Synthesis and Theoretical Studies of a New High Explosive, N,N,-Bis(3-aminofurazan-4-yl)-4,4´-diamino- 2,2´,3,3´,5,5´,6,6´-octanitroazobenzene

• Autorzy: Jing S. , Liu Y. , Liu D. , Guo J.
• Języki publikacji: EN

Abstrakty

EN

A new high energy, low sensitivity material N,N,-bis(3-aminofurazan- 4-yl)-4,4´-diamino-2,2´,3,3´,5,5´,6,6´-octanitroazobenzene (BAFDAONAB) was synthesized from 4-chlorobenzoic acid and diaminofurazan. The structure of BAFDAONAB was characterized by FT-IR, NMR and Elemental Analyses and its purity was determined by HPLC. The optimized structure and thermodynamic parameters were obtained at the DFT- B3LYP/6-31+G** theoretical level. Its detonation properties were also predicted by the formulae of Kamlet-Jacobs and the Monte-Carlo method. The results show that the density, heat of formation, detonation velocity, detonation pressure, impact sensitivity and purity were 1.93 g/cm3, 4487.44 kJ/mol, 9.01 km/s, 35.03 GPa, 63 cm and 99.3%, respectively. In addition, the compound was an insensitive high explosive which could meet the requirements of high energetic materials.

Słowa kluczowe

EN

BAFDAONAB; density functional theory; detonation properties

• Wydawca: Sieć Badawcza Łukasiewicz - Instytut Przemysłu Organicznego
• Czasopismo: Central European Journal of Energetic Materials
• Rocznik: 2015
• Tom: Vol. 12, no. 4
• Strony: 745--755
• Opis fizyczny: Bibliogr. 21 poz., rys., tab.

Twórcy

autor

Jing S.

• School of Chemical Engineering and Environment, North University of China, Taiyuan 030051, China

autor

Liu Y.

• School of Chemical Engineering and Environment, North University of China, Taiyuan 030051, China

autor

Liu D.

• School of Chemical Engineering and Environment, North University of China, Taiyuan 030051, China

autor

Guo J.

• School of Chemical Engineering and Environment, North University of China, Taiyuan 030051, China

