Synthesis of high density and low freezing point jet fuels range cycloalkanes with cyclopentanone and lignin-derived vanillins

doi:10.1016/j.jechem.2022.12.017

Abstract

Abstract: In this work, a ‘‘cyclopentanone-vanillin” strategy was proposed for the preparation of jet fuel range cycloalkanes from lignocellulose-derived ketones and lignin-derived aldehydes via aldol condensation and hydrodeoxygenation (HDO). Ethanolamine lactate ionic liquid (LAIL) exhibited excellent catalytic activity in the aldol condensation of cyclopentanone and vanillin. Desired mono-condensation and bi-condensation products were obtained with yield of 95.2% at 100 °C. It is found that the synergy effects between amino group of ethanolamine and hydroxyl group of lactic acid play a key role in the aldol con-densation. The condensation products were converted into cycloalkanes by HDO over 5%Pd/Nb₂O₅ cata-lyst. The density of the obtained HDO products is 0.89 g/cm³ and the freezing point is lower than —60 °C. These results suggest that the resulted cycloalkanes can be used as additives to improve the density and low-temperature fluidity of the jet fuels.

Key words: Aldol condensation, Cyclopentanone-vanillin, Ionic liquid catalysts, Hydrodeoxygenation, Jet fuel

Xinghua Zhang, Miaojia Song, Jianguo Liu, Qi Zhang, Lungang Chen, Longlong Ma. Synthesis of high density and low freezing point jet fuels range cycloalkanes with cyclopentanone and lignin-derived vanillins[J]. Journal of Energy Chemistry, 2023, 79(4): 22-30.

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URL: https://www.jenergychem.com/EN/10.1016/j.jechem.2022.12.017

