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含能材料ChineseJournalofEnergeticMaterials,Vol.
27,No.
4,2019(326-347)SabrinaHanafi,DjalalTrache,SlimaneAbdous,ZineddineBensalem,AbderrahmaneMezroua5Nitro1,2,4triazole3one:AReviewofRecentAdvancesSabrinaHanafi,DjalalTrache,SlimaneAbdous,ZineddineBensalem,AbderrahmaneMezroua(UERProcédésEnergétiques,EcoleMilitairePolytechnique,Algiers16046,Algeria)Abstract:The3Nitro1,2,4triazole5one(NTO)isahighenergydensitymaterialsofkeeninterestforbothcommercialandscientificworldsowingtoitsreducedsensitivity,betterthermalstabilityandhighperformances.
Itplaysasignificantroletoreplacethecurrentenergeticingredients.
Inthisreview,wesummarizevariousstrategiesinvolvedinthesynthesisofNTOaswellastheexistingapproachestotailoritsparticlemorphologyandsizes.
ThemostprominentpropertiesofNTO,suchasinsensitivityandperformance,whichareusuallyrequiredtoproduceefficientformulations,havebeenconciselydiscussed.
Inaddition,thisoverviewreportsonsomenewerformsofNTOincludingderivativesandcocrystalsavailableintheliterature,whichcanenhancetheNTOfeaturesandextenditsapplications.
TheadvantagesandshortcomingsofvariousNTOformsforspecificandpotentialusearealsohighlightedtogetherwiththeattemptsmadetoovercometheseissues.
Therefore,effortswillcertainlycontinuetoimprovecharacteristicsandperformancesofNTOeitherbychemicalmodificationorbycocrystallizationinordertoproducepromisingformulationsforwidespreadapplicationsinthenearfuture.
Keywords:Triazolone;3nitro1,2,4triazole5one(NTO);synthesis;properties;particlemorphology;derivatives;cocrystals;applicationsCLCnumber:TJ55Documentcode:ADOI:10.
11943/CJEM20183711IntroductionThestudyofhighenergeticmaterials,e.
g.
,explosives,propellants,andpyrotechnics,hasdrawnmuchattentioninmilitaryandcivilianengineeringscience.
Themostcommonlyusedenergeticmaterials(EMs)are1,3,5,7tetranitro1,3,5,7tetraazacyclooctane(HMX),1,3,5trinitro1,3,5triazacyclohexane(RDX),2,4,6trinitrotoluene(TNT),ammoniumperchlorate(AP),nitroglycerin(NG),andnitrocellulose(NC)[1-4].
Recently,someofnewenergeticmaterialshaveshownprominentapplications,suchashexaazahexanitroisowurtzitane(HNIW,CL20),2,6diamino3,5dinitropyrazine1oxide(LLM105),1,1diamino2,2dinitroethylene(FOX7),1,3,3trinitroazetidine(TNAZ),2,4,6triamino1,3,5trinitrobenzene(TATB)and3nitro1,2,4triazole5one(NTO)[5-8].
Thesynthesis,modificationandapplicationofsuchmaterialsarestillveryactive.
MajoreffortsaredevotedtodevelophighperformanceEMswithnotonlyexcellentcombustion/detonationproperties,highdensities,andpositiveoxygenbalances,butalsogoodthermalstabilities,insensitivitiestoexternalforces,inexpensivesynthesis,safehandlingandgoodenvironmentalcompatibility,amongothers.
However,achievingafinebalancebetweenthevariousrequirementsofphysicochemicalpropertiesisaninterestingbutchallengingtaskbecauseenhancementinsomeproperties(e.
g.
performance)oftencomesattheexpenseoftheothers(e.
g.
molecularstability).
NTOhascapturedamajorroleinresearchof文章编号:10069941(2019)04032622ReceivedDate:20181229;RevisedDate:20190125PublishedOnline:20190301Biography:SabrinaHanafi(1993-),female,PhD,Researchfield:energeticmaterials,nanocatalysts,propellant,characterization.
email:sabrinahnf@yahoo.
comCorrespondingauthor:DjalalTrache(1982-),male,TeacherResearcher,Researchfield:propellant,stability,newenergeticmaterials,analyticalchemistry,nanocatalysts,kinetics,biobasedmaterials,advancedmaterials.
email:djalaltrache@gmail.
com引用本文:SabrinaHanafi,DjalalTrache,SlimaneAbdous,etal.
5Nitro1,2,4triazole3one:AReviewofRecentAdvances[J].
ChineseJournalofEnergeticMaterials(HannengCailiao),2019,27(4):326-347.
326CHINESEJOURNALOFENERGETICMATERIALS含能材料2019年第27卷第4期(326-347)5Nitro1,2,4triazole3one:AReviewofRecentAdvancesEMsasoneoftheimportantinsensitivehighexplosive.
