2-Tetrazene Derivatives as New Energetic Materials; Synthesis, Characterization and Energetic Properties

• Autorzy: Miró Sabaté C. , Delalu H.
• Języki publikacji: EN

Abstrakty

EN

The oxidation of 1,1-dimethylhydrazine with aqueous monochloramine yielded (E)-1,1,4,4-tetramethyl-2-tetrazene (1) as a pale yellow liquid with hypergolic properties. 1 can be oxidized with potassium permanganate to form (E)-1-formyl-1,4,4-trimethyl-2-tetrazene (2) and (E)-1,4-diformyl-1,4dimethyl-2-tetrazene (3). Additionally, 1 reacts with a diethyl ether solution of monochloramine to form a stable 1,1,4,4-tetramethyl-2-tetrazenium chloride salt (4). The chloride in salt 4 was exchanged with various energetic anions, such as nitrate (5), perchlorate (6), 5,5´-azobistetrazolate (7*6H2O), picrate (8) and azide (9). All materials were characterized by analytical and spectroscopic methods and the solid state structures of compounds 2-8 were elucidated. Due to the energetic nature of these materials, they were submitted to friction and impact sensitivity tests and DSC analysis was used to assess their thermal stabilities. Furthermore, the heats of formation of compounds 2-8 were computed using quantum mechanical methods (CBS-4M) and their detonation parameters (pressure and velocity) and specific impulses were also calculated. Lastly, the 2-tetrazene derivatives presented here are of potential interest either as building blocks or as a new class of low toxicity, low sensitivity energetic materials.

Słowa kluczowe

EN

2-tetrazene; energetic materials; X-ray diffraction; NMR spectroscopy

• Wydawca: Sieć Badawcza Łukasiewicz - Instytut Przemysłu Organicznego
• Czasopismo: Central European Journal of Energetic Materials
• Rocznik: 2014
• Tom: Vol. 11, no. 4
• Strony: 515--537
• Opis fizyczny: Bibliogr. 24 poz., rys., tab.

Twórcy

autor

Miró Sabaté C.

• Hydrazines and Polynitrogen Energetic Compounds, University of Lyon, Bât. Berthollet, 3è étage, 22, av. Gaston Berger, 69622 Villeurbanne, France

autor

Delalu H.

• Hydrazines and Polynitrogen Energetic Compounds, University of Lyon, Bât. Berthollet, 3è étage, 22, av. Gaston Berger, 69622 Villeurbanne, France

Bibliografia

• [1] a) Klapötke T.M., Miró Sabaté C., 5,5´-Hydrazinebistetrazole: an Oxidationstable Nitrogen-rich Compound and Starting Material for the Synthesis of 5,5´- Azobistetrazolates, Z. Anorg. Allg. Chem., 2007, 633, 2671-2677;
• b) Klapötke T.M., Miró Sabaté C., Welch J.M., Z. Anorg. Allg. Chem., 1,5-Diamino-4-methyltetrazolium 5-Nitrotetrazolate – Synthesis, Testing and Scale-up, 2008, 634(5), 857-866;
• c) Klapötke T.M., Miró Sabaté C., Bistetrazoles: Nitrogen-rich, High-performing, Insensitive Energetic Compounds, Chem. Mater., 2008, 20(11), 3629-3637.
• [2] a) Karaghiosoff K., Klapötke T.M., Miró Sabaté C., Energetic Silver Salts with 5-Aminotetrazole Ligands, Chem. Eur. J., 2009, 15, 1164-1176;
• b) Ebespächer M., Klapötke T.M., Miró Sabaté C., Nitrogen-rich Salts Based on the Energetic 5,5´-Hydrazinebistetrazolate Anion, Helv. Chim. Acta, 2009, 92, 977-996;
• c) Klapötke T.M., Miró Sabaté C., Rasp M., Synthesis and Properties of 5-Nitrotetrazole Derivatives as New Energetic Materials, J. Mater. Chem., 2009, 19, 2240-2252;
• d) Klapötke T.M., Miró Sabaté C., Low Energy Monopropellants Based on the Guanylurea Cation, Z. Anorg. Allg. Chem., 2010, 636, 163-175;
• e) Delalu H., Karaghiosoff K., Klapötke T.M., Miró Sabaté C., 5-Aminotetrazoles and Silver-based Primary Explosives, Cent. Eur. J. Energ. Mater., 2010, 7(3), 115-129.
• [3] a) Göbel M., Klapötke T.M., Potassium-, Ammonium-, Hydrazinium-,Guanidinium-, Aminoguanidinium-, Diaminoguanidinium-, Triaminoguanidiniumand Melaminium nitroformate – Synthesis, Characterization and Energetic Properties, Z. Anorg. Allg. Chem., 2007, 633(7), 1006-1017;
• b) Geisberger G., Klapötke T.M., Stierstorfer J., Copper Bis(1-methyl-5-nitriminotetrazolate): A Promising New Primary Explosive, Eur. J. Inorg. Chem., 2007, 30, 4743-4750;
• c) Klapötke T.M., Stierstorfer J., Nitration Products of 5-Amino-1H-tetrazole and Methyl-5-amino-1H-tetrazoles – Structures and Properties of Promising Energetic Materials, Helv. Chim. Acta, 2007, 90(11), 2132-2150;
• d) Klapötke T.M., Stierstorfer J., Hammerl A., Chapman R.D., 5-Azido-1H-tetrazole – Improved Synthesis, Crystal Structure and Sensitivity Data, Z. Anorg. Allg. Chem., 2008, 634, 1051-1057;
• e) Klapötke T.M., Stierstorfer J., Tarantik K., New Energetic Materials: Functionalized 1-Ethyl-5-aminotetrazoles and 1-Ethyl-5-nitriminotetrazoles, Chem. Eur. J., 2009, 15(23), 633, 5775-5792.
• [4] a) Joo Y.-H., Twamley B., Garg S., Shreeve J.M., In Situ Generated Energetic Nitrogen Rich Derivatives of 1,5-Diaminotetrazole, Angew. Chem,. 2009, 47, 6236-6239;
• b) Abe T., Joo Y.-H., Tao G.-H., Shreeve J.M., Disubstituted Azidotetrazoles as Energetic Compounds, Chem. Eur. J., 2009, 15, 4102-4110;
• c) Steinhauser G., Klapötke, T.M., Using the Chemistry of Fireworks to Engage Students in Learning Basic Chemical Principles: A Lesson in Eco-Friendly Pyrotechnics, J. Chem. Educ., 2010, 87(2), 150-156;
• d) Knoll C., Müller D., Giester G., Ofner J., Lendl B., Weinberger P., Steinhauser G., An Unusually Water-poor 5,5′-Azobistetrazolate of Dysprosium: Stabilization of a Nitrogenrich Heterocycle by a Minimum of Hydrogen Bonds, New J. Chem., 2013, 37, 3840-3844;
• e) Giester G., Lendl B., Weinberger P., Steinhauser G., Wagner C., Zachhuber B., Ramer G., Villa M., Nitrogen-rich Compounds of the Actinoids: Dioxouranium(VI) 5,5′-Azobis[tetrazolide] Pentahydrate and Its Unusually Small Uranyl Angle, Inorg. Chem., 2012, 51(12), 6739-6745;
• f) Steinhauser G., Giester G., Wagner C., Leopold N., Sterba J.H., Lendl B., Bichler M., Nitrogen-Rich Compounds of the Lanthanoids: The 5,5′-Azobis[1H-tetrazol-1-ides] of some Yttric Earths (Tb, Dy, Ho, Er, Tm, Yb, and Lu), Helv. Chim. Acta, 2009, 92(7), 1371-1384.
