated with carbon balances in the product (>93% for Pt; <75% for Ru), deactivation appears to be caused by deposition of humins on the catalyst.},
doi = {10.1016/j.apcata.2015.10.009},
journal = {Applied Catalysis. A, General},
number = C,
volume = 508,
place = {United States},
year = {Thu Oct 22 00:00:00 EDT 2015},
month = {Thu Oct 22 00:00:00 EDT 2015}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Cited by: 61 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:
Catalytic dehydration of C 6 carbohydrates for the production of hydroxymethylfurfural (HMF) as a versatile platform chemical
journal, January 2014
- Wang, Tianfu; Nolte, Michael W.; Shanks, Brent H.
- Green Chem., Vol. 16, Issue 2
Continuous production of 5-hydroxymethylfurfural from fructose: a design case study
journal, January 2010
- Torres, Ana I.; Daoutidis, Prodromos; Tsapatsis, Michael
- Energy & Environmental Science, Vol. 3, Issue 10
Cycloaddition of Biomass-Derived Furans for Catalytic Production of Renewable p -Xylene
journal, April 2012
- Williams, C. Luke; Chang, Chun-Chih; Do, Phuong
- ACS Catalysis, Vol. 2, Issue 6
Selective Transformation of 5-Hydroxymethylfurfural into the Liquid Fuel 2,5-Dimethylfuran over Carbon-Supported Ruthenium
journal, February 2014
- Hu, Lei; Tang, Xing; Xu, Jiaxing
- Industrial & Engineering Chemistry Research, Vol. 53, Issue 8
Zinc-Assisted Hydrodeoxygenation of Biomass-Derived 5-Hydroxymethylfurfural to 2,5-Dimethylfuran
journal, September 2014
- Saha, Basudeb; Bohn, Christine M.; Abu-Omar, Mahdi M.
- ChemSusChem, Vol. 7, Issue 11
Hydrodeoxygenation of HMF over Pt/C in a continuous flow reactor
journal, October 2014
- Luo, Jing; Arroyo-Ramírez, Lisandra; Gorte, Raymond J.
- AIChE Journal, Vol. 61, Issue 2
Chemisorption–XRD particle size discrepancy of carbon supported palladium: Carbon decoration of Pd?
journal, May 2015
- Tengco, John Meynard M.; Lugo-José, Yuliana K.; Monnier, John R.
- Catalysis Today, Vol. 246
Hydrodeoxygenation of Furfural Over Supported Metal Catalysts: A Comparative Study of Cu, Pd and Ni
journal, March 2011
- Sitthisa, Surapas; Resasco, Daniel E.
- Catalysis Letters, Vol. 141, Issue 6
Catalytic Reduction of Biomass-Derived Furanic Compounds with Hydrogen
journal, October 2013
- Nakagawa, Yoshinao; Tamura, Masazumi; Tomishige, Keiichi
- ACS Catalysis, Vol. 3, Issue 12
Selective hydrogenation of biomass-derived 5-hydroxymethylfurfural (HMF) to 2,5-dimethylfuran (DMF) under atmospheric hydrogen pressure over carbon supported PdAu bimetallic catalyst
journal, September 2014
- Nishimura, Shun; Ikeda, Naoya; Ebitani, Kohki
- Catalysis Today, Vol. 232
Selective conversion of furfural to methylfuran over silica-supported NiFe bimetallic catalysts
journal, November 2011
- Sitthisa, Surapas; An, Wei; Resasco, Daniel E.
- Journal of Catalysis, Vol. 284, Issue 1
Reaction Pathways of Propanal and 1-Propanol on Fe/Ni(111) and Cu/Ni(111) Bimetallic Surfaces
journal, May 2014
- Myint, MyatNoeZin; Yan, Yushan; Chen, Jingguang G.
- The Journal of Physical Chemistry C, Vol. 118, Issue 21
Aqueous-phase hydrogenation and hydrodeoxygenation of biomass-derived oxygenates with bimetallic catalysts
journal, January 2014
- Lee, Jechan; Kim, Yong Tae; Huber, George W.