AkeycharacteristicofthethermallystableNTOisitsinsensitivitytoimpact,friction,heat,sparkandshockwaves[9].
Itisrelativelyeasytosynthesize.
Itdisplaysperformancecharacteristicscomparabletothoseofthecurrentlycommonlyemployedsecondaryexplosivesandpossessesanappropriatepotentialtobeusedasanexplosiveandpropellantingredient[10].
Thiscompoundhasbeenshowntobelessharmfultohumanhealththantraditionalexplosives[11].
Itcanbealsopressedwithoutabinderintodesiredmorphologyhavingahighdensity[12].
Severalauthorshavetailoreditsparticlesizeandmorphologyinordertomeettherequirementofenergeticmaterialsformulations.
Sphericalmorphologyisrevealedtobeappropriateforbetterprocessabilityandhasgreatimpactonscaletoaltertheperformanceandinsensitivitytowardsasuddenmechanicalstimulithannonsphericalcrystals[13-14].
However,thisnitrogenheterocyclicenergeticcompoundpresentssomedrawbacks,whatlimititsfurtherapplications,suchasnegativeoxygenbalance,negativeenthalpyofformationandacidity.
Toovercomesuchshortcomings,theresearchershaveadoptedtwomainapproaches.
ThefirstoneconcernsthepreparationofNTOderivativesowingtoitsacidityandthesecondoneisdedicatedtotheformationofNTOcocrystals.
Thefirstapproachisthefamousone,whereseveralmetalandaminesalts,andotherderivativesofNTOhavebeenproducedandothercontinuetoappear.
Severalofthelattercompoundsexhibitinterestingphysicochemicalproperties.
Thesecondnewapproach,whichisthecocrystallization,mayprovideapromisingpathwaytouseNTO.
Acocrystalisatypeofamolecule,displayingintermolecularinteractionarisingfromhydrogenbonds,πstacking,vanderWaalsforces,andhalogenbonds.
ItisreportedthatcocrystallizationcantailorthecrystaldensityofEMswithoutchangingtheirchemicalstructure.
Besides,theinsensitivitymaybedecreasedwithoutsacrificingtheperformance[15].
VariousNTOcocrystalshavebeenrecentlyinvestigatedtheoreticallyandexperimentally.
Itisshownthatthismethodologyprovidesanopportunitytomodifythephysicochemicalpropertiesandpreparesuperiorcocrystalswithbetterintegratedpropertiesatamolecularlevel[16].
SeveralreviewpapersandbookchaptershavebeenpublishedinthelasttwodecadesdealingwithNTO,itsderivativesaswellastheconventionalsynthesisproceduresandapplications[5,14,17-21].
However,thefocusofthecurrentarticleisdifferentfromthepublishedliteratureandwhereappropriate,specificpointscoveredinpublishedliteraturearesummarizedand/orreferencedouttothecorrespondingpaper/book/patent.
OneoftheprimeobjectivesofthisreviewistosummarizeandemphasizetheuptodateproceduresusedtoproduceNTOshowingtheiradvantagesanddrawbacks.
Webelievethatitmayprovideastrongbaseforthefuturedevelopmentinthisemergingareaofresearch.
AnoverviewoftheNTOparticlemorphologyandsizecontrolwillbeprovidedaswellastheireffectsonthephysicochemicalproperties.
TherecentNTOderivativesandthedifferentNTObasedcocrystalsaspotentialsubstances,thatcouldreplacethecurrentenergeticingredients,arediscussed.
CurrentapplicationsofNTOinenergeticformulationsarealsohighlighted.
2SynthesisofNTOManchotandNolleareconsideredasthepioneersinthesynthesisofNTO,althoughtheirstructureassignmentwaswrong,byusingatwostepprocess[22].
Thefirststepisdedicatedtotheproductionoftriazolone,whichundergonethenitrationprocessinthesecondstep.
Chipenetal.
andotherscientistshavefollowedthisapproachfewdecadeslater[23-26].
SlightmodificationsonthesynthesisprocedurehavebeenperformedbyLeeetal.
atLosAlamosNationalLaboratory,USA,andpublishedthefirstreportontheexplosivenatureofNTOduring1980s[27].
Therecognitionofsuchenergeticfeatureshaspromoteditsextensivetheoreticalstudies,synthesisandcharacterization[19,28].
Varioussynthesismethodshavebeenexploredworldwideforpreparingthisenerget327www.
energetic-materials.
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cn含能材料ChineseJournalofEnergeticMaterials,Vol.
27,No.
