Isomerization of tetrahydrodicyclopentadiene using ionic liquid: Green alternative for Jet Propellant-10 and adamantane

Fuel

Volumn 91, Issue 1, 2012, Pages 164-169

  Wang, Lei ^a   Zou, Ji Jun ^a   Zhang, Xiangwen ^a   Wang, Li ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

Adamantane; Ionic liquid; Isomerization; Jet Propellant 10; Tetrahydrodicyclopentadiene

Indexed keywords

1-BROMOADAMANTANE; ACID CATALYST; ADAMANTANES; EXO-ISOMERIZATION; HIGHER TEMPERATURES; METAL CHLORIDES; REACTION TEMPERATURE; TETRAHYDRODICYCLOPENTADIENE;

CHLORINE COMPOUNDS; IONIC LIQUIDS; IONS; ISOMERS; PROPELLANTS;

ISOMERIZATION;

EID: 80055014557     PISSN: 00162361     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fuel.2011.07.038     Document Type: Article

References (33)

1. T.J. Bruno, M.L. Huber, A. Laesecke, E.W. Lemmon, and R.A. Perkins Thermophysical properties of JP-10, NISTIR 6640 2006 Boulder, CO National Institute of Standards and Technology
2. J.-J. Zou, X. Zhang, J. Kong, and L. Wang Hydrogenation of dicyclopentadiene over amorphous nickel alloy catalyst SRNA-4 Fuel 87 2008 3655 3659
3. R.C. Fort Adamantane: The Chemistry of Diamond Molecules 1976 Dekker New York
4. J.E. Dahl, S.G. Liu, and R.M.K. Carlson Isolation and structure of higher diamondoids, nanometer-sized diamond molecules Science 299 2003 96 99 (Pubitemid 36042408)
5. S.J. Cristol, W.K. Seifert, and S.B. Soloway Bridged polycyclic compounds. X. the synthesis of endo and exo-1, 2-dihydrodicyclopentadienes and related compounds J Am Chem Soc 82 1960 2351 2356
6. Schneider A, Ware RE, Janoski EJ. Isomerization of endo- tetrahydrodicyclopentadiene to a missile fuel diluent. US Patent 4086284; 1978.
7. Norton RV, Howe SC. Production of high energy fuel. US Patent 4270014; 1981.
8. P.v.R. Schleyer A simple preparation of adamantane J Am Chem Soc 79 1957 3292
9. P.v.R. Schleyer, and M.M. Donaldson The relative stability of bridged hydrocarbons. II. endo- and exo-trimethylenenorbornane. The formation of adamantane J Am Chem Soc 82 1960 4645 4651
10. 3 catalyst systems for the synthesis of adamantane Petrochem Techn 28 1999 546 548
11. G.A. Olah, and O. Farooq Chemistry in superacids. 7. Superacid-catalyzed isomerization of endo- to exo-trimethylenenorbornane (tetrahydrodicyclopentadiene) and to adamantane J Org Chem 51 1986 5410 5413
12. B.H. Jeong, J.S. Han, S.W. Ko, J.H. Lee, and B.J. Lee Deactivation and reuse of cesium-containing heteropolyacid for the isomerization of THDCPD J Ind Eng Chem 2 2007 310 313
13. 3 Green Chem 9 2007 589 593
14. M. Navrátilová, and K. Sporka A Synthesis of adamantane on commercially available zeolitic catalysts Appl Catal A 203 2000 127 132
15. L. Wu, M. Ji, M. He, and T. Cai Synthesis of adamantane catalyzed by an active immobilized aluminium chloride catalyst Chin J Catal 28 2007 585 587
16. V.I. Parvulescu, and C. Hardacre Catalysis in ionic liquids Chem Rev 107 2007 2615 2665 (Pubitemid 47029102)
17. R.D. Rogers, and K.R. Seddon Ionic liquids-solvents of the future Science 302 2003 792 793
18. H. Olivier-Bourbigou, L. Magna, and D. Morvan Ionic liquids and catalysis: recent progress from knowledge to applications Appl Catal A 373 2010 1 56
19. R. Zhang, X. Meng, Z. Liu, J. Meng, and C. Xu Isomerization of n-pentane catalyzed by acidic chloroaluminate ionic liquids Ind Eng Chem Res 47 2008 8205 8210
20. A.S. Berenblyum, E.A. Katsman, and Y.Z. Karasev The nature of catalytic activity and deactivation of chloroaluminate ionic liquid Appl Catal A 315 2006 128 134 (Pubitemid 44709852)
21. M. Huang, J. Wu, F. Shieu, and J. Lin Isomerization of exo-tetrahydrodicyclopentadiene to adamantane using an acidity-adjustable chloroaluminate ionic liquid Catal. Commun. 10 2009 1747 1751
22. Huang M, Chang J, Lin J, Lin K, Wu J. Method for producing exo-tetrahydrodicyclopentadiene using ionic liquid catalyst. US Patent 7488860; 2009.
23. M. Huang, J. Wu, F. Shieu, and J. Lin Isomerization of endo-tetrahydrodicyclopentadiene over clay-supported chloroaluminate ionic liquid catalysts J Mol Catal A 315 2010 69 75
24. K. Yoo, V.V. Namboodiri, R.S. Varma, and P.G. Smirniotis Ionic liquid-catalyzed alkylation of isobutane with 2-butene J Catal 222 2004 511 519
25. 4] ionic liquid as catalyst for alkylation of benzene with 1-dodecene Appl Catal A 276 2004 61 66
26. V. Ladnak, N. Hofmann, N. Brausch, and P. Wasserscheid Continuous, ionic liquid-catalysed propylation of toluene in a liquid-liquid biphasic reaction mode using a loop reactor concept Adv Synth Catal 349 2007 719 726
27. M.H. Valkenberg, C. Castro, and W.F. Holderich Friedel-crafts acylation of aromatics catalysed by supported ionic liquids Appl Catal A 215 2001 185 190 (Pubitemid 32573606)
28. D. Thiele, and R.F. Souza The role of aluminum species in biphasic butene dimerization catalyzed by nickel complexes J Mol Catal A 264 2007 293 298 (Pubitemid 46329588)
29. 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 2001 309 316
30. X. Liang, G. Gong, H. Wu, and J. Yang Highly efficient procedure for the synthesis of biodiesel from soybean oil using chloroaluminate ionic liquid as catalyst Fuel 88 2009 613 616
31. 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 331 2007 34 38 (Pubitemid 47405209)
32. Y. Yang, and Y. Kou Determination of the Lewis acidity of ionic liquids by means of an IR spectroscopic probe Chem Commun 2 2004 226 227 (Pubitemid 38130559)
33. Q. Wu, B. Dong, M. Han, H. Xin, Y. Zuo, and Y. Jin Studies on acidity of chloroaluminate ionic liquids and its catalytic performance for alkylation of benzene with long-chain alkenes Spectrosc Spectr Anal 27 2007 460 464 (Pubitemid 46619961)