The synthesis and energetic properties of 5,7-dinitrobenzo-1,2,3,4- tetrazine-1,3-dioxide (DNBTDO)

Propellants, Explosives, Pyrotechnics

Volumn 37, Issue 5, 2012, Pages 527-535

  Klapötke, Thomas M ^a,b   Piercey, Davin G ^a   Stierstorfer, Jörg ^a   Weyrauther, Michael ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF MARYLAND   (United States)

Author keywords

DNBTDO; Nitrogen heterocycles

Indexed keywords

3-DIOXIDE; DNBTDO; ENERGETIC PROPERTIES; GRAIN SIZE; MECHANICAL SENSITIVITY; NITROGEN HETEROCYCLES;

CHEMISTRY;

CHEMICAL ENGINEERING;

EID: 84867203220     PISSN: 07213115     EISSN: 15214087     Source Type: Journal    
DOI: 10.1002/prep.201100151     Document Type: Article

References (59)

1. 10 Chain, Inorg. Chem. 2011, 50, 2732-2734.
2. M. Göbel, K. Karaghiosoff, T. M. Klapötke, D. G. Piercey, J. Stierstorfer, Nitrotetrazolate-2-N-oxides and the Strategy of N-Oxide Introduction, J. Am. Chem. Soc. 2010, 132, 17216-17226.
3. T. M. Klapötke, D. G. Piercey, J. Stierstorfer, The Facile Synthesis and Energetic Properties of an Energetic Furoxan Lacking Traditional "Explosophore" Moieties: (E,E)-3,4-Bis(oximomethyl)furoxan (DPX1), Propellants Explos. Pyrotech. 2011, 36, 160-167.
4. -: The Azidotetrazolate 2-Oxide Anion, Chem. Eur. J. 2011, 17, 13068-13077.
5. 8 Structure and Photochromism, J. Am. Chem. Soc. 2010, 132, 12172-12173.
6. W. McLellan, W. R. Hartley, M. Brower, Health Advisory for Hexahydro-1,3,5-trinitro-1,3,5-triazine, Technical Report PB90-273533; Office of Drinking Water, U. S. Environmental Protection Agency, Washington, D.C., USA, 1988.
7. A. Provatas, Formulation and Performance Studies of Polymer Bonded Explosives (PBX) Containing Energetic Binder Systems, Part 1, Weapons Systems Division Systems Sciences Laboratory, Edinburg South Australia, Australia. DSTO-TR-1397, 2003, AR 012-585.
8. T. Altenburg, T. M. Klapötke, A. Penger, J. Stierstorfer, Two Outstanding Explosives Based on 1,2-Dinitroguanidine: Ammonium Dinitroguanidine and 1,7-Diamino-1,7-dinitrimino-2,4,6-trinitro-2,4,6-triazaheptane, Z. Anorg. Allg. Chem. 2010, 636, 463-471.
9. T. M. Klapötke, C. M. Sabaté, 5-Aminotetrazolium 5-Aminotetrazolates-New Insensitive Nitrogen-Rich Materials, Z. Anorg. Allg. Chem. 2009, 635, 1812-1822.
10. T. Wei, W. Zhu, X. Zhang, Y.-F. Li, H. Xio, Molecular Design of 1,2,4,5-Tetrazine-Based High-Energy Density Materials, J. Phys. Chem. A 2009, 113, 9404-9412.
11. T. Kaihoh, T. Itoh, K. Yamaguchi, A. Ohsawa, First Synthesis of A 1,2,3,4-Tetrazine, J. Chem. Soc., Chem. Commun. 1988, 1608-1609
12. A. M. Churakov, V. A. Tartakovsky, Progress in 1,2,3,4-Tetrazine Chemistry, Chem. Rev. 2004, 104, 2601-2616.
13. M. N. Glukhovtsev, B. Y. Simkin, V. I. Minkin, Stabilization of the Hexaazabenzene Heterocyclic System in Hexazine 1,3,5-Trioxide, Zh. Organicheskoi Khim. 1988, 24, 2486-2488.
14. S. Inagake, N. Goto, Nature of Conjugation in Hydronitrogens and Fluoronitrogens. Excessive Flow of Unshared Electron Pairs into Ï-Bonds, J. Am. Chem. Soc. 1987, 109, 3234-3240.
15. M. Noyman, S. Zilberg, Y. Haas, Stability of Polynitrogen Compounds: The Importance of Separating the Ï- and π-Electron Systems, J. Phys. Chem. A 2009, 113, 7376-7382.