4,2019(326-347)SabrinaHanafi,DjalalTrache,SlimaneAbdous,ZineddineBensalem,AbderrahmaneMezrouaiccompound,wherethefocusisthedevelopmentandimprovementofthesynthesispathwaysofsuchheterocycliccompound.
Thedetailedmethodologiesoftheefficientsynthesismethodsaregivenbellow.
2.
1SynthesisofTriazolone(TO)Bothofthetwoisomers1,2,4triazol5oneand1,2,4triazol3oneareabbreviatedastriazoloneoroxytriazole.
Itisconsideredasanintermediateproduct.
Triazoloneisaheterocycliccompoundcontainingthreenitrogenatoms,oneCNdoublebondandcarbonylgroup.
ItcanbepreparedbydifferentwaysasdepictedinFig.
1.
Thethermaldecarboxylationof1,2,4triazol3onecarboxylicacidisusedbyManchotetal.
tosynthesistriazolone[29-30].
Theobtainedyieldwaslow.
Fewyearslater,Chipenetal.
havetriedtoenhancetheyieldofsuchreactionbyimprovingtheyieldof1,2,4triazol3onecarboxylicacid(Ⅲ)usingdifferentconcentrationsofsulfuricacid(15%,25%and35%)todecomposethe3diazo1,2,4triazole5carboxylicacid(Ⅱ)togeneratethecompoundⅢ[29].
Thislatterwasdecarboxylatedat205-210℃toproduce75%ofTO.
ThereactionprocessisdisplayedinScheme1.
ThesimilarauthorshavesynthesizedTObyacylationofacetonesemicarbazonewithformicacid,theintermediatereactionhasproduceddiformylsemicarbazide,whichonprolongedheatinggeneratesTO.
Theauthorsmentionedthatthereactionyielddoesnotexceed10%.
Inanotherwork,Krgeretal.
havepreparedTObythedeaminationof4amino1,2,4triazol5onewithnitrousacid[26].
During1990s,Becaweetal.
haveboiledeithersemicarbazidealoneorsemicarbazidehydrochloridewithformicacid(90%)[5,31-32].
Theyrevealedthatthebestwaytogetabetteryield(70%)andgreatestpurity(99%)istouseeitherasolidsemicarbazidehydrochloride(SC)itselforbyformingSCinsituemployingsemicarbazideandaqueoushydrochloricacid.
ThismethodbasedonsolidSCremainsthemostandwidelyemployedmethodtoproduceTO[9,12,33-35].
2.
2NitrationofTOAnumberofresearchworksdealingwiththenitrationofTOhavebeenundertakenbyseveralscientists.
ThesynthesisofNTOwasachievedusingoneofthefollowingnitratingagents:fumingnitricacid[22],nitricacidatdifferentconcentrations[5,27,36]orsulfuricnitricacidmixture[37].
Manysynthesisstrategieswereadoptedtoimprovebothreactionprocessandyield(Table1).
Thisprocesscanbeperformedinoneortwosteps.
2.
2.
1NitrationofTOwithNitricAcidNTOcanbeobtainedbynitrationoftriazoloneFig.
1Differentmethodstosynthesizetriazolone.
TO:1,2,4triazole5one;SC:semicarbazide;ASCO:acetonesemicarbazone;ATO:4amino1,2,4triazol5one;TOCA:3carboxylicacid1,2,4triazol5oneScheme1TOsynthesisfromthethermaldecarboxylationof1,2,4triazol3onecarboxylicacid[29]Table1YieldofNTOproductionusingdifferentnitratingagentsnitratingagentfumingnitricacid(98%)fumingnitricacid/waterfumingnitricacid(withinitialcooling)nitricacid(70%)(onepotreaction)nitricacid(70%)(twostepreaction)nitricacid/sulfuricacid(onepot)nitricacid/sulfuricacid/heatingwithmicrowavecyclodextrinnitrateester/sulfuricacid/watermetalnitrate/sulfuricacidyield/%-6770-75758077748880reference[22][29][25][38][21][38][34][12][39]328CHINESEJOURNALOFENERGETICMATERIALS含能材料2019年第27卷第4期(326-347)5Nitro1,2,4triazole3one:AReviewofRecentAdvances(TO)indiluted/concentratednitricacidorsimplybyusingfumingnitricacid,whichmaybepreparedbyaddingexcessnitrogendioxidetonitricacid.
Broadly,thesynthesisprocedureisnotaneasyprocess,becauseseveralparameterscanaffectthechemicalreactionsuchastheconcentrationoftheacid,itspurity,theratio,thedurationandtemperatureofthereaction,tonameafew.
During1980s,varioussynthesisrouteshavebeendeveloped.
Spearsetal.
havemadeaconcisereviewdealingwiththepreparationmethodsofNTO,wheretheypointedouttheemploymentofdifferentratiosofsemicarbazide,formicacid,nitricacidaloneormixedwithsulfuricacidunderdifferentexperimentalconditions[38].
