Korean Chemical Engineering Research

The Korean Institute of Chemical Engineers (한국화학공학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Renewable Jet Fuel Precursors from C-C Bond Condensation of Furfural and Ethyl Levulinate in Water

  • Cai, Chiliu (Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences) ;
  • Liu, Qiying (Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences) ;
  • Tan, Jin (Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences) ;
  • Wang, Tiejun (Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences) ;
  • Zhang, Qi (Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences) ;
  • Ma, Longlong (Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences)
  • Received : 2016.01.25
  • Accepted : 2016.04.14
  • Published : 2016.08.01
Download PDF
⟨ Previous Next ⟩

Abstract

Biomass derived jet fuel is proven as a potential alternative for the currently used fossil oriented energy. The efficient production of jet fuel precursor with special molecular structure is prerequisite in producing biomass derived jet fuel. We synthesized a new jet fuel precursor containing branched $C_{15}$ framework by aldol condensation of furfural (FA) and ethyl levulinate (EL), where the latter of two could be easily produced from lignocellulose by acid catalyzed processes. The highest yield of 56% for target jet fuel precursor could be obtained at the optimal reaction condition (molar ratio of FA/EL of 2, 323 K, 50 min) by using KOH as catalyst. The chemical structure of $C_{15}$ precursor was specified as (3E, 5E)-6-(furan-2-yl)-3-(furan-2-ylmethylene)-4-oxohex-5-enoic acid ($F_2E$). For stabilization, this yellowish solid precursor was hydrogenated at low temperature to obtain C=C bonds saturated product, and the chemical structure was proposed as 4-oxo-6-(tetrahydrofuran-2-yl)-3-(tetrahydrofuran-2-yl)-methyl hexanoic acid ($H-F_2E$). The successful synthesis of the new jet fuel precursors showed the significance that branched jet fuel could be potentially produced from biomass derived FA and EL via fewer steps.

