Abstract
1,3,3-Trinitroazetidine (Molecular Formula: C3H4N4O6, TNAZ) has been assessed as a potential high energy replacement for TNT. Australian industrial plant is a melt-castable explosive that has been proposed as a potential replacement for TNT. The structure of the compound has been confirmed by IR, NMR, mass, elemental analysis and by X-ray crystallography. HPLC technique has been employed to confirm the purity of TNAZ (>99%). The compound is further characterized by thermal techniques and is found to undergo limited decomposition at its melting point. Small scale sensitivity tests have also been carried out and the results show that TNAZ is significantly more sensitive to mechanical stimuli than TNT.
References
Archibald TG, Gilardi R, Baum K, George C (1990) Synthesis and x-ray crystal structure of 1,3,3-trinitroazetidine. J Org Chem 55(9):2920–2924
Agrawal PM, Rice BM, Zheng L, Velardez GF, Thompson DL (2006) Molecular dynamics simulations of the melting of 1,3,3-Trinitroazetidine. J Phys Chem B 110(11):5721–5726
Yu C-L, Zhang Y-X, Bauer SH (1998) Estimation of the equilibrium distribution of products generated during high temperature pyrolyses of 1,3,3-trinitroazetidine; thermochemical parameters. J Mol Structure (Theochem) 432:63–68
Watt DS, Cliff MD (1998) TNAZ based melt-cast explosives: technology review and AMRL Research Directions, DSTO Aeronautical and Maritime Research Laboratory, AR-010-600, July 1998
Katritzky AR, Cundy DJ, Chen J (1994) Novel syntheses of 1,3,3-trinitroazetidine. J Heterocycl Chem 31(2):271–275
Marchand AP, Rajagopal D, Bott SG, Archibald TG (1995) A novel approach to the synthesis of 1,3,3-trinitroazetidine. J Org Chem 60(15):4943–4946
Coburn MD, Hiskey MA, Archibald TG (1998) Scale-up and waste-minimization of the Los Alamos process for 1,3,3-trinitroazetidine (TNAZ). Waste Manage (Oxford) 17(2/3):143–146
Nissan R, Ruppert W (2005) More than a decade of green energetics R&D research. Joint Services Environmental Management Conference Columbus, OH, US. Army RDECOM/ Hughes Assoc. INC
Axenrod T, Watnick C, Yazdekhasti H, Dave PR (1993) Synthesis of 1,3,3-trinitroazetidine. Tetrahedron Lett 34(42):6677–6680
Agrawal JP, Hogdson RD (2007) Organic chemistry of explosives. Wiley, New York, NY, pp 265–269
Jadhav HS, Talawar MB, Dhavale DD, Asthana SN, Krishnamurthy VN (2006) Alternate method for synthesis of 1,3,3-trinitroazetidine (TNAZ): next generation melt-castable high-energy material. Indian J Chem Technol 13(1):41–46
Stepanova EV, Stepanova AI (2015) Synthesis and properties of 1,3,3-trinitroazetidine, 58(11):3–15
Sućeska M, Rajić M, Mateĉić-Muśyanić S, Zeman S, Jalovŷ Z (2003) Kinetics and heats of sublimation and evaporation of 1,3,3-trinitroazetidine (TNAZ). J Therm Anal Calorim 74(3):853–866
Akhavan J (2004) Chemistry of explosives. 2nd edn. RSC Paperbacks, Cambridge, UK, p 47
Politzer P, Lane ME, Concha MC, Redfern PC (1995) Comparative computational analysis of some nitramine and difluoramine structures, dissociation energies and heats of formation. J Mol Struct (Theochem) 338(1–3):249–255
Garland NL, McElvany SW (1998) Ionization potentials of TNAZ and its decomposition products. Chem Phys Lett 297:147–153
Simpson RL, Garza RG, Foltz MF, Ornellas DL, Urtiew PA (1994) Characterisation of TNAZ. UCRL-ID-119672, Lawerence Livermore National Laboratory
Dewey MA, Blau RJ, Doll DW, Lee KE, Braithwaite PC (2003) ARDEC explosives development: melt/pour explosives containing TNAZ. Thiokol Corporation. In: Insensitive munitions & energetic materials technology symposium, March 10–13, 2003. Orlando, FL
Liu M-H, Chen C, Hong Y-S (2005) Theoretical study of the unimolecular decomposition mechanisms of energetic TNAD and TNAZ explosives. Int J Quantum Chem 102(4):398–408