16. H. Schechter, M. Venugopal, D. Srinivasulu, Synthesis of 1,2,3,4-Tetrazines, 1,2,3,4-Tetrazine Di-N-oxides, Pentazole Derivatives, Pentazine Poly N-oxides, and Nitroacetylenes, Ohio State University Research Foundations, DARPA/AFOSR Sponsored, Project 746566. March 8, 2006.
17. X. Song, J. Li, H. Hou, B. Wang, Extensive Theoretical Studies of a New Energetic Material: Tetrazino-tetrazine-tetraoxide, J. Comput. Chem. 2009, 30, 1816-1820.
18. V. A. Tartakovsky, I. E. Filatov, A. M. Churakov, S. L. Ioffe, Y. A. Strelenko, V. S. Kuz'min, G. L. Rusinov, K. I. Pashkevich, Synthesis and Structure of Pyridoannelated 1,2,3,4-Tetrazine 1,3-dioxides, Izvest. Akad. Nauk. Ser. Khim. 2004, 11, 2471-2477.
19. A. M. Churakov, S. L. Ioffe, V. A. Tartakovsky, The First Synthesis of 1,2,3,4-Tetrazine-1,3-di-N-oxides, Mendeleev Commun. 1991, 1, 101-103.
20. A. Y. Tyurin, A. M. Churakov, Y. A. Strelenko, M. O. Ratnikov, V. A. Tartakovsky, Synthesis of First Nonannulated 1,2,3,4-Tetrazine-1,3-dioxides, Izvest. Akad. Nauk. Ser. Khim. 2006, 9, 1589-1594.
21. K. L. Altman, L. H. Merwin, W. P. Norris, W. S. Wilson, R. Gilardi, High Nitrogen Explosives. Part 2. Dibenzo-1,3a,4,6a-tetraazapentalenes and Benzo-1,2,3,4-tetrazine-1,3-dioxides, Report NAWCWPNS TP 8277, Naval Air Warfare Center Weapons Division, China Lake, CA, USA, 1996.
22. CrysAlis Pro, Oxford Diffraction Ltd., Version 1.171.33.41 beta (release 2009 CrysAlis171.NET).
23. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release April 01, 2005, CrysAlis171.NET).
24. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, A Program for Crystal Structure Solution, SIR-92, J. Appl. Crystallogr. 1993, 26, 343.
25. G. M. Sheldrick, SHELXS-97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.
26. A. L. Spek, PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, 1999.
27. NATO Standardization Agreement (STANAG) on Explosives, Impact Sensitivity Tests, No. 4489, Ed. 1, Brussels, Sept. 17, 1999.
28. WIWEB-Standardarbeitsanweisung 4-5.1.02, Ermittlung der Explosionsgefährlichkeit, hier der Schlagempfindlichkeit mit dem Fallhammer, Erding, November 8, 2002.
29. http://www.bam.de.
30. http://www.reichel-partner.de.
31. NATO Standardization Agreement (STANAG) on Explosives, Friction Sensitivity Tests, No. 4487, Ed. 1, Brussels, August 22, 2002.
32. WIWEB-Standardarbeitsanweisung 4-5.1.03, Ermittlung der Explosionsgefährlichkeit oder der Reibeempfindlichkeit mit dem Reibeapparat, Erding, November 8, 2002.
33. S. Zeman, V. Pelikán, J. Majzlík, Electric Spark Sensitivity of Nitramines, Part II. A Problem of "Hot Spots", Cent. Eur. J. Energ. Mater. 2006, 3, 45-51.
34. D. Skinner, D. Olson, A. Block-Bolten, Electrostatic Discharge Ignition of Energetic Materials, Propellants Explos. Pyrotech. 1998, 23, 34-42.
35. http://www.ozm.cz/testinginstruments/ small-scale-electrostatic- discharge-tester.htm.
36. According to the UN Recommendations on the Transport of Dangerous Goods. ISBN 92-1-139087-7: Impact: Insensitive >40 J, less sensitive ≥35 J, sensitive ≥4 J, very sensitive ≤3 j Friction Insensitive >N, less sensitive =360 N, sensitive ≤80N a. >80N, very sensitive ≤80 N, extremely sensitive 10 N
37. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 09, Revision A1, Gaussian, Inc., Wallingford CT, USA, 2009.
