Energetic Nitrogen-rich Salts

• Autorzy: Wu J.-W. , Zhang J.-G. , Zhang T.-L. , Yang L.
• Języki publikacji: EN

Abstrakty

EN

Energetic salts as a unique class of energetic materials have recently been investigated widely, since they possess advantages over their atomically similar nonionic analogues – they tend to exhibit lower vapor pressures, higher densities and better thermal stabilities. Furthermore, these salts are readily improved upon by the appropriate combination of different cations and anions. Over the last twenty years, our group has continued to synthesize and study novel ionic energetic materials. Here, we have summarized all of the series of nitrogen-rich energetic salts. This review gives an overview of the various studies dealing with synthetic aspects and some of the physicochemical properties of ionic compounds that are based on ammonia, guanidine, semicarbazide, carbohydrazide, tetrazine, tetrazole, triazole and imidazole. In addition, their potential applications in the fields of explosives and propellants are discussed. We hope these investigations will be helpful in providing a wider insight for future research in the area of energetic salts.

Słowa kluczowe

EN

energetic salts; synthesis; characterization; crystal structure; review

• Czasopismo: Central European Journal of Energetic Materials
• Rocznik: 2015
• Tom: Vol. 12, no. 3
• Strony: 417--437
• Opis fizyczny: Bibliogr. 29 poz., rys.

Twórcy

autor

Wu J.-W.

• State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, China

autor

Zhang J.-G.

• State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, China

autor

Zhang T.-L.

• State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, China

autor

Yang L.

