5-Nitro-1,2,4-triazole-3-one:A Review of Recent Advances
|
摘要
The 3?Nitro?1,2,4?triazole?5?one(NTO)is a high energy density materials of keen interest for both commercial and scientific worlds owing to its reduced sensitivity,better thermal stability and high performances. It plays a significant role to replace the current energetic ingredients. In this review,we summarize various strategies involved in the synthesis of NTO as well as the existing approaches to tailor its particle morphology and sizes. The most prominent properties of NTO,such as insensitivity and performance,which are usually required to produce efficient formulations,have been concisely discussed. In addition,this overview reports on some newer forms of NTO including derivatives and co?crystals available in the literature,which can enhance the NTO features and extend its applications. The advantages and shortcomings of various NTO forms for specific and potential use are also highlighted together with the attempts made to overcome these issues. Therefore,efforts will certainly continue to improve characteristics and performances of NTO either by chemical modification or by co?crystallization in order to produce promising formulations for widespread applications in the near future.
The 3?Nitro?1,2,4?triazole?5?one(NTO)is a high energy density materials of keen interest for both commercial and scientific worlds owing to its reduced sensitivity,better thermal stability and high performances. It plays a significant role to replace the current energetic ingredients. In this review,we summarize various strategies involved in the synthesis of NTO as well as the existing approaches to tailor its particle morphology and sizes. The most prominent properties of NTO,such as insensitivity and performance,which are usually required to produce efficient formulations,have been concisely discussed. In addition,this overview reports on some newer forms of NTO including derivatives and co?crystals available in the literature,which can enhance the NTO features and extend its applications. The advantages and shortcomings of various NTO forms for specific and potential use are also highlighted together with the attempts made to overcome these issues. Therefore,efforts will certainly continue to improve characteristics and performances of NTO either by chemical modification or by co?crystallization in order to produce promising formulations for widespread applications in the near future.
The 3?Nitro?1,2,4?triazole?5?one(NTO)is a high energy density materials of keen interest for both commercial and scientific worlds owing to its reduced sensitivity,better thermal stability and high performances. It plays a significant role to replace the current energetic ingredients. In this review,we summarize various strategies involved in the synthesis of NTO as well as the existing approaches to tailor its particle morphology and sizes. The most prominent properties of NTO,such as insensitivity and performance,which are usually required to produce efficient formulations,have been concisely discussed. In addition,this overview reports on some newer forms of NTO including derivatives and co?crystals available in the literature,which can enhance the NTO features and extend its applications. The advantages and shortcomings of various NTO forms for specific and potential use are also highlighted together with the attempts made to overcome these issues. Therefore,efforts will certainly continue to improve characteristics and performances of NTO either by chemical modification or by co?crystallization in order to produce promising formulations for widespread applications in the near future.
引文
[1]Klap?tke T M.Chemistry of high?energy materials[M].Berlin:Walter de Gruyter GmbH&Co KG,2017.
[2]Agrawal J P.High energy materials:propellants,explosives and pyrotechnics[M].Weinheim:John Wiley&Sons,2010.
[3]Trache D,Khimeche K,Mezroua A,et al.Physicochemical properties of microcrystalline nitrocellulose from Alfa grass fibres and its thermal stability[J].Journal of Thermal Analysis and Calorimetry,2016,124(3):1485-1496.
[4]Trache D,Tarchoun A F.Stabilizers for nitrate ester?based energetic materials and their mechanism of action:a state?of?the?art review[J].Journal of Materials Science,2018,53(1):100-123.
[5]Klap?tke T M,Witkowski T G.Covalent and ionic insensitive high?explosives[J].Propellants,Explosives,Pyrotechnics,2016,41(3):470-483.
[6]Williamson D M,Gymer S,Taylor N E,et al.Characterisation of the impact response of energetic materials:observation of a low?level reaction in 2,6?diamino?3,5?dinitropyr?azine?1?oxide(LLM?105)[J].RSC Advances,2016,6(33):27896-27900.
[7]Viswanath D S,Ghosh T K,Boddu V M.Emerging Energetic Materials:Synthesis,Physicochemical,and Detonation Properties[M].The Netherlands:Springer,2018.
[8]Trache D,Klap?tke T M,Maiz L,et al.Recent advances in new oxidizers for solid rocket propulsion[J].Green Chemistry,2017,19(20):4711-4736.
[9]Zhao Y,Chen S,Jin S,et al.Heat effects of NTO synthesis in nitric acid solution[J].Journal of Thermal Analysis and Calorimetry,2017,128(1):301-310.
[10]Pourmortazavi S M,Rahim?Nasrabadi M,Kohsari I,et al.Non?isothermal kinetic studies on thermal decomposition of energetic materials:KNF and NTO[J].Journal of thermal analysis and calorimetry,2011,110(2):857-863.
[11]Krzmarzick M J,Khatiwada R,Olivares C I,et al.Biotransformation and degradation of the insensitive munitions compound,3?nitro?1,2,4?triazol?5?one,by soil bacterial commu?nities[J].Environmental science&technology,2015,49(9):5681-5688.
[12]Deshmukh M B,Wagh N D,Skider A K,et al.Cyclodextrin nitrate ester/H2SO4 as a novel nitrating system for efficient synthesis of insensitive high explosive 3?nitro?1,2,4?triazol?5?one[J].Industrial&Engineering Chemistry Research,2014,53(50):19375-19379.
[13]Sarangapani R,Ramavat V,Reddy T S,et al.Effect of particle size and shape of NTO on micromeritic characteristics and its explosive formulations[J].Powder Technology,2014,253:276-283.
[14]Lasota J,Chy?ek Z,Trzciński W.Methods for preparing spheroidal particles of 3?nitro?1,2,4?triazol?5?one(NTO)[J].Central European Journal of Energetic Materials,2015,12(4):769-783.
[15]Lin H,Zhu S G,Zhang L,et al.Intermolecular interactions,thermodynamic properties,crystal structure,and detonation performance of HMX/NTO cocrystal explosive[J].International Journal of Quantum Chemistry,2013,113(10):1591-1599.
[16]Zhao G,Yang D.Periodic DFT study of structural transformations of cocrystal NTO/TZTN under high pressure[J].RSC Advances,2018,8(56):32241-32251.
[17]Viswanath D S,Ghosh T K,Boddu V M.5?Nitro?2,4?Dihy?dro?3H?1,2,4?Triazole?3?One(NTO),in Emerging Energetic Materials:Synthesis,Physicochemical,and Detonation Prop?erties[M].Springer,2018,163-211.
[18]BadgujarD M,Talawar M B,Mahulikar P P.Review of promising insensitive energetic materials[J].Central European Journal of Energetic Materials,2017,14(4):821-843.
[19]Singh G.Recent Advances on Energetic Materials[M].New York:Nova Science Publishers,2015.
[20]Zbarskii V,Kuz′min V,Yudin N.Synthesis and properties of 1?nitro?4,5?dihydro?1H?1,2,4?triazol?5?one[J].Russian Journal of Organic Chemistry,2004,40(7):1069-1070.
[21]Smith M W,Cliff M D.NTO?based explosive formulations:Atechnology review[R].DTSO Aeronautial Maritime Research Laboratory,Melbourne,1999.
[22]Manchot V W,Noll R.Ueber derivate des Triazols[J].Justus liebigs annalen der chemie,1905,343(1):1-27.
[23]Chipen G I,Bokalder R P,Rinshtein V Y.1,2,4?Triazol?3?one and its nitro and amino derivatives[J].Chem Heterocycl Compds,1966,2(1):110-116.
[24]Gehlen HSchmidt J.Zur Kenntnis der 1,2,4?Triazolone?(5),V?der einfluss von substituenten auf die geschwindigkeit der hydrolyse von 1,2,4?triazolonen?(5)in halbkonzentrierter schwefels?ure[J].Justus Liebigs Annalen der Chemie,1965,682(1):123-135.
[25]Kr?ger C F,Miethchen R,Frank H,et al.über 1,2,4?Tri?azole,XVII.die nitrierung und bromierung von 1,2,4?tri?azolonen[J].Chemische Berichte,1969,102(3):755-766.
[26]Kr?ger C F,Hummel L,Mutscher M,et al.über 1,2,4?Tri?azole,IX:Synthesen und Reaktionen von 4?Amino?1,2,4?triazolonen?(5)[J].Chemische Berichte,1965,98(9):3025-3033.
[27]Lee K Y,Chapman L B,Cobura M D.3?Nitro?1,2,4?tri?azol?5?one,a less sensitive explosive[J].Journal of Energetic Materials,1987,5(1):27-33.
[28]Bolotina N,Kirschbaum K,Pinkerton A A.Energetic materials:a?NTO crystallizes as a four?component triclinic twin[J].Acta Crysstallographia,2005,B61:577-584.
