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Abstrakty
The polycyclic nitramine 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12- hexaazaisowurtzitane (HNIW, CL-20) is synthesized via hydrodebenzylation of 2,4,6,8,10,12-hexabenzyl-2,4,6,8,10,12-hexaazaisowurtzitane (HBIW) over a palladium-based catalyst. This process is the key step in the synthesis of CL-20, a compound with unique energetic and explosive characteristics. The use of CL-20 is restricted at present by the high cost of the hydrodebenzylation process, during which the palladium-based catalyst becomes rapidly deactivated. The catalyst deactivation has now been shown to consist of deposition of the reaction products on the carbon support with simultaneous blocking of the active centers by these products. The HBIW decomposition products can permanently combine with palladium, thereby reducing the number of the active centers on the catalyst. Other byproducts clog the pores of the active carbon and reduce both the surface area of the active carbon and the pore volume. The reaction yield is also reduced by aggregation of palladium particles. A palladium catalyst regeneration procedure which has now been developed, consists of heating the catalyst for a specific time at 350 °C in a nitrogen and water vapour stream, and allows partial recovery of the activity of the palladium catalyst in a subsequent HBIW hydrodebenzylation reaction. The specific area and overall pore volume of the regenerated catalyst are also enhanced. The yield from the HBIW hydrodebenzylation reaction using the regenerated catalyst was ca. 42%.
Rocznik
Tom
Strony
333--348
Opis fizyczny
Bibliogr. 11 poz., rys., tab.
Twórcy
autor
- Faculty of Chemistry, The Division of High Energetic Materials, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
autor
- Faculty of Chemistry, The Division of High Energetic Materials, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
autor
- Faculty of Chemistry, The Division of High Energetic Materials, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland
Bibliografia
- [1] Maksimowski P., Golofit T., 4,10-Dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo [5.5.0.05,9.03,11]dodecane Synthesis, J. Energ. Mater., 2013, 31(3), 224-237.
- [2] Krysztopa J., Maksimowski P., The Effect of the Conditions of Condensation of Benzylamine with Glyoxal Run in Methanol on the Yield of 2,4,6,8,10,12-Hexabenzyl-2,4,6,8,10,12-hexaazatetracyclo[5.5.0.05,9. 03,11]dodecane, Przemysł Chemiczny, 2005, 84(04), 260-263.
- [3] Jefimczyk J., Antczak A., Maksimowski P., Studies on Synthesis of Hexabenzylhexaazaisowurtzitane (HBIW) in the Menthol-sulfuric Acid System, Przemysł Chemiczny, 2008, 87(03), 296-299.
- [4] Maksimowski P., Fabijańska A., Adamiak J., Tetraacetyl-dibenzyl-hexaazaisowurtzitane Nitrosation, Propellants Explos. Pyrotech., 2010, 35, 353-358.
- [5] Bellamy A.J., Reductive Debenzylation of Hexabenzylhexaazaisowurtzitane, Tetrahedron, 1995, 51, 4711.
- [6] Nielsen A.T., Nissan R.A., Vanderah D.J., Coon C.L., Gilardi R.D., George C.F., Flippen-Andersen J., Polyazapolycyclics by Condensation of Aldehydes with Amines. Formation of 2,4,6,8,10,12-Hexabenzyl-2,4,6,8,10,12-hexaazatetracyclo[ 5,5,0,05,9,03,11]dodecanes from Glyoxal and Benzylamines, J. Org. Chem., 1990, 55, 1459.
- [7] Wardle R.B., Edwards W.W., Hydrogenolysis of 2,4,6,8,10,12-Hexabenzyl-2,4,6,8,10,12-hexaazatetracyclo[5,5,0,05.9,03,11]dodecanes, US Patent 5,739,325, 1996.
- [8] Toebes M.L., Dillen J.A., Jong K.P., Synthesis of Supported Palladium Catalysts, J. Mol. Cat. A, 2001, 173, 75.
- [9] Koskin A.P., Simakova I.L., Parmon, V.N., Reductive Debenzylation of Hexabenzylhexaazaisowurtzitane − the Key Step of the Synthesis of Polycyclic Nitramine Hexanitrohexaazaisowurtzitane, Russian Chemical Bulletin, 2007, 56(12), 2370-2375.
- [10] Koskin A.P., Simakova I.L., Parmon V.N., Study of Palladium Catalyst Deactivation in Synthesis of 4,10-Diformyl-2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazaisowurtzitane, Reaction Kinetics and Catalysis Letters, 2007, 92(2), 293-302.
- [11] Klapötke T.M., Krumm B., Holl G., Kaiser M., Synthesis, Characterization and Quantum Chemical Computations of Hexanitrohexaaza-isowurtzitane, Energetic Materials − Modeling of Phenomena, Experimental Characterization, Environmental Engineering, Fraunhofer Institut, Karlsruhe, 1999, P-120.
Uwagi
Opracowanie ze środków MNiSW w ramach umowy 812/P-DUN/2016 na działalność upowszechniającą naukę.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-9ad0c5a3-0323-499e-b6e5-b93fa87e672d