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Review / Przegląd New Energetic Materials Derived from Common 90 This article is available in PDF-format, in colour, at: http://www.wydawnictwa.ipo.waw.pl/materialy-wysokoenergetyczne/materialy-wysokoenergetyczne12_1/HEM_0114_E.pdf Materiały Wysokoenergetyczne / High Energy Materials, 2020, 12 (1), 90 − 110; DOI 10.22211/matwys/0114E ISSN 2083-0165 Copyright © 2020 Łukasiewicz Research Network - Institute of Industrial Organic Chemistry, Poland Article is available under the Creative Commons Attribution-Noncommercial-NoDerivs 3.0 license CC BY-NC-ND 3.0. Review / Przegląd First published in Polish in 2015. New energetic materials derived from common explosives. Review 2,4,6-Trinitrotoluen jako źródło nowoczesnych materiałów wybuchowych. Przegląd Mateusz Szala*,1), Tomasz Sałaciński2) 1) Military University of Technology, Faculty of Advanced Technologies and Chemistry, Laboratory of Explosives, 2 gen. S. Kaliskiego Street, 00-908 Warsaw, Poland 2) Institute of Industrial Organic Chemistry**, 6 Annopol Street, 03-236 Warsaw, Poland * E-mail: [email protected] ** now called: Łukasiewicz Research Network – Institute of Industrial Organic Chemistry Abstract: The review discusses the products of 2,4,6-trinitrotoluene reactions which have explosive properties or are potentially high-energy compounds. The following compounds are discussed: trinitrobenzene, cyanotrinitrobenzene, trinitroxylene, aminotrinitrotoluenes, trinitronitromethylbenzene, methylene bis(2,4,6-trinitrobenzene), hexanitrostilbene, nitromethyldiphenylamines, 4,4’,6,6’-tetranitro- 2,2’-azoxytoluene and 2,4,6-trinitrobenzylideneamine derivatives. The synthesis pathways are provided for all compounds and the detonation parameters are presented for selected compounds. Streszczenie: Omówiono wybrane, mające właściwości wybuchowe lub będące potencjalnie związkami energetycznymi, produkty reakcji w których 2,4,6-trinitrotoluen jest substratem. Opisano między innymi: trinitrobenzen, cyjanotrinitrobenzen, trinitroksylen, amino-trinitrotolueny, trinitro-nitrometylo-benzen, metylenobis(2,4,6-trinitrobenzen), heksanitrostilben, nitro-metylo-difenyloaminy, 4,4’,6,6’-tetranitro- 2,2’-azoksytoluen oraz pochodne 2,4,6-trinitrobenzylidenoaminy. Dla każdego opisanego związku przedstawiono ścieżkę syntezy oraz dla wybranych materiałów podano parametry detonacyjne. Keywords: 2,4,6-trinitrotoluene (TNT), synthesis, cyanotrinitrobenzene, trinitro-nitromethyl-benzene, nitro- methyl-diphenylamine, ATNT, BTNHT, DATNT, DNTN, HNDFM, HNS, TNAT, TNB, TNBHT, TNX Słowa kluczowe: 2,4,6-trinitrotoluen (TNT), synteza, cyjano-2,4,6-trinitrobenzen, 1,3,5-trinitro-2-(nitrometylo) benzen, nitro-metylo-difenyloamina, ATNT, BTNHT, DATNT, DNTN, HNDFM, HNS, TNAT, TNB, TNBHT, TNX 1. Introduction 2,4,6-Trinitrotoluene (TNT) was first developed in 1863 [1]. However, due to its low sensitivity to mechanical stimuli and relatively high critical detonation diameter, the explosive properties of the material were not immediately noticed. We can safely assume that TNT has been used in munitions since 1900 [2, 3], however, during the First World War, 2,4,6-trinitrophenol (picric acid) was the most commonly used secondary explosive. Even though 2,4,6-trinitrophenol was