TheyhavereportedthattheyieldofNTOvariedbetween36%-75%.
ManyresearchworkshavebeendevotedtoenhancetheyieldofNTObystudyingthenitrationofTOusingdifferentconcentrationofnitricacid(65%to100%)[22-24,26-27,31,40].
In1993,BecaweandDelcos[31]optimizedthenitrationprocesspreviouslyintroducedbyManchotandNoll[22].
Theyinvestigatedvariousparameterssuchasthenitrationtemperature,thenitrationratio(HNO3/triazolone),reactiontime,anddilutionratio.
Theydeducedthatthenitrationratioof5isanacceptablepromise,thetemperaturevaluesbetween20℃and30℃areperfectlyacceptable,thereactiontimeofthreehoursprovidesamaximumyield,andthedilutionratioofslightlylessthanunityseemstobeoptimum.
However,theypointedoutthatthedissolutionofTOinnitricacidshouldbestartedatatemperaturecloseto0℃becauseitishighlyexothermicbeforeallowingthereactionmediumtoreachtheroomtemperature.
Theprocesswasdoneintwostepsasgivenbellow(Scheme2).
Mukundanetal.
havealsousedthesametwostepprocess,wheretheysynthesizedTOfollowedbyNTOafternitrationusingHNO3[41].
Theyreportedayieldof80%aftercrystallizationfromwater.
Singhetal.
employedthesimilarsynthesisroutebyusing70%nitricacidfornitrationofTOtoNTO[42].
ZbarskyandYudinperformedadetailedinvestigationofthenitrationkineticsofTOin70%-100%nitricacid,andtheyfoundthattheprocesscanbesimulatedbypseudofirstorder[43].
TheyreportedthattheyieldofNTOdidnotdependontemperatureintherangeof0-30℃.
Thereactiontime,whichdecreasesbytheincreaseoftemperature,wasindependentonboththeinitialacidconcentrationintherangeof90%-98%HNO3andtheratioofHNO3totriazoloneintherangeof4-8molHNO3permoleTO.
Nevertheless,atacidconcentrationexceeding77%,1nitro1,2,4triazoloneisobtainedwithinthefirstminutesofthenitration.
ItwasfoundthatatotaldestructionoftheTOringoccurredwiththeformationofNxOy,CH2OandCOasdecompositionproductswhenH0>1;whereas,ifH0CN—chemicalgroupinadditiontoC—NO2linkage.
Itexhibitsgoodthermalstability,lowsensitivitytoradiationdamage,accidentalandsympatheticinitiation[69,77-78].
TheacidiccharacterofNTOandthepresenceoftworeactive(N—H)protonsinitsmoleculeallowedthepreparationofnumeroussaltsofmetalsaswellasaromaticandaliphaticamines,whichcanbetailoredforawiderangeofapplications[69,79].
Inaddition,NTOisnitrogenrichandcontainsotherfunctionalgroupssuitableforinteractionssuchashydrogenbonding.
Thederivedsaltshaveanumberofadvantagesovernonionicmolecules,sincethesesaltsdisplayhigherdensityandlowervaporpressurethantheirrespectiveatomicallynonionicanalogues[71].
However,NTOpresentedsomedrawbackssuchasthehighsolubilityinwater,theacidreactionbyhydrolysisandthelargecriticaldiameterneededforthecontinuationofthedetonation[80].
TheformerissuecanleadtotheincreaseofNTOamountinindustrialwastewaterproducedduringTable2SomephysicochemicalpropertiesofNTONTOnameCASNo.
structuralformulamolecularmass/g·mol-1density/g·cm-3solubilitydecompositiontemperature/℃heatofformation/kJ·mol-1oxygenbalanceacidity1HNMR13CNMR14NNMRIRspectrum/cm-1NearIRspectrum/cm-1RamanIRspectrum/cm-1C2H2N4O33Nitro1,2,4triazole5one,5Nitro1,2,4triazole3one,5oxy3nitro1,2,4triazole(ONTA),nitrotriazolone9326491301.
93,1.
911,2.
06solublein:water,acetone,acetonitrile,dioxin,NMP,DMF,trifluoroaceticacidandDMSO.
limiltedsolubilityin:toluene,chloroform,diethylether,ethylacetate.
insolublein:dichloromethane.
271-273-101.
1-24.
6adibasicacid:pK1=3.
76,pK2=11.
2513.
5(H—NadjacentNO2)and12.
8(DMSOd6)154.
4(CO)and148.
0(C—NO2)(DMSOd6)-34.
5.
5(H—N),-112.
9(N—H),-205.
4,-207.
4,-243.