Keywords

References

  1. Roman-Leshkov, Y., Barrett, C. J., Liu, Z. Y. and Dumesic, J. A., "Production of Dimethylfuran for Liquid Fuels from Biomass-Derived Carbohydrates," Nature, 447, 982-985(2007). https://doi.org/10.1038/nature05923
  2. Li, G. Y., Li, N., Li, S. S., Wang, A.Q., Cong, Y., Wang, X. and Zhang, T., "Synthesis of Renewable Diesel with Hydroxyacetone and 2-methyl-furan," Chem. Commun., 49, 5727-5729(2013). https://doi.org/10.1039/c3cc42296h
  3. Climent, M. J., Corma, A. and Iborra, S., "Conversion of Biomass Platform Molecules Intofuel Additives and Liquid Hydrocarbon Fuels," Green Chem., 16, 516-547(2014). https://doi.org/10.1039/c3gc41492b
  4. Corma, A., Torre, D. L., Renz, M. and Villandier, N., "Production of High-Quality Diesel from Biomass Waste Products," Angew. Chem. Int. Edit., 123, 2423-2426(2011). https://doi.org/10.1002/ange.201007508
  5. Xu, G. Q., Li, Q., Feng, J., Liu, Q., Zhang, Z. J., Wang, X. C., Zhang, X. Y. and Mu, X. D., "Direct a-Alkylation of Ketones with Alcohols in Water," Chemsuschem., 7, 105-109(2014). https://doi.org/10.1002/cssc.201300815
  6. Pestman, R., Koster, R. M., Duijne, A., Pieterse, J. A. and Ponec, V., "Reaction of Carboxylic Acids on Oxides: 2. Bimolecular Reaction of Aliphatic Acids to Ketones," J. Catal., 168, 265-272(1997). https://doi.org/10.1006/jcat.1997.1624
  7. Yang, J. F., Li, N., Li, G. Y., Wang, W. T., Wang, A. Q., Wang, X. D., Cong, Y. and Zhang, T., "Synthesis of Renewable High-Density Fuels Using Cyclopentanone Derived from Lignocelluloses," Chem.Commun., 50, 2572-2574(2014). https://doi.org/10.1039/c3cc46588h
  8. Lee, W. M. and Kim, K. L., "A Study of Hydrocracking and Hydroisomerization of N-Heptane over Supported Ru Catalysts," Korean Chemical Engineering Research, 28, 255-255(1990).
  9. Lee, J. G. and Lee, H. G., "Effect of Metal / Acid Balance in Pt - Loaded Large Pore Zeolites on the Hydroisomerization of N-Hexenes and N-Heptane," Korean Chemical Engineering Research, 14, 451-451(1997). https://doi.org/10.1007/BF02706591
  10. Kunkes, E. L., Gubuz, E. I. and Dumesic, J. A., "Vapour-Phase C-C Coupling Reactions of Biomass-Derived Oxygenates over Pd/CeZrOx Catalysts," J. Catal., 266, 236-249(2009). https://doi.org/10.1016/j.jcat.2009.06.014
  11. Li, G. Y., Li, N., Wang, X. K., Sheng, X. R., Li, S. S., Wang, A. Q., Cong, Y., Wang, X. D. and Zhang, T., "Synthesis of Diesel or Jet Fuel Range Cycloalkanes with 2-Methylfuran and Cyclopentanone from Lignocellulose," Energy Fuels, 28, 5112-5118(2014). https://doi.org/10.1021/ef500676z
  12. Cortright, R. D., Davda, R. R. and Dumesic, J. A., "Hydrogen from Catalytic Reforming of Biomass-Derived Hydrocarbons in Liquid Water," Nature, 418, 964-967(2002). https://doi.org/10.1038/nature01009
  13. Chheda, J. N., Huber, G. W. and Dumesic, J. A., "Liquid-Phase Catalytic Processing of Biomass-Derived Oxygenated Hydrocarbons to Fuels and Chemicals," Angew. Chem. Int. Edit., 46, 7164-7183(2007). https://doi.org/10.1002/anie.200604274
  14. West, R. M., Liu, R. M., Peter, M., Gartner, C. A. and Dumesic, J. A., "Carbon-Carbon Bond Formation Forbiomass-Derived Furfurals And Ketones by Aldol Condensation in A Biphasic System," J. Mol. Catal. A-Chem., 296, 18-27(2008). https://doi.org/10.1016/j.molcata.2008.09.001
  15. Huber, G. W., Chheda, J. N., Barrett, C. J. and Dumesic, J. A., "Production of Liquid Alkanes by Aqueous-Phase Processing of Biomass-Derived Carbohydrates," Science, 308, 1446-1450(2005). https://doi.org/10.1126/science.1111166
  16. Huber, G. W., Iborra, S. and Corma, A., "Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering," Chem. Rev., 106, 4044-4098(2006). https://doi.org/10.1021/cr068360d
  17. Li, G. Y., Li, N., Wang, Z. Q., Li, C. Z., Wang, A. Q., Wang, X. D., Cong, Y. and Zhang, T., "Synthesis of High-Quality Diesel with Furfural and 2-Methylfuran from Hemicellulose," Chemsuschem., 5, 1958-1966(2012). https://doi.org/10.1002/cssc.201200228
  18. Huang, Y. B., Yang, Z., Dai, J. J., Guo, Q. X. and Fu, Y., "Production of High Quality Fuels from Lignocellulose-Derived Chemicals: A Convenient C-C Bond Formation of Furfural, 5-Methylfurfural and Aromatic Aldehyde," RSC Advances, 2, 11211-11214(2012). https://doi.org/10.1039/c2ra22008c