McKenney RL, Floyd TG, Stevens WE (1997) Binary phase diagram series: 1,3,3-trinitroazetidine (TNAZ)/2,4,6-trinitrotoluene (TNT). Wright Laboratory, Armament Directorate Report, WL-TR-1997–7001, January 1997
Osmont L, Catoire I, Gökalp V, Yang V (2007) Ab initio quantum chemical predictions of enthalpies of formation, heat capacities, and entropies of gas-phase energetic compounds. Combust Flame 151(1–2):262–273
Jenkins TF, Bartolini C, Ranney TA (2003) Stability of CL-20, TNAZ, HMX, RDX, NG, and PETN in moist, unsaturated soil. ERDC/CRREL TR-03-7, April 2003
Liu Y, Liu Z-N, C-m Yin (2004) Phase diagram and eutectic of binary systems for 1,3,3-trinitroazetidine (TNAZ) with some energetic materials. Hanneng Cailiao 12(Suppl. 1):227–230
Annex DS, Allman JC, Lee YT (1991) Chemistry of energetic materials. In Olah GA, Squire DR (eds) Academic Press, New York, NY, pp 27–54
Additional Scholarly Articles for Further Reading
Agrawal PM, Rice BM, Zheng L, Velardez GF, Thompson DL (2006) Molecular dynamics simulations of the melting of 1,3,3-trinitroazetidine. J Phys Chem B 110(11):5721–5726. https://doi.org/10.1021/jp056690
Alavi S, Reilly LM, Thompson DL (2003) Theoretical predictions of the decomposition mechanism of 1,3,3-trinitroazetidine (TNAZ). J Chem Phys 119(16):8297–8304. https://doi.org/10.1063/1.1611471
Anderson K, Homsy J, Behrens R, Bulusu S (1997) Mechanistic and kinetic studies of the thermal decomposition of TNAZ and NDNAZ. CPIA Publ 657 (JANNAF Propulsion Systems Hazards Subcommittee Meeting, vol 1), pp 37–51
Anex DS, Allman JC, Lee YT (1991) Studies of initial dissociation processes in 1,3,3-trinitroazetidine by photofragmentation translational spectroscopy. Academic, pp 27–54
Archibald TG, Gilardi R, Baum K, George C (1990) Synthesis and x-ray crystal structure of 1,3,3-trinitroazetidine. J Org Chem 55(9):2920–2924. https://doi.org/10.1021/jo00296a066
Astrat’ev AA, Stepanov AI, Dashko DV (2013) Synthesis, energetic and some chemical properties of new explosive—3,4-bis(4’-nitrofurazan-3’-yl)furazan (BNTF). University of Pardubice, Institute of Energetic Materials, pp 482–496
Aubuchon CM, Rector KD, Holmes W, Fayer MD (1999) Nitro group asymmetric stretching mode lifetimes of molecules used in energetic materials. Chem Phys Lett 299(1):84–90. https://doi.org/10.1016/S0009-2614(98)01241-X
Axenrod T, Watnick C, Yazdekhasti H, Dave PR (1995) Synthesis of 1,3,3-trinitroazetidine via the Oxidative Nitrolysis of N-p-Tosyl-3-azetidinone Oxime. J Org Chem 60(7):1959–1964. https://doi.org/10.1021/jo00112a014
Bakhtiar R, Bulusu S (1995) Molecular complexes of cyclodextrins: application of ion-spray mass spectrometry to the study of complexes with selected nitramines. Rapid Commun Mass Spectrom 9(14):1391–1394. https://doi.org/10.1002/rcm.1290091413
Bartnik R, Cal D, Marchand AP, Alihodzic S, Devasagayaraj A (1998) New method for the generation and trapping of 1-azabicyclo [1.1.0] butane. Application to the synthesis of 1,3-dinitroazetidine. Synth Commun 28(21):3949–3954. https://doi.org/10.1080/00397919808004953
Bartnik R, Marchand AP (1997) Synthesis and chemistry of substituted 1-azabicyclo [1.1.0] butanes. Synlett (9):1029–1039. http://doi.org/10.1055/s-1997-1520
Bauer SH, Zhang Y-X (1999) Stability tests of TNAZ—thermal and shock impact. J Energ Mater 17(2 & 3):161–176. https://doi.org/10.1080/07370659908216101
Bottaro JC (1996) Recent advances in explosives and solid propellants. Chem Ind (London) (7):249–252
Braithwaite PC, Hatch RL, Lee K, Wardle RB (1998) Development of high performance CL-20 explosive formulations. In: International annual conference on ICT 29th (Energetic Materials), pp 4.1–4.7