38. J. W. Ochterski, G. A. Petersson, J. A. Montgomery Jr., A Complete Basis Set Model Chemistry. V. Extensions to Six or More Heavy Atoms, J. Chem. Phys. 1996, 104, 2598
39. J. A. Montgomery Jr., M. J. Frisch, J. W. Ochterski, G. A. Petersson, A Complete Basis Set Model Chemistry. VII. Use of the Minimum Population Localization Method, J. Chem. Phys. 2000, 112, 6532.
40. L. A. Curtiss, K. Raghavachari, P. C. Redfern, J. A. Pople, Assessment of Gaussian-2 and Density Functional Theories for the Computation of Enthalpies of Formation, J. Chem. Phys. 1997, 106, 1063
41. E. F. C. Byrd, B. M. Rice, Improved Prediction of Heats of Formation of Energetic Materials Using Quantum Chemical Methods, J. Phys. Chem. A 2006, 110, 1005-1013
42. B. M. Rice, S. V. Pai, J. Hare, Predicting Heats of Formation of Energetic Materials Using Quantum Chemical Calculations, Combust. Flame 1999, 118, 445-458.
43. P. J. Linstrom, W. G. Mallard (Eds.), NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg MD, 20899, http://webbook.nist.gov, (retrieved March 30, 2010).
44. M. S. Westwell, M. S. Searle, D. J. Wales, D. H. Williams, Empirical Correlations Between Thermodynamic Properties and Intermolecular Forces, J. Am. Chem. Soc. 1995, 117, 5013-5015
45. F. Trouton, On Molecular Latent Heat, Philos. Mag. 1884, 18, 54-57.
46. M. Súeska, EXPLO5.3 Program, Zagreb, Croatia, 2009.
47. M. Súeska, Calculation of Detonation Parameters by EXPLO5 Computer Program, Mater. Sci. Forum, 2004, 465-466, 325-330
48. M. Súeska, Calculation of Detonation Properties of Ci-Hi-Ni-O Explosives, Propellants Explos. Pyrotech. 1991, 16, 197-202
49. M. Súeska, Evaluation of Detonation Energy from EXPLO5 Computer Code Results, Propellants Explos. Pyrotech. 1999, 24, 280-285
50. M. L. Hobbs, M. R. Baer: Calibration of the BKW-EOS with a Large Product Species Data Base and Measured C-J Properties, 10th Symposium (International) on Detonation, ONR 33395-12, Boston, MA, USA, July 12-16, 1993, p. 9.
51. J. E. Felts, H. W. Sandusky, R. H. Granholm, Development of the Smallscale Shock Sensitivity Test (SSST), 16th Conference of the American Physical Society Topical Group on Shock Compression of Condensed Matter, Nashville, TN, USA, June 28-July 1, 2009, AIP Conference Proceedings 1195, p. 3
52. H. W. Sandusky, R. H. Granholm, D. G. Bohl, Small-Scale Shock Reactivity Test (SSRT), IHTR 2701, Naval Surface Warfare Center, Indian Head, MD, USA, August 12, 2005.
53. R. Mayer, J. Köhler, A. Homburg, Explosives, 5 th ed., Wiley VCH, Weinheim, 2002, pp. 7-200.
54. R. Mayer, J. Köhler, A. Homburg, Explosives, 5 th ed., Wiley VCH, Weinheim, 2002, p. 8.
55. T. M. Klapötke, Chemistry of High-Energy Materials, Walter de Gruyter, Berlin, New York, 2011, Ch. 3.
56. R. W. Gurney, Internal Report BRL-405, 1943, Ballistic Research Laboratory, Aberdeen Proving Ground, MD, USA.
57. A. Koch, N. Arnold, M. Estermann, A Simple Relation Between the Detonation Velocity of An Explosive and its Gurney Energy, Propellants Explos. Pyrotech. 2002, 27, 365-368.
58. R. Meyer, J. Köhler, A. Homburg, Explosives, 6 th ed., Wiley-VCH, Weinheim, 2007.
59. Cheetah 2.0, Energetic Materials Center, Lawrence Livermore National Laboratory, Livermore, CA, USA, 1998.