Nitrogen-Rich Energetic Materials

446 Pages·2023·11.36 MB·English

by  Gozin M., Fershtat L.L. (ed.)

Nitrogen-RichEnergeticMaterials
Nitrogen-Rich Energetic Materials
Edited by Michael Gozin and Leonid L. Fershtat
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v
Contents
Preface xi
AbouttheEditors xv
1 ChemistryofPentazole 1
MingLu,PengchengWang,YuangangXu,andQiuhanLin
1.1 Introduction 1
1.2 SubstitutedPentazoles 1
1.2.1 Arylpentazoles(ArN ) 2
5
1.2.2 HeterocyclePentazoles 3
1.2.3 Benzylpentazole(BzN ) 3
5
1.2.4 OtherSubstitutedPentazoles 3
1.2.5 PolypentazolesClusters 4
1.3 StrategiesforthePreparationofcyclo-N − 5
5
1.3.1 UsingHigh-EnergyElectronstoCleavetheC—NBondinArN 6
5
1.3.2 CleavingtheC—NBondofArN UsingRedoxChemistry 7
5
1.3.3 Possible[3+2]ReactionofN −andN atHighPressure 8
3 2
1.4 ComplexesofMetalandcyclo-N − 9
5
1.4.1 MetalSaltsofcyclo-N −(0D) 9
5
1.4.2 Metal–InorganicFrameworks(MIFs)ofcyclo-N − 10
5
1.4.3 CoordinationPolymers 12
1.4.4 StructuralCharacterization 14
1.4.4.1 MSandNMRCharacterization 14
1.4.4.2 TopologyAnalysis 14
1.4.4.3 RamanandIRAnalysis 15
1.4.4.4 StabilityAnalysis 16
1.4.4.5 BondingStudy 18
1.4.4.6 DetonationProperties 21
1.5 cyclo-N −-BasedNonmetallicIonicSalts 25
5
1.5.1 Synthesis 25
1.5.2 Single-CrystalX-RayStructures 26
1.5.3 Properties 37
1.5.3.1 15NNMR 37
1.5.3.2 IRSpectrum 38
vi Contents
1.5.3.3 ThermalStability 38
1.5.3.4 Sensitivity 40
1.5.3.5 Density 40
1.5.3.6 HeatofFormationandDetonationPerformance 40
1.6 Conclusions 43
References 43
2 AromaticFused-Ring-BasedEnergeticCompounds 47
KangcaiWangandQinghuaZhang
2.1 Introduction 47
2.2 Fused-RingAromaticEnergeticCompounds 49
2.2.1 [5,5]-Bicyclic-Backbone-BasedEnergeticCompounds 49
2.2.2 [5,6]-BicyclicEnergeticCompounds 53
2.2.3 OtherMulticyclicEnergeticCompounds 63
2.3 Conclusions 68
References 69
3 AdvancesinComputationsofNitrogen-RichMaterials 73
LeiZhangandChuangYao
3.1 WhyComputationandWhatRoleItPlays? 73
3.2 WhyNitrogen-RichHEDMsandHowTheyWork? 74
3.3 AdvancesinComputationofFirst-GenerationNitrogen-Rich
HEDMs 75
3.4 AdvancesinComputationofSecond-GenerationNitrogen-Rich
HEDMs 81
3.5 AdvancesinComputationofThird-GenerationNitrogen-RichHEDMs:
PolynitrogenMaterials 84
3.5.1 Nitrogen-RichHEDMsComposedofN + 85
3
3.5.2 Nitrogen-RichHEDMsComposedofN + 86
5
3.5.3 Nitrogen-RichHEDMsComposedofcyclo-N − 87
5
3.5.3.1 SynthesisandRelatedMechanismatAmbientandHigh
Pressures 87
3.5.3.2 PentazoleCompoundswithNon-nitrogenStabilizer 88
3.5.3.3 ArgumentontheProtonationofcyclo-N −in(N ) (H O) (NH ) Cl 90
5 5 6 3 3 4 4
3.5.3.4 StabilizationMechanismofDual-Aromaticcyclo-N − 91
5
3.5.4 All-NitrogenClusterN 93
4
3.5.5 All-NitrogenClusterN 93
6
3.5.6 All-NitrogenCrystalsComposedofN 94
8
3.5.7 All-NitrogenCrystalsComposedofN 95
10
3.5.8 All-NitrogenHEDMswithCubicGaucheStructure 96
3.6 FinalRemarks 97
Acknowledgement 98
References 98
Contents vii
4 LaserIgnitionofEnergeticTransitionMetalComplexes 107
MaximilianWurzenberger,DanielShem-Tov,andJörgStierstorfer
4.1 Introduction 107
4.2 SynthesisofEnergeticCoordinationCompounds 116
4.3 SynthesisofEnergeticTetrazoleLigands 116
4.4 SynthesisEnergeticCoordinationComplexes 121
4.5 ExamplesofMolecularStructures 122
4.6 EnergeticPropertiesofLigandsandCorrespondingEnergetic
CoordinationCompounds 122
4.7 UV–VisSpectroscopyofEnergeticCoordinationCompounds 128
4.8 StudiesofIgnitionMechanism 128
4.9 Conclusions 134
References 135
5 Energetic1,2,3,4-Tetrazines 139
AleksandrM.Churakov,MichaelS.Klenov,AlekseyA.Voronin,and
VladimirA.Tartakovsky
5.1 Introduction 139
5.2 MethodsofSynthesisandReactivityof1,2,3,4-Tetrazines 141
5.2.1 1,2,3,4-TetrazineswithCarbonSubstituentsatNitrogenAtoms 141
5.2.2 Annulated1,2,3,4-TetrazineswithBridgeheadNitrogenAtoms 142
5.2.3 FullyUnsaturated1,2,3,4-Tetrazines 142
5.2.3.1 Annulated1,2,3,4-Tetrazines 142
5.2.3.2 1,2,3,4-Tetrazine1-OxidesandBenzotetrazine1-Oxides 143
5.2.3.3 1,2,3,4-Tetrazine1,3-Dioxides 144
5.3 NMRandX-rayStudies 164
5.4 ThermalStability 168
5.4.1 TheoreticalStability 168
5.4.2 HeatResistance 169
5.4.2.1 Non-annulated1,2,3,4-Tetrazine1,3-Dioxides(TDOs) 171
5.4.2.2 Benzo-1,2,3,4-Tetrazine1,3-Dioxides(BTDOs) 172
5.4.2.3 BTDOsAnnulatedwithTDORing 173
5.4.2.4 BTDOsAnnulatedwithTetraazapentaleneSystem 174
5.4.2.5 BTDOsAnnulatedwithFuroxanRing 174
5.4.2.6 Tetrazine-1,3-Dioxides(TDOs)AnnulatedwithFive-Membered
Heterocycles 175
5.4.2.7 TDOsAnnulatedwithTetraazapentaleneSystems 175
5.4.2.8 TDOAnnulatedwithSix-MemberedHeterocycle 175
5.4.2.9 1,2,3,4-TetrazineswithTwoBridgeheadNitrogenAtoms 177
5.5 Applications 177
References 179
viii Contents
6 RecentAdvancesinChemistryofNitrogen-RichEnergetic
PolymersandPlasticizers 189
MichaelGozinandLeonidL.Fershtat
6.1 Introduction 189
6.2 HeterocyclicEnergeticPolymersandPlasticizers 189
6.3 Nitrogen-RichEnergeticPolymersLackingTraditionalExplosophoric
Groups 201
6.4 Azido-RichEnergeticPolymersandPlasticizers 202
6.5 AzidoFluoropolymers 216
6.6 AzidoPlasticizers 219
6.7 NitroGroupContainingPolymers 225
6.8 AromaticC-NO ContainingPolymers 230
2
6.9 Conclusions 234
References 234
7 TetrazoleEnergeticSaltsBasedonVariousExplosophores:
RecentOverviewofSynthesisandEnergeticProperties 239
SairaManzoor,Qamar-un-nisaTariq,andJian-GuoZhang
7.1 Introduction 239
7.2 Tetrazole-BasedEnergeticSalts 241
7.2.1 SynthesisofNitro,Nitramino,orAzidoTetrazoleEnergeticSalts 242
7.2.2 SynthesisofAmino/Hydrazine-TetrazoleEnergeticSalts 263
7.2.3 SynthesisofTetrazoleN-oxideEnergeticSalts 266
7.2.4 SynthesisofBistetrazoleorBridgedBistetrazoleEnergeticSalts 269
7.3 ConclusionandFutureTrends 278
7.4 Cautions 280
Acknowledgments 280
References 280
8 PropertiesandApplicationofNitrogen-RichCompoundBTATz
inLow-SignaturePropellants 285
JianhuaYi,ZhihuaSun,YiXu,ZhaoQin,ChangjianWang,BozhouWang,
HuiLi,HaijianLi,ChaoChen,XiaoXie,andFengqiZhao
8.1 Introduction 285
8.2 SynthesisofBTATz 286
8.2.1 Experimental 286
8.2.2 Synthesisof3,6-Bis(3,5-Dimethylpyrazole)-1,2-Dihydro-1,2,4,5-
Tetrazine(3) 286
8.2.3 Synthesisof3,6-Bis(3,5-Dimethylpyrazole)-1,2,4,5-Tetrazine(4) 287
8.2.4 SynthesisofBTATz(5) 287
8.3 StructureofBTATz 287
8.3.1 GeometricConfiguration 287
8.3.2 BondOrders 289
8.3.3 VibrationandInfraredSpectrum 289
8.4 PropertiesofBTATz 290
Contents ix
8.4.1 EnergyPropertiesofBTATzandOtherEnergeticCompounds 290
8.4.2 PhysicochemicalPropertiesDetectedforBTATz 291
8.5 EnergeticPropertiesofthePropellants 291
8.6 PlumeSmokeSignatureofthePropellants 295
8.7 PreparationofthePropellants 296
8.7.1 BTATz–CMDBPropellantsinDINASystem 296
8.7.2 BTATz–HNIW–CMDBPropellantsinDIANPSystem 296
8.8 DecompositionReactionKineticsandThermalSafetyofthe
Propellants 297
8.8.1 BTATz–CMDBPropellantsinDINASystem 297
8.8.1.1 ConditionsforThermalDecompositionReaction 297
8.8.1.2 ThermalBehavior 297
8.8.1.3 NonisothermalReactionKinetics 302
8.8.1.4 ThermalSafety 306
8.8.2 BTATz–HNIW–CMDBPropellantsinDIANPSystem 311
8.8.2.1 ConditionsforThermalDecompositionReaction 311
8.8.2.2 ThermalBehavior 311
8.8.2.3 NonisothermalReactionKinetics 313
8.8.2.4 ThermalSafety 314
8.9 CombustionPropertiesofthePropellants 319
8.9.1 BTATz–CMDBPropellantsinDINASystem 319
8.9.1.1 BurningRateProperties 319
8.9.1.2 StructuresofCombustionFlamesandQuenchedSurfaces 320
8.9.2 BTATz–HNIW–CMDBPropellantsinDIANPSystem 322
8.9.2.1 BurningRateProperties 322
8.9.2.2 StructuresofCombustionFlamesandQuenchedSurfaces 323
8.10 CorrelationBetweenPDSCCharacteristicValuesandBurning
Rates 324
8.11 Conclusions 326
References 327
9 Nitro-substitutedOxadiazoles:ImportantBuildingBlocksin
theSynthesisofEnergeticCompounds 331
PhilipPagoria
9.1 Introduction 331
9.2 EnthalpyofFormationofOxadiazoles 331
9.3 1,2,4-Oxadiazoles 332
9.4 1,3,4-Oxadiazoles 339
9.5 Furazans(1,2,5-Oxadiazole)andFuroxans
(1,2,5-Oxadiazole-2-Oxides) 344
9.6 Summary 365
Abbreviations 366
References 367
x Contents
10 InsensitiveHighExplosivesContainingTetraazapentalene
Moiety 377
Ernst-ChristianKoch
10.1 Introduction 377
10.2 SynthesisofTACOTDerivatives 377
10.3 CrystalandMolecularStructure 383
10.4 Spectroscopy 385
10.4.1 NMRSpectroscopy 385
10.5 Thermochemistry 386
10.6 DetonationPerformance 388
10.7 ThermalBehavior 390
10.8 Sensitivity 391
10.9 Conclusions 392
Acknowledgments 392
Abbreviations 392
References 393
11 Nitrogen-RichPyrotechnicMaterialsforLightand
Smoke 397
ThomasM.KlapötkeandMagdalenaRusan
11.1 Light-GeneratingPyrotechnics 397
11.2 Smokes 405
11.2.1 WhiteSmoke 411
11.2.2 ColoredSmoke 412
Acknowledgments 413
References 413
Index 415