Cahill S, Bulusu S (1993) Molecular complexes of explosives with cyclodextrins. I. Characterization of complexes with the nitramines RDX, HMX and TNAZ in solution by proton NMR spin-lattice relaxation time measurements. Magn Reson Chem 31(8):731–735. https://doi.org/10.1002/mrc.1260310808
Cahill S, Rinzler AG, Owens FJ, Bulusu S (1994) Molecular complexes of explosives with cyclodextrins. II. Preparation and characterization of a solid complex ofβ-cyclodextrin with the nitramine 1,3,3-trinitroazetidine (TNAZ). J Phys Chem 98(28):7095–7100. https://doi.org/10.1021/j100079a033
Calculated using Advanced Chemistry Development (ACD/Labs) Software V8.14 for Solaris (© 1994–2008 ACD/Labs)
Chakka S, Boddu VM, Maloney SW, Toghiani RK, Damavarapu R (2009) Vapor pressures and melting points of select munitions compounds. American Institute of Chemical Engineers, pp chakk1/1-chakk1/9
Chapman RD et al (1995) Phase behavior in TNAZ-based and other explosive formulations. American Defense Preparedness Association, pp 192–197
Coburn MD, Hiskey MA, Archibald TG (1998) Scale-up and waste-minimization of the Los Alamos process for 1,3,3-trinitroazetidine (TNAZ). Waste Manage (Oxford) 17(2/3):143–146. https://doi.org/10.1016/S0956-053X(97)10013-7
Coburn MD, Hiskey MA, Oxley JC, Smith JL, Zheng W, Rogers E (1998) Synthesis and spectra of some 2H-, 13C-, and 15 N-labeled isomers of 1,3,3-trinitroazetidine and 3,3-dinitroazetidinium nitrate. J Energ Mater 16(2 & 3):73–99. https://doi.org/10.1080/07370659808217506
Crowder GA, McKenney RL Jr (1999) Vibrational analysis of high-energy compounds: 1,3,3-trinitroazetidine and 1-acetyl-3,3-dinitroazetidine. J Energ Mater 17(1):49–68. https://doi.org/10.1080/07370659908216095
Dubovik AV, Kozak GD, Aleshkina EA (2007) Theoretical estimation of explosion hazard of NTO, FOX-7, TNAZ, and CL-20. University of Pardubice, pp 484–495
Dudek K, Marecek P, Jalovy Z (2002) Some properties of cast TNAZ mixtures. In: International annual conference on ICT 33rd (Energetic Materials), pp 53/1–53/7
Dudek K, Marecek P, Jalovy Z (2001) Synthesis and some properties of 1,3,3-trinitroazetidine (TNAZ). University of Pardubice, pp 75–80
Dudek K, Marecek P, Vavra P (2000) Laboratory testing of HNIW mixtures. In: International annual conference on ICT 31st (Energetic Materials), pp 110/1–110/6
Fan X, Li J, Zhang Y, Zhang W, Kang X (2005) Characteristics of the smokeless CMDB propellants with 1,3,3-trinitroazetidine. Huozhayao Xuebao 28(4):35–40
Florczak B, Lipinska K (2001) Thermochemical properties of composite propellants combustion products. University of Pardubice, pp 86–98
Fuchs B, Stec D, III (2007) Computational survey of representative energetic materials as propellants for microthruster applications. In: Proceedings of SPIE-international society optics engineering 6556 (Micro (MEMS) and Nanotechnologies for Defense and Security), pp 65561B/1–65561B/12. http://doi.org/10.1117/12.721756
Garland NL, McElvany SW (1998) Ionization potentials of TNAZ and its decomposition products. Chem Phys Lett 297(1,2):147–153. http://doi.org/10.1016/S0009-2614(98)01113-0
Garland NL, Nelson HH (1998) Laser-induced decomposition of TNAZ. J Phys Chem B 102(15):2663–2667. https://doi.org/10.1021/JP980201D
Hayashi K, Kumagai T, Nagao Y (2000) Improved synthesis of an energetic material, 1,3,3-trinitroazetidine exploiting 1-azabicyclo [1.1.0] butane. Heterocycles 53(2):447–452
Hill LG, Seitz WL, Kramer JF, Murk DM, Medina RS (1996) Wedge test data for three new explosives: LAX112, 2,4-DNI, and TNAZ. In: AIP conference on proceedings 370 (Pt. 2, Shock Compression of Condensed Matter–1995), pp 803–806