  19. Olson, E. S. and Heide, C., "Multiproduct Biorefinery for Synthesis of Fuel Components and Chemicals from Lignocellulosic via Levulinate Condensations," U.S. Patent No.0,312,028(2010).
  20. Hachihama, Y. and Hayashi, L., "The Preparation of Polyamides Containing Heterocyclic Groups from Furfural and Levulinic Acid," Makromol. Chem., 13, 201-209(1954). https://doi.org/10.1002/macp.1954.020130120
  21. Barrett, C. J.,Chheda, J. N., Huber, G. W. and Dumesic, J. A., "Single-Reactor Process for Sequential Aldol-Condensation and Hydrogenation of Biomass-Derived Compounds in Water," Appl. Catal. B-Environ., 66,111-118(2006). https://doi.org/10.1016/j.apcatb.2006.03.001
  22. Corma, A., Torre, D. and Renz, M., "High-Quality Diesel from Hexose- and Pentose-Derived Biomass Platform Molecules," Chemsuschem., 4, 1574-1577(2011). https://doi.org/10.1002/cssc.201100296
  23. Li, G. Y., Li, N., Yang, J. F., Li, L., Wang, A. Q., Wang, X. D., Cong, Y. and Zhang, T., "Synthesis of Renewable Diesel Range Alkanes by Hydrodeoxygenation of Furans over Ni/$H{\beta}$ under Mild Conditions," Green Chem., 16, 594-599(2014). https://doi.org/10.1039/C3GC41356J
  24. Amarasekara, A. S., Singh, T. B., Larkin, E., Hasan, M. A. and Fan, H. J., "NaOH Catalyzed Condensation Reactions between Levulinic Acid and Biomass Derived Furan-Aldehydes in Water," Industrial Crops and Products, 65, 546-549(2015). https://doi.org/10.1016/j.indcrop.2014.10.005
  25. Mark, M., Saikat, D. and Inaki, G., "Hydrodeoxygenation of the Angelica Lactone Dimer, A Cellulose-Based Feedstock: Simple, High-Yield Synthesis of Branched C7-C10 Gasoline-Like Hydrocarbons," Angew. Chem. Int. Edit., 53, 1854-1857(2014). https://doi.org/10.1002/anie.201308143
  26. Fakhfakh, N., Cognet, P., Cabassud, M., Lucchese, Y. and Ros, M. D. L., "Stoichio-Kinetic Modeling and Optimization of Chemical Synthesis: Application to The Aldolic Condensation of Furfural on Acetone," Chem. Eng. Process., 47, 349-362(2008). https://doi.org/10.1016/j.cep.2007.01.015
  27. Lange, J. P., Heide, C. and Buijtenen, J., "Furfural - A Promising Platform for Lignocellulosic Biofuels," Chem Sus Chem., 5, 150-166(2012). https://doi.org/10.1002/cssc.201100648
  28. Wu, M. S., "The Regioselective Study of Ethyl Levulinate and Benzaldehyde'S Nucleophilic Addition Reaction," M. S. Dissertation, Hebei Normal University, Shi Jia Zhuang(2009).
  29. Huber, G. W. and Dumesic, J. A., "An Overview of Aqueous-Phase Catalytic Processes for Production of Hydrogen and Alkanes In A Biorefinery," Catal. Today, 111, 119-132(2006). https://doi.org/10.1016/j.cattod.2005.10.010
  30. Cho, H. B., Lee, B. U., Ryu, C. H., Nakayama, T. and Park, Y. H., "Selective Hydrogenation of 4-Isobutylacetophenone over A Sodium-Promoted Pd/C Catalyst," Korean J Chem. Eng., 30, 306-313(2013). https://doi.org/10.1007/s11814-012-0184-z
  31. Ryan, M., Liu, Z. Y. and Maximilian, P., "Liquid Alkanes with Targeted Molecular Weights from Biomass-Derived Carbohydrates," Chemsuschem., 1, 417-424(2008). https://doi.org/10.1002/cssc.200800001
  32. Faba, L., Diaz, E. and Ordonez, S., "Improvement on the Catalytic Performance of Mg-Zr Mixed Oxides for Furfural-Acetone Aldol Condensation by Supporting on Mesoporous Carbons," Chemsuschem., 6, 463-473(2013). https://doi.org/10.1002/cssc.201200710

Cited by

  1. Synthesis and Characterization of Furans and Levulinates Polymers: Derived from Cellulosic Carbohydrates via Aldol Condensation vol.53, pp.2267-1242, 2018, https://doi.org/10.1051/e3sconf/20185303011
  2. Production of renewable long-chained cycloalkanes from biomass-derived furfurals and cyclic ketones vol.8, pp.25, 2018, https://doi.org/10.1039/C8RA01723A
  3. n-Octadecane 으로부터 항공유 제조를 위한 Pt-Mg/mesoporous aluminosilicate 촉매 연구 vol.54, pp.5, 2016, https://doi.org/10.9713/kcer.2016.54.5.712
  4. One-Pot Condensation of Furfural and Levulinates: A Novel Method for Cassava Use in Synthesis of Biofuel Precursors vol.32, pp.6, 2016, https://doi.org/10.1021/acs.energyfuels.8b00396