discovered over 100 years before TNT [4], due to its unsatisfactory properties [3], its bulk use ended with the end of the First World War. Currently, many different explosives New energetic materials derived from common explosives. Review Table 1. Properties of selected explosives Molecular formula Substance Sensitivity to Melting point and/or Detonation velocity [km/s] (density (nitrogen content Abbreviation 3 Name decomposition temperature [°C] [g/cm ]) impact [N∙m] friction [N] [%]) [CAS No.] 266.0 [5] 267-269 [6] 7.992 (1.84) [12] 269 [7] 8.4 (1.91) [11] C2H2N4O3 3-Nitro-1,2,4-triazol- NTO >40 [14] 252 [15] 270 [8, 9] 8.510a) (1.93b) [7, 12] (43.1) 5-on [932-64-9] 51 [7] >353 [9, 11] 270 (decomposition 270-273) [10] 8.558a) (1.930b)) [13] 274.8 [5] 8.564 (1.93) [9] Decomposition: ~270 [11] Decomposition: 215 [16, 17] 168-288 [18] FOX-7, 8.870 (1.88-1.885) [16, 17] 15-40 [13] C2H4N4O4 1,1-Diamino-2,2- Decomposition: 226 [18] 216 [13] DADNE 9.044a) (1.885b)) [13] 24 [7] (37.8) dinitroethylene Decomposition: >240 [13] >350 [16, 17] [145250-81-3] 9.090 (1.885) [9] >30 [17] Decomposition: 254 [9, 19] >360 [9] 99.0 [20] 99-101 [21] C3H4N4O6 TNAZ 1,3,3-Trinitroazetidine 101 [22-24] 9.006a) (1.840b)) [13] 6 [13] 324 [13] (29.2) [97645-24-4] 103-104 [25] Decomposition: >240 [13] 203 [26] 8.5 (1.81) [10] 204 [7, 27-32] 8.600 (1.806) [9] 5.6 [39] 205 [33] 8.700 (1.80) [12] 96 [15] C3H6N6O6 1,3,5-Trinitro-1,3,5- RDX, hexogen 7 [17] 205 (215 decomposition) [9, 10] 8.75 (1.76) [30, 35] 114 [10] (37.8) triazacyclohexane [121-82-4] 7.4 [13, 30] 205-206 [34] 8.780 (1.78) [7] 120 [17, 19, 30, 35, 39] 7.5 [7, 35] Decomposition: 220 [17] 8.930 (1.82) [17] Decomposition: 230 [13] 8.977a) (1.816b)) [13] 246 [7] 275 [27, 30] 276-286 (278 decomposition) [9] 6.4 [39] 9.1 (1.9) [38] 1,3,5,7-Tetranitro- 276 [28] 7.4 [13] C4H8N8O8 HMX, octogen 9.1 (1.905-1.910) [13, 27] 95 [39] 1,3,5,7-tetraza- 278.5-280 [26, 36] 7.5 [7, 38] (37.8) [2691-41-0] 9.120 (1.90) [7] 120 [13, 38] cyclooctane 283 (decomposition ~280) [10] 10.20 (α-) [40] 9.320a) (1.910b)) [13] 285 [37] 11.90 (ε-) [40] 286 [33] Decomposition: 287 [13, 38] 321-326 [5] 7.35 [27] 120.17 [40] 330 [9] 7.95 [40] C6H6N6O6 1,3,5-Triamino-2,4,6- TATB 240 [15] 347 (97% pure) [6] 8.000) (1.94 b)) [7] 50 [7, 13] (32.6) trinitrobenzene [3058-38-6] 353 [13] 350 (decomposition) [6, 7, 26, 27, 8.108 (1.94) [9] >360 [9] 36, 41] 8.114a) (1.937b)) [13] 220 (decomposition) [42] 2,4,6,8,10,12-Hexanitro- (α- 1.97, β- 1.99, γ- 1.92, ε- 2.04) [9] C6H6N12O12 CL-20, HNIW 228 (decomposition) [9] 78-110 [43] 2,4,6,8,10,12- 9.580 [9] 2 [42] (38.4) [135285-90-4] 240 (ε-) [5] 80 [42] hexaazaiso-wurtzitane 10.000 (!) (2.02-2.04) [42] 247 [42] 91 a) calculated value; b) total maximum density (TMD) Copyright © 2020 Łukasiewicz Research Network – Institute of Industrial Organic Chemistry, Poland 92 M. Szala, T. Sałaciński are being tested and used with the most popular examples being given in Table 1. Table 2 shows the properties of asymmetrical trinitrotoluene isomers; Table 3 shows the properties of TNT and explosives discussed in the study. Even though modern secondary explosives are classified into a variety of chemical component groups, they all include carbon, hydrogen, nitrogen and oxygen. In recent years, new designs of explosives