Bibliografia

• [1] Joo Y.H., Twamley B., Garg S., Shreeve J.M., Energetic Nitrogen-Rich Derivatives of 1,5-Diaminotetrazole, Angew. Chem., Int. Ed., 2008, 47, 6236.
• [2] Singh R., Gao H., Meshri D., Shreeve J.M., Nitrogen-Rich Heterocycles, Struct. Bonding , 2007, 125, 35-38.
• [3] Fischer A., Antonietti M., Thomas A., Growth Confined by the Nitrogen Source: Synthesis of Pure Metal Nitride Nanoparticles in Mesoporous Graphitic Carbon Nitride, Adv. Mater., 2007, 19, 264-267.
• [4] Gao H., Wang R., Twamley B., Hiskey M.A., Shreeve J.M., 3-Amino-6-nitroaminotetrazine (ANAT)-based energetic salts, Chem. Commun., 2006, 4007-4009.
• [5] Huynh M.H.V., Hiskey M.A., Chavez D.E., Naud D.L., Gilardi R.D., Synthesis, Characterization, and Energetic Properties of Diazido Heteroaromatic High-Nitrogen C−N Compound, J. Am. Chem. Soc., 2005, 127, 12537-12543.
• [6] Gao H., Shreeve J.M., Azole-Based Energetic Salts, Chem. Rev., 2011, 111, 7377-7436.
• [7] Klapötke T.M., New Nitrogen-rich High Explosives, in: High Energy Density Materials, (Klapötke T.M., Ed.), Structure and Bonding, Springer, 2007, 125, 85-121.
• [8] Fendt T., Fischer N., Klapötke T.M., Stierstorfer J., N-Rich Salts of 2-Methyl-5-nitraminotetrazole: Secondary Explosives with Low Sensitivities, Inorg. Chem., 2011, 50, 1447-1458.
• [9] Izsak D., Klapötke T.M., Reuter S., Salts of 5-(5-Azido-1H-1,2,4-triazol-3-yl)tetrazol-1-ol: From Highly Sensitive Primary Explosives to Insensitive Nitrogen-Rich Salts, Eur. J. Inorg. Chem., 2013, 5641-5651.
• [10] Dippold A.A., Klapötke T.M., A Study of Dinitro-bis-1,2,4-triazole-1,1′-diol and Derivatives: Design of High-Performance Insensitive Energetic Materials by the Introduction of N-Oxides, J. Am. Chem. Soc., 2013, 135, 9931-9938.
• [11] Talawar M.B., Sivabalan R., Polke B.G., Nair U.R., Gore G.M., Asthana S.N.,Establishment of Process Technology for the Manufacture of Dinitrogen Pentoxide and Its Utility for the Synthesis of most Powerful Explosive of Today − CL-20, J. Hazard. Mater., 2005, 124, 153-164.
• [12] Mehilal, Sikder N., Sikder A.K., Agrawal J.P., N,N’-Bis(1,2,4-triazol-3-yl)-4,4’-diamino-2,2’,3,3’,5,5’,6,6’-octanitroazobenzene (BTDAONAB), Indian J. Eng. Mater. Sci., 2004, 11, 516-520.
• [13] Mousavi S., Esmaeilpour K., Kesharvarz M.H., A New Thermally-stable Insensitive High Explosive: N,N-Bis[1,2,3,4-tetrazol-5-yl]-4,4′-diamino-2,2′,3,3′,5,5′,6,6′-octanitroazobenzene [BAFDAONAB], Cent. Eur. J. Energ. Mater., 2013, 10(4), 455-465.
• [14] Gao H., Ye C., Piekarski C.M., Shreeve J.M., Computational Characterization of Energetic Salts, J. Phys. Chem. C, 2007, 111, 10718-10731.
• [15] Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Montgomery, Jr., J.A.; Vreven, T.; Kudin, K.N.; Burant, J.C.; Millam, J.M.; Iyengar, S.S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G.A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J.E.; Hratchian, H.P.; Cross, J.B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Austin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Ayala, P.Y.; Morokuma, K.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Zakrzewski, V.G.; Dapprich, S.; Daniels, A.D.; Strain, M.C.; Farkas, O.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Ortiz, J.V.; Cui, Q.; Baboul, A.G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M.W.; Johnson, B.; Chen, W.; Wong, M.W.; Gonzalez, C.; and Pople, J.A. Gaussian 03, Revision D.02, Gaussian, Inc.: Wallingford, CT, 2004.
• [16] Parr R.G., Yang W., Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989; ISBN 0195092767.
• [17] Suleimenov O.M., Ha T.K., Ab initio Calculation of the Thermochemical Properties of Polysulphanes (H2Sn), Chem. Phys. Lett., 1998, 290, 451-457.
• [18] Kamlet M.J., Jacobs S.J., Chemistry of Detonations. I. A Simple Method for Calculating Detonation Properties of C-H-N-O Explosives, J. Chem. Phys., 1968, 48, 23-35.
• [19] Kamlet M.J., Ablard J.E., Chemistry of Detonations. II. Buffered Equilibria, J. Chem. Phys., 1968, 48, 36-42.
• [20] Kamlet M.J., Dickinson C., Chemistry of Detonations. III. Evaluation of the Simplified Calculational Method for Chapman-Jouguet Detonation Pressures on the Basis of Available Experimental Information, J. Chem. Phys., 1968, 48, 43-50.
• [21] Pospíšil M., Vávra P., Concha M., Murray J., Politzer P., A Possible Crystal Volume Factor in the Impact Sensitivities of some Energetic Compounds, J. Mol. Model., 2010, 16, 895-901.