• State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, China

Bibliografia

• [1] a) Guo Y., Tao G.H., Zeng Z., Gao H.X., Parrish D.A., Shreeve J.M., Energetic Salts Based on Monoanions of N,N-Bis(1H-tetrazol-5-yl)amine and 5,5’-Bis(tetrazole), Chem. - Eur. J., 2010, 16, 3753-3762; b) Singh R.P., Verma R.D., Meshri D.T., Shreeve J.M., Energetic Nitrogen-rich Salts and Ionic Liquids, Angew. Chem., Int. Ed., 2006, 45, 3584-3601; c) Gao H.X., Shreeve J.M., Azole-based Energetic Salts, Chemical Reviews, 2011, 111, 7377-7436; d) Huang H.F., Meng Z.H., Zhou Z.M., Gao H.X., Zhang J., Wu Y.K., Energetic Salts and Energetic Ionic Liquids (in Chinese), Prog. Chem., 2009, 154-163.
• [2] a) Liu X.J., Zhang H.J., Lin Q.H., Li Y.C., Li Y.Y., Pang S.P., Progress of Study on the Synthesis of Azole Energetic Ionic Compounds (in Chinese), Chin. J. Explos. Propellants (Huozhayao Xuebao), 2010, 32(1), 6-10; b) Klapötke T.M., Nitrogenrich Salts of 1-Methyl-5-nitriminotetrazolate: an Auspicious Class of Thermally Stable Energetic Materials, Chem. Mater., 2008, 20, 4519-4530.
• [3] a) Zhang Y.Q., Huang Y.G., Parrish D.A., Shreeve J.M., 4-Amino-3,5-dinitropyrazolate Salts − Highly Insensitive Energetic Materials, J. Mater. Chem., 2011, 21, 6891-6897; b) Wang R., Guo Y., Zeng Z., Shreeve J.M., Nitrogen-rich Nitroguanidyl-functionalized Tetrazolate Energetic Salts, Chem. Commun., 2009, 19, 2697-2699.
• [4] a) Crawford M.J., Klapötke T.M., Martin F.A., Sabate C.M., Rusan M., Energetic Salts of the Binary 5-Cyanotetrazolate Anion ([C2N5](-)) with Nitrogen-rich Cations, Chem. − Eur. J., 2011, 17, 1683-1695; b) Joo Y.H., Gao H.X., Parrish D.A., Cho S.G., Goh E.M., Shreeve J.M., Energetic Salts Based on Nitroiminotetrazolecontaining Acetic Acid, J. Mater. Chem., 2012, 22, 6123-6130; c) Fischer N., Klapötke T.M., Reymann M., Stierstorfer J., Nitrogen-rich Salts of 1H,1H-5,5-Bitetrazole-1,1-diol: Energetic Materials with High Thermal Stability, Eur. J. Inorg. Chem., 2013, 12, 2167-2180.
• [5] a) Darwich C., Klapötke T.M., Sabate C.M., 1,2,4-Triazolium-cation-based Energetic Salts, Chem. − Eur. J., 2008, 5756-5771; b) Karaghiosoff K., Klapötke T.M, Mayer P., Sabate C.M., Penger A., Welch J.M., Salts of Methylated 5-Aminotetrazoles with Energetic Anions, Inorg. Chem., 2008, 47, 1007-1019; c) Bachmann W.E., Sheehan J.C., A New Method of Preparing the High Explosive RDX, J. Am. Chem. Soc., 1949, 71, 1842-1845.
• [6] a) Klapötke T.M., Piercey D.G., Stierstorfer J., The 1,3-Diamino-1,2,3-triazolium Cation: a Highly Energetic Moiety, Eur. J. Inorg. Chem., 2013, 14(19), 1509-1517; b) Huang H.F., Meng Z.H., Zhou Z.M., Zhang H.X., Zhang J., Wu Y.K., Energetic Salts and Energetic Ionic Liquids (in Chinese), Progress in Chemistry, 2009, 21(1), 152-163.
• [7] a) He L., Tao G.-H., Parrish D.A., Shreeve J.M., Impact Insensitive Dinitromethanide Salts, Chem. Commun., 2013, 49, 10329-10331; b) Zhang Y., Parrish D.A., Shreeve J.M., 4-Nitramino-3,5-dinitropyrazole-based Energetic Salts, Chem. − Eur. J., 2012, 18, 987-994; c) Thottempudi V., Shreeve J.M., Synthesis of Trinitromethyl- and Dinitromethyl-substituted Azoles Using Nitrate Salts in Sulfuric Acid, Synthesis, 2012, 44, 1253-1257; d) Zhang Y., Huang Y., Parrish D.A., Shreeve J.M., 4-Amino-3,5-dinitropyrazolate Salts Highly Insensitive Energetic Materials, J. Mater. Chem., 2011, 21, 6891-6897; e) Wang K., Parrish D.A., Shreeve J.M., 3-Azido-Nnitro-1H-1,2,4-triazol-5-amine Based Energetic Salts, Chem. − Eur. J., 2011, 17, 14485-14492; f) Thottempudi V., Shreeve J.M., Synthesis and Promising Properties of a New Family of High-density Energetic Salts of 5-Nitro-3-trinitromethyl-1H-1,2,4-triazole and 5,5’-Bis(trinitronnethyl)-3,3’-azo-1H-1,2,4-triazole, J. Am. Chem. Soc., 2011, 133, 19982-19992; g) Singh R.P., Shreeve J.n.M., New Energetic Polynitro Cyclic Esters: Ammonium, Hydrazinium, and Hydroxylammonium Salts of Polynitramines, Chem. − Eur. J., 2011, 17, 11876-11881; h) Huang Y., Zhang Y., Shreeve J.n.M., Nitrogen-rich Salts Based on Energetic Nitroaminodiazido-1,3,5-triazine and Guanazine, Chem. − Eur. J., 2011, 17, 1538-1546; i) He L., Tao G.