The upgrading of biomass-derived feedstocks to liquid transportation fuels is complex because of the chemical differences between biomass-derived chemicals and conventional fuels. Aldol condensation may play an important role in converting biomass-derive components to fuels because it allows smaller species to be converted to larger species that are more similar to conventional fuels. This review covers recent progress in aldol condensation of biomass-derived 5-hydroxymethylfurfural, acetone, methyl ketones, acetoin, levulinic acid, furfural, cyclopentanone and levulinic acid. The corresponding catalytic mechanisms and future research directions in these areas are also discussed.
Cite this paper
Jiang, C. (2020). Upgrading of Biomass-Derived Feedstocks to Liquid Transportation Fuel Precursors by Aldol Condensation. Open Access Library Journal, 7, e6185. doi: http://dx.doi.org/10.4236/oalib.1106185.
Conti, J., Holtberg, P., Diefenderfer, J., LaRose, A., Turnure, J.T. and Westfall, L. International Energy Outlook 2016 with Projections to 2040. 1-5.
https://www.osti.gov/biblio/1296780
Hronec, M., Fulajtárova, K., Liptaj, T., Prónayová, N. and Soták, T. (2015) Bio-Derived Fuel Additives from Furfural and Cyclopentanone. Fuel Processing Technology, 138, 564-569. https://doi.org/10.1016/j.fuproc.2015.06.036
Huber, G.W., Iborra, S. and Corma, A. (2006) Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering. Chemical Reviews, 106, 4044-4098. https://doi.org/10.1021/cr068360d
Patel, M. and Kumar, A. (2016) Production of Renewable Diesel through the Hydroprocessing of Lignocellulosic Biomass-Derived Bio-Oil: A Review. Renewable and Sustainable Energy Reviews, 58, 1293-1307.
https://doi.org/10.1016/j.rser.2015.12.146
Bridgwater, A.V. (2012) Review of Fast Pyrolysis of Biomass and Product Upgrading. Biomass and Bioenergy, 38, 68-94.
https://doi.org/10.1016/j.biombioe.2011.01.048
López Barreiro, D., Ronsse, F. and Brilman, W. (2013) Hydrothermal Liquefaction (HTL) of Microalgae for Biofuel Production: State of the Art Review and Future Prospects. Biomass and Bioenergy, 53, 113-127.
https://doi.org/10.1016/j.biombioe.2012.12.029
Kumar, S., Lange, J.P., Van Rossum, G. and Kersten, S.R.A. (2015) Liquefaction of Lignocellulose in Fluid Catalytic Cracker Feed: A Process Concept Study. ChemSusChem, 8, 4086-4094. https://doi.org/10.1002/cssc.201500457
Snehesh Shivananda Ail, S.D. (2016) Biomass to Liquid Transportation Fuel via Fischer Tropsch Synthesis—Technology Review and Current Scenario. Renewable and Sustainable Energy Reviews, 58, 267-286.
https://doi.org/10.1016/j.rser.2015.12.143
Lan, W., Chen, G., Zhu, X., Wang, X. and Xu, B. (2015) Progress in Techniques of Biomass Conversion into Syngas. Journal of the Energy Institute, 88, 151-156.
https://doi.org/10.1016/j.joei.2014.05.003
Shylesh, S., Hanna, D., Gomes, J., Canlas, C.G., Head-Gordon, M. and Bell, A.T. (2015) The Role of Hydroxyl Group Acidity on the Activity of Silica-Supported Secondary Amines for the Self-Condensation of n-Butanal. ChemSusChem, 8, 466-472.
https://doi.org/10.1002/cssc.201402443
Bohre, A., Saha, B. and Abu-Omar, M.M. (2015) Catalytic Upgrading of 5-Hydro- xymethylfurfural to Drop-In Biofuels by Solid Base and Bifunctional Metal-Acid Catalysts. ChemSusChem, 8, 4022-4029. https://doi.org/10.1002/cssc.201501136
Wang, L. and Chen, E.Y.X. (2015) Recyclable Supported Carbene Catalysts for High-Yielding Self-Condensation of Furaldehydes into C10 and C12 Furoins. ACS Catalysis, 5, 6907-6917. https://doi.org/10.1021/acscatal.5b01410
Dea, S. and Basudeb Saha, R.L. (2015) Hydrodeoxygenation Processes: Advances on Catalytic Transformations of Biomass-Derived Platform Chemicals into Hydrocarbon Fuels. Bioresource Technology, 178, 108-118.
https://doi.org/10.1016/j.biortech.2014.09.065
Charles, L. (2016) Perrin and Kuei-Lin Chang. The Complete Mechanism of an Aldol Condensation. The Journal of Organic Chemistry, 81, 5631-5635.