93212(NH),1714(CO),and1547(NO2)6250and45501361and1329reference[5,17]-[69][21][27,70-71][19,21][72-73][71][73-74][71,75][2021][19]Fig.
2AperformancecomparisonofNTOwiththoseofotherhighexplosives[17,19,21]333www.
energetic-materials.
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cn含能材料ChineseJournalofEnergeticMaterials,Vol.
27,No.
4,2019(326-347)SabrinaHanafi,DjalalTrache,SlimaneAbdous,ZineddineBensalem,AbderrahmaneMezrouathemanufacturingandprocessingofitsformulations.
RecentreportsonthetoxicityofaqueousNTOonCeriodaphniadubia,northernleopard,frogandrat,citetoxiceffectwhentheconcentrationreachesandexceedstherangeof1kg/1000L[81-82].
Forthispurpose,ahugeamountofworkhavebeendoneworldwideinordertofindefficientprocedurestoremovesuchaharmfulexplosivefromsolutionsandreducetheriskofenvironmentalcontamination[35,67,83].
3.
2MorphologyofNTOMorphologies,sizes(distribution),defects,etc.
arethestructuresabovethecrystalpackingandnotintrinsic.
Theyaregovernedbypreparationmethodsinsteadofemergentmolecularpackingincrystal.
Itiswidelyacceptedthatstructure,sizeandmorphologyhavegreatinfluenceonpropertiesofdifferentmaterials.
Theparticlesizesignificantlyaffectsvariousfeaturesofparticulatematerialsandoffersappropriateindicationforqualitycontrolandperformance.
Coarsesphericalparticlescanfloweasilyandgeneratehighbulkdensity.
Fineparticleswithsuitablemorphology,however,areoftennecessitatedtoenhancetheballisticparametersandincreasetheenergyoutputowingtothehighsurfacearea[13].
Inaddition,someauthorsreportedthatflowpropertiessuchaswettability,packability,andcompatibilitycanbeincreasedtoagreatextentoncesphericalparticlesareused[84].
Consequently,suchphysicalcharacteristicsplayvitalroleinachievinginsensitivity,solidloadingandmixfluidityinprocessingandhighperformanceofEMs.
Oneapproachtodecreasethesensitivitytowardsmechanicalstimuliconcernsthealterationofparticlesizeandmorphologytocubicorsphericaldesiredmorphology,whichcanbereachedbyappropriatecrystallizationmethodalongwithsuitableoperationalconditions[48,85-86].
TheconventionalprocessofNTOpreparationfromsemicarbazidehydrochlorideintwostepsgivesrisetorodlikemorphologythatisnonsphericalinnature,whichreadilyagglomeratesandeventuallybecomessensitivetounexpectedshock.
LargescaleproductionofNTOinvolvescrystallizationfromwater,andthisyieldsirregularrodsandjaggedcrystals.
Thisundesiredirregularmorphologyleadstohighviscosity,poorprocessabilityandconsequentlyreducessolidloading.
Thismaycreateissueswithexplosiveformulations,whereadversemorphologyandsizegeneratehandlingsdifficultiesandformulationmaybehighlyviscousandnoteasytopour.
Thus,watercanonlybeutilizedtopurifytheproductsandnotforobtaininggoodmorphology.
Forthatpurpose,severalauthorshavetestedvariousprocedurestoproduceadesiredNTOmorphology(Table3).
Collignon,asoneofthepioneersinthecrystallizationofcrudeNTO,studiedawayforobtainingspheroidalNTOafteritscrystallizationfromaliphatTable3SomeprocedurestoproducedifferentmorphologiesofNTOmethodcoolingrecrystallizationwater/oilmicroemulsionfreezedryingintoliquidrapidexpansionofsupercriticalsolutioninfluencingfactorsconcentration,volumeration,agitatorconfiguration,speedtemperature,ratiosolvent/antisolventconcentration,temperatureconcentrationextractiontemperatureandpressure,nozzlesize,flowratekeypointscoolingratesurfactantnozzlediameterandfreezetemperatureselectionofpropersolventmorphologysphericalsphericalgridsneedlelikecosolventwater/1methyl2pyrolidonenalkanolpolyoxyethylenealkylphenolether-commentbulkdensity:0.
65-1.
15g·mL-1size:10-200μmsize:10-30nmparticlesize:70-90nmparticlesize:540nmRef.
[48,87-88][89][90][91]334CHINESEJOURNALOFENERGETICMATERIALS含能材料2019年第27卷第4期(326-347)5Nitro1,2,4triazole3one:AReviewofRecentAdvancesicalcoholscontaining1to4carbonatomsortheiradmixturewithwater[92].
Thesolutionwasheatedfrom40℃toaboilingtemperatureofalcoholfollowedbyafastcooling(6-20℃·min-1)understirring.