Jadhav HS, Dhavale DD, Talawar MB, Asthana SN, Krishnamurthy VN (2003) 1-(3’,5’-dinitrophenyl)-3,3-dinitroazetidine: a new energetic materials. University of Pardubice, pp 153–159
Jadhav HS, Talawar MB, Dhavale DD, Asthana SN, Krishnamurthy VN (2006) Alternate method for synthesis of 1,3,3-trinitroazetidine (TNAZ): next generation melt-castable high-energy material. Indian J Chem Technol 13(1):41–46
Jalovy Z, Zeman S, Suceska M, Vavra P, Dudek K, Rajic M (2001) 1,3,3-trinitroazetidine (TNAZ), Part I syntheses and properties. J Energ Mater 19(2 & 3):219–239. https://doi.org/10.1080/07370650108216127
Jizhen L, Xuezhong F, Xiping F, Fengqi Z, Rongzu H (2006) Compatibility study of 1,3,3-trinitroazetidine with some energetic components and inert materials. J Therm Anal Calorim 85(3):779–784. https://doi.org/10.1007/s10973-005-7370-8
Katorov DV, Rudakov GF, Ladonin AV, Zhilin VF, Veselova EV, Vyalova NA (2007) Preparation of low-melting explosive compositions based on 1,3,3-trinitroazetidine. Cent Eur J Energ Mater 4(1–2):125–133
Katritzky AR, Cundy DJ, Chen J (1994) Novel syntheses of 1,3,3-trinitroazetidine. J Heterocycl Chem 31(2):271–275. https://doi.org/10.1002/jhet.5570310202
Keshavarz MH (2007) Determining heats of detonation of non-aromatic energetic compounds without considering their heats of formation. J Hazard Mater 142(1–2):54–57. https://doi.org/10.1016/j.jhazmat.2006.07.057
Keshavarz MH, Moghadas MH, Tehrani MK (2009) Relationship between the electrostatic sensitivity of nitramines and their molecular structure. Propellants Explos Pyrotech 34(2):136–141. https://doi.org/10.1002/prep.200700264
Keshavarz MH, Yousefi MH (2008) Heats of sublimation of nitramines based on simple parameters. J Hazard Mater 152(3):929–933. https://doi.org/10.1016/j.jhazmat.2007.07.067
Kim JS, Kim H, Kwon Y (2009) Synthesis of glycidyldinitroazetidine (GDNAZ) as an energetic monomers containing explosophoric group. In: International annual conference on ICT 40th (Energetic Materials), pp 53/1–53/11
Konrad S, Doris K (2000) Synthesis and properties of TNAZ. In: International annual conference on ICT 31st (Energetic Materials), pp 10/1–10/12
Lanzerotti MYD, Autera J, Sharma J (1996) Crystal growth of TNAZ during high acceleration. In: AIP conference proceedings 370 (Pt. 1, Shock Compression of Condensed Matter–1995), pp 243–246
Lanzerotti Y, Sharma J (2002) Mechanical behavior of energetic materials during high acceleration. In: AIP conference proceedings on 620 (Shock Compression of Condensed Matter, Pt. 2), pp 853–855
Lanzerotti Y, Sharma J (2003) Mechanical behavior of energetic materials during high acceleration. In: Materials research society symposium proceedings 759(Granular Material-Based Technologies), pp 155–159
Lanzerotti Y, Sharma J (2001) Mechanical behavior of energetic materials at high acceleration. Kluwer Academic/Plenum Publishers, pp 367–369
Li J, Zhang W, Wang B, Fan X, Liu Z (2005) Studies on the combustion characteristics and the thermal behavior of CMDB and NEPE propellants with 1,3,3-trinitroazetidine. Huozhayao Xuebao 28(2):16–20, 38
J-z Li, G-f Zhang, Fan X-z Hu, R-z Pan Q (2006) Thermal behavior of 1,3,3-trinitroazetidine. J Anal Appl Pyrolysis 76(1–2):1–5. https://doi.org/10.1016/j.jaap.2005.04.008
Liao L-Q et al (2012) Compatibility of PNIMMO with some energetic materials. J Therm Anal Calorim 109(3):1571–1576. https://doi.org/10.1007/s10973-011-1905-y
Liu M-H, Chen C, Hong Y-S (2004) Empirical methods for estimating the detonation properties of energetic TNAZ molecular derivatives. J Theor Comput Chem 3(3):379–389. https://doi.org/10.1142/S0219633604001100
Liu M-H, Chen C, Hong Y-S (2005) Theoretical study of the unimolecular decomposition mechanisms of energetic TNAD and TNAZ explosives. Int J Quantum Chem 102(4):398–408. https://doi.org/10.1002/qua.20284