https://doi.org/10.1021/acs.joc.6b00959
Hernandez, W.Y., Alic, F., Verberckmoes, A. and Tuning, P.V.D.V. (2017) The Acidic-Basic Properties by Zn-Substitution in Mg-Al Hydrotalcites as Optimal Catalysts for the Aldol Condensation Reaction. Journal of Materials Science, 52, 628-642. https://doi.org/10.1007/s10853-016-0360-3
Yong, G., Zhang, Y. and Ying, J.Y. (2008) Efficient Catalytic System for the Selective Production of 5-Hydroxymethylfurfural from Glucose and Fructose. Angewandte Chemie—International Edition, 47, 9345-9348.
https://doi.org/10.1002/anie.200803207
Chheda, J.N. and Dumesic, J.A. (2007) An Overview of Dehydration, Aldol-Con- densation and Hydrogenation Processes for Production of Liquid Alkanes from Biomass-Derived Carbohydrates. Catalysis Today, 123, 59-70.
https://doi.org/10.1016/j.cattod.2006.12.006
Li, S., Chen, F., Li, N., et al. (2017) Synthesis of Renewable Triketones, Diketones, and Jet-Fuel Range Cycloalkanes with 5-Hydroxymethylfurfural and Ketones. ChemSusChem, 10, 711-719.
Lee, R., et al. (2016) CO2-Catalysed Aldol Condensation of 5-Hydroxy-Methylfurfural and Acetone to a Jet Fuel Precursor. Green Chemistry, 18, 5118-5121.
https://doi.org/10.1039/C6GC01697A
Pupovac, K. and Palkovits, R. (2013) Cu/MgAl2O4 as Bifunctional Catalyst for Aldol Condensation of 5-Hydroxymethylfurfural and Selective Transfer Hydrogenation. ChemSusChem, 6, 2103-2110. https://doi.org/10.1002/cssc.201300414
Chen, S., Yang, H.Q., et al. (2015) Theoretical Study on the Reaction Mechanisms of the Aldol-Condensation of 5-Hydroxymethylfurfural with Acetone Catalyzed by MgO and MgO . Catalysis Today, 245, 100-107.
https://doi.org/10.1016/j.cattod.2014.05.004
Anbarasan, P., Baer, Z.C., Sreekumar, S., et al. (2012) Integration of Chemical Catalysis with Extractive Fermentation to Produce Fuels. Nature, 491, 235-239.
https://doi.org/10.1038/nature11594
Multer, A., McGraw, N., Hohn, K. and Vadlani, P. (2013) Production of Methyl Ethyl Ketone from Biomass Using a Hybrid Biochemical/Catalytic Approach. Industrial & Engineering Chemistry Research, 52, 56-60.
https://doi.org/10.1021/ie3007598
Koutinas, A.A., Yepez, B., Kopsahelis, N., Freire, D.M.G., de Castro, A.M., Papanikolaou, S. and Kookos, I.K. (2016) Techno-Economic Evaluation of a Complete Bioprocess for 2,3-Butanediol Production from Renewable Resources. Bioresource Technology, 204, 55-64. https://doi.org/10.1016/j.biortech.2015.12.005
Balakrishnan, M., et al. (2015) Novel Pathways for Fuels and Lubricants from Biomass optimized Using Life-Cycle Greenhouse Gas Assessment. Proceedings of the National Academy of Sciences of the United States of America, 112, 7645-7649.
https://doi.org/10.1073/pnas.1508274112
Balakrishnan, M., Arab, G.E., Kunbargi, O.B., Gokhale, A.A., Grippo, A.M., Toste, F.D. and Bell, A.T. (2016) Production of Renewable Lubricants via Self-Condensation of Methyl Ketones. Green Chemistry, 18, 1-5. https://doi.org/10.1039/C6GC00579A
Nakajima, K., Baba, Y., Noma, R., et al. (2011) Nb2O5 3nH2O as a Heterogeneous Catalyst with Water-Tolerant Lewis Acid Sites. Journal of the American Chemical Society, 133, 4224-4227. https://doi.org/10.1021/ja110482r
Lebarbier, V., Houalla, M. and Onfroy, T. (2012) New Insights into the Development of Bronsted Acidity of Niobic Acid. Catalysis Today, 192, 123-129.
https://doi.org/10.1016/j.cattod.2012.02.061
Zhang, B., Li, X.-L., Fu, J., et al. (2016) Production of Acetoin through Simultaneous Utilization of Glucose, Xylose, and Arabinose by Engineered Bacillus subtilis. PLoS ONE, 11, e0159298. https://doi.org/10.1371/journal.pone.0159298
Zhu, C.J., Shen, T., Liu, D., et al. (2016) Production of Liquid Hydrocarbon Fuels with Acetoin and Platform Molecules Derived from Lignocellulose. Green Chemistry, 18, 2165-2174. https://doi.org/10.1039/C5GC02414E
Li, X.D., Jia, P., et al. (2016) Furfural: A Promising Platform Compound for Sustainable Production of C4 and C5 Chemicals. ACS Catalysis, 6, 7621-7640.