SpheroidalparticlesofNTOwererecoveredat5-10℃.
Similarauthorusedamethodofcrystallizationfromwaterwiththeadditionofasurfactant(perfluorinatedsaltsofaliphaticcompounds)andmethylcelluloseinordertoformspheroidalNTO[40].
SomeauthorsreportedthatcrashprecipitationfromDMSOcouldprovidemoresuitablecrystalmorphologies.
DissolutionofNTOinDMSOandsubsequentinjectionthroughanopeningsmallerthan0.
7mmintodichloromethanegivesrisetoNTOasfinelydividedparticleswithsurfaceareaoftheorderof5.
7m2·cm-3[19].
KimproducedsphericalNTObycoolingcrystallizationusingcosolventNmethyl2pyrrolidone(NMP)andwater[87].
Theyfoundthatthecoolingrateof10℃·min-1gavebetterresults.
ItwasreportedthatthemassratioofNTO/NMPaffectedthemorphologyofNTO.
Porousparticleswithcracksandfissuresweregeneratedwhentheratioisover0.
6.
Fromthedifferenttestedmixtures,thecombinationwater/NP=1.
0,NTO/NMP=0.
39providedthemostadvantageousmorphology.
Furthermore,itwasestablishedthatthewaterquantityinthemixturewithNMPaffectedthediameterandthemorphologyoftherecrystallizedNTO[93].
Thesizeofparticleshadanaveragediameterof50-220m,whichdependedproportionallyonthecontentofwaterinthemixture.
Similarapproachbasedonwater/NMPmixturewasusedbyVijayalakshmi[48].
TheyfocusedonthesynthesisofsphericalNTObyrapidcoolingcrystallizationandoptimizedthecrystallizationprocesstoachievefineandsphericalparticles.
Theymentionedthathigheragitationspeedandcoolingrateleadtotherelativelyfineparticles.
TheyrevealedalsothatsphericalNTOpossessedabout40%reductioninviscositywithrespecttotheconventionaljaggedandrodtypeones.
TheseauthorsalsotriedtorecrystallizeNTOfromothersolvents,suchasaliphaticalcoholsandtheiradmixtureswithwater.
Itwaspointedoutthatnoneoftheselattersolventsappearedtoadequatelyobtainbettermorphology.
ThecrystallizedNTOgranules,inthiscase,werepartlyrounded.
Recently,theTrzcinskigrouppreparedsphericalparticlesofNTOwithdiametersrangingfrom50μmto500musingawater/NMPmixture(H2O/NMP=60/40V/V,coolingrate1K·min-1)[88].
TheobtainedNTOwastestedintheformulationscontainingDNAN(2,4dinitroanisole)orTNTwithRDX.
Morerecently,thesimilarresearchgrouphaveinvestigatedtheeffectofadditionofdifferentsurfactantstothemixturewater/NMP[14].
TheauthorsdemonstratedthatthesystemNTO/H2O/NMP/Polyvinylalcohol(9-10/80/20/0.
008-0.
1)at5-15℃provideddesirablemorphologyofNTO.
Theobtainedproducthadahighbulkdensityandpresentedgoodresistancetomechanicalstimuli,suchasfriction(353N)andimpact(minimumsensitivityequalto13J).
Similartothemorphology,theparticlesizeofEMsalsoownsavitalroletoachievegoodperformanceinenergeticmaterialformulation,sinceitaffectspackingdensity,porosity,cohesion,flowability,andinteractionwithfluids/binders.
NanosizingofEMsleadstoalargeavailablesurfaceareaandconsequentlybetterheattransmission.
Thereareotheradvantagesofusingnanoenergeticmaterials(NEM)suchasimprovinginsensitivity,decreasingthermaldecompositiontemperatureandnanomeltingpointeffect.
TheseNEMmayexhibitsomewhatfasterreactioncomparedtoconventionalmicronsizedones.
Yang[90]producednanoNTObyemployingsprayfreezinginliquidmethodfrom90%pureNTO.
Theobtainednanoparticlesshowedanaveragesizeof70-90nmwithelongatedmorphology.
TheseauthorscomparedthethermaldecompositionaswellastheimpactsensitivityofbothnanoNTOandmicroNTO.
TheyconcludedthatthedecompositionofnanoNTOoccurredatalowertemperatureanditislesssensitivetoimpactstimuliwithrespecttomicroNTO.
335www.
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cn含能材料ChineseJournalofEnergeticMaterials,Vol.
27,No.
4,2019(326-347)SabrinaHanafi,DjalalTrache,SlimaneAbdous,ZineddineBensalem,AbderrahmaneMezrouaWangetal.
utilizedareversemicroemulsionofsolventevaporationtechniquetoproducenanoscaleNTO[89].