have shown a tendency to decrease the hydrogen content and increase the nitrogen content. A reduction in the amount of hydrogen increases the heat of explosion, whereas an increase in nitrogen content increases the standard enthalpy of formation as well as the amount of gaseous explosion products. Despite a limited upper temperature range of application due to its low melting point (Table 3), susceptibility to photolytic decomposition [44] and susceptibility to numerous reactions in alkaline environment [45] and alternatives to it having been sought for over 115 years, TNT is one of the most commonly used secondary explosives. The main purpose of the research is the implementation of insensitive munitions (IM). The requirements for this type of munition has been discussed in [46]. It is partially due to the technological developments and hazards related to the properties listed in Table 1. TNT is much less sensitive to mechanical stimuli than other materials listed in Table 1: TNAZ, RDX, HMX and CL-20. The materials with lower sensitivity to impact and/ or friction (NTO and FOX-7), including a TNT structure (TATB) cannot compete with TNT in low-melting compositions, since they decompose during melting or melt at significantly higher temperatures and require much higher expenditure of energy. Since the melted explosive shows increased sensitivity to external stimuli compared to its solid form, a difference between the melting point (81 °C) and the decomposition temperature (min. 240 °C) of 160 °C for the TNT is its significant advantage. It provides a safety margin in the event of local overheating of the molten material. A strong impulse for developing competitors to TNT is its significant impact on the environment and explosive hazard in its production. In Poland, the problem of effluents was resolved several decades ago e.g. [47] by obtaining the purest 2,4,6- isomer and is still the subject of research [48, 49]. As shown in Table 2, asymmetrical trinitrotoluene isomers, characterized by higher melting points, which also affects the TNT crystallization temperature, are treated as impurities in TNT designated for military use. Table 2. Melting point and/or decomposition temperature of asymmetrical trinitrotoluene isomers [°C] Melting point and/or decomposition temperature Abbreviation [CAS] Source [°C] 112 [50] 2,3,4-TNT [602-29-9] Decomposition: starts at 282 [26, 30] Decomposition: 290-310 [50] 97 [30] 97.2 [50] 2,3,5-TNT 97.5 [26] [609-74-5] Decomposition: starts at 283 [30] Decomposition: 333-337 [50] 108 [30] 2,3,6-TNT 111 [26, 50] [18292-97-2] Decomposition: starts at 280 [30] Decomposition: 327-335 [50] 104 [26, 30, 50] 2,4,5-TNT [610-25-3] Decomposition: starts at 262 [30] Decomposition: 288-293 [50] 132 [30] 3,4,5-TNT 137.5 [26, 50] [603-15-6] Decomposition: starts at 288 [30] Decomposition: 305-318 [50] The so called “red waters”, i.e. TNT-contaminated effluents have also been studied abroad, e.g. [51-53]. New methods of disposing of asymmetrical trinitrotoluenes are also being developed. One of the latest methods is Copyright © 2020 Łukasiewicz Research Network – Institute of Industrial Organic Chemistry, Poland New energetic materials derived from common explosives.
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