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http://dx.doi.org/10.14478/ace.2015.1054

A Study on the Reaction Pathway for Isomerization of Tetrahydrotricyclopentadiene Using Ionic Liquid Catalyst  

Kim, Dae Hyun (Division of Advanced material Engineering, Kongju National University)
Han, Jeong-Sik (Agency for Defense Development)
Jeon, Jong-Ki (Department of Chemical engineering, Kongju National University)
Yim, Jin-Heong (Division of Advanced material Engineering, Kongju National University)
Publication Information
Applied Chemistry for Engineering / v.26, no.3, 2015 , pp. 366-371 More about this Journal
Abstract
The kinetic behavior of tetrahydrotricyclopentadiene (THTCPD) isomerization was studied by using two kinds of chloroaluminate ionic liquid (IL) catalyst with different Lewis acidity. THTCPD isomerization pathway was discussed under the different temperature and time as reaction parameters using IL catalysts consisting of 1-butyl-3-methylimidazolun chloride $(BMIC)/AlCl_3$ with low acidity and pyridine hydrochloride $(PHC)/AlCl_3$ with high acidity. The conversion of THTCPD isomerization increased with increasing Lewis acidity of IL catalyst. The THTCPD isomerization pathway changed as a function of reaction temperature and catalyst acidity. In the case of $BMIC/AlCl_3$ IL catalyst, THTCPD isomerization pathway was similar to that of using conventional $AlCl_3$ catalyst. However, two different types of additional pathways (endo, exo, endo-NB ${\rightarrow}$ exo, exo, endo-NB ${\rightarrow}$ exo, exo, exo-NB and endo, exo, endo-NB ${\rightarrow}$ exo, exo, endo-NB ${\rightarrow}$ exo, exo, exo-CP) were appeared when using $PHC/AlCl_3$ IL catalyst.
Keywords
High energy density fuels; Isomerization; Kinetic study; Tetrahydrotricyclopentadiene; Ionic liquid catalyst;
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1 H. S. Chung, C. S. H. Chen, R. A. Kremer, and J. R. Boulton, Recent Developments in High-Energy Density Liquid Hydrocarbon Fuels, Energy Fuels, 13, 641-649 (1999).   DOI   ScienceOn
2 T. Edward, Liquid Fuels and Propellants for Aerospace Propulsion: 1903-200, J. of PROP. & POW., 19, 1089-1107 (2003).   DOI   ScienceOn
3 L. Wang, X. Zhang, J.-J. Zou, H. Han, Y. Li, and L. Wang, Acid-Catalyzed Isomerization of Tetrahydrotricyclopentadiene: Synthesis of High-Energy-Density Liquid Fuel, Energy Fuels, 23, 2383-2388 (2009).   DOI
4 Y. Li, J.-J. Zou, X. Zhang, L. Wang, and Z. Mi, Product distribution of tricyclopentadiene from cycloaddition of dicyclopentadiene and cyclopentadiene: A theoretacal and expermental study, Fuel, 89, 2522-2527 (2010).   DOI   ScienceOn
5 L. Wang, J.-J. Zou, X. Zhang, and L. Wang, Rearrangement of Tetrahydrotricyclopentadiene Using Acidic Ionic Liquid: Synthesis of Diamondoid Fuel, Energy Fuels, 25, 1342-1347 (2011).   DOI   ScienceOn
6 G. W. Burdette and A. I. Schneider, Exo-tetrahydrotricyclopentadiene, a high density liquid fuel, US Patent 4,401,837 (1983).
7 J. R. Boulton and R. A. Kremer, Oligomers of cyclopentadiene and process for making them, US Patent 5,446,222 (1995).
8 Z. Xiong, Z. Mi, and X. Zhang, Study on the oligomerization of cyclopentadiene and dicyclopentadiene to tricyclopentadiene through Diels-Alder reaction, React. Kinet. Catal. Lett., 85, 89-97 (2005).   DOI
9 J.-J. Zou, Z. Xiong, L. Wang, X. Zhang, and Z. Mi, Preparation of Pd-B/${\gamma}-Al_2O_3$ amorphous catalyst for the hydrogenation of tricyclopentadiene, J. Mol. Catal. A: Chemical, 271, 209-215 (2007).   DOI
10 M.-Y. Huang, J.-C. Chang, J.-C. Lin, K.-H. Lin, and J.-C. Wu, Method for producing exo-tetrahydrodicyclopentadiene using ionic liquid catalyst, US Patent 7,488,862 (2009).
11 M.-Y. Huang, J.-C. Wu, F.-S. Shieu, and J.-J. Lin, Isomerization of endo-tetrahydrodicyclopentadiene over clay-supported chloroaluminate ionic liquid catalysts, J. Mol. Catal. A: Chemical, 315, 69-75 (2010).   DOI
12 V. I. Pavulescu and C. Hardacre, Catalysis in Ionic Liquids, Chem. Rev., 107, 2615-2665 (2007).   DOI   ScienceOn
13 K. Yoo, V. V. Namboodiri, R. S. Varma, and P. G. Smirniotis, Ionic liquid-catalyzed alkylation of isobueane with 2-butene, J. Catal., 222, 511-519 (2004).   DOI   ScienceOn
14 H. W. Bae, J.-S. Han, S. Jung, M. Cheong, H. S. Kim, and J. S. Lee, Polymer-supported chloroaluminate catalysts for the Diels-Alder reaction of cyclopentadiene with methyl methacrylate, Appl. Catal. A: General, 331, 34-38 (2007).   DOI
15 C.-Z. Qial, Y.-F. Zhang, J.-C. Zhang, and C.-Y. Li, Activity and stability investigation of [BMIM][$AlCl_4$] ionic liquid as catalyst for alkylation of benzene with 1-dodecene, Appl. Catal. A: General., 276, 61-66 (2004).   DOI
16 P. Wasserscheid and M. Eichmann, Selective dimerisation of 1-butene in biphasic mode using buffered chloroaluminate ionic liquid solvents-design and application of a continuous loop reactor, Catal. Today, 66, 309-316 (2001).   DOI   ScienceOn
17 D. Thiele and R. F. de Souza, The role of aluminum species in biphasic butene dimerization catalyzed by nickel complexes, J. of Mol. Catal. A: Chemical, 264, 293-298 (2007).   DOI
18 S.-G. Kim, J. Han, J.-K. Jeon, and J.-H. Yim, Ionic liquid-catalyzed isomerization of tetrahydrotricyclopentadiene using various chloroaluminate complexes, Fuel, 137, 109-114 (2014).   DOI   ScienceOn