-H., Parrish D.A., Shreeve J.n.M., Liquid Dinitromethanide Salts, Inorg. Chem., 2011, 50, 679-685; j) Joo Y.-H., Shreeve J.n.M., High Energy 3-Diazido-2-(azidomethyl)propan-2-ammonium Salts, Abstracts of Papers of the American Chemical Society, 2009, 238; k) Joo Y.-H., Shreeve J.n.M., 1,3-Diazido-2-(azidomethyl)-2-propylammonium Salts, Inorg. Chem., 2009, 48, 8431-8438; l) Klapötke T.M., Sabate C.M., 5-Aminotetrazolium 5-Aminotetrazolates − New Insensitive Nitrogen-rich Materials, Z. Anorg. Allg. Chem., 2009, 635, 1812-1822; m) Klapötke T.M., Stierstorfer J., Wallek A.U., Nitrogen-rich Salts of 1-Methyl-5-nitriminotetrazolate: an Auspicious Class of Thermally Stable Energetic Materials, Chem. Mater., 2008, 20, 4519-4530; n)Klapötke T.M., Stein M., Stierstorfer J., Salts of 1H-Tetrazole - Synthesis, Characterization and Properties, Z. Anorg. Allg. Chem., 2008, 634, 1711-1723; o) Klapötke T.M., Sabate C.M., Stierstorfer J., Hydrogenbonding Stabilization in Energetic Perchlorate Salts: 5-Amino-1H-tetrazolium Perchlorate and Its Adduct with 5-Amino-1H-tetrazole, Z. Anorg. Allg. Chem., 2008, 634, 1867-1874; p) Klapötke T.M., Sabate C.M., Nitrogen-rich Tetrazolium Azotetrazolate Salts: a New Family of Insensitive Energetic Materials, Chem. Mater., 2008, 20, 1750-1763; q) Klapötke T.M., Miro Sabate C., 1,2,4-Triazolium and Tetrazolium Picrate Salts: “On the Way” from Nitroaromatic to Azole-based Energetic Materials, Eur. J. Inorg. Chem., 2008, 5350-5366; r) Klapötke T.M., Mayer P., Sabate C.M., Welch J.M., Wiegand N., Simple, Nitrogen-rich, Energetic Salts of 5-Nitrotetrazole, Inorg. Chem., 2008, 47, 6014-6027; s) Darwich C.,Klapötke T.M., Sabate C.M., Structural and Preliminary Explosive Property Characterizations of New 3,4,5-Triamino-1,2,4-triazolium (Guanazinium) Salts, Propellants Explos. Pyrotech., 2008, 33, 336-346; t) Darwich C., Karaghiosoff K., Klapötke T.M., Sabate M., Synthesis and Characterization of 3,4,5-Triamino-1,2,4-triazolium and 1-Methyl-3,4,5-triamino-1,2,4-triazolium Iodides, Z. Anorg. Allg. Chem., 2008, 634, 61-68; u) Crawford M.-J., Klapötke T.M., Radies H., Synthesis and Characterization of Perfluorinated Nitriles and the Corresponding Sodium 5-Perfluoroalkyltetrazolate Salts, J. Fluorine Chem., 2008, 129, 1199-1205.
• [8] a) Lv C.H., Zhang T.L., Lu Z., Cai R.J., Yu K.B., Preparation and Crystal Structure of (NH4)2[C6H(NO2)3O2], Initiators Pyrotech. (Huogongpin), 1999, 01, 2-5; b) Chen H.Y., Zhang T.L., Zhang J.G., Yu K.B., Synthesis and Structure Analysis of Diammonium 3,5-Dnitro-1,2,4-cyclopentanetrione, J. Chem. Crystallogr., 2005, 36, 181-187; c) Hu X.C., Zhang T.L., Liu Z.H., Zhang J.G., Qiao X.J., Yang L., Synthesis, Crystal Structure, Thermal Analysis and Sensitivity of Mono-Ammonium Trinitrophloroglucinolate (in Chinese), Chin. J. Energ. Mater. (Hanneng Cailiao), 2008, 16, 376-382; d) Lv C.H., Zhang T.L., Ren L.B., Zhang Z.G., Yu K.B., Preparation and Molecular Structure of Ammonium Picrate (in Chinese), Journal of Beijing Institute of Technology, 1999, 19, 25-28; e) Zhang J.G., Zhang T.L., Yu K.B., Preparation and Crystal Structure of NH4·NTO (in Chinese), Chemistry, 2000, 9, 28.
• [9] Zhang J.G., Zhang T.L., Yang L., A Study of Crystal Structure and Explosive Properties of Ammonium Perchlorate (in Chinese), Chin. J. Explos. Propellants (Huozhayao Xuebao), 2002, 3, 33-34.