Long GT, Wight CA (2002) Thermal decomposition of a melt-castable high explosive: isoconversional analysis of TNAZ. J Phys Chem B 106(10):2791–2795. https://doi.org/10.1021/jp012859o
Ma H-X et al (2010) Molecular structure, thermal behavior and adiabatic time-to-explosion of 3,3-dinitroazetidinium picrate. J Mol Struct 981(1–3):103–110. https://doi.org/10.1016/j.molstruc.2010.07.036
Makhova NN, Ovchinnikov IV (2008) New variant of 1,3,3-trinitroazetidine synthesis. vol Pt. 2. University of Pardubice, pp 639–641
Marchand AP, Rajagopal D, Bott SG, Archibald TG (1995) A novel approach to the synthesis of 1,3,3-trinitroazetidine. J Org Chem 60(15):4943–4946. https://doi.org/10.1021/jo00120a049
Marecek P, Dudek K (2002) Cast TNAZ mixtures. University of Pardubice, pp 164–168
Marecek P, Dudek K, Vavra P (2001) Laboratory testing of TNAZ mixtures. In: International annual conference on ICT 32nd (Energetic Materials), pp 90/1–90/8
McKenney RL Jr. et al (1998) Synthesis and thermal properties of 1,3-dinitro-3- (1’,3’-dinitroazetidin-3’-yl)azetidine (TNDAZ) and its admixtures with 1,3,3-trinitroazetidine (TNAZ). [Erratum to document cited in CA129:161458]. J Energ Mater 16(2 & 3):198–235
McKenney RL Jr et al (1998) Synthesis and thermal properties of 1,3-dinitro-3-(1,3-dinitro-3-azetidinyl) azetidine (TNDAZ) and its admixtures with 1,3,3-trinitroazetidine (TNAZ). J Energ Mater 16(1):1–22. https://doi.org/10.1080/07370659808216090
McKenney RL Jr, Stevens WE (2000) Binary phase diagram series: 1,3,3-trinitroazetidine (TNAZ)/1,3,5-trinitrobenzene (TNB). J Energ Mater 18(4):241–273. https://doi.org/10.1080/07370650008219112
McKenney RL Jr, Stevens WE, Floyd TG (1998) Binary phase diagram series: 1,3,3-trinitroazetidine (TNAZ)/2,4,6-trinitrotoluene (TNT). J Energ Mater 16(4):245–278. https://doi.org/10.1080/07370659808230234
McKenney RL Jr, Stevens WE, Floyd TG (1999) Binary phase diagram series: 1,3,3-trinitroazetidine (TNAZ)/N-Acetyl-3,3-dinitroazetidine (ADNAZ). J Energ Mater 17(2 & 3):113–140. https://doi.org/10.1080/07370659908216099
Mondal T, Saritha B, Ghanta S, Roy TK, Mahapatra S, Durga Prasad M (2009) On some strategies to design new high energy density molecules. J Mol Struct Theochem 897(1–3):42–47. https://doi.org/10.1016/j.theochem.2008.11.013
Mostak P, Stancl M (2006) New trends in detection of explosives. University of Pardubice, pp 61–74
Nedel’ko VV et al (2009) Thermal decomposition of 1,3,3-trinitroazetidine in the gas phase, solution, and melt. Russ Chem Bull 58(10):2028–2034. https://doi.org/10.1007/s11172-009-0277-y
Nedelko VV, Korsounskii BL, Chukanov NV, Larikova TS, Makhova NN, Ovchinnikov IV (2006) Thermal decomposition of 1,3,3-trinitroazetidine in gas, solution and melt. In: International annual conference on ICT 37th (Energetic Materials), pp 154/1–154/12
Oehrle SA (1994) Analysis of CL-20 and TNAZ in the presence of other nitroaromatic and nitramine explosives using HPLC with photodiode array (PDA) detection. J Energ Mater 12(4):211–222. https://doi.org/10.1080/07370659408018651
Oehrle SA (1996) Analysis of nitramine and nitroaromatic explosives by micellar electrokinetic capillary chromatography (MECC). J Energ Mater 14(1):47–56. https://doi.org/10.1080/07370659608216057
Oftadeh M, Khozani MH, Radhoosh M, Keshavarz MH (2011) DFT molecular orbital calculations of initial step in decomposition pathways of TNAZ and some of its derivatives with -F, -CN and -OCH3 groups. Comput Theor Chem 964(1–3):262–268. https://doi.org/10.1016/j.comptc.2011.01.007
Oftadeh M, Selahvarzi S, Keshavarz MH (2013) Intermolecular interactions between TNAZ and H2O: a DFT study. Cent Eur J Energ Mater 10(2):289–300
