Synthesis and energetic properties of 4,4′,5,5′-tetranitro-2, 2′-biimidazolate(N4BIM) salts

Propellants, Explosives, Pyrotechnics

Volumn 37, Issue 6, 2012, Pages 647-652

  Chavez, David E ^a   Parrish, Damon ^b   Preston, Daniel N ^a   Mares, Isaac W ^a  

^a LOS ALAMOS NATIONAL LABORATORY   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

Explosives; Propellants

Indexed keywords

BURN RATES; BURNING RATE; COMBUSTION BEHAVIOR; ENERGETIC PROPERTIES; PRESSURE DEPENDENCE; PROPELLANT INGREDIENT;

COMBUSTION; ELECTROSTATIC DEVICES; EXPLOSIVES; PROPELLANTS;

SALTS;

EID: 84871334596     PISSN: 07213115     EISSN: 15214087     Source Type: Journal    
DOI: 10.1002/prep.201200040     Document Type: Article

References (27)

1. -: The Azidotetrazolate 2-Oxide Anion, Chem. Eur. J. 2011, 17, 13068.
2. N. Fischer, T.M. Klapötke, B., J. Stierstorfer, Energetic Nitrogen-Rich Salts of 1-(2-Hydroxyethyl)-5-nitriminotetrazole, Eur. J. Inorg. Chem. 2011, 28, 4471.
3. 10 Chain, Inorg. Chem. 2011, 50, 2732.
4. K. Wai, D.A. Parrish, J.M. Shreeve, 3-Azido-N-nitro-1H-1,2,4-triazol-5- amine-Based Energetic Salts, Chem. Eur. J. 2011, 17, 3629.
5. V. Thottempudi, J.M. Shreeve, Trinitromethyl-Substituted 5-Nitro- or 3-Azo-1,2,4-triazoles: Synthesis, Characterization, and Energetic Properties, J. Am. Chem. Soc. 2011, 133, 6464.
6. Y. Zhang, Y. Huang, D.A. Parrish, J.M. Shreeve, 4-Amino-3,5- dinitropyrazolate Salts-Highly Insensitive Energetic Materials, J. Mater. Chem. 2011, 21, 6891.
7. M.A. Hiskey, D.E. Chavez, R.L. Bishop, J.F. Kramer, S.A. Kinkead, Use of 3,3'-Diamino-4,4'-azoxyfurzan and 3,3'-Diamino-4,4'-azofurazan as Insensitive High Explosives, US Patent 6358339, The Regents of the University of California, Los Alamos, NM, USA, 2002.
8. D.E. Chavez, M.A. Hiskey, D.L. Naud, Preparation of 3,3'-Azobis(6-amino- 1,2,4,5-tetrazine), US Patent 6342589, The United States of America as Represented by The United States Department of Energy, Washington, DC, USA, 2002.
9. D. Chavez, L. Hill, M. Hiskey, S. Kinkead, Preparation and Explosive Properties of Azo- and Azoyfurazans, J. Energ. Mater. 1999, 17, 219.
10. D. E. Chavez, M. A. Hiskey, M. H. V. Huynh, D. L. Naud, S. F. Son, B. C. Tappan, The Combustion Studies of High-Nitrogen Energetic Materials, J. Pyrotech. 2006, 23, 70.
11. M. A. Hiskey, N. Goldman, J. R. Stine, High-Nitrogen Energetic Materials Derived from Azotetrazolate, J. Energ. Mater. 1998, 16, 119.
12. H.F. Hayden, C.M. Michienzi, B.A. Mason, S.F. Son, B.C. Tappan, Burning Rate Studies of Triaminoguanidinium Azotetrazolate (TAGzT) and Hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) Mixtures, 41st JANNAF Combustion Subcommittee (CS) Meeting, San Diego CA, USA, December 4-8, 2006.
13. R. Behrens, D. Wiese-Smith, H. Hayden, Reaction Processes that Control the Thermal Decomposition of Mixtures of TAGZT and RDX, 41st JANNAF Combustion Subcommittee (CS) Meeting, San Diego CA, USA, December 4-8, 2006.
14. A. Hammerl, G. Holl, M. Kaiser, T.M. Klapötke, P. Mayer, H. Piotrowsky, M. Vogt, Methylated Ammonium and Hydrazinium Salts of 5,5'-Azotetrazolates, Z. Naturforsch. 2001, 56b, 857.
15. D.E. Chavez, B.C. Tappan, B.A. Mason, D.A. Synthesis and Energetic Properties of Bis(Triaminoguanidinium) 3,3'-Dinitro-5,5'-azo-1,2,4-triazolate (TAGDNAT): A New High-Nitrogen Material, Propellants Explos. Pyrotech. 2009, 34, 475.
16. S.G. Cho, R. Jin, M. Eun, J.-K. Kim, R. Damavarapu, R. Surapaneni, Synthesis and Characterization of 4,4'5,5'-Tetranitro-2,2'-bis-1H-imidazole (TNBI), Propellants Explos. Pyrotech. 2005, 30, 445.
17. V.V. Semenov, B.I. Ugrak, S.A. Shevelev, M.I. Kanischev, A.T. Baryshnikov, A.A. Fainzil'berg, Nitrozazole Alkylation with α-Haloketones- Carbon-13, Nitrogen-15, Nitrogen-14 NMR Study,Izvest. Akad. Nauk Ser. Khim. 1990, 8, 1827.
18. D.T. Cromer, C.B. Storm, Structure of 4,4′5,5′-Tetranitro-2, 2′-biimidazole Dihydrate, Acta Crystallogr., Sect. C 1990, 46, 1957.
19. 4, Acta Crystallogr., Sect. C 1990, 46, 1959.
20. M.A. Hiskey, M.M. Stinecipher, J.E. Brown, Synthesis and Initial Characterization of Some Energetic Salts of 3,3-Dinitroazetidine, J. Energ. Mater. 1993, 11, 157.
21. D.E. Chavez, M.A. Hiskey, 1,2,4,5-Tetrazine-Based Energetic Materials, J. Energ. Mater. 1999, 17, 357.
22. Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre, CCDC, 12 Union Road, Cambridge CB21EZ, UK. Copies of the data can be obtained free of charge on quoting the depository number CCDC-861601 (Fax: +44-1223-336-033; E-Mail: deposit@ccdc.cam.ac.uk, http://www.ccdc.cam.ac.uk).
23. S. Bastea, L.E. Fried, K.R. Glaesemann, W.M. Howard, P.C. Souers, P.A. Vitello, Cheetah, User's Manual, Lawrence Livermore National Laboratory, Livermore, CA, USA, 2006.
24. M.J. Ward, S.F. Son, M.Q. Brewster, Steady Deflagration of HMX with Simple Kinetics: A Gas Phase Chain Reaction Model, Combust. Flame 1998, 114, 556.
25. B. C. Tappan, A. N. Ali, S. F. Son, T. B. Brill, Decomposition and Ignition of the High-Nitrogen Compound Triaminoguanidinium Azotetrazolate (TAGzT), Propellants Explos. Pyrotech. 2006, 31, 163-168.
26. A. N. Ali, S. F. Son, M. A. Hiskey, D. L. Naud, Novel High Nitrogen Propellant Used in Solid Fuel Micropropulsion, J. Propul. Power 2004, 20, 120.
27. D.E. Chavez, B.C. Tappan, M.A. Hiskey, S.F. Son, H.H. Harry, D. Montoya, S. Hagelberg, New High-Nitrogen Materials Based on Nitroguanyl-Tetrazines: Explosive Properties, Thermal Decomposition and Combustion Studies, Propellants Explos. Pyrotech. 2005, 30, 412.