[29]Chipen G,Bokalder R,Grinshtein V Y.1,2,4?Triazol?3?one and its nitro and amino derivatives[J].Chemistry of heterocyclic compounds,1966,2(1):79-83.
[30]Rozin Y A,Belyaeve N A,Bakulev V A,et al.Rearrangement of 1?aminoimidazolidine?4,5?triones to 5?oxo?4,5?dihydro?1,2,4?triazole?3?carboxylic acid[J].Chemistry of Heterocyclic Compounds,2011,12(46):1534-1535.
[31]Becuwe A,Delclos A.Low?sensitivity explosive compounds for low vulnerability warheads[J].Propellants,Explosives,Pyrotechnics,1993,18(1):1-10.
[32]Bojarskaolejnik E,Stefaniak L,Witanowski M,et al.Preparation and C?13 NMR?spectra of some azolones,azolothiones and their methoxy and methylmercapto relatives[J].Bulletin of The Polish Academy of Sciences-Chemistry,1986,34(7-8):295-303.
[33]Trzciński W A,Szala M,Rejmer W.Study of the heat and kinetics of nitration of 1,2,4?triazol?5?one(TO)[J].Propellants,Explosives,Pyrotechnics,2015,40(4):498-505.
[34]Saikia A,Sivabalan R,Gore G M,et al.Microwave?assisted quick synthesis of some potential high explosives[J].Propellants,Explosives,Pyrotechnics,2012,37(5):540-543.
[35]Khatiwada R,Abrell L,Li G,et al.Adsorption and oxidation of 3?nitro?1,2,4?triazole?5?one(NTO)and its transformation product(3?amino?1,2,4?triazole?5?one,ATO)at ferrihydrite and birnessite surfaces[J].Environmental Pollution,2018,240:200-208.
[36]Fan L,Dass C,Burkey T J.Synthesis and thermal decomposi?tion of 15N?labelled NTO[J].Journal of Labelled Compounds and Radiopharmaceuticals,1996,38(1):87-94.
[37]Kim H S,Goh E M,Park B S.Preparation method of 3?nitro?1,2,4?triazol?5?one by a process minimizing heat generation during crystallization[P].US patent6583296 B1,Agency for Defence Development:Korea,2003.
[38]Spear R J,Louey C N,Wolfson M G.A preliminary assessment of 3?nitro?1,2,4?triazol?5?one(NTO)as an insensitive high explosive[R].DSTO Materals Research Laboratory,Aus?tralia,Report No.MLR?TR?89?18,1989.
[39]Saikia A,Sivabalan R,Gore G M,et al.Synthesis of some po?tential high energy materials using metal nitrates;an approach towards environmental benign process[J].Journal of Scientific&Industrial Research,2014,73:485-488.
[40]Collignon S L,Farncomb R.Preparation of spheroidal 3?Ni?tro?1,2,4?triazole?5one by crystallization[P].US Patent H719,US Secretary of Navy:USA,1989.
[41]Mukundan T,Purandare G N,Nair J K,et al.Explosive nitro?triazolone formulates[J].Defence Science Journal,2002,52(2):127-133.
[42]Singh G,Kapoor I P S,Tiwari S K,et al.Studies on energetic compounds:Part 16.Chemistry and decomposition mechanisms of 5?nitro?2,4?dihydro?3H?1,2,4?triazole?3?one(NTO)[J].Journal of Hazardous Materials,2001,81(1-2):67-82.
[43]Zbarsky V L,Yudin N V.Kinetics of the synthesis of NTO in nitric acid[J].Propellants,Explosives,Pyrotechnics,2005,30(4):298-302.
[44]Zhao Y,Chen S,Jin S,et al.Empirical kinetics equation of the synthesis of NTO in nitric acid[J].Propellants,Explosives,Pyrotechnics,2016,41(6):1085-1091.
[45]Delaude L,Laszlo P,Smith K.Heightened selectivity in aro?matic nitrations and chlorinations by the use of solid supports and catalysts[J].Accounts of chemical research,1993,26:607-613.
[46]Li J.One?pot synthesis of 3?nitro?1,2,4?triazol?5?one[J].Beijing Ligong Dexue Xuebao,1998,18(4):518-519.
[47]Zecheru T,Rotariu T,Matache L C,et al.Synthesis and applications of 3?nitro?1,2,4?triazol?5?one based hybrid energetic compositions[J].Revista de Chimie,2014,65:1186?1189.
[48]Vijayalakshmi R,Radhakrishnan S,Rajendra P S,et al.Particle size management studies on spherical 3?nitro?1,2,4?triazol?5?one[J].Particle&Particle Systems Characterization,2011,28(3?4):57-63.
[49]Gaba M,Dhingra N.Microwave chemistry:general features and applications[J].Indian Journal of Pharmaceutical Education and Research,2011,45(2):175-183.
[50]Kumar R S,Gnanavel B.High performance catalytic activity of pure and silver(Ag)doped TiO2 nanoparticles by a novel microwave irradiation technique[J].Journal of Materials Science:Materials in Electronics,2017,28(5):4253-4259.
[51]Liu,D,Wu Z,Tian F,et al.Synthesis of N and La codoped TiO2/AC photocatalyst by microwave irradiation for the photo?catalytic degradation of naphthalene[J].Journal of Alloys and Compounds,2016,676:489-498.
[52]Jiang Y,Wang Y,Meng F,et al.N?doped carbon dots synthe?sized by rapid microwave irradiation as highly fluorescent probes for Pb2+ detection[J].New Journal of Chemistry,2015.39(5):3357-3360.
[53]Qiu H,Cui B,Li G,et al.Novel Fe3O4@ZnO@mSiO2 nano?carrier for targeted drug delivery and controllable release with microwave irradiation[J].The Journal of Physical Chemistry C,2014,118(27):14929-14937.
[54]Ekezie F G C,Sun D W,Han Z,et al.Microwave?assisted food processing technologies for enhancing product quality and process efficiency:A review of recent developments[J].Trends in Food Science&Technology,2017,67:58-69.
[55]Rashad M,Hamdalla T A,Al Gani S E,et al.Optical and electrical behaviors in NiO/xFe2O3 nanoparticles synthesized by microwave irradiation method[J].Optical Materials,2018,75:869-874.
[56]Kshirsagar A D,Mahulikar P P.Microwave?assisted synthesis of poly(glycidyl azide?co?tetrahydrofuran)[J].Polymer Bulletin,2017,74(5):1727-1742.
[57]ZhangC,Li J,Luo Y J,et al.Microwave?assisted azidation reaction for rapid synthesis of poly(3,3′?bisazidomethyl oxetane)[J].Journal of Energetic Materials,2016,34(2):197-204.
[58]Fatimah I.Green synthesis of silver nanoparticles using extract of Parkia speciosa Hassk pods assisted by microwave irradiation[J].Journal of Advanced Research,2016,7(6):961-969.
[59]Saif M J,Naveed M,Asif H M,et al.Irradiation applications for polymer nano?composites:A state?of?the?art review[J].Journal of industrial and engineering chemistry,2018,60:218-236.
[60]Yang Q,Ge J,Gong Q,et al.Two energetic complexes incorporating 3,5?dinitrobenzoic acid and azole ligands:micro?wave?assisted synthesis,favorable detonation properties,insensitivity and effects on the thermal decomposition of RDX[J].New Journal of Chemistry,2016,40(9):7779-7786.
[61]Badgujar D,Talawar M B,Asthana S N,et al.Synthesis and characterization of methyl nitramino?2,4,6?trinitrobenzenes using bismuth nitrate pentahydrate as an eco friendly nitrating agent[J].Journal of Scientific&Industrial Research,2010,69:208-210.
[62]Kshirsagar A,Gite V,Hundiwale D,et al.Microwave assisted synthesis and characterization of glycidyl azide polymers containing different initiating diol units[J].Central European Journal of Energetic Materials,2015,12:757-767.
[63]Cova T F,Murtinho D,Pais A A C C,et al.Combining cellulose and cyclodextrins:fascinating designs for materials and pharmaceutics[J].Frontiers in Chemistry,2018,6:271-289.
[64]Ruebner A,Statton G L,Consaga J P.Polymeric cyclodextrin nitrate esters[M].PA:Mach I,Inc.,King of Prussia,2003.
[65]Ma H,Song J,Hu R.A review on 3?nitro?1,2,4?triazol?5?one and its salts[J].Chinese Journal of Explosives and Propellants,2006,29(6):9?15.
[66]Kondrikov B N,Smirniv S P,Minakin A V,et al.Chemical kinetics of the thermal decomposition of NTO[J].Propellants,Explosives,Pyrotechnics,2004,29(1):27-33.