Annalkanolwasemployedasacosurfactant.
Themassratiobetweensurfactantandcosurfactantwas7∶1andthewatercontentofthesolutionwas24%.
Theexperimentwasperformedat298-303Kunderavacuumbetween-0.
6and-0.
85MPa.
Theparticlesize10-30nmwasobtained.
3.
3CrystalStructuresofNTOTwopolymorphicmodificationsarerecognizedforcrystallineNTO.
LeeandGilardireportedthedetailedmethodologiestopreparetheseforms[94].
Thefirstpolymorph,αfrom,wasproducedbyslowcoolingofahotsolutionofNTOinvarioussolvent(suchaswater)followedbyrefrigeration.
Theobtainedcrystalsappearedaslongneedles,whichshatterwhencutperpendiculartothecrystalaxis.
Thisformisconsideredasthemoststablebuttendstotwinning,andthatisthereasonwhyparametersofitscrystalstructurewereobtainedquiterecently.
TheαformbelongstothetriclinicspacegroupP1andcontainseightmoleculesinacellunit.
ExperimentalanalysisforαNTO(withdensityof1.
903g·cm-3)wascarriedoutat223.
2KbyXraydiffractionmethod.
ItwasfoundthatmoleculesintheNTOcrystalsformribbons,andareconnectedbyanethydrogenbondsandweakvanderWaalsinteractions[95].
Thesecondform,βpolymorph,waspreparedbyrecrystallizationfrommethanoloramixedethanol/dichloromethanesolvent.
ItwasmentionedthatβNTOremainedstableforsixmonthafterwhichitdecomposed.
TheunitcellofβNTOismonoclinicofthespacegroupP21/cwithfourmoleculesintheunitcell,whereeachmoleculeislinkedtootherbyfourhydrogenbonds.
AtambientconditionstheβNTO(withdensityof1.
876g·cm-3)islessdensethanαNTO[96].
ThelatticeparametersofthetwopolymorphsaredepictedinTable4[17,95,97].
Bolotinaetal.
haveinvestigatedtheeffectoftemperaturefrom100Kto298KonthecrystalstructureofthemetastableβNTOusingsinglecrystalXraydiffractiontechniques[96].
Theyreportedthatthethermalexpansionoccurredinaplane,whichisalmostperpendiculartotheplanesofallNTOmolecules.
Thecrystallatticeindicatedanharmonicityoftheatomicthermalmotion.
ThesimilarresearchgroupreportedthecrystalstructureofαNTOat298K[28].
Theyexhibitedthatαformcrystalizedasafourcomponenttriclinictwinwithfourcrystallographicindependentmoleculesinthesymmetricunit.
Hydrogenbondingcreatedtwoindependentribbonsinthecrystalstructure.
Recently,Rykounovhasstudiedtheeffectoffinitepressuresonthestructuralandthermodynamicpropertiesofthetwopolymorphicformsusingtheabinitioapproach[95].
Nosignificantstructurewasfoundunderpressureof50GPaforαNTO,whereasβNTOshowedastructuralchangeevenat17.
5GPa.
IntheworkofWuetal.
,thestructuralpropertiesofβNTOhavebeeninvestigatedunderhydrostaticpressureof0-160GPa[98].
ThebandcparametersaresensitivetovanderWaalsinteractions.
Thestructurewasthestiffestinadirectioninthewholepressurerange.
ItwasrevealedthatNTOdecomposesat150GPabybreakingofN—Obondinnitrogroup,andpolymerizedbyforminganewN—Hcovalentbondbetweenonenitrogenatomintheringandonehydrogenatomconnectedtotheringinanothermolecule.
4NTObasedCocrystalsArelativelynewconceptthatisreceivingsubTable4ThecrystallatticeparametersofαandβpolymorphsofNTOcrystalpolymorphcrystalsystemspacegroupa/b/c/α/(°)β/(°)γ/(°)density/g·cm-3αNTOtriclinic,8molecules/cellP15.
1210.
3017.
90106.
797.
7090.
201.
903βNTOmonoclinic,4molecules/cellP21/c9.
3105.
4509.
03090.
00101.
4690.
001.
876336CHINESEJOURNALOFENERGETICMATERIALS含能材料2019年第27卷第4期(326-347)5Nitro1,2,4triazole3one:AReviewofRecentAdvancesstantialinteresttotailorthephysicochemicalpropertiesofEMsiscocrystallization[99].
Althoughnowadaysestablishedwithinthepharmaceuticalfield,asameansforenhancingthesolubility,bioavailability,physicochemicalandstabilitypropertiesofactivepharmaceuticalcomponentswithoutmodificationsintheirchemicalstructure[100-101],cocrystallizationisnowatanearlyphaseofdevelopmentwithinthefieldofEMs,butitisstartingtodemonstrateconsequentpromise.