• [10] Ao G.J., Liu Z.H., Zhang T.L., Yang L., Zhang J.G., Progress in Triaminoguanidine Energetic Compounds (in Chinese), Chin. J. Energ. Mater. (Hanneng Cailiao), 2008, 16, 450-457.
• [11] a) Chen H.Y., Zhang T.L., Qiao X.J., Yang L., Shao F.L., Molecular Structure of Aminoguanidine Sulfate Monohydrate (in Chinese), Journal of Beijing Institute of Technology, 2006, 15, 473-477; b) Liu Z.H., Ao G.J., Zhang T.L., Yang L., Zhang J.G., Synthesis, Crystal Structure and Thermal Analysis of (TAGH)2(TNR) (in Chinese), Acta Phys.-Chim. Sin. (Wuli Huaxue Xuebao), 2008, 24, 1155-1159; c) Qi S.Y., Zhang T.L., Ao G.J., Zhang J.G., Yang L., Structure, hermodynamics and Sensitivity Property of (TAGH)ClO4 (in Chinese), Chin. J. Explo. Propellants, 2009, 6, 35-39; d) X. J. Qiao, R. G. Yu, T. L. Zhang and J. G. Zhang, Prepration and Structure Charaterization of (AG)(DNP) (in Chinese), Chin.J. Org. Chem. (Youji Huaxue), 2004, 9, 1095-1098; e) YangL., Zhang T.L., Yang Y.M., Feng C.G., Yu K.B., Preparation and Crystal Structure of M2TNR (M=AG, CHZ) (in Chinese), Chin. J. Org. Chem. (Youji Huaxue), 2001, 12, 1132-1136; f) Yuan Q.S., Zhang T.L., Ao G.J., Zhang J.G., Yang L., Synthesis, Crystal Structure and Thermal Analysis of (TAGH)(HTNR) (in Chinese), Acta Chim. Sin., 2009, 67(8), 729-734; g) Zhang Z.G., Zhang T.L., Zhang J.G., Yu K.B., Molecular Structure and Crystal Structure of [NH2NHC(NH2)2]NO3 (in Chinese), Chin. J. Energ. Mater., 2001, 9, 142-144.
• [12] Yang L., Zhang T.L., Feng C.G., Yu K.B., Preparation and Molecular Structure of AGNTO (in Chinese), Acta Phys.-Chim. Sin., 2001, 17, 438-442.
• [13] a) Chen H.Y., Zhang T.L., Zhang J.G., Synthesis, X-ray Crystal Structure and Thermal Decomposition Character of Semicarbazidium 3,5-Dihydroxy-2,4,6-trinitrophenolate Hemihydrate Chin. J. Chem., 2005, 23, 963-969; b) Chen H.Y., Zhang T.L., Zhang J.G., Preparation and Molecular Structure of (SCZ) (TNPG)·2H20, Chinese Journal of Structure Chemistry, 2005, 24(8), 973-979; c) Yang L., Zhang T.L., Zhang J.G., Shao B., Feng C.G., Yu K.B., Preparation and Molecular Structure of Semicarbazide Picric (in Chinese), Chin. J. Energ. Mater., 2001, 9(2), 73-76.
• [14] a) Kamlet M.J., Jacobs S.J., J. Chem. Phys., 1968, 48, 23-25; b) 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, 23-25.
• [15] Li Z.M., Yan Y.J., Gong H.Y., Zhang J.G., Zhang T.L., Yang L., Theoretical Study on Structure, Heat of Formation and Detonation Properties of Picrate-based Energetic Ionic Salt (in Chinese), Chin. J. Explo. Propellants, 2009, 32(6), 6-10.
• [16] a) Yang L., Zhang J.G., Zhang T.L., Feng C.G., Yu K.B., Preparation and Molecular Structure of CHZPA (in Chinese), Chin. J. Explos. Propellants, 2002, 25(3), 66-68; b) Yang L., Zhang T.L., Zhang J.G., Yang Y.M., Feng C.G., Yu K.B., Praperation and Crystal Structure of M2TNR (M=AG, CHZ) (in Chinese), Chin. J. Org. Chem., 2001, 21(12), 1132-1136; c) Feng C.G., Yang L., Zhang J.G., Zhang T.L., Yu K.B., Preparation and Molecular Structure of CHZ NTO·H2O (in Chinese), Chinese Journal of Structure Chemistry, 2002, 21(3), 309-312; d) Liu Z.H., Zhang T.L., Hu X.C., Zhang J.G., Yang L., Qiao X.J., Preparation, Crystal Structure, and Thermal Analysis of Carbohydrazide Trinitrophloroglucinolate, Chemical Research in Chinese Universities, 2008, 24(6), 683-687.
• [17] a) Sheng T.B., Ming H., Ping L.X., Shan L.J., De N.F., Lun H.J., Theoretical Investigation of Several 1,2,3,4-Tetrazine-based High-energy Compounds, Propellants Explos. Pyrotech., 2013, 38, 372-378; b) Feng J.L., Zhang J.G., Wang K., Zhang T.L., Crystal Structure and Theoretical Studies of 3,6-Dihydrazino-1,2,4,5-tetrazine, Chemical Journal of Chinese Universities, 2011, 32, 1519-1525.