[67]Madeira C L,Field J A,Simonich M T,et al.Ecotoxicity of the insensitive munitions compound 3?nitro?1,2,4?triazol?5?one(NTO)and its reduced metabolite 3?amino?1,2,4?tri?azol?5?one(ATO)[J].Journal of Hazardous Materials,2018,343:340-346.
[68]Richard T,Weidhaas J.Biodegradation of IMX?101 explosive formulation constituents:2,4?dinitroanisole(DNAN),3?nitro?1,2,4?triazol?5?one(NTO),and nitroguanidine[J].Journal of Hazardous Materials,2014,280:372-379.
[69]Singh G,Felix S P.Studies on energetic compounds.Part 32:crystal structure,thermolysis and applications of NTO and its salts[J].Journal of molecular structure,2003,649(1?2):71-83.
[70]LeeK Y,Coburn M D.3?nitro?1,2,4?triazol?5?one,a less sensi?tive explosive[P].US Patent S4733610,US Department of Energy:USA,1988.
[71]Xue H,Gao H,Twamley B,et al.Energetic salts of 3?nitro?1,2,4?triazole?5?one,5?nitroaminotetrazole,and other nitro?substituted azoles[J].Chemistry of Materials,2007,19(7):1731-1739.
[72]Kulkarni P,Purandare G N,Nair J K,et al.Synthesis,charac?terization,thermolysis and performance evaluation studies on alkali metal salts of TABA and NTO[J].Journal of hazardous materials,2005.119(1-3):53-61.
[73]Zhang M,Li C,Gao H,et al.Promising hydrazinium 3?Ni?tro?1,2,4?triazol?5?one and its analogs.Journal of materials science,2016,51:10849-10862.
[74]Volk F,Bathelt H.Influence of energetic materials on the energy?output of gun propellants[J].Propellants,Explosives,Pyrotechnics,1997,22(3):120-124.
[75]Langlet,A.3?Nitro?1,2,4?triazole?5?one(NTO),A new explosive with high performance and low sensitivity[R].National Defence Research Establishment,Stockholm,Sweden,FOAReport C?20789?2.3,1990.
[76]Hussein A K,Elbeih A,Zeman S.Thermal decomposition kinetics and explosive properties of a mixture based on cis?1,3,4,6?tetranitrooctahydroimidazo?[4,5?d]imidazole and 3?ni?tro?1,2,4?triazol?5?one(BCHMX/NTO)[J].Thermochimica Acta,2017,655:292-301.
[77]Rothgery E,Audette D E,Wedlich R C,et al.The study of the thermal decomposition of 3?nitro?1,2,4?triazol?5?one(NTO)by DSC,TGA?MS,and ARC[J].Thermochimica Acta,1991,185(2):235-243.
[78]Yi X,Rongzu H,Xiyou W,et al.Thermal behaviour of 3?ni?tro?1,2,4?triazol?5?one and its salts[J].Thermochimica Acta,1991,189(2):283-296.
[79]Szala M,Trzciński W A.Synthesis and energetic properties of imidazolium and 2?methylimidazolium salts of 3?nitro?1,2,4?triazol?5?one[J].Propellants,Explosives,Pyrotechnics,2017,42(9):1027-1031.
[80]Mathieu J,Stucki H.Military high explosives[J].Chimia,2004,58(6):383-389.
[81]Lent E M,Crouse L C B,Jackovitz A M,et al.An extended one?generation reproductive toxicity test of 1,2,4?Tri?azol?5?one(NTO)in rats[J].Journal of Toxicology and Environmental Health,Part A,2016,79(24):1159-1178.
[82]Kennedy A J,Poda A R,Melby N L,et al.Aquatic toxicity of photo?degraded insensitive munition 101(IMX?101)constituents[J].Environmental toxicology and chemistry,2017,36(8):2050-2057.
[83]Chew S C,Tennant M,Mai N,et al.Practical Remediation of 3?nitro?1,2,4?triazol?5?one wastewater[J].Propellants,Explosives,Pyrotechnics,2018,43(2):198-202.
[84]Patil S,Sahoo S.Improvement in compressibility,flowability and drug release of glibenclamide by spherical crystallization with additives[J].Digest journal of Nanomaterials&Biostructures,2011,6(4):1463-1477.
[85]Kumar R,Siril P F,Soni P.Tuning the particle size and mor?phology of high energetic material nanocrystals[J].Defence Technology,2015,11(4):382-389.
[86]Vijayalakshmi R,Radhakrishnan S,Shitole P,et al.Spherical3?nitro?1,2,4?triazol?5?one(NTO)based melt?cast compositions:heralding a new era of shock insensitive energetic mate?rials[J].RSC Advances,2015,5(123):101647-101655.
[87]Kim K J,Kim K M.Growth kinetics in seeded cooling crystalli?zation of 3?nitro?1,2,4?triazol?5?one in water?N?methylpyrrol?idone[J].Powder technology,2002,122(1):46-53.
[88]Trzciński,W,Cudzilo S,Dyjak S,et al.A comparison of the sensitivity and performance characteristics of melt?pour explosives with TNT and DNAN binder[J].Central European Journal of Energetic Materials,2014,11(3):443-455.
[89]Dun?ju W,Zhang J,Jin?ying W,et al.Preparation of Nanome?ter NTO by W/O microemulsion[J].Initiators&Pyrotechnics,2007,14(1):9-11.
[90]Yang G,Nie F,Li J,et al.Preparation and characterization of nano?NTO explosive[J].Journal of Energetic Materials,2007,25(1):35-47.
[91]Teipel U,Kr?ber H,Krause H H.Formation of energetic mate?rials using supercritical fluids[J].Propellants,Explosives,Pyrotechnics,2001,26(4):168-173.
[92]Collignon S L.Preparation of spheroidal 3?nitro?1,2,4?tri?azole?5?one[P].US patent 4894462,US Secretary of Navy:USA,1990.
[93]Kim K J.Spherulitic crystallization of 3?nitro?1,2,4?tri?azol?5?one in water+N?methyl?2?pyrrolidone[J].Journal of Crystal Growth,2000,208(1-4):569-578.
[94]Lee K,Gilardi R,Armstrong R W,et al.Structure and properties of energetic materials[M].Materials Research Society,Pittsburgh,PA,1993,296:237.
[95]Rykounov A.Structural and thermodynamic properties of two polymorphic modifications of the insensitive high explosive5?nitro?2,4?dihydro?1,2,4?triazol?3?one(NTO)under finite pressures and temperatures from ab initio calculations[J].Cryst Eng Comm,2015,17(40):7653-7662.
[96]Bolotina N B,Zhurova E,Pinkerton A A.Energetic materials:variable?temperature crystal structure ofβ?NTO[J].Journal of applied crystallography,2003,36(2):280?285.
[97]Hang G Y,Yu W L,Wang J T,et al.Theoretical investigations on stabilities,sensitivity,energetic performance and mechanical properties of CL?20/NTO cocrystal explosives by molecular dynamics simulation[J].Theoretical Chemistry Accounts,2018,137(8):1-14.
[98]Wu Q,Zhu W,Xiao H.Dispersion?corrected DFT study on the structure and absorption properties of crystalline 5?nitro?2,4?dihydro?1,2,4?triazole?3?one under compression[J].Structural Chemistry,2015,26(2):477-484.
[99]Aaker?y C B.Sinha A S.Co?crystals:Preparation,Characterization and Applications[M].UK:Royal Society of Chemistry,2018.
[100]York P,Paradkar A.Crystal engineering and particle design for the powder compaction process[M].in Pharmaceutical Powder Compaction Technology,Second Edition,CRC Press,2016:248-265.
[101]Duggirala N K,Perry M L,Almarsson?,et al.Pharmaceutical cocrystals:along the path to improved medicines[J].Chemical Communications,2016,52(4):640-655.
[102]Spitzer D,Risse B,Schnell F,et al.Continuous engineering of nano?cocrystals for medical and energetic applications[J].Scientific reports,2014,4:6575-6575.
[103]Bolton O,Matzger A J.Improved stability and smart?material functionality realized in an energetic cocrystal[J].Angewandte Chemie,2011,123(38):9122-9125.
[104]Bennion J C,Siddiqi Z R,Matzger A J.A melt castable energetic cocrystal[J].Chemical Communications,2017,53(45):6065-6068.
[105]Viswanath J V,Venugopal K J,Rao N V S,et al.An overview on importance,synthetic strategies and studies of 2,4,6,8,10,12?hexanitro?2,4,6,8,10,12?hexaazaisowurtzitane(HNIW)[J].Defence technology,2016,12(5):401-418.
[106]Landenberger K B,Matzger A J.Cocrystal engineering of a prototype energetic material:supramolecular chemistry of 2,4,6?trinitrotoluene[J].Crystal Growth&Design,2010,10(12):5341-5347.
[107]Landenberger K B,Matzger A J.Cocrystals of 1,3,5,7?tetrani?tro?1,3,5,7?tetrazacyclooctane(HMX)[J].Crystal Growth&Design,2012,12(7):3603-3609.
[108]Yang Z,Wang Y,Zhou J,et al.Preparation and performance of a BTF/DNB cocrystal explosive[J].Propellants,Explosives,Pyrotechnics,2014,39(1):9-13.
[109]Wei X,Ma Y,Long X,et al.A strategy developed from the observed energetic?energetic cocrystals of BTF:cocrystallizing and stabilizing energetic hydrogen?free molecules with hydrog?enous energetic coformer molecules[J].CrystEngComm,2015,17(37):7150-7159.
[110]Zhang X,Chen S,Wu Y,et al.A novel cocrystal composed of CL?20 and energetic ionic salt[J].Chemical Communications,2018,54:13268-13270.
[111]Sun S,Zhang H,Liu Y,et al.Transitions from separately crys?tallized CL?20 and HMX to CL?20/HMX cocrystal based on solvent media[J].Crystal Growth&Design,2017,18(1):77-84.
[112]Hang G,Yu W,Wang T,et al.Theoretical investigations on the structures and properties of CL?20/TNT cocrystal and its defective models by molecular dynamics simulation[J].Journal of molecular modeling,2018,24(7):1-9.
[113]Aaker?y C B,Wijethunga T K,Desper J.Crystal engineering of energetic materials:co?crystals of ethylenedinitramine(EDNA)with modified performance and improved chemical stability[J].Chemistry-A European Journal,2015,21(31):11029-11037.
[114]Hussein A K,Zeman S,Elbeih A.Synthesis,performance,and thermal behavior of a novel insensitive EDNA/DAT co?crystal[J].Zeitschrift für anorganische und allgemeine Chemie,2018,644(8-9):430-437.
[115]Landenberger K B,Bolton O,Matzger A J.Energetic?energetic cocrystals of diacetone diperoxide(DADP):Dramatic and divergent sensitivity modifications via cocrystallization[J].Journal of the American Chemical Society,2015,137(15):5074-5079.
[116]Gao H,Zhang S,Gou R,et al.Theoretical insight into the temperature?dependent acetonitrile(ACN)solvent effect on the diacetone diperoxide(DADP)/1,3,5?tribromo?2,4,6?trini?trobenzene(TBTNB)cocrystallization[J].Computational Materials Science,2016,121:232-239.
[117]Bennion J C,McBain A,Son S F,et al.Design and synthesis of a series of nitrogen?rich energetic cocrystals of 5,5′?dini?tro?2H,2H′?3,3′?bi?1,2,4?triazole(DNBT)[J].Crystal Growth&Design,2015,15(5):2545-2549.
[118]Zhang J,Parrish D A,Shreeve J M.Curious cases of 3,6?dini?tropyrazolo[4,3?c]pyrazole?based energetic cocrystals with high nitrogen content:an alternative to salt formation[J].Chemical Communications,2015,51(34):7337-7340.
[119]Song K,Zhang S,Shi W.Theoretical insights into the stabili?ties,detonation performance,and electrostatic potentials of cocrystals containing α?or β?HMX and TATB,FOX?7,NTO,or DMF in various molar ratios[J].Journal of molecular modeling,2016,22(10):249.
[120]Li J,Jiao Q L,Gong Y G,et al.Explosive performance of HMX/NTO co?crystal[J].IOP Conference Series:Materials Science and Engineering,2018,292:012032.
[121]Wu J T,Zhang J G,Li T,et al.A novel cocrystal explosive NTO/TZTN with good comprehensive properties[J].RSC Advances,2015,5(36):28354-28359.
[122]Anderson S R,Ende D J,Salan J S,et al.Preparation of an energetic?energetic cocrystal using resonant acoustic mixing[J].Propellants,Explosives,Pyrotechnics,2014,39(5):637-640.
[123]Hope K S,Lloyd H J,Ward D,et al.Resonant acoustic mixing and its applications to energetic materials[C]//18th Seminar on New Trend in Research of Energetic Materials.Institute of Energetic Materials University of Pardubice,Pardupice,Czech Republic,2015.
[124]Lloyd H J.Co?crystallisation of energetic materials?a step?change in the control of properties and performance of munitions[D].Edinburgh:University of Edinburgh,2017.
[125]RenY,Zhao F Q,Yi,J H,et al.Studies on an ionic com?pound(3?ATz)+(NTO)-:crystal structure,specific heat capacity,thermal behaviors and thermal safety[J].Journal of the Iranian Chemical Society,2012,9(3):407-414.
[126]Ma H,Song J,Hu R,et al.Molecular structure,the quantum chemical investigation and the thermal behavior of the dimeth?ylamine salt of 3?nitro?1,2,4?triazol?5?one,(CH3)2NH2+C2N4O3H-[J].Journal of Molecular Structure:THEOCHEM,2004,678(1):217-222.
[127]Lee K Y,Stinecipher M M.Synthesis and initial characterization of amine salts of 3?nitro?1,2,4?triazol?5?one[J].Propellants,Explosives,Pyrotechnics,1989,14(6):241-244.
[128]De Paz J L,Ciller J.Structure and tautomerism of ANTA(Ami?nonitrotriazole)[J].Propellants,Explosives,Pyrotechnics,1994,19:32-41.
[129]Singh G,Kapoor I P S,Prem Felix S,et al.Studies on energetic compounds Part 23:Preparation,thermal and explosive characteristics of transition metal salts of 5?nitro?2,4?dihydro?3H?1,2,4?triazole?3?one(NTO)[J].Propellants,Explosives,Pyrotechnics,2002,27(1):16-22.
[130]Singh G,Felix S P.Studies on energetic compounds:25.An overview of preparation,thermolysis and applications of the salts of 5?nitro?2,4?dihydro?3H?1,2,4?triazol?3?one(NTO)[J].Journal of hazardous materials,2002,90(1):1-17.
[131]Li Z,Ma H,Yan B,et al.Synthesis,crystal structure,theoretical calculation and thermal behavior of DNAZ·NTO[J].Chinese Journal of Chemistry,2009,27(11):2284-2290.
[132]Dong S,Zhang G,Chen B,et al.A new energetic material:an azidoethylamine salt of triazole[J].Acta Crystallographica Section C:Crystal Structure Communications,1996,52(8):2057-2058.
[133]Jadhav H,Talawar M B,Dhavale D D,et al.Synthesis,characterization and thermolysis of 2,4?dihydro?2,4,5?trini?tro?3H?1,2,4?triazol?3?one(DTNTO):A new derivative of3?nitro?1,2,4?triazol?5?one(NTO)[J].Indian Journal Engineering and Materials Sciences,2005,12:467-471.
[134]Najafi M,Moghimi A,Moumenian H,et al.New 3?nitro?1,2,4 triazol?5?one(nto)salts synthesized from amines[J].Journalof Energetic Materials,2008,3(1):2-12.
[135]Najafi M,Samangani A K.Non?Isothermal kinetic study of the thermal decomposition of melamine 3?nitro?1,2,4?triazol?5?one salt[J].Propellants,Explosives,Pyrotechnics,2011,36(6):487-492.
[136]Wallace L,Underwood C J,Day A I,et al.Electrochemical reduction of nitrotriazoles in aqueous media as an approach to the synthesis of new green energetic materials[J].New Journal of Chemistry,2011,35(12):2894-2901.
[137]Underwood C J,Wall C,Provatas A,et al.New high nitrogen compounds azoxytriazolone(AZTO)and azotriazolone(azo?TO)as insensitive energetic materials[J].New Journal of Chemistry,2012,36(12):2613-2617.
[138]Cronin M P,Day A I,Wallace L.Electrochemical remediation produces a new high?nitrogen compound from NTO wastewa?ters[J].Journal of hazardous materials,2007,149(2):527-531.
[139]Coburn M D,Lee K Y.Picryl derivatives of 5?nitro?2,4?dihydro?3H?1,2,4?triazol?3?one[J].Journal of heterocyclic chemistry,1990,27(3):575-577.
[140]Türker L,Bayar??.NTO?picryl constitutional isomers-ADFT study[J].Journal of Energetic Materials,2012,30(1):72-96.
[141]Tappan B C,Bowden P R,Lichthardt J P,et al.Evaluation of the detonation performance of insensitive explosive formula?tions based on 3,3′?diamino?4,4′?azoxyfurazan(DAAF)and3?nitro?1,2,4?triazol?5?one(NTO)[J].Journal of Energetic Materials,2018,36(2):169-178.
[142]Bécuwe A,Delclos A,Donzel G,et al.Improvements in NTO Based PBXs.A New Powerful and Insensitive Class of PBX[C]//Insensitive Munitions and Energetic Materials Tech?nology Symposium,Event#854,Florida,USA,6?9th Octo?ber.National Defense Industrial Association,1997.
[143]Lee J S,Jaw K S.Thermal decomposition properties and compatibility of CL?20,NTO with silicone rubber[J].Journal of thermal analysis and calorimetry,2006,85(2):463-467.
[144]Baudin G,Roudot M,Genetier M,et al.Shock?to?detonation transition of RDX,HMX and NTO based composite high explosives:Experiments and modelling[J].Journal of Physics:Conference Series,2014,500:052004.
[145]Belaada A,Trzcinski W A,Chylek Z,et al.A melt?cast composition based on NTO and FOX?7[J].Central European Journal of Energetic Materials,2016,13(4):882-902.
[146]Oxley J C,Smith J L,Donnelly M A,et al.Thermal stability studies comparing IMX?101(dinitroanisole/nitroguanidine/NTO)to analogous formulations containing dinitrotoluene[J].Propellants,Explosives,Pyrotechnics,2016,41(1):98?113.
[147]Cuddy M F,Poda A R,Chappell M A.Estimations of vapor pressures by thermogravimetric analysis of the insensitive mu?nitions IMX?101,IMX?104,and individual components[J].Propellants,Explosives,Pyrotechnics,2014,39(2):236-242.
[148]Singh G,Felix S P.Studies on energetic compounds:Part 36:Evaluation of transition metal salts of NTO as burning rate modifiers for HTPB?AN composite solid propellants[J].Combustion and Flame,2003,135(1-2):145-150.
[2]Agrawal J P.High energy materials:propellants,explosives and pyrotechnics[M].Weinheim:John Wiley&Sons,2010.
[3]Trache D,Khimeche K,Mezroua A,et al.Physicochemical properties of microcrystalline nitrocellulose from Alfa grass fibres and its thermal stability[J].Journal of Thermal Analysis and Calorimetry,2016,124(3):1485-1496.
[4]Trache D,Tarchoun A F.Stabilizers for nitrate ester?based energetic materials and their mechanism of action:a state?of?the?art review[J].Journal of Materials Science,2018,53(1):100-123.
[5]Klap?tke T M,Witkowski T G.Covalent and ionic insensitive high?explosives[J].Propellants,Explosives,Pyrotechnics,2016,41(3):470-483.
[6]Williamson D M,Gymer S,Taylor N E,et al.Characterisation of the impact response of energetic materials:observation of a low?level reaction in 2,6?diamino?3,5?dinitropyr?azine?1?oxide(LLM?105)[J].RSC Advances,2016,6(33):27896-27900.
[7]Viswanath D S,Ghosh T K,Boddu V M.Emerging Energetic Materials:Synthesis,Physicochemical,and Detonation Properties[M].The Netherlands:Springer,2018.
[8]Trache D,Klap?tke T M,Maiz L,et al.Recent advances in new oxidizers for solid rocket propulsion[J].Green Chemistry,2017,19(20):4711-4736.
[9]Zhao Y,Chen S,Jin S,et al.Heat effects of NTO synthesis in nitric acid solution[J].Journal of Thermal Analysis and Calorimetry,2017,128(1):301-310.
[10]Pourmortazavi S M,Rahim?Nasrabadi M,Kohsari I,et al.Non?isothermal kinetic studies on thermal decomposition of energetic materials:KNF and NTO[J].Journal of thermal analysis and calorimetry,2011,110(2):857-863.
[11]Krzmarzick M J,Khatiwada R,Olivares C I,et al.Biotransformation and degradation of the insensitive munitions compound,3?nitro?1,2,4?triazol?5?one,by soil bacterial commu?nities[J].Environmental science&technology,2015,49(9):5681-5688.
[12]Deshmukh M B,Wagh N D,Skider A K,et al.Cyclodextrin nitrate ester/H2SO4 as a novel nitrating system for efficient synthesis of insensitive high explosive 3?nitro?1,2,4?triazol?5?one[J].Industrial&Engineering Chemistry Research,2014,53(50):19375-19379.
[13]Sarangapani R,Ramavat V,Reddy T S,et al.Effect of particle size and shape of NTO on micromeritic characteristics and its explosive formulations[J].Powder Technology,2014,253:276-283.
[14]Lasota J,Chy?ek Z,Trzciński W.Methods for preparing spheroidal particles of 3?nitro?1,2,4?triazol?5?one(NTO)[J].Central European Journal of Energetic Materials,2015,12(4):769-783.
[15]Lin H,Zhu S G,Zhang L,et al.Intermolecular interactions,thermodynamic properties,crystal structure,and detonation performance of HMX/NTO cocrystal explosive[J].International Journal of Quantum Chemistry,2013,113(10):1591-1599.
[16]Zhao G,Yang D.Periodic DFT study of structural transformations of cocrystal NTO/TZTN under high pressure[J].RSC Advances,2018,8(56):32241-32251.
[17]Viswanath D S,Ghosh T K,Boddu V M.5?Nitro?2,4?Dihy?dro?3H?1,2,4?Triazole?3?One(NTO),in Emerging Energetic Materials:Synthesis,Physicochemical,and Detonation Prop?erties[M].Springer,2018,163-211.
[18]BadgujarD M,Talawar M B,Mahulikar P P.Review of promising insensitive energetic materials[J].Central European Journal of Energetic Materials,2017,14(4):821-843.
[19]Singh G.Recent Advances on Energetic Materials[M].New York:Nova Science Publishers,2015.
[20]Zbarskii V,Kuz′min V,Yudin N.Synthesis and properties of 1?nitro?4,5?dihydro?1H?1,2,4?triazol?5?one[J].Russian Journal of Organic Chemistry,2004,40(7):1069-1070.
[21]Smith M W,Cliff M D.NTO?based explosive formulations:Atechnology review[R].DTSO Aeronautial Maritime Research Laboratory,Melbourne,1999.
[22]Manchot V W,Noll R.Ueber derivate des Triazols[J].Justus liebigs annalen der chemie,1905,343(1):1-27.
[23]Chipen G I,Bokalder R P,Rinshtein V Y.1,2,4?Triazol?3?one and its nitro and amino derivatives[J].Chem Heterocycl Compds,1966,2(1):110-116.
[24]Gehlen HSchmidt J.Zur Kenntnis der 1,2,4?Triazolone?(5),V?der einfluss von substituenten auf die geschwindigkeit der hydrolyse von 1,2,4?triazolonen?(5)in halbkonzentrierter schwefels?ure[J].Justus Liebigs Annalen der Chemie,1965,682(1):123-135.
[25]Kr?ger C F,Miethchen R,Frank H,et al.über 1,2,4?Tri?azole,XVII.die nitrierung und bromierung von 1,2,4?tri?azolonen[J].Chemische Berichte,1969,102(3):755-766.
[26]Kr?ger C F,Hummel L,Mutscher M,et al.über 1,2,4?Tri?azole,IX:Synthesen und Reaktionen von 4?Amino?1,2,4?triazolonen?(5)[J].Chemische Berichte,1965,98(9):3025-3033.
[27]Lee K Y,Chapman L B,Cobura M D.3?Nitro?1,2,4?tri?azol?5?one,a less sensitive explosive[J].Journal of Energetic Materials,1987,5(1):27-33.
[28]Bolotina N,Kirschbaum K,Pinkerton A A.Energetic materials:a?NTO crystallizes as a four?component triclinic twin[J].Acta Crysstallographia,2005,B61:577-584.
[29]Chipen G,Bokalder R,Grinshtein V Y.1,2,4?Triazol?3?one and its nitro and amino derivatives[J].Chemistry of heterocyclic compounds,1966,2(1):79-83.
[30]Rozin Y A,Belyaeve N A,Bakulev V A,et al.Rearrangement of 1?aminoimidazolidine?4,5?triones to 5?oxo?4,5?dihydro?1,2,4?triazole?3?carboxylic acid[J].Chemistry of Heterocyclic Compounds,2011,12(46):1534-1535.
[31]Becuwe A,Delclos A.Low?sensitivity explosive compounds for low vulnerability warheads[J].Propellants,Explosives,Pyrotechnics,1993,18(1):1-10.
[32]Bojarskaolejnik E,Stefaniak L,Witanowski M,et al.Preparation and C?13 NMR?spectra of some azolones,azolothiones and their methoxy and methylmercapto relatives[J].Bulletin of The Polish Academy of Sciences-Chemistry,1986,34(7-8):295-303.
[33]Trzciński W A,Szala M,Rejmer W.Study of the heat and kinetics of nitration of 1,2,4?triazol?5?one(TO)[J].Propellants,Explosives,Pyrotechnics,2015,40(4):498-505.
[34]Saikia A,Sivabalan R,Gore G M,et al.Microwave?assisted quick synthesis of some potential high explosives[J].Propellants,Explosives,Pyrotechnics,2012,37(5):540-543.