Thelatterstrategycanimprovethecomprehensivepropertieswithoutsacrificingtheenergyoutput.
Moreandmoreenergeticcocrystals(ECC)arebeingproduced,openingaroadtonewhighEMswithrequiredfeatures[99,102-104].
ECCarecrystalsencompassingtwoormoreneutralmolecularcompoundsinwhichatleastoneisenergeticinacertainratiothroughnonbondedinteractions.
Theintermolecularinteractionsandhydrogenbondsformedbetweenthecomponentsofcocrystalshelptoachieveprominentfeaturesthantheirrespectiveconstituents.
RecentresearchactivitiesonsynthesisofnewEMsbycombiningasensitiveandalesssensitivematerialtoobtainbetterpackingdensity,desiredmorphology,higherperformanceandincreasedsafetythroughtheprocessofcocrystallizationarereported[105].
Todate,severalECChavebeensynthesizedexperimentallyandcalculatedtheoretically.
Forinstance,17cocrystalsofTNTwithvariousaromaticorheterocycliccoformershavebeenpreparedbyLandenbergerandMatzgeranddemonstratedanalterationofkeycharacteristicssuchasmeltingpoint,decompositiontemperatures,anddensity[106].
SimilarauthorsproducedvariousHMXcocrystalsandrevealedatremendousdecreaseinsensitivitycomparedtopureHMX[107].
Othercocrystalshavebeenachievedsuchasthoseofbenzotrifuroxan(BTF)[108-109],2,4,6,8,10,12hexanitrohexaazaisowurtzitane(CL20)[110-112],ethylenedinitramine[113-114],diacetonediperoxide[115-116],azolederivatives[117-118],amongothers.
AzolebasedEMsareofpotentialinterestforcocrystallizationinvestigationsastheyexhibitrelativelygoodhydrogenbonddonororacceptormolecules.
NTOisanexampleofsuchazolederivatives.
Linetal.
exploredNTOascocrystalformertococrystallizewithHMX[15].
Theycalculatedthebondingenergies,thermodynamicproperties,detonationproperties,andthermalstabilityusingdensityfunctionaltheorymethods.
Furthermore,theystudiedthecrystalstructureofHMX/NTOcocrystalusingMonteCarlosimulationandfirstprinciplesmethods.
TheauthorsdemonstratedthattheintermolecularinteractionsweregovernedbyCH…OandNH…Ointeractions,aswellasO…OandN…Oweakinteractions.
Thecocrystalformationwasexothermicwithlowentropy.
ThechangeofGibbsfreeenergywasnegativeat300K,showingthatlowertemperatureallowstheformationofHMX/NTOcocrystals.
ItwasalsoexhibitedthatthedetonationvelocityofthecocrystalwaslowerthanthatofHMX,anditsthermalstabilitymeetstherequirementofhighenergydensitymaterials.
Recently,Songetal.
employedamoleculardynamicsmethodtoinvestigatethebondingenergiesassociatedwiththecocrystallizationofNTOwitheitherαandβHMX[119].
TheyexhibitedthatHMX/NTOwithlowmolecularrations(2∶1,1∶1,1∶2,1∶3),arethemoststable.
ThebindingenergiesofsuchcocrystalarelargerthanthoseofHMX/TATBandHMX/FOX7cocrystals.
ItwasshownthatCO…H—Chydrogenbondinginteractionswerethemaindrivingforceforcocrystallization.
Inaddition,theβformwaspreferredwhenmoleculesinNTOsupercellsweresubstitutedwithHMX,asinαform.
TheauthorsrevealedthattheincreaseofHMXproportionwouldincreasethedenotationvelocityandpressuretothedetrimentofthesensitivity.
Inanotherwork,Lietal.
preparedacocrystalofHMX/NTOinamolarratioof1∶1bysolvent/antisolventmethod[120].
Itwasshown,asmentionedinTable5,thatthemorphologyofthecocrystalisdifferentfromitsrespectivecoformers.
TheproducedcocrystalspossessedlowsensitivitytoimpactandfrictioncomparedtoHMX.
Recently,Wuetal.
reportedthecocrystallizationofNTOwithanitrogenrichcompound5,6,7,8tetrahydrotetrazolo[1,5b][1,2,4]triazine337www.
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4,2019(326-347)SabrinaHanafi,DjalalTrache,SlimaneAbdous,ZineddineBensalem,AbderrahmaneMezroua(TZTN)[121].
ThislatterwaschosenasitisaweakbaseanditcouldpotentiallytheacidityofNTO.
StrongintermolecularNH…NandNH…OhydrogenbondinginteractionsaretheprimarydrivingforceinthepreparