Abstract
Diminishing fossil fuel reserves and growing concerns about global warming indicate that sustainable sources of energy are needed in the near future. For fuels to be useful in the transportation sector, they must have specific physical properties that allow for efficient distribution, storage and combustion; these properties are currently fulfilled by non-renewable petroleum-derived liquid fuels. Ethanol, the only renewable liquid fuel currently produced in large quantities, suffers from several limitations, including low energy density, high volatility, and contamination by the absorption of water from the atmosphere. Here we present a catalytic strategy for the production of 2,5-dimethylfuran from fructose (a carbohydrate obtained directly from biomass or by the isomerization of glucose) for use as a liquid transportation fuel. Compared to ethanol, 2,5-dimethylfuran has a higher energy density (by 40 per cent), a higher boiling point (by 20 K), and is not soluble in water. This catalytic strategy creates a route for transforming abundant renewable biomass resources1,2 into a liquid fuel suitable for the transportation sector, and may diminish our reliance on petroleum.
This is a preview of subscription content, access via your institution
Relevant articles
Open Access articles citing this article.
-
A unique Co@CoO catalyst for hydrogenolysis of biomass-derived 5-hydroxymethylfurfural to 2,5-dimethylfuran
Nature Communications Open Access 27 June 2022
Access options
Subscribe to this journal
Receive 51 print issues and online access
$199.00 per year
only $3.90 per issue
Rent or buy this article
Get just this article for as long as you need it
$39.95
Prices may be subject to local taxes which are calculated during checkout



References
Parikka, M. Global biomass fuel resources. Biomass Bioenergy 27, 613–620 (2004)
Ragauskas, A. J. et al. The path forward for biofuels and biomaterials. Science 311, 484–489 (2006)
Barlow, M. T., Smith, D. J. & Steward, D. G. Fuel composition. European patent EP0082689. (1983)
Román-Leshkov, Y., Chheda, J. N. & Dumesic, J. A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 312, 1933–1937 (2006)
Brown, D. W., Floyd, A. J., Kinsman, R. G. & Roshan-Ali, Y. Dehydration reactions of fructose in non-aqueous media. J. Chem. Technol. Biotechnol. 32, 920–924 (1982)
Kuster, B. M. F. 5-Hydroxymethylfurfural (HMF). A review focussing on its manufacture. Starch 42, 314–321 (1990)
Moreau, C., Belgacem, M. N. & Gandini, A. Recent catalytic advances in the chemistry of substituted furans from carbohydrates and in the ensuing polymers. Top. Catal. 27, 11–30 (2004)
Szmant, H. H. & Chundury, D. D. The preparation of 5-hydroxymethylfurfuraldehyde from high fructose corn syrup and other carbohydrates. J. Chem. Technol. Biotechnol. 31, 135–145 (1981)
van Dam, H. E., Kieboom, A. P. G. & van Bekkum, H. The conversion of fructose and glucose in acidic media: Formation of hydroxymethylfurfural. Starch 38, 95–101 (1986)
Eisen, E. O. & Joffe, J. Salt effects in liquid-liquid equilibria. J. Chem. Eng. Data 11, 480–484 (1966)
Tan, T. C. & Aravinth, S. Liquid-liquid equilibria of water/acetic acid/1-butanol system—effects of sodium (potassium) chloride and correlations. Fluid Phase Equil. 163, 243–257 (1999)
Neier, W., Webers, W., Ruckhaber, R., Osterburg, G. & Ostwald, W. Continuous production of sec-butanol. German patent DE3040997. (1982)
Jones, D. T. & Woods, D. R. Acetone-butanol fermentation revisited. Microbiol. Rev. 50, 484–524 (1986)
Ramey, E. D. Continuous two-stage dual path anaerobic fermentation of butanol and other organic solvents using two different strains of bacteria. US patent US5753474. (1998)
Manly, D. G. & Dunlop, A. P. Catalytic hydrogenation. I. Kinetics and catalyst composition in the preparation of 2-methylfuran. J. Org. Chem. 23, 1093–1095 (1958)
Rao, R. S., Baker, R. T. & Vannice, M. A. Furfural hydrogenation over carbon-supported copper. Catal. Lett. 60, 51–57 (1999)
Zheng, H.-Y. et al. Towards understanding the reaction pathway in vapour phase hydrogenation of furfural to 2-methylfuran. J. Mol. Catal. Chem. 246, 18–23 (2006)
Twigg, M. V. & Spencer, M. S. Deactivation of supported copper metal catalysts for hydrogenation reactions. Appl. Catal. A 212, 161–174 (2001)
Helms, C. R. & Sinfelt, J. H. Electron spectroscopy (ESCA) studies of ruthenium-copper catalysts. Surf. Sci. 72, 229–242 (1978)
Sinfelt, J. H. Supported bimetallic cluster catalysts. J. Catal. 29, 308–315 (1973)
Sinfelt, J. H., Lam, Y. L. & Cusumano, J. A. Nature of ruthenium-copper catalysts. J. Catal. 42, 227–237 (1976)
Broughton, D. B. & Gerhold, C. G. Continuous sorption process employing fixed beds of sorbent and moving inlets and outlets. US Patent US2985589. (1961)
Hashimoto, K., Adachi, S. & Shirai, Y. in Preparative and Production Scale Chromatography (eds Ganestos, G. & Barker, P. E.) 395–417 (CRC Publishing, New York, 1993)
Jones, J. H., Fenske, M. R. & Rusk, R. A. Vapor-phase oxidation as a process for raising octane number. Ind. Eng. Chem. Prod. Res. Dev. 10, 57–65 (1971)
Graboski, M. S. An Analysis of Alternatives for Unleaded Petrol Additives for South Africa (Technical Report, United Nations Environment Programme, Nairobi, Kenya, 2003); available at 〈http://www.unep.org/PCFV/PDF/PubGraboskiReport.pdf〉
Acknowledgements
This work was supported by the National Science Foundation Chemical and Transport Systems Division of the Directorate for Engineering, and the US Department of Energy Office of Basic Energy Sciences. We thank R. McClain and the UW Chemistry Department for access to their mass spectrometer. We also thank D. Simonetti, R. West, J. Chheda, E. Kunkes, S. Chen and S. Laumann for discussions and technical assistance.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Competing interests
Reprints and permissions information is available at www.nature.com/reprints. The authors declare no competing financial interests.
Supplementary information
Supplementary Information
This file contains Supplementary Figures 1-2 with an annotated version of Figure 2 in the main text summarizing the main findings of the work and a diagram depicting the vapor-phase hydrogenolysis flow reactor; Supplementary Methods used for compound quantification and characterization; Supplementary Discussion regarding vapor-phase hydrogenolysis experiments; Supplementary Tables 1-4 summarizing results regarding the use of additional inorganic salts for the dehydration experiments, as well as results for both liquid and vapor-phase hydrogenolysis experiments; Supplementary Notes with additional information regarding the estimation for the energy consumption in a distillation process for DMF and ethanol, toxicology data for DMF and additional references. (PDF 450 kb)
Rights and permissions
About this article
Cite this article
Román-Leshkov, Y., Barrett, C., Liu, Z. et al. Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates. Nature 447, 982–985 (2007). https://doi.org/10.1038/nature05923
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1038/nature05923
This article is cited by
-
Mechanistic kinetic comparison of terrestrial biomass-derived cellulose and marine algae-derived agarose acidic degradation to monosaccharides and 5-hydroxymethylfurfural
Biomass Conversion and Biorefinery (2023)
-
Effects of Mixing and Particle Size on the Kinetics and Dynamics of Enzymatically Treated Cotton Cellulose (MCC) in Continuous Flow Reactor
Applied Biochemistry and Biotechnology (2023)
-
A unique Co@CoO catalyst for hydrogenolysis of biomass-derived 5-hydroxymethylfurfural to 2,5-dimethylfuran
Nature Communications (2022)
-
Ionic liquid-based nanocomposites for organic transformations
Journal of the Iranian Chemical Society (2022)
-
Catalytic Transfer Hydrogenation of Biomass-Derived 5-Hydroxymethylfurfural into 2,5-Dihydroxymethylfuran over Co/UiO-66-NH2
Catalysis Letters (2022)
Comments
By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.