[35]Khatiwada R,Abrell L,Li G,et al.Adsorption and oxidation of 3?nitro?1,2,4?triazole?5?one(NTO)and its transformation product(3?amino?1,2,4?triazole?5?one,ATO)at ferrihydrite and birnessite surfaces[J].Environmental Pollution,2018,240:200-208.
[36]Fan L,Dass C,Burkey T J.Synthesis and thermal decomposi?tion of 15N?labelled NTO[J].Journal of Labelled Compounds and Radiopharmaceuticals,1996,38(1):87-94.
[37]Kim H S,Goh E M,Park B S.Preparation method of 3?nitro?1,2,4?triazol?5?one by a process minimizing heat generation during crystallization[P].US patent6583296 B1,Agency for Defence Development:Korea,2003.
[38]Spear R J,Louey C N,Wolfson M G.A preliminary assessment of 3?nitro?1,2,4?triazol?5?one(NTO)as an insensitive high explosive[R].DSTO Materals Research Laboratory,Aus?tralia,Report No.MLR?TR?89?18,1989.
[39]Saikia A,Sivabalan R,Gore G M,et al.Synthesis of some po?tential high energy materials using metal nitrates;an approach towards environmental benign process[J].Journal of Scientific&Industrial Research,2014,73:485-488.
[40]Collignon S L,Farncomb R.Preparation of spheroidal 3?Ni?tro?1,2,4?triazole?5one by crystallization[P].US Patent H719,US Secretary of Navy:USA,1989.
[41]Mukundan T,Purandare G N,Nair J K,et al.Explosive nitro?triazolone formulates[J].Defence Science Journal,2002,52(2):127-133.
[42]Singh G,Kapoor I P S,Tiwari S K,et al.Studies on energetic compounds:Part 16.Chemistry and decomposition mechanisms of 5?nitro?2,4?dihydro?3H?1,2,4?triazole?3?one(NTO)[J].Journal of Hazardous Materials,2001,81(1-2):67-82.
[43]Zbarsky V L,Yudin N V.Kinetics of the synthesis of NTO in nitric acid[J].Propellants,Explosives,Pyrotechnics,2005,30(4):298-302.
[44]Zhao Y,Chen S,Jin S,et al.Empirical kinetics equation of the synthesis of NTO in nitric acid[J].Propellants,Explosives,Pyrotechnics,2016,41(6):1085-1091.
[45]Delaude L,Laszlo P,Smith K.Heightened selectivity in aro?matic nitrations and chlorinations by the use of solid supports and catalysts[J].Accounts of chemical research,1993,26:607-613.
[46]Li J.One?pot synthesis of 3?nitro?1,2,4?triazol?5?one[J].Beijing Ligong Dexue Xuebao,1998,18(4):518-519.
[47]Zecheru T,Rotariu T,Matache L C,et al.Synthesis and applications of 3?nitro?1,2,4?triazol?5?one based hybrid energetic compositions[J].Revista de Chimie,2014,65:1186?1189.
[48]Vijayalakshmi R,Radhakrishnan S,Rajendra P S,et al.Particle size management studies on spherical 3?nitro?1,2,4?triazol?5?one[J].Particle&Particle Systems Characterization,2011,28(3?4):57-63.
[49]Gaba M,Dhingra N.Microwave chemistry:general features and applications[J].Indian Journal of Pharmaceutical Education and Research,2011,45(2):175-183.
[50]Kumar R S,Gnanavel B.High performance catalytic activity of pure and silver(Ag)doped TiO2 nanoparticles by a novel microwave irradiation technique[J].Journal of Materials Science:Materials in Electronics,2017,28(5):4253-4259.
[51]Liu,D,Wu Z,Tian F,et al.Synthesis of N and La codoped TiO2/AC photocatalyst by microwave irradiation for the photo?catalytic degradation of naphthalene[J].Journal of Alloys and Compounds,2016,676:489-498.
[52]Jiang Y,Wang Y,Meng F,et al.N?doped carbon dots synthe?sized by rapid microwave irradiation as highly fluorescent probes for Pb2+ detection[J].New Journal of Chemistry,2015.39(5):3357-3360.
[53]Qiu H,Cui B,Li G,et al.Novel Fe3O4@ZnO@mSiO2 nano?carrier for targeted drug delivery and controllable release with microwave irradiation[J].The Journal of Physical Chemistry C,2014,118(27):14929-14937.
[54]Ekezie F G C,Sun D W,Han Z,et al.Microwave?assisted food processing technologies for enhancing product quality and process efficiency:A review of recent developments[J].Trends in Food Science&Technology,2017,67:58-69.
[55]Rashad M,Hamdalla T A,Al Gani S E,et al.Optical and electrical behaviors in NiO/xFe2O3 nanoparticles synthesized by microwave irradiation method[J].Optical Materials,2018,75:869-874.
[56]Kshirsagar A D,Mahulikar P P.Microwave?assisted synthesis of poly(glycidyl azide?co?tetrahydrofuran)[J].Polymer Bulletin,2017,74(5):1727-1742.
[57]ZhangC,Li J,Luo Y J,et al.Microwave?assisted azidation reaction for rapid synthesis of poly(3,3′?bisazidomethyl oxetane)[J].Journal of Energetic Materials,2016,34(2):197-204.
[58]Fatimah I.Green synthesis of silver nanoparticles using extract of Parkia speciosa Hassk pods assisted by microwave irradiation[J].Journal of Advanced Research,2016,7(6):961-969.
[59]Saif M J,Naveed M,Asif H M,et al.Irradiation applications for polymer nano?composites:A state?of?the?art review[J].Journal of industrial and engineering chemistry,2018,60:218-236.
[60]Yang Q,Ge J,Gong Q,et al.Two energetic complexes incorporating 3,5?dinitrobenzoic acid and azole ligands:micro?wave?assisted synthesis,favorable detonation properties,insensitivity and effects on the thermal decomposition of RDX[J].New Journal of Chemistry,2016,40(9):7779-7786.
[61]Badgujar D,Talawar M B,Asthana S N,et al.Synthesis and characterization of methyl nitramino?2,4,6?trinitrobenzenes using bismuth nitrate pentahydrate as an eco friendly nitrating agent[J].Journal of Scientific&Industrial Research,2010,69:208-210.
[62]Kshirsagar A,Gite V,Hundiwale D,et al.Microwave assisted synthesis and characterization of glycidyl azide polymers containing different initiating diol units[J].Central European Journal of Energetic Materials,2015,12:757-767.
[63]Cova T F,Murtinho D,Pais A A C C,et al.Combining cellulose and cyclodextrins:fascinating designs for materials and pharmaceutics[J].Frontiers in Chemistry,2018,6:271-289.
[64]Ruebner A,Statton G L,Consaga J P.Polymeric cyclodextrin nitrate esters[M].PA:Mach I,Inc.,King of Prussia,2003.
[65]Ma H,Song J,Hu R.A review on 3?nitro?1,2,4?triazol?5?one and its salts[J].Chinese Journal of Explosives and Propellants,2006,29(6):9?15.
[66]Kondrikov B N,Smirniv S P,Minakin A V,et al.Chemical kinetics of the thermal decomposition of NTO[J].Propellants,Explosives,Pyrotechnics,2004,29(1):27-33.
[67]Madeira C L,Field J A,Simonich M T,et al.Ecotoxicity of the insensitive munitions compound 3?nitro?1,2,4?triazol?5?one(NTO)and its reduced metabolite 3?amino?1,2,4?tri?azol?5?one(ATO)[J].Journal of Hazardous Materials,2018,343:340-346.
[68]Richard T,Weidhaas J.Biodegradation of IMX?101 explosive formulation constituents:2,4?dinitroanisole(DNAN),3?nitro?1,2,4?triazol?5?one(NTO),and nitroguanidine[J].Journal of Hazardous Materials,2014,280:372-379.
[69]Singh G,Felix S P.Studies on energetic compounds.Part 32:crystal structure,thermolysis and applications of NTO and its salts[J].Journal of molecular structure,2003,649(1?2):71-83.
[70]LeeK Y,Coburn M D.3?nitro?1,2,4?triazol?5?one,a less sensi?tive explosive[P].US Patent S4733610,US Department of Energy:USA,1988.
[71]Xue H,Gao H,Twamley B,et al.Energetic salts of 3?nitro?1,2,4?triazole?5?one,5?nitroaminotetrazole,and other nitro?substituted azoles[J].Chemistry of Materials,2007,19(7):1731-1739.
[72]Kulkarni P,Purandare G N,Nair J K,et al.Synthesis,charac?terization,thermolysis and performance evaluation studies on alkali metal salts of TABA and NTO[J].Journal of hazardous materials,2005.119(1-3):53-61.
[73]Zhang M,Li C,Gao H,et al.Promising hydrazinium 3?Ni?tro?1,2,4?triazol?5?one and its analogs.Journal of materials science,2016,51:10849-10862.
[74]Volk F,Bathelt H.Influence of energetic materials on the energy?output of gun propellants[J].Propellants,Explosives,Pyrotechnics,1997,22(3):120-124.
[75]Langlet,A.3?Nitro?1,2,4?triazole?5?one(NTO),A new explosive with high performance and low sensitivity[R].National Defence Research Establishment,Stockholm,Sweden,FOAReport C?20789?2.3,1990.
[76]Hussein A K,Elbeih A,Zeman S.Thermal decomposition kinetics and explosive properties of a mixture based on cis?1,3,4,6?tetranitrooctahydroimidazo?[4,5?d]imidazole and 3?ni?tro?1,2,4?triazol?5?one(BCHMX/NTO)[J].Thermochimica Acta,2017,655:292-301.
[77]Rothgery E,Audette D E,Wedlich R C,et al.The study of the thermal decomposition of 3?nitro?1,2,4?triazol?5?one(NTO)by DSC,TGA?MS,and ARC[J].Thermochimica Acta,1991,185(2):235-243.
[78]Yi X,Rongzu H,Xiyou W,et al.Thermal behaviour of 3?ni?tro?1,2,4?triazol?5?one and its salts[J].Thermochimica Acta,1991,189(2):283-296.
[79]Szala M,Trzciński W A.Synthesis and energetic properties of imidazolium and 2?methylimidazolium salts of 3?nitro?1,2,4?triazol?5?one[J].Propellants,Explosives,Pyrotechnics,2017,42(9):1027-1031.
[80]Mathieu J,Stucki H.Military high explosives[J].Chimia,2004,58(6):383-389.
[81]Lent E M,Crouse L C B,Jackovitz A M,et al.An extended one?generation reproductive toxicity test of 1,2,4?Tri?azol?5?one(NTO)in rats[J].Journal of Toxicology and Environmental Health,Part A,2016,79(24):1159-1178.
[82]Kennedy A J,Poda A R,Melby N L,et al.Aquatic toxicity of photo?degraded insensitive munition 101(IMX?101)constituents[J].Environmental toxicology and chemistry,2017,36(8):2050-2057.
[83]Chew S C,Tennant M,Mai N,et al.Practical Remediation of 3?nitro?1,2,4?triazol?5?one wastewater[J].Propellants,Explosives,Pyrotechnics,2018,43(2):198-202.
[84]Patil S,Sahoo S.Improvement in compressibility,flowability and drug release of glibenclamide by spherical crystallization with additives[J].Digest journal of Nanomaterials&Biostructures,2011,6(4):1463-1477.
[85]Kumar R,Siril P F,Soni P.Tuning the particle size and mor?phology of high energetic material nanocrystals[J].Defence Technology,2015,11(4):382-389.
[86]Vijayalakshmi R,Radhakrishnan S,Shitole P,et al.Spherical3?nitro?1,2,4?triazol?5?one(NTO)based melt?cast compositions:heralding a new era of shock insensitive energetic mate?rials[J].RSC Advances,2015,5(123):101647-101655.
[87]Kim K J,Kim K M.Growth kinetics in seeded cooling crystalli?zation of 3?nitro?1,2,4?triazol?5?one in water?N?methylpyrrol?idone[J].Powder technology,2002,122(1):46-53.
[88]Trzciński,W,Cudzilo S,Dyjak S,et al.A comparison of the sensitivity and performance characteristics of melt?pour explosives with TNT and DNAN binder[J].Central European Journal of Energetic Materials,2014,11(3):443-455.
[89]Dun?ju W,Zhang J,Jin?ying W,et al.Preparation of Nanome?ter NTO by W/O microemulsion[J].Initiators&Pyrotechnics,2007,14(1):9-11.
[90]Yang G,Nie F,Li J,et al.Preparation and characterization of nano?NTO explosive[J].Journal of Energetic Materials,2007,25(1):35-47.
[91]Teipel U,Kr?ber H,Krause H H.Formation of energetic mate?rials using supercritical fluids[J].Propellants,Explosives,Pyrotechnics,2001,26(4):168-173.
[92]Collignon S L.Preparation of spheroidal 3?nitro?1,2,4?tri?azole?5?one[P].US patent 4894462,US Secretary of Navy:USA,1990.
[93]Kim K J.Spherulitic crystallization of 3?nitro?1,2,4?tri?azol?5?one in water+N?methyl?2?pyrrolidone[J].Journal of Crystal Growth,2000,208(1-4):569-578.
[94]Lee K,Gilardi R,Armstrong R W,et al.Structure and properties of energetic materials[M].Materials Research Society,Pittsburgh,PA,1993,296:237.
[95]Rykounov A.Structural and thermodynamic properties of two polymorphic modifications of the insensitive high explosive5?nitro?2,4?dihydro?1,2,4?triazol?3?one(NTO)under finite pressures and temperatures from ab initio calculations[J].Cryst Eng Comm,2015,17(40):7653-7662.
[96]Bolotina N B,Zhurova E,Pinkerton A A.Energetic materials:variable?temperature crystal structure ofβ?NTO[J].Journal of applied crystallography,2003,36(2):280?285.
[97]Hang G Y,Yu W L,Wang J T,et al.Theoretical investigations on stabilities,sensitivity,energetic performance and mechanical properties of CL?20/NTO cocrystal explosives by molecular dynamics simulation[J].Theoretical Chemistry Accounts,2018,137(8):1-14.
[98]Wu Q,Zhu W,Xiao H.Dispersion?corrected DFT study on the structure and absorption properties of crystalline 5?nitro?2,4?dihydro?1,2,4?triazole?3?one under compression[J].Structural Chemistry,2015,26(2):477-484.
[99]Aaker?y C B.Sinha A S.Co?crystals:Preparation,Characterization and Applications[M].UK:Royal Society of Chemistry,2018.
[100]York P,Paradkar A.Crystal engineering and particle design for the powder compaction process[M].in Pharmaceutical Powder Compaction Technology,Second Edition,CRC Press,2016:248-265.
[101]Duggirala N K,Perry M L,Almarsson?,et al.Pharmaceutical cocrystals:along the path to improved medicines[J].Chemical Communications,2016,52(4):640-655.
[102]Spitzer D,Risse B,Schnell F,et al.Continuous engineering of nano?cocrystals for medical and energetic applications[J].Scientific reports,2014,4:6575-6575.
[103]Bolton O,Matzger A J.Improved stability and smart?material functionality realized in an energetic cocrystal[J].Angewandte Chemie,2011,123(38):9122-9125.
[104]Bennion J C,Siddiqi Z R,Matzger A J.A melt castable energetic cocrystal[J].Chemical Communications,2017,53(45):6065-6068.
[105]Viswanath J V,Venugopal K J,Rao N V S,et al.An overview on importance,synthetic strategies and studies of 2,4,6,8,10,12?hexanitro?2,4,6,8,10,12?hexaazaisowurtzitane(HNIW)[J].Defence technology,2016,12(5):401-418.
[106]Landenberger K B,Matzger A J.Cocrystal engineering of a prototype energetic material:supramolecular chemistry of 2,4,6?trinitrotoluene[J].Crystal Growth&Design,2010,10(12):5341-5347.
[107]Landenberger K B,Matzger A J.Cocrystals of 1,3,5,7?tetrani?tro?1,3,5,7?tetrazacyclooctane(HMX)[J].Crystal Growth&Design,2012,12(7):3603-3609.
[108]Yang Z,Wang Y,Zhou J,et al.Preparation and performance of a BTF/DNB cocrystal explosive[J].Propellants,Explosives,Pyrotechnics,2014,39(1):9-13.
[109]Wei X,Ma Y,Long X,et al.A strategy developed from the observed energetic?energetic cocrystals of BTF:cocrystallizing and stabilizing energetic hydrogen?free molecules with hydrog?enous energetic coformer molecules[J].CrystEngComm,2015,17(37):7150-7159.
[110]Zhang X,Chen S,Wu Y,et al.A novel cocrystal composed of CL?20 and energetic ionic salt[J].Chemical Communications,2018,54:13268-13270.
[111]Sun S,Zhang H,Liu Y,et al.Transitions from separately crys?tallized CL?20 and HMX to CL?20/HMX cocrystal based on solvent media[J].Crystal Growth&Design,2017,18(1):77-84.
[112]Hang G,Yu W,Wang T,et al.Theoretical investigations on the structures and properties of CL?20/TNT cocrystal and its defective models by molecular dynamics simulation[J].Journal of molecular modeling,2018,24(7):1-9.
[113]Aaker?y C B,Wijethunga T K,Desper J.Crystal engineering of energetic materials:co?crystals of ethylenedinitramine(EDNA)with modified performance and improved chemical stability[J].Chemistry-A European Journal,2015,21(31):11029-11037.
