화학공학소재연구정보센터
Korean Chemical Engineering Research, Vol.54, No.4, 519-526, August, 2016
Synthesis of Renewable Jet Fuel Precursors from C-C Bond Condensation of Furfural and Ethyl Levulinate in Water
E-mail:,
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 C15 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 C15 precursor was specified as (3E, 5E)-6-(furan-2-yl)-3-(furan-2-ylmethylene)-4-oxohex-5-enoic acid (F2E). 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-F2E). 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.
  1. Roman-Leshkov Y, Barrett CJ, Liu ZY, Dumesic JA, Nature, 447, 982 (2007)
  2. Li GY, Li N, Li SS, Wang AQ, Cong Y, Wang X, Zhang T, Chem. Commun., 49, 5727 (2013)
  3. Climent MJ, Corma A, Iborra S, Green Chem., 16, 516 (2014)
  4. Corma A, Torre DL, Renz M, Villandier N, Angew. Chem.-Int. Edit., 123, 2423 (2011)
  5. Xu GQ, Li Q, Feng J, Liu Q, Zhang ZJ, Wang XC, Zhang XY, Mu XD, Chemsuschem., 7, 105 (2014)
  6. Pestman R, Koster RM, Vanduijne A, Pieterse JA, Ponec V, J. Catal., 168(2), 265 (1997)
  7. Yang JF, Li N, Li GY, Wang WT, Wang AQ, Wang XD, Cong Y, Zhang T, Chem. Commun., 50, 2572 (2014)
  8. Lee WM, Kim KL, Korean Chem. Eng. Res., 28, 255 (1990)
  9. Lee JG, Lee HG, Korean Chem. Eng. Res., 14, 451 (1997)
  10. Kunkes EL, Gurbuz EI, Dumesic JA, J. Catal., 266(2), 236 (2009)
  11. Li GY, Li N, Wang XK, Sheng XR, Li SS, Wang AQ, Cong Y, Wang XD, Zhang T, Energy Fuels, 28(8), 5112 (2014)
  12. Cortright RD, Davda RR, Dumesic JA, Nature, 418, 964 (2002)
  13. Chheda JN, Huber GW, Dumesic JA, Angew. Chem.-Int. Edit., 46, 7164 (2007)
  14. West RM, Liu ZY, Peter M, Gartner CA, Dumesic JA, J. Mol. Catal. A-Chem., 296(1-2), 18 (2008)
  15. Huber GW, Chheda JN, Barrett CJ, Dumesic JA, Science, 308, 1446 (2005)
  16. Huber GW, Iborra S, Corma A, Chem. Rev., 106(9), 4044 (2006)
  17. Li GY, Li N, Wang ZQ, Li CZ, Wang AQ, Wang XD, Cong Y, Zhang T, Chemsuschem., 5, 1958 (2012)
  18. Huang YB, Yang Z, Dai JJ, Guo QX, Fu Y, RSC Advances, 2, 11211 (2012)
  19. Olson ES, 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, Hayashi L, Makromol. Chem., 13, 201 (1954)
  21. Barrett CJ, Chheda JN, Huber GW, Dumesic JA, Appl. Catal. B: Environ., 66(1-2), 111 (2006)
  22. Corma A, Torre D, Renz M, Chemsuschem., 4, 1574 (2011)
  23. Li GY, Li N, Yang JF, Li L, Wang AQ, Wang XD, Cong Y, Zhang T, Green Chem., 16, 594 (2014)
  24. Amarasekara AS, Singh TB, Larkin E, Hasan MA, Fan HJ, Ind. Crop. Prod., 65, 546 (2015)
  25. Mark M, Saikat D, Inaki G, Angew. Chem.-Int. Edit., 53, 1854 (2014)
  26. Fakhfakh N, Cognet P, Cabassud M, Lucchese Y, Rios MDDL, Chem. Eng. Process., 47(3), 349 (2008)
  27. Lange JP, Heide C, Buijtenen J, Chem Sus Chem., 5, 150 (2012)
  28. Wu MS, “The Regioselective Study of Ethyl Levulinate and Benzaldehyde’S Nucleophilic Addition Reaction,” M. S. Dissertation, Hebei Normal University, Shi Jia Zhuang(2009).
  29. Huber GW, Dumesic JA, Catal. Today, 111(1-2), 119 (2006)
  30. Cho HB, Lee BU, Ryu CH, Nakayama T, Park YH, Korean J. Chem. Eng., 30(2), 306 (2013)
  31. Ryan M, Liu ZY, Maximilian P, Chemsuschem., 1, 417 (2008)
  32. Faba L, Diaz E, Ordonez S, Chemsuschem., 6, 463 (2013)