Oxley J, Smith J, Zheng W, Rogers E, Coburn M (1997) Thermal Decomposition Pathways of 1,3,3-Trinitroazetidine (TNAZ), Related 3,3-Dinitroazetidium Salts, and 15 N, 13C, and 2H Isotopomers. J Phys Chem A 101(24):4375–4383. https://doi.org/10.1021/JP9700950
Oxley JC, Kooh AB, Szekeres R, Zheng W (1994) Mechanisms of nitramine thermolysis. J Phys Chem 98(28):7004–7008. https://doi.org/10.1021/j100079a019
Oyumi Y, Brill TB (1985) Thermal decomposition of energetic materials. 4. High-rate, in situ, thermolysis of the four, six, and eight membered, oxygen-rich, gem-dinitroalkyl cyclic nitramines, TNAZ, DNNC, and HNDZ. Combust Flame 62(3):225–231.https://doi.org/10.1016/0010-2180(85)90148-8
Parr TP, Hanson-Parr DM (1996) Solid propellant diffusion flame structure. In: Symposium (International) combust, [Proceedings] 26th (vol 2):1981–1987
Persson B, Ostmark H, Bergman H (1997) An HPLC method for analysis of HNIW and TNAZ in an explosive mixture. Propellants Explos Pyrotech 22(4):238–239. https://doi.org/10.1002/prep.19970220411
Pietrzyk S, Nowaczewski J, Bladek J (2007) Analysis of novel high energetic explosives: HNIW, TEX, TNAZ, DADNE. University of Pardubice, pp 853–858
Politzer P, Seminario JM (1993) Energy changes associated with some decomposition steps of 1,3,3-trinitroazetidine. A non-local density functional study. Chem Phys Lett 207(1):27–30. https://doi.org/10.1016/0009-2614(93)85006-A
Porollo AA, Pivina TS, Ivshin VP (1998) Theoretical technique for modeling of 1,3,3-trinitroazetidine (TNAZ) thermal decomposition. In: Proceedings on international pyrotech seminar 24th, pp 445–455
Rice VM et al (2001) Theoretical chemistry: applications in energetic materials research. Khim Fiz 20(10):9–13
Sarlauskas J et al (2014) Modern nitramines TNAZ and CL-20 (HNIW): their electron-accepting potency, enzymatic reactivity and cytotoxicity. vol 2. University of Pardubice, Institute of Energetic Materials, pp 987–1004
Shao Y-H, Ren X-N, Liu Z-R (2010) An investigation on eutectic binary phase diagram of volatilizable energetic materials by high pressure DSC. J Therm Anal Calorim 101(3):1135–1141. https://doi.org/10.1007/s10973-009-0620-4
Shao YH, Ren XN, Liu ZR, Zhang X (2011) Ternary phase diagrams of DNTF and TNAZ and their eutectics. J Therm Anal Calorim 103(2):617–623. https://doi.org/10.1007/s10973-010-0993-4
Sheffield SA, Gustavsen RL, Alcon RR (1996) Hugoniot and initiation measurements on TNAZ explosive. In: AIP conference on proceedings 370 (Pt. 2, Shock Compression of Condensed Matter–1995), pp 879–882
Shu Y, Li H, Huang Y, Liu S (2003) Synthesis of N-acetyl-3,3-dinitroazetidine. University of Pardubice, pp 543–546
Sikder N, Sikder AK, Bulakh NR, Gandhe BR (2004) 1,3,3-Trinitroazetidine (TNAZ), a melt-cast explosive: synthesis, characterization and thermal behaviour. J Hazard Mater 113(1–3):35–43. https://doi.org/10.1016/j.jhazmat.2004.06.002
Sikder N, Sikder AK, Bulakh NR, Gandhe BR (2004) 1,3,3-Trinitroazetidine (TNAZ), a melt-cast explosive: synthesis, characterization and thermal behaviour. J Hazard Mater 113(1–3):35–43
Sikder N, Sikder AK, Bulakh NR, Gandhe BR (2004) 1,3,3-Trinitroazetidine (TNAZ), a melt-cast explosive: synthesis, characterization and thermal behaviour. J Hazard Mater 113(1–3):35–43. https://doi.org/10.1016/j.jhazmat.2004.06.002
Simpson RL, Urtiew PA, Tarver CM (1996) Shock initiation of 1,3,3-trinitroazetidine (TNAZ). In: AIP conference on proceedings 370 (Pt. 2, Shock Compression of Condensed Matter–1995), pp 883–886
Sinditskii VP, Egorshev VY, Berezin MV, Rudakov GF, Ladonin AV, Katorov DV (2005) Combustion behavior and flame structure of a melt-castable high explosive 1,3,3-trinitroazetidine (TNAZ). In: International annual conference on ICT 36th (Energetic Materials), pp 78/1–78/7