https://www.jenergychem.com/EN/Y2023/V79/I4/22

References

[1] K.T. Malladi, T. Sowlati,Appl. Energy 267(2020).
[2] E.O. Jåstad, T.F. Bolkesjø, E. Trømborg, P.K. Rørstad,Appl. Energy 274(2020).
[3] S. Ebrahimi, S.A.H.Esmaeili, A. Sobhani, J. Szmerekovsky, Appl. Energy 310(2020).
[4] S. Shylesh, A.A. Gokhale, C.R. Ho, A.T. Bell, Acc. Chem. Res. 50(2017) 2589-2597.
[5] J.Q. Bond, A.A. Upadhye, H. Olcay, G.A. Tompsett, J. Jae, R. Xing, D.M. Alonso, D. Wang, T.Y. Zhang, R. Kumar, A. Foster, S.M. Sen, C.T. Maravelias, R. Malina, S.R.H.Barrett, R. Lobo, C.E. Wyman, J.A. Dumesic, G.W. Huber, Energy Environ. Sci. 7(2014) 1500-1523.
[6] E.R. Sacia, M. Balakrishnan, M.H. Deaner, K.A. Goulas, F.D. Toste, A.T. Bell, ChemSusChem 8(2015) 1726-1736.
[7] R. Xing, A.V. Subrahmanyam, H. Olcay, W. Qi, G.P.van Walsum, H. Pendse, G.W. Huber, Green Chem. 12(2010) 1933-1946.
[8] X. Luo, R. Lu, X. Si, H. Jiang, Q. Shi, H. Ma, C. Zhang, J. Xu, F. Lu, J. Energy Chem. 69(2022) 231-236.
[9] X. Zhang, L. Pan, L. Wang, J. Zou, Chem. Eng. Sci. 180(2018) 95-125.
[10] Q. Deng, J. Xu, P. Han, L. Pan, L. Wang, X. Zhang, J. Zou, Fuel Process. Technol. 148(2016) 361-366.
[11] T.V. Bui, T. Sooknoi, D.E. Resasco, ChemSusChem 10(2017) 1631-1639.
[12] Y. Jing, Q. Xia, J. Xie, X. Liu, Y. Guo, J. Zou, Y. Wang, ACS Catal. 8(2018) 3280-3285.
[13] Q. Liu, X. Zhang, Q. Zhang, Q. Liu, C. Wang, L. Ma, Energy Fuels 34(2020) 7149-7159.
[14] F. Chen, N. Li, S. Li, J. Yang, F. Liu, W. Wang, A. Wang, Y. Cong, X. Wang, T. Zhang, Catal. Commun. 59(2015) 229-232.
[15] T. Shen, C. Zhu, C. Tang, Z. Cao, L. Wang, K. Guo, H. Ying, RSC Adv. 6(2016) 62974-62980.
[16] C. Zhu, T. Shen, D. Liu, J. Wu, Y. Chen, L. Wang, K. Guo, H. Ying, P. Ouyang, Green Chem. 18(2016) 2165-2174.
[17] G. Li, N. Li, X. Wang, X. Sheng, S. Li, A. Wang, Y. Cong, X. Wang, T. Zhang, Energy Fuels 28(2014) 5112-5118.
[18] G. Nie, X. Zhang, L. Pan, M. Wang, J. Zou, Chem. Eng. Sci. 180(2018) 64-69.
[19] S. Liu, C. Shi, Z. Shen, L. Pan, Z. Huang, X. Zhang, J. Zou,J. Energy Chem. https://doi.org/10.1016/j.jechem.2022.10.050.
[20] S. Xie, T.H. Huynh, P. Qin, T. Tan, H. Lin, J. Energy Chem. 49(2020) 42-50.
[21] Q. Deng, G. Nie, L. Pan, J. Zou, X. Zhang, L. Wang, Green Chem. 17(2015) 4473-4481.
[22] X. Sheng, G. Li, W. Wang, Y. Cong, X. Wang, G.W. Huber, N. Li, A. Wang, T. Zhang, AIChE J. 62(2016) 2754-2761.
[23] W. Wang, N. Li, G. Li, S. Li, W. Wang, A. Wang, Y. Cong, X. Wang, T. Zhang, ACS Sustain. Chem. Eng. 5(2017) 1812-1817.
[24] S. Chen, W. Wang, X. Li, P. Yan, W. Han, T. Shen, T. Deng, W. Zhu, H. Wang, J. Energy Chem. 66(2022) 576-586.
[25] G. Nie, X. Zhang, P. Han, J. Xie, L. Pan, L. Wang, J. Zou, Chem. Eng. Sci. 158(2017) 64-69.
[26] J. Bai, Y. Zhang, X. Zhang, C. Wang, L. Ma, ACS Sustain. Chem. Eng. 9(2021) 7112-7119.
[27] J. Xie, L. Zhang, X. Zhang, P. Han, J. Xie, L. Pan, D.R. Zou, S.H. Liu, J. Zou, Sustain. Energy Fuels 2(2018) 1863-1869.
[28] F. Chen, N. Li, S. Li, G. Li, A.Q. Wang, Y. Cong, X. Wang, T. Zhang, Green Chem. 18(2016) 5751-5755.
[29] W. Wang, Y. Liu, N. Li, G. Li, W. Wang, A. Wang, X. Wang, T. Zhang, Sci. Rep. 7(2017) 6111.
[30] G. Nie, X. Zhang, L. Pan, P. Han, J. Xie, Z. Li, J. Xie, J. Zou, Chem. Eng. Sci. 173(2017) 91-97.
[31] G. Nie, Y. Dai, Y. Liu, J. Xie, S. Gong, N. Afzal, X. Zhang, L. Pan, J. Zou, Chem. Eng. Sci. 207(2019) 441-447.
[32] R. Ramos, A. Grigoropoulos, N. Perret, M. Zanella, A.P. Katsoulidis, T.D. Manning, J.B. Claridge, M.J. Rosseinsky, Green Chem. 19(2017) 1701-1713.
[33] Y. Zhang, G. Fan, L. Yang, F. Li, Appl. Catal. A-Gen. 561(2018) 117-126.
[34] A.R.C.Morais, M.D.D.J. Matuchaki, J. Andreaus, R. Bogel-Lukasik, Green Chem. 18(2016) 2985-2994.
[35] A. Mittal, S.K. Black, T.B. Vinzant, M. O’Brien, M.P. Tucker, D.K. Johnson, ACS Sustain. Chem. Eng. 5(2017) 5694-5701.
[36] C. Liu, X. Yin, X. Pan, J. Hu, N. Li, J. Xu, J. Jiang, K. Wang,Chem. Eng. J. 425(2021).
[37] S. Wang, Y. Zhao, H. Lin, J. Chen, L. Zhu, Z. Luo, Green Chem. 19(2017) 3869-3879.
[38] W. Jeon, I.H. Choi, J.Y. Park, J.S. Lee, K.R. Hwang, Catal. Today. 352(2020) 95-103.
[39] H. Guo, B. Zhang, Z. Qi, C. Li, J. Ji, T. Dai, A. Wang, T. Zhang, ChemSusChem 10(2017) 523-532.
[40] L. Jiang, H. Guo, C. Li, P. Zhou, Z. Zhang, Chem. Sci. 10(2019) 4458-4468.
[41] X. Li, Y. Ding, X. Pan, Y. Xing, B. Zhang, X. Liu, Y. Tan, H. Wang, C. Li, J. Energy Chem. 67(2022) 492-499.
[42] X. Cui, X. Zhao, D. Liu, Green Chem. 20(2018) 2018-2026.
[43] O. Kikhtyanin, D. Kadlec, R. Velvarska, D. Kubicka, ChemCatChem 10(2018) 1464-1475.
[44] X. Zhang, H. An, H. Zhang, X. Zhao, Y. Wang, Ind. Eng. Chem. Res. 53(2014) 16707-16714.
[45] L.Q. Kang, Y.Q. Cai, H. Wang, L.H. Li, Monatsh Chem. 145(2014) 337-340.
[46] M. Iglesias, R. Gonzalez-Olmos, I. Cota, F. Medina, Chem. Eng. J. 162(2010) 802-808.
[47] J. Xu, N. Li, G. Li, F. Han, A. Wang, Y. Cong, X. Wang, T. Zhang, Green Chem. 20(2018) 3753-3760.
[48] A.-B.Watheq, J Solution Chem. 41(2012) 1495-1506.
[49] N. Asprion, H. Hasse, G. Maurer, Fluid Phase Equilibr. 186(2001) 1-25.
[50] E.A. Velcheva, B.A. Stamboliyska, P.J. Boyadjieva, J. Mol. Struct. 963(2010) 57-62.
[51] D. Simijonović, Z.D. Petrović, V.P. Petrović, J. Mol Liq. 179(2013) 98-103.
[52] J.L. Anderson, J. Ding, T. Welton, D.W. Armstrong, J. Am. Chem.Soc. 124(2014) 14247-14254.
[53] Q. Liu, M.H.A.Janssen, F. van Rantwijk, R.A. Sheldon, Green Chem. 7(2005) 39-42.
[54] A. Osatiashtiani, L.J. Durndell, J.C. Manayil, A.F. Lee, K. Wilson, Green Chem. 18(2016) 5529-5535.
[55] J.L. Fiorio, A.H. Braga, C.L.B.Guedes, L.M. Rossi, ACS Sustain. Chem. Eng. 7(2019) 15874-15883.
[56] Y. Shao, Q. Xia, L. Dong, X. Liu, X. Han, S.F. Parker, Y. Cheng, L.L. Daemen, A.J.Ramirez-Cuesta, S.Yang, Y. Wang, Nat. Commun. 8(2017) 16104.