- Green Chemistry, Vol. 16, Issue 2
Nickel-Tungsten Carbide Catalysts for the Production of 2,5-Dimethylfuran from Biomass-Derived Molecules
journal, February 2014
- Huang, Yao-Bing; Chen, Meng-Yuan; Yan, Long
- ChemSusChem, Vol. 7, Issue 4
Efficient production of the liquid fuel 2,5-dimethylfuran from 5-hydroxymethylfurfural over Ru/Co3O4 catalyst
journal, March 2014
- Zu, Yanhong; Yang, Panpan; Wang, Jianjian
- Applied Catalysis B: Environmental, Vol. 146
Works referencing / citing this record:
Fundamentals of C–O bond activation on metal oxide catalysts
journal, February 2019
- Goulas, Konstantinos A.; Mironenko, Alexander V.; Jenness, Glen R.
- Nature Catalysis, Vol. 2, Issue 3
Study of PtOx/TiO2 Photocatalysts in the Photocatalytic Reforming of Glycerol: The Role of Co-Catalyst Formation
journal, October 2018
- Majrik, Katalin; Pászti, Zoltán; Korecz, László
- Materials, Vol. 11, Issue 10
Fractionation of Lignocellulosic Biomass over Core-Shell Ni@Al 2 O 3 Catalysts with Formic Acid as a Cocatalyst and Hydrogen Source
journal, March 2019
- Park, Jaeyong; Riaz, Asim; Verma, Deepak
- ChemSusChem, Vol. 12, Issue 8
Continuous Flow Organic Chemistry: Successes and Pitfalls at the Interface with Current Societal Challenges: Continuous Flow Organic Chemistry: Successes and Pitfalls at the Interface with Current Societal Challenges
journal, May 2018
- Gérardy, Romaric; Emmanuel, Noémie; Toupy, Thomas
- European Journal of Organic Chemistry, Vol. 2018, Issue 20-21
An Efficient and Reusable Embedded Ru Catalyst for the Hydrogenolysis of Levulinic Acid to γ-Valerolactone
journal, March 2017
- Wei, Zuojun; Lou, Jiongtao; Su, Chuanmin
- ChemSusChem, Vol. 10, Issue 8
A Non‐Noble Monometallic Catalyst Derived from Cu–MOFs for Highly Selective Hydrogenation of 5‐Hydroxymethylfurfural to 2,5‐Dimethylfuran
journal, December 2019
- Zhang, Qingtu; Zuo, Jianliang; Peng, Feng
- ChemistrySelect, Vol. 4, Issue 46
Metal Catalysts for the Efficient Transformation of Biomass-derived HMF and Furfural to Value Added Chemicals
journal, March 2018
- Gupta, Kavita; Rai, Rohit K.; Singh, Sanjay K.
- ChemCatChem, Vol. 10, Issue 11
Spectroscopic characterization of a highly selective NiCu 3 /C hydrodeoxygenation catalyst
journal, January 2018
- Goulas, Konstantinos A.; Lee, Jennifer D.; Zheng, Weiqing
- Catalysis Science & Technology, Vol. 8, Issue 23
Selective Hydrodeoxygenation of 5-Hydroxymethylfurfural to 2,5-Dimethylfuran over Heterogeneous Iron Catalysts
journal, March 2017
- Li, Jiang; Liu, Jun-ling; Liu, He-yang
- ChemSusChem, Vol. 10, Issue 7
The H2 Pressure Dependence of Hydrodeoxygenation Selectivities for Furfural Over Pt/C Catalysts
journal, February 2016
- Luo, Jing; Monai, Matteo; Yun, Hongseok
- Catalysis Letters, Vol. 146, Issue 4
Ruthenium on Carbonaceous Materials for the Selective Hydrogenation of HMF
journal, August 2018
- Cattaneo, Stefano; Naslhajian, Hadi; Somodi, Ferenc
- Molecules, Vol. 23, Issue 8
Ruthenium on Carbonaceous Materials for the Selective Hydrogenation of HMF
journal, August 2018
- Cattaneo, Stefano; Naslhajian, Hadi; Somodi, Ferenc
- Molecules, Vol. 23, Issue 8