Singh A, Sikder N, Sikder AK (2005) Improved synthesis of an energetic material, 1,3,3-trinitroazetidine (TNAZ) exploiting 2-iodoxy benzoic acid (IBX) as an oxidising agent. Indian J Chem, Sect B: Org Chem Incl Med Chem 44B(12):2560–2563
Suceska M, Rajic M, Zeman S, Jalovy Z (2001) 1,3,3-trinitroazetidine (TNAZ). Study of thermal behaviour. Part II. J Energ Mater 19(2 & 3):241–254 http://doi.org/10.1080/07370650108216128
Suceska M, Zeman S, Rajic M, Jalovy Z (2001) Theoretical prediction of TNAZ detonation properties. University of Pardubice, pp 308–318
Suseska M, Rajis M, Matecis-Musanis S, Zeman S, Jalovy Z (2003) Kinetics and heats of sublimation and evaporation of 1,3,3-trinitroazetidine (TNAZ). J Therm Anal Calorim 74(3):853–866. https://doi.org/10.1023/B:JTAN.0000011017.65451.96
Talawar MB et al (2006) Effect of organic additives on the mitigation of volatility of 1-nitro-3,3’-dinitroazetidine (TNAZ): next generation powerful melt castable high energy material. J Hazard Mater 134(1–3):8–18. https://doi.org/10.1016/j.jhazmat.2003.10.008
Thompson CA, Rice JK, Russell TP, Seminario JM, Politzer P (1997) Vibrational analysis of 1,3,3-trinitroazetidine using matrix isolation infrared spectroscopy and quantum chemical calculations. J Phys Chem A 101(42):7742–7748. https://doi.org/10.1021/JP971173M
Thompson CA, Russell TP, Concha MC, Politzer P (1997) Comparing quantum chemical calculations for azetidine strained ring compounds. American Chemical Society, pp COMP-125
Turker L (2013) Detonation velocity—a molecular aspect. Adv Chem Model 4:223–236
Turker L, Atalar T (2011) 1,3,3-Trinitroazetidine (TNAZ) and some of its constitutional isomers: a DFT study. vol 2. University of Pardubice, Institute of Energetic Materials, pp 982–993
Turker L, Varis S (2012) Desensitization of TNAZ via molecular structure modification and explosive properties—a DFT study. Acta Chim Slov 59(4):749–759
Veals JD, Thompson DL (2014) Thermal decomposition of 1,3,3-trinitroazetidine (TNAZ): A density functional theory and ab initio study. J Chem Phys 140(15):154306/1–154306/10 http://doi.org/10.1063/1.4870652
Wakeham GP, Chung DD, Nelson KA (2002) Femtosecond time-resolved spectroscopy of energetic materials. Thermochim Acta 384(1–2):7–21. https://doi.org/10.1016/S0040-6031(01)00774-2
Wilcox CF, Zhang YX, Bauer SH (2000) The thermochemistry of TNAZ (1,3,3-trinitroazetidine) and related species: models for calculating heats of formation. J Mol Struct: THEOCHEM 528:95–109. https://doi.org/10.1016/S0166-1280(99)00475-3
Wilcox CF, Zhang YX, Bauer SH (2001) The thermochemistry of TNAZ (1,3,3-trinitroazetidine) and related species: G3(MP2)//B3LYP heats of formation. J Mol Struct: THEOCHEM 538:67–72. https://doi.org/10.1016/S0166-1280(00)00646-1
Xue L, Zhao F-Q, Xing X-L, Gao H-X, Yi J-H, Hu R-Z (2009) Dissolution properties of 1,3,3-trinitroazetidine in ethyl acetate and N. N-dimethylformamide. Wuli Huaxue Xuebao 25(12):2413–2416
Yan B et al (2014) Thermodynamic properties, detonation characterization and free radical of N-2’,4’-dinitrophenyl-3,3-dinitroazetidine. J Chem Thermodyn 69:152–156. https://doi.org/10.1016/j.jct.2013.10.014
Yan Q-L, Zeman S, Elbeih A (2012) Recent advances in thermal analysis and stability evaluation of insensitive plastic bonded explosives (PBXs). Thermochim Acta 537:1–12. https://doi.org/10.1016/j.tca.2012.03.009
Yu CL, Zhang YX, Bauer SH (1998) Estimation of the equilibrium distribution of products generated during high temperature pyrolyses of 1,3,3-trinitroazetidine; thermochemical parameters. J Mol Struct: THEOCHEM 432(1):63–68. https://doi.org/10.1016/S0166-1280(97)87495-7