https://doi.org/10.1021/acscatal.6b01838
Kikhtyanin, O., Hora, L., et al. (2015) Unprecedented Selectivities in Aldol Condensation over Mg-Al Hydrotalcite in a Fixed Bed Reactor Setup. Catalysis Communications, 58, 89-92. https://doi.org/10.1016/j.catcom.2014.09.002
Thanh, D.N., Kikhtyanin, O., Ramos, R., et al. (2016) Nanosized TiO2—A Promising Catalyst for the Aldol Condensation of Furfural with Acetone in Biomass Upgrading. Catalysis Today, 277, 97-107. https://doi.org/10.1016/j.cattod.2015.11.027
Hora, L., et al. (2014) Aldol Condensation of Furfural and Acetone over Mg-Al Layered Double Hydroxides and Mixed Oxides. Catalysis Today, 223, 138-147.
https://doi.org/10.1016/j.cattod.2013.09.022
Kikhtyanin, O., Bulánek, R., Frolich, K., et al. (2016) Aldol Condensation of Furfural with Acetone over Ion-Exchanged and Impregnated Potassium BEA Zeolites. Journal of Molecular Catalysis A: Chemical, 424, 358-368.
https://doi.org/10.1016/j.molcata.2016.09.014
Pileidis, F.D. and Titirici, M.M. (2016) Levulinic Acid Biorefineries: New Challenges for Efficient Utilization of Biomass. ChemSusChem, 9, 562-582.
https://doi.org/10.1002/cssc.201501405
Liang, G.F., Wang, A.Q., Zhao, X.C., et al. (2016) Selective Aldol Condensation of Biomass-Derived Levulinic Acid and Furfural in Aqueous-Phase over MgO and ZnO. Green Chemistry, 18, 3430-3438. https://doi.org/10.1039/C6GC00118A
Zhang, L., Pham, T.N., Faria, J., Santhanaraj, D., Sooknoi, T., Tan, Q., Zhao, Z. and Resasco, D.E. (2016) Synthesis of C4 and C8 Chemicals from Ethanol on MgO-In- corporated Faujasite Catalysts with Balanced Confinement Effects and Basicity. ChemSusChem, 9, 736-748. https://doi.org/10.1002/cssc.201501518
Hronec, M., Fulajtárová, K., Vávra, I., Soták, T., Dobro?ka, E. and Mi?u?ík, M. (2016) Carbon Supported Pd-Cu Catalysts for Highly Selective Rearrangement of Furfural to Cyclopentanone. Applied Catalysis B: Environmental, 181, 210-219.
https://doi.org/10.1016/j.apcatb.2015.07.046
Hronec, M., et al. (2016) Nickel Catalysed Hydrogenation of Aldol Condensation Product of Furfural with Cyclopentanone to C15 Cyclic Ethers. ChemistrySelect, 2, 331-336. https://doi.org/10.1002/slct.201500001
Hronec, M., Fulajtárova, K., Liptaj, T., ?tolcová, M., Prónayová, N. and Soták, T. (2014) Cyclopentanone: A Raw Material for Production of C15 and C17 Fuel Precursors. Biomass and Bioenergy, 63, 291-299.
https://doi.org/10.1016/j.biombioe.2014.02.025
Matzker, G. and Burtoloso, A.C.B. (2015) Conversion of Levulinic Acid into c-Valerolactone Using Fe3(CO)12: Mimicking a Biorefinery Setting by Exploiting Crude Liquors from Biomass acid Hydrolysis. Chemical Communications, 51, 14199-14202. https://doi.org/10.1039/C5CC02993G
Faba, L., Díaz, E. and Ordó?ez, S. (2016) Base-Catalyzed Condensation of Levulinic Acid: A New Biorefinery Upgrading Approach. ChemCatChem, 8, 1490-1494.
https://doi.org/10.1002/cctc.201600064
Jing, Y., Xin, Y., Guo, Y., Liu, X. and Wang, Y. (2019) Highly Efficient Nb2O5 Catalyst for Aldol Condensation of Biomass-Derived Carbonyl Molecules to Fuel Precursors. Chinese Journal of Catalysis, 40, 1168-1177.
https://doi.org/10.1016/S1872-2067(19)63371-1
Cueto, J., Faba, L., Díaz, E. and Ordó?ez, S. (2020) Optimization of the Process Conditions for Minimizing the Deactivation in the Furfural-Cyclopentanone Aldol Condensation in a Continuous Reactor. Applied Catalysis B: Environmental, 263, Article ID: 118341. https://doi.org/10.1016/j.apcatb.2019.118341
Ngo, D.T., Tan, Q., Wang, B. and Resasco, D.E. (2019) Aldol Condensation of Cyclopentanone on Hydrophobized MgO. Promotional Role of Water and Changes in Rate-Limiting Step upon Organosilane Functionalization. ACS Catalysis, 9, 2831- 2841. https://doi.org/10.1021/acscatal.8b05103