Single-step catalytic conversion of furfural to 2-pentanol over bimetallic Co–Cu catalysts

Seemala, Bhogeswararao; Kumar, Rajeev; Cai, Charles M.; Wyman, Charles E.; Christopher, Phillip

doi:10.1039/C8RE00195B

Title: Single-step catalytic conversion of furfural to 2-pentanol over bimetallic Co–Cu catalysts

Journal Article · Wed Oct 10 00:00:00 EDT 2018 · Reaction Chemistry & Engineering

DOI:https://doi.org/10.1039/C8RE00195B· OSTI ID:1581906

^[1];

^[2];

^[2]; Wyman, Charles E. ^[2];

^[1]

Univ. of California, Riverside, CA (United States); Univ. of California, Santa Barbara, CA (United States)
Univ. of California, Riverside, CA (United States)

The conversion of biomass derived furfural to 2-pentanol, a useful organic solvent and precursor for various types of fuels, was demonstrated in this work with ~71.1% yield in a single step over a Co–Cu/Al₂O₃ catalyst at 240 °C and 45 bar H₂ pressure. The catalyst shown here sustained activity and selectivity for four subsequent recycles without regeneration. Co was proposed as the primary active site that enabled hydrodeoxygenation of furfural to produce methyl furan followed by ring opening, while Cu mitigated product degradation that occurred on pure Cu catalysts.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Univ. of California, Riverside, CA (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Sustainable Transportation Office. Bioenergy Technologies Office; USDOE Office of Energy Efficiency and Renewable Energy (EERE), Office of Sustainable Transportation. Bioenergy Technologies Office (BETO)

Grant/Contract Number:: EE0007006

OSTI ID:: 1581906

Alternate ID(s):: OSTI ID: 1477892

Journal Information:: Reaction Chemistry & Engineering, Vol. 4, Issue 2; ISSN 2058-9883

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 14 works

Citation information provided by
Web of Science

References (39)