[114]Hussein A K,Zeman S,Elbeih A.Synthesis,performance,and thermal behavior of a novel insensitive EDNA/DAT co?crystal[J].Zeitschrift für anorganische und allgemeine Chemie,2018,644(8-9):430-437.
[115]Landenberger K B,Bolton O,Matzger A J.Energetic?energetic cocrystals of diacetone diperoxide(DADP):Dramatic and divergent sensitivity modifications via cocrystallization[J].Journal of the American Chemical Society,2015,137(15):5074-5079.
[116]Gao H,Zhang S,Gou R,et al.Theoretical insight into the temperature?dependent acetonitrile(ACN)solvent effect on the diacetone diperoxide(DADP)/1,3,5?tribromo?2,4,6?trini?trobenzene(TBTNB)cocrystallization[J].Computational Materials Science,2016,121:232-239.
[117]Bennion J C,McBain A,Son S F,et al.Design and synthesis of a series of nitrogen?rich energetic cocrystals of 5,5′?dini?tro?2H,2H′?3,3′?bi?1,2,4?triazole(DNBT)[J].Crystal Growth&Design,2015,15(5):2545-2549.
[118]Zhang J,Parrish D A,Shreeve J M.Curious cases of 3,6?dini?tropyrazolo[4,3?c]pyrazole?based energetic cocrystals with high nitrogen content:an alternative to salt formation[J].Chemical Communications,2015,51(34):7337-7340.
[119]Song K,Zhang S,Shi W.Theoretical insights into the stabili?ties,detonation performance,and electrostatic potentials of cocrystals containing α?or β?HMX and TATB,FOX?7,NTO,or DMF in various molar ratios[J].Journal of molecular modeling,2016,22(10):249.
[120]Li J,Jiao Q L,Gong Y G,et al.Explosive performance of HMX/NTO co?crystal[J].IOP Conference Series:Materials Science and Engineering,2018,292:012032.
[121]Wu J T,Zhang J G,Li T,et al.A novel cocrystal explosive NTO/TZTN with good comprehensive properties[J].RSC Advances,2015,5(36):28354-28359.
[122]Anderson S R,Ende D J,Salan J S,et al.Preparation of an energetic?energetic cocrystal using resonant acoustic mixing[J].Propellants,Explosives,Pyrotechnics,2014,39(5):637-640.
[123]Hope K S,Lloyd H J,Ward D,et al.Resonant acoustic mixing and its applications to energetic materials[C]//18th Seminar on New Trend in Research of Energetic Materials.Institute of Energetic Materials University of Pardubice,Pardupice,Czech Republic,2015.
[124]Lloyd H J.Co?crystallisation of energetic materials?a step?change in the control of properties and performance of munitions[D].Edinburgh:University of Edinburgh,2017.
[125]RenY,Zhao F Q,Yi,J H,et al.Studies on an ionic com?pound(3?ATz)+(NTO)-:crystal structure,specific heat capacity,thermal behaviors and thermal safety[J].Journal of the Iranian Chemical Society,2012,9(3):407-414.
[126]Ma H,Song J,Hu R,et al.Molecular structure,the quantum chemical investigation and the thermal behavior of the dimeth?ylamine salt of 3?nitro?1,2,4?triazol?5?one,(CH3)2NH2+C2N4O3H-[J].Journal of Molecular Structure:THEOCHEM,2004,678(1):217-222.
[127]Lee K Y,Stinecipher M M.Synthesis and initial characterization of amine salts of 3?nitro?1,2,4?triazol?5?one[J].Propellants,Explosives,Pyrotechnics,1989,14(6):241-244.
[128]De Paz J L,Ciller J.Structure and tautomerism of ANTA(Ami?nonitrotriazole)[J].Propellants,Explosives,Pyrotechnics,1994,19:32-41.
[129]Singh G,Kapoor I P S,Prem Felix S,et al.Studies on energetic compounds Part 23:Preparation,thermal and explosive characteristics of transition metal salts of 5?nitro?2,4?dihydro?3H?1,2,4?triazole?3?one(NTO)[J].Propellants,Explosives,Pyrotechnics,2002,27(1):16-22.
[130]Singh G,Felix S P.Studies on energetic compounds:25.An overview of preparation,thermolysis and applications of the salts of 5?nitro?2,4?dihydro?3H?1,2,4?triazol?3?one(NTO)[J].Journal of hazardous materials,2002,90(1):1-17.
[131]Li Z,Ma H,Yan B,et al.Synthesis,crystal structure,theoretical calculation and thermal behavior of DNAZ·NTO[J].Chinese Journal of Chemistry,2009,27(11):2284-2290.
[132]Dong S,Zhang G,Chen B,et al.A new energetic material:an azidoethylamine salt of triazole[J].Acta Crystallographica Section C:Crystal Structure Communications,1996,52(8):2057-2058.
[133]Jadhav H,Talawar M B,Dhavale D D,et al.Synthesis,characterization and thermolysis of 2,4?dihydro?2,4,5?trini?tro?3H?1,2,4?triazol?3?one(DTNTO):A new derivative of3?nitro?1,2,4?triazol?5?one(NTO)[J].Indian Journal Engineering and Materials Sciences,2005,12:467-471.
[134]Najafi M,Moghimi A,Moumenian H,et al.New 3?nitro?1,2,4 triazol?5?one(nto)salts synthesized from amines[J].Journalof Energetic Materials,2008,3(1):2-12.
[135]Najafi M,Samangani A K.Non?Isothermal kinetic study of the thermal decomposition of melamine 3?nitro?1,2,4?triazol?5?one salt[J].Propellants,Explosives,Pyrotechnics,2011,36(6):487-492.
[136]Wallace L,Underwood C J,Day A I,et al.Electrochemical reduction of nitrotriazoles in aqueous media as an approach to the synthesis of new green energetic materials[J].New Journal of Chemistry,2011,35(12):2894-2901.
[137]Underwood C J,Wall C,Provatas A,et al.New high nitrogen compounds azoxytriazolone(AZTO)and azotriazolone(azo?TO)as insensitive energetic materials[J].New Journal of Chemistry,2012,36(12):2613-2617.
[138]Cronin M P,Day A I,Wallace L.Electrochemical remediation produces a new high?nitrogen compound from NTO wastewa?ters[J].Journal of hazardous materials,2007,149(2):527-531.
[139]Coburn M D,Lee K Y.Picryl derivatives of 5?nitro?2,4?dihydro?3H?1,2,4?triazol?3?one[J].Journal of heterocyclic chemistry,1990,27(3):575-577.
[140]Türker L,Bayar??.NTO?picryl constitutional isomers-ADFT study[J].Journal of Energetic Materials,2012,30(1):72-96.
[141]Tappan B C,Bowden P R,Lichthardt J P,et al.Evaluation of the detonation performance of insensitive explosive formula?tions based on 3,3′?diamino?4,4′?azoxyfurazan(DAAF)and3?nitro?1,2,4?triazol?5?one(NTO)[J].Journal of Energetic Materials,2018,36(2):169-178.
[142]Bécuwe A,Delclos A,Donzel G,et al.Improvements in NTO Based PBXs.A New Powerful and Insensitive Class of PBX[C]//Insensitive Munitions and Energetic Materials Tech?nology Symposium,Event#854,Florida,USA,6?9th Octo?ber.National Defense Industrial Association,1997.
[143]Lee J S,Jaw K S.Thermal decomposition properties and compatibility of CL?20,NTO with silicone rubber[J].Journal of thermal analysis and calorimetry,2006,85(2):463-467.
[144]Baudin G,Roudot M,Genetier M,et al.Shock?to?detonation transition of RDX,HMX and NTO based composite high explosives:Experiments and modelling[J].Journal of Physics:Conference Series,2014,500:052004.
[145]Belaada A,Trzcinski W A,Chylek Z,et al.A melt?cast composition based on NTO and FOX?7[J].Central European Journal of Energetic Materials,2016,13(4):882-902.
[146]Oxley J C,Smith J L,Donnelly M A,et al.Thermal stability studies comparing IMX?101(dinitroanisole/nitroguanidine/NTO)to analogous formulations containing dinitrotoluene[J].Propellants,Explosives,Pyrotechnics,2016,41(1):98?113.
[147]Cuddy M F,Poda A R,Chappell M A.Estimations of vapor pressures by thermogravimetric analysis of the insensitive mu?nitions IMX?101,IMX?104,and individual components[J].Propellants,Explosives,Pyrotechnics,2014,39(2):236-242.
[148]Singh G,Felix S P.Studies on energetic compounds:Part 36:Evaluation of transition metal salts of NTO as burning rate modifiers for HTPB?AN composite solid propellants[J].Combustion and Flame,2003,135(1-2):145-150.