Zeman S, Atalar T (2009) A new view of relationships of the N–N bond dissociation energies of cyclic nitramines. Part III. Relationship with detonation velocity. J Energ Mater 27(3):217–229. http://doi.org/10.1080/07370650802640374
Zhang J, Hu J-W, Wang J-L, Chen L-Z (2011) Solubility of 1,3,3-trinitroazetidine in ethanol + water systems from (293.15 K to 323.15 K). J Solution Chem 40(4):703–708. http://doi.org/10.1007/s10953-011-9673-7
Zhang J, Hu R, Zhu C, Feng G, Long Q (1997) Thermal behavior of 1,3,3-trinitroazetidine. Thermochim Acta 298(1–2):31–35. https://doi.org/10.1016/S0040-6031(97)00056-7
Zhang J, Hu R, Zhu C, Feng G, Long Q (1996) Thermal behavior of 1,3,3-trinitroazetidine. Beijing Institute of Technology Press, pp 133–138
Zhang M, Shi Z, Bai Y, Gao Y, Hu R, Zhao F (2006) Using molecular recognition of β-Cyclodextrin to determine molecular weights of low-molecular-weight explosives by MALDI-TOF mass spectrometry. J Am Soc Mass Spectrom 17(2):189–193. https://doi.org/10.1016/j.jasms.2005.10.005
Zhang X, Yang J, Wang T, Gong X, Wang G (2014) A theoretical study on the stability and detonation performance of 2,2,3,3-tetranitroaziridine (TNAD). J Phys Org Chem 27(6):532–539. https://doi.org/10.1002/poc.3297
Zhang Y-X, Bauer SH (1998) Gas-Phase Pyrolysis of 1,3,3-trinitroazetidine: shock tube kinetics. J Phys Chem A 102(29):5846–5856. https://doi.org/10.1021/JP980931L
Zhang Y-X, Bauer SH (1999) Gas-phase decomposition mechanisms of C-NO2, N-NO2 energetic materials: reevaluations. Int J Chem Kinet 31(9):655–673 http://doi.org/10.1002/(SICI)1097-4601(1999)31:9<655::AID-KIN7>3.0.CO;2-M
Zhang Y-X, Bauer SH (1999) Gas-phase decomposition mechanisms of C-NO2, N-NO2 energetic materials: reevaluations. Int J Chem Kinet 31(9):655–673. http://doi.org/10.1002/(SICI)1097-4601(1999)31:9<655::AID-KIN7>3.0.CO;2-M
Zhao Q, Zhang S, Li QS (2005) A direct ab initio dynamics study of the initial decomposition steps of gas phase 1,3,3-trinitroazetidine. Chem Phys Lett 412(4–6):317–321. https://doi.org/10.1016/j.cplett.2005.07.014
Zhao Q, Zhang S, Li QS (2005) The influence of ring strain and conjugation on the reaction energies of the NO2 fission of nitramines: a DFT study. Chem Phys Lett 407(1–3):105–109. https://doi.org/10.1016/j.cplett.2005.03.059
Zheng W, Dong X, Rogers E, Oxley JC, Smith JL (1997) Improvements in the determination of decomposition gases from 1,3,3-trinitroazetidine and 5-nitro-2,4-dihydro-3H-1,2,4-traizol-3-one using capillary gas chromatography-mass spectrometry. J Chromatogr Sci 35(10):478–482. https://doi.org/10.1093/chromsci/35.10.478
Zheng W, Dong X, Rogers E, Oxley JC, Smith JL (1997) Improvements in the determination of decomposition gases from 1,3,3-trinitroazetidine and 5-nitro-2,4-dihydro-3H-1,2,4-traizol-3-one using capillary gas chromatography-mass spectrometry. J Chromatogr Sci 35(10):478–482. https://doi.org/10.1093/chromsci/35.10.478
Zheng W, Rogers E, Coburn M, Oxley J, Smith J (1997) Mass spectral fragmentation pathways in 1,3,3-trinitroazetidine. J Mass Spectrom 32(5):525–532. https://doi.org/10.1002/(SICI)1096-9888(199705)32:5<525:AID-JMS505>3.0.CO;2-7
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2018 US Government (outside the USA)
About this chapter
Cite this chapter
Viswanath, D.S., Ghosh, T.K., Boddu, V.M. (2018). 1,3,3-Trinitroazetidine (TNAZ). In: Emerging Energetic Materials: Synthesis, Physicochemical, and Detonation Properties. Springer, Dordrecht. https://doi.org/10.1007/978-94-024-1201-7_11
Download citation
DOI: https://doi.org/10.1007/978-94-024-1201-7_11
Published:
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-024-1199-7
Online ISBN: 978-94-024-1201-7
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)