One-step Conversion of Furfural into 2-Methyltetrahydrofuran under Mild Conditions Dong, Fang; Zhu, Yulei; Ding, Guoqiang ChemSusChem, Vol. 8, Issue 9 https://doi.org/10.1002/cssc.201500178	journal	April 2015
Integrated furfural production as a renewable fuel and chemical platform from lignocellulosic biomass: Furfural production from lignocellulosic biomass Cai, Charles M.; Zhang, Taiying; Kumar, Rajeev Journal of Chemical Technology & Biotechnology, Vol. 89, Issue 1 https://doi.org/10.1002/jctb.4168	journal	August 2013
Understanding the stability of Co-supported catalysts during ethanol reforming as addressed by in situ temperature and spatial resolved XAFS analysis Ávila-Neto, C. N.; Liberatori, J. W. C.; da Silva, A. M. Journal of Catalysis, Vol. 287 https://doi.org/10.1016/j.jcat.2011.12.013	journal	March 2012
Efficient Preparation of Liquid Fuel 2,5-Dimethylfuran from Biomass-Derived 5-Hydroxymethylfurfural over Ru–NaY Catalyst Nagpure, Atul S.; Lucas, Nishita; Chilukuri, Satyanarayana V. ACS Sustainable Chemistry & Engineering, Vol. 3, Issue 11 https://doi.org/10.1021/acssuschemeng.5b00857	journal	October 2015
Nonenzymatic Sugar Production from Biomass Using Biomass-Derived -Valerolactone Luterbacher, J. S.; Rand, J. M.; Alonso, D. M. Science, Vol. 343, Issue 6168 https://doi.org/10.1126/science.1246748	journal	January 2014
Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates Román-Leshkov, Yuriy; Barrett, Christopher J.; Liu, Zhen Y. Nature, Vol. 447, Issue 7147, p. 982-985 https://doi.org/10.1038/nature05923	journal	June 2007
Support Induced Control of Surface Composition in Cu–Ni/TiO ₂ Catalysts Enables High Yield Co-Conversion of HMF and Furfural to Methylated Furans Seemala, Bhogeswararao; Cai, Charles M.; Wyman, Charles E. ACS Catalysis, Vol. 7, Issue 6 https://doi.org/10.1021/acscatal.7b01095	journal	May 2017
“Try and Fall Sick …︁”-The Composer, Chemist, and Surgeon Aleksandr Borodin Podlech, Joachim Angewandte Chemie International Edition, Vol. 49, Issue 37 https://doi.org/10.1002/anie.201002023	journal	August 2010
Production of renewable petroleum refinery diesel and jet fuel feedstocks from hemicellulose sugar streams Olcay, Hakan; Subrahmanyam, Ayyagari V.; Xing, Rong Energy Environ. Sci., Vol. 6, Issue 1 https://doi.org/10.1039/C2EE23316A	journal	January 2013
Effects of Cu–Ni Bimetallic Catalyst Composition and Support on Activity, Selectivity, and Stability for Furfural Conversion to 2-Methyfuran Seemala, Bhogeswararao; Cai, Charles M.; Kumar, Rajeev ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 2 https://doi.org/10.1021/acssuschemeng.7b03572	journal	December 2017
Coupling metal halides with a co-solvent to produce furfural and 5-HMF at high yields directly from lignocellulosic biomass as an integrated biofuels strategy Cai, Charles M.; Nagane, Nikhil; Kumar, Rajeev Green Chem., Vol. 16, Issue 8 https://doi.org/10.1039/C4GC00747F	journal	January 2014
Single pot selective hydrogenation of furfural to 2-methylfuran over carbon supported iridium catalysts Date, Nandan S.; Hengne, Amol M.; Huang, K. -W. Green Chemistry, Vol. 20, Issue 9 https://doi.org/10.1039/C8GC00284C	journal	January 2018
Interplay between particle size, composition, and structure of MgAl2O4-supported Co–Cu catalysts and their influence on carbon accumulation during steam reforming of ethanol Ávila-Neto, C. N.; Zanchet, D.; Hori, C. E. Journal of Catalysis, Vol. 307 https://doi.org/10.1016/j.jcat.2013.07.025	journal	November 2013
Reduced Cu–Co–Al Mixed Metal Oxides for the Ring-Opening of Furfuryl Alcohol to Produce Renewable Diols Sulmonetti, Taylor P.; Hu, Bo; Lee, Sungsik ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 10 https://doi.org/10.1021/acssuschemeng.7b01769	journal	August 2017
An Investigation of the Metabolism of Isoleucine to Active Amyl Alcohol in Saccharomyces cerevisiae Dickinson, J. Richard; Harrison, Scott J.; Dickinson, Jenny A. Journal of Biological Chemistry, Vol. 275, Issue 15, p. 10937-10942 https://doi.org/10.1074/jbc.275.15.10937	journal	April 2000
The effects of oxidation–reduction treatment on the structure and activity of cobalt-based catalysts Tang, Liangguang; Yamaguchi, Doki; Leita, Ben Catalysis Communications, Vol. 59 https://doi.org/10.1016/j.catcom.2014.10.021	journal	January 2015
Connecting Biomass and Petroleum Processing with a Chemical Bridge Bozell, Joseph J. Science, Vol. 329, Issue 5991, p. 522-523 https://doi.org/10.1126/science.1191662	journal	July 2010
Catalytic conversion of furfural to industrial chemicals over supported Pt and Pd catalysts Bhogeswararao, S.; Srinivas, D. Journal of Catalysis, Vol. 327 https://doi.org/10.1016/j.jcat.2015.04.018	journal	July 2015
Alumina supported Ni and Co catalysts modified by Y2O3 via different impregnation strategies: Comparative analysis on structural properties and catalytic performance in methane reforming with CO2 Li, Baitao; Su, Wenfeng; Wang, Xiaona International Journal of Hydrogen Energy, Vol. 41, Issue 33 https://doi.org/10.1016/j.ijhydene.2016.06.219	journal	September 2016
One-pot selective conversion of furfural into 1,5-pentanediol over a Pd-added Ir–ReO _x /SiO ₂ bifunctional catalyst Liu, Sibao; Amada, Yasushi; Tamura, Masazumi Green Chem., Vol. 16, Issue 2 https://doi.org/10.1039/C3GC41335G	journal	January 2014
Research Octane Numbers of Primary and Mixed Alcohols from Biomass-Based Syngas Rapp, Vi H.; Mack, J. Hunter; Tschann, Philipp Energy & Fuels, Vol. 28, Issue 5 https://doi.org/10.1021/ef5001453	journal	April 2014
Catalytic Reduction of Biomass-Derived Furanic Compounds with Hydrogen Nakagawa, Yoshinao; Tamura, Masazumi; Tomishige, Keiichi ACS Catalysis, Vol. 3, Issue 12 https://doi.org/10.1021/cs400616p	journal	October 2013
Ni-Co/Al ₂ O ₃ Bimetallic Catalysts for CH ₄ Steam Reforming: Elucidating the Role of Co for Improving Coke Resistance You, Xiaojuan; Wang, Xiang; Ma, Youhe ChemCatChem, Vol. 6, Issue 12 https://doi.org/10.1002/cctc.201402695	journal	October 2014
Selective conversion of furfural to methylfuran over silica-supported NiFe bimetallic catalysts Sitthisa, Surapas; An, Wei; Resasco, Daniel E. Journal of Catalysis, Vol. 284, Issue 1 https://doi.org/10.1016/j.jcat.2011.09.005	journal	November 2011
An XPS and TPR study of the reduction of promoted cobalt-kieselguhr Fischer-Tropsch catalysts Sexton, B. Journal of Catalysis, Vol. 97, Issue 2 https://doi.org/10.1016/0021-9517(86)90011-4	journal	February 1986
Electronic Structure Effects in Transition Metal Surface Chemistry Vojvodic, A.; Nørskov, J. K.; Abild-Pedersen, F. Topics in Catalysis, Vol. 57, Issue 1-4 https://doi.org/10.1007/s11244-013-0159-2	journal	November 2013
Hybrid Catalytic Biorefining of Hardwood Biomass to Methylated Furans and Depolymerized Technical Lignin Seemala, Bhogeswararao; Meng, Xianzhi; Parikh, Aakash ACS Sustainable Chemistry & Engineering, Vol. 6, Issue 8 https://doi.org/10.1021/acssuschemeng.8b01930	journal	June 2018
Pentanol isomer synthesis in engineered microorganisms Cann, Anthony F.; Liao, James C. Applied Microbiology and Biotechnology, Vol. 85, Issue 4 https://doi.org/10.1007/s00253-009-2262-7	journal	October 2009
Chemicals from Biomass: Combining Ring-Opening Tautomerization and Hydrogenation Reactions to Produce 1,5-Pentanediol from Furfural Brentzel, Zachary J.; Barnett, Kevin J.; Huang, Kefeng ChemSusChem, Vol. 10, Issue 7 https://doi.org/10.1002/cssc.201700178	journal	March 2017
What could be possible with mature biofuels technologies? Wyman, Charles E.; Huber, George Biofuels, Bioproducts and Biorefining, Vol. 3, Issue 2 https://doi.org/10.1002/bbb.139	journal	March 2009
Versatile catalysis of iron: tunable and selective transformation of biomass-derived furfural in aliphatic alcohol Zhang, Zhenya; Tong, Xinli; Zhang, Haigang Green Chemistry, Vol. 20, Issue 13 https://doi.org/10.1039/C8GC00852C	journal	January 2018
A versatile bi-metallic copper–cobalt catalyst for liquid phase hydrogenation of furfural to 2-methylfuran Srivastava, Sanjay; Jadeja, G. C.; Parikh, Jigisha RSC Advances, Vol. 6, Issue 2 https://doi.org/10.1039/C5RA15048E	journal	January 2016
Levulinic Acid as a Catalyst for the Production of 5-Hydroxymethylfurfural and Furfural from Lignocellulose Biomass Seemala, Bhogeswararao; Haritos, Victoria; Tanksale, Akshat ChemCatChem, Vol. 8, Issue 3 https://doi.org/10.1002/cctc.201501105	journal	December 2015
Solvent Applications of 2-Methyltetrahydrofuran in Organometallic and Biphasic Reactions Aycock, David F. Organic Process Research & Development, Vol. 11, Issue 1 https://doi.org/10.1021/op060155c	journal	January 2007
2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry Pace, Vittorio; Hoyos, Pilar; Castoldi, Laura ChemSusChem, Vol. 5, Issue 8 https://doi.org/10.1002/cssc.201100780	journal	August 2012
Silica-immobilized piperazine: A sustainable organocatalyst for aldol and Knoevenagel reactions Shanmuganathan, Saravanakumar; Greiner, Lasse; Domínguez de María, Pablo Tetrahedron Letters, Vol. 51, Issue 50 https://doi.org/10.1016/j.tetlet.2010.10.080	journal	December 2010
Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels Atsumi, Shota; Hanai, Taizo; Liao, James C. Nature, Vol. 451, Issue 7174, p. 86-89 https://doi.org/10.1038/nature06450	journal	January 2008
Electroless Deposition of Ferromagnetic Cobalt Nanoparticles in Propylene Glycol Balela, Mary Donnabelle L.; Yagi, Shunsuke; Lockman, Zainovia Journal of The Electrochemical Society, Vol. 156, Issue 9 https://doi.org/10.1149/1.3169776	journal	January 2009
Hydrogenation/dehydrogenation reactions: isopropanol dehydrogenation over copper catalysts Rioux, R. M.; Vannice, M. A. Journal of Catalysis, Vol. 216, Issue 1-2 https://doi.org/10.1016/S0021-9517(02)00035-0	journal	May 2003

Cited By (1)

Solid Acids for the Reaction of Bioderived Alcohols into Ethers for Fuel Applications Zaccheria, Federica; Scotti, Nicola; Ravasio, Nicoletta Catalysts, Vol. 9, Issue 2 https://doi.org/10.3390/catal9020172	journal	February 2019

Similar Records

Effects of Cu–Ni Bimetallic Catalyst Composition and Support on Activity, Selectivity, and Stability for Furfural Conversion to 2-Methyfuran

Journal Article · Tue Dec 05 00:00:00 EST 2017 · ACS Sustainable Chemistry & Engineering · OSTI ID:1581906

Seemala, Bhogeswararao; Cai, Charles M.; Kumar, Rajeev; +2 more

Support Induced Control of Surface Composition in Cu–Ni/TiO₂ Catalysts Enables High Yield Co-Conversion of HMF and Furfural to Methylated Furans

Journal Article · Mon May 08 00:00:00 EDT 2017 · ACS Catalysis · OSTI ID:1581906

Seemala, Bhogeswararao; Cai, Charles M.; Wyman, Charles E.; +1 more

Direct synthesis of furfuryl alcohol from furfural: catalytic performance of monometallic and bimetallic Mo and Ru phosphides

Journal Article · Tue Jun 18 00:00:00 EDT 2019 · Catalysis Science and Technology · OSTI ID:1581906

Bonita, Yolanda; Jain, Varsha; Geng, Feiyang; +4 more

Related Subjects

09 BIOMASS FUELS

Title: Single-step catalytic conversion of furfural to 2-pentanol over bimetallic Co–Cu catalysts

Citation Formats

References (39)

Cited By (1)

Similar Records

Related Subjects