• [18] a) Li Z.M., Xie S.H., Zhang J.G., Feng J.L., Wang K., Zhang T.L., Two High Nitrogen Content Energetic Compounds: 3,6-Diguanidino-1,2,4,5-tetrazine and its Diperchlorate, Journal of Chemical and Engineering Data, 2012, 57, 729-736; b) Liang Y.H., Zhang J.G., Xie S.H., Zhang T.L., Shu Y.J., Yang L., Zhou Z.N., Synthesis, Themal Decomposition and Sensitivity Properties of a series of Salts of Di-guanidine-s-tetrazine of Nitro-phenol (in Chinese), Chin. J. Explos. Propellants, 2011, 34(3), 28-31; c) Zhang J.G., Liang Y.H., Feng J.L., Wang K., Zhang T.L., Zhou Z.N., Yang L., Synthesis, Crystal Structures, Thermal Decomposition and Explosive Properties of a Series of Novel Energetic Nitrophenol Salts of Dihydrazino-stetrazine, Z. Anorg. Allg. Chem., 2012, 638(7-8), 1212-1218; d) Zhang J.G., Xin Y., Wu J.T., Mou S., Feng J.L., Zhang T.L., Two High-nitrogen Energetic Salts Based on 3,6-Dihydrazino-1,2,4,5-tetrazine, Chin. J. Inorg. Chem., 2013, 29.
• [19] Li N., Chai C.P., Gan Z.Y., Luo Y.J., Review on Molecular Design and Performance of Energetic Ionic Compounds (in Chinese), Chin. J. Energ. Mater., 2010, 18, 467-475.
• [20] a) Cui Y., Zhang T.L., Zhang J.G., Hu X.C., Zhang J., Huang H.S., Preparation, Crystal Structure and Thermal Analyses of 1,5-Diamino-4-hydro-1,2,3,4-tetrazolium 3,5-Dihydroxy-2,4,6-trinitrophenolate, Chin. J. Chem., 2008, 26, 426-432; b) Hu X.C., Zhang T.L., Qiao X.J., Yang L., Zhang J.G., Cui Y., Zhang J., Crystal Structure and Thermal Decomposition of 5-Aminotetrazole Trinitrophloroglucinolate, Acta Phys.-Chim. Sin., 2008, 24(4), 578-580.
• [21] Wei L., J. G. Zhang, J. Y. Li, T. L. Zhang, L. Yang and Z. N. Zhou, Synthesis and Properties of 5-Nitraminotetrazole High Nitrogen Salts (in Chinese), Chin. J. Explos. Propellants (Huozhayao Xuebao), 2011, 34(2), 6-11.
• [22] Chai Y.P.,Zhang T.L., Yao J., Synthesis and Characterization of Bitetrazole Salts (in Chinese), J. Solid Rocket Technol. (Guti Huojian Jishu), 2007, 30(3), 248-252.
• [23] Q. H. Lin, Y. C. Li, C. Qi, W. Liu, Y. Wang and S. P. Pang, Nitrogen-rich Salts Based on 5-Hydrazino-1H-tetrazole: a New Family of High-density Energetic Materials, J. Mater. Chem. A 2013, 1, 6776-6785.
• [24] a) Agrawal J.P., Recent Trends in High-energy Materials, Progress in Energy and Combustion Science, 1998, 24, 1-30; b) Gao H., Shreeve J,M, Azole-based Energetic Salts, Chemical Reviews, 2011, 111, 7377-7436.
• [25] Klapötke T.M., Stierstorfer J., The CN7- Anion, J. Amer. Chem. Soc., 2009, 131, 1122-1134.
• [26] a) Wu J.T., Zhang J.G., Xin Y., Mou S., Zhang T.L., Synthesis, Characterization, and Thermal Analysis of Two Energetic Ionic Salts Based on 3,4-Diamino-1,2,4-triazole (DATr), Z. Anorg. Allg. Chem., 2013, 639(12-13), 2354-2358; b) Wu J T., Zhang J.G., Mou S., Yin X., Zhang T.L., Preparation, Structure and Kinetic Analysis of the Thermal Behaviour of Some Energetic Salts of 3-Hydrazino-4-amino-1,2,4-triazole, Cent. Eur. J. Energ. Mater., 2013, 10(4), 481-493.
• [27] Ou Y.X., Explosives, 2006, Beijing Institute of Technology, China, ISBN 9787564004750.
• [28] Wu B.D., Lu L.Y., Li F.G., Zhou Z.N., Yang L., Zhang J.G., Zhang T.L., Preparation, Crystal Structures and Thermal Decomposition of Three Energetic Manganese compounds and a Salt Based on Imidazole and Picrate, Polyhedron, 2013, 55, 73-79.
• [29] a) Zhan T., Yang L., Qiao X.J., Zhang T.L., Zhang J.G., Liang Y.H., Synthesis, Crystal Structure and Thermal Analysis of Two New Energetic Compounds (AIM) NO3 and (AIM)(HTNR)•H2O (in Chinese), Acta Chim. Sin., 2012, 70(4), 471-478; b) Denault C.C., Marx P.C., Takimoto H.H., Energy of Combustion and Differential Thermograms of Organic Azides, J. Chem. Eng. Data, 1968, 13, 514-516.