• [5] Gao H., Joo Y.-H., Twamley B., Shreeve J.M., Novel Hypergolic Ionic Liquids with the 2,2-Dialkyltriazanium Cation, Angew. Chem., 2009, 48, 2792--2795.
• [6] a) Forquet V., Darwich C., Miró Sabaté C., Delalu H., Study of Energetic Materials Based on the 2,2-Dimethyltriazanium Cation, New Trends Res. Energ. Mater., Proc. Semin., 15th, Pardubice, Czech Republic, 2010, 468-470;
• b) Miró Sabaté C., Jeanneau E., Delalu H., Energetic Ionic Compounds Based on the 2-Tetrazenium Cation, Eur. J. Inorg. Chem., 2012, 14, 2418-2428.
• [7] Heppekausen J., Klapötke T.M., Sproll S.M., Synthesis of Functionalized Tetrazenes as Energetic Compounds, J. Org. Chem., 2009, 74(6), 2460-2466.
• [8] Klapötke T.M., Minar N.K., Stierstorfer J., Investigations of Bis(methyltetrazolyl) triazenes as Nitrogen-Rich Ingredients in Solid Rocket Propellants − Synthesis, Characterization and Properties, Polyh., 2009, 28(1), 13-26.
• [9] Klapötke T.M., Mayer P., Schulz A., Weigand J.J., 1,4-Bis-[1-methyltetrazol-5-yl]-1,4-dimethyl-2-tetrazene: a Stable, Highly Energetic Hexamer of Diazomethane (CH2N2)6, Propellants Explos. Pyrotech., 2004, 29, 325.
• [10] Wiberg N., Bayer H., Bachhuber H., Isolation of Tetrazene, N4H4, Angew. Chem., 1975, 87(6), 202-203.
• [11] Sutton G.P., History of Liquid Propellant Rocket Engines in the United States, J. Propul. Power, 2003, 19, 978-1007.
• [12] a) Nonnenberg C., Frank I., Klapötke T.M., Ultrafast Cold Reactions in the Bipropellant Monomethylhydrazine/Nitrogen Tetroxide: CPMD Simulations, Angew. Chem., 2004, 116, 4686-4689, Angew. Chem. Int. Ed., 2004, 43, 4586-4589;
• b) Catoire L., Chaumeix N., Paillard C., Chemical Kinetic Model for Monomethylhydrazine/Nitrogen Tetroxide Gas Phase Combustion and Hypergolic Ignition, Visualizations of Gas-Phase NTO/MMH Reactivity, J. Propul. Power, 2004, 20, 87-92.
• [13] Frank I., Hammerl A., Klapötke T.M., Nonnenberg C., Zewen H., Processes During the Hypergolic Ignition Between Monomethylhydrazine (MMH) and Dinitrogen Tetroxide (N2O4) in Rocket Engines, Propellants Explos. Pyrotech., 2005, 30, 44-52.
• [14] Catoire L., Chaumeix N., Pichon S., Paillard C., Visualizations of Gas-Phase NTO/ MMH Reactivity, J. Propul. Power, 2006, 22, 120-126.
• [15] Ishikawa Y., McQuaid M.J., Reactions of NO2 with CH3NHNH and CH3NNH2: a Direct Molecular Dynamics Study, J. Mol. Struct., 2007, 825-846, 119-124.
• [16] Osmont A., Catoire L., Klapötke T.M., Vaghjiani G.L., Swihart M.T., Thermochemistry of Species Potentially Formed During NTO/MMH Hypergolic Ignition, Propellants Explos. Pyrotech., 2008, 33, 209-212.
• [17] 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.
• [18] Klapötke T.M., Krumm B., Steemann F.X., Steinhauser G., Hands on Explosives: Safety Testing of Protective Measures, Safety Science, 2010, 48(1), 28-34.
• [19] Thun W.E., McBride W.R., Permanganate Oxidation of Tetrasubstituted 2-Tetrazenes, J. Org. Chem., 1969, 34(10), 2997-3002.
• [20] Liu A., Fang, T., Zhenyou X., Xiao Q., Zhang C., Synthesis of 4-Amino-1,2,4-triazole, Wuhan Gongcheng Daxue Xuebao, 2008, 30(4), 28-30.
• [21] Sisler H.H., Kren R.M., Utvary K., Reaction of Chloramine with 1,1-Dimethylhydrazine. Formation of Tetramethyl-2-tetrazene, Inorg Chem., 1969, 8(9), 2007-2008.
• [22] Taylor R., Kennard O., Crystallographic Evidence for the Existence of CH•••O, CH•••N and CH•••Cl Hydrogen Bonds, J. Am. Chem. Soc., 1982, 104, 5063-5070.
• [23] a) Klapötke T.M., Miró Sabaté C., 1,2,4-Triazolium and Tetrazolium Picrate Salts: “On the Way” from Nitroaromatic to Azole-based Energetic Materials, Eur. J. Inorg. Chem., 2008, 34, 5350-5366; b) Klapötke T.M., Miró Sabaté C., Synthesis and Spectroscopic Characterization of Azolium Picrate Salts, Z. Anorg. Allg. Chem., 2008, 634, 1017-1024.
• [24] Köhler J., Meyer R., Explosivstoffe, 9th ed., Wiley-VCH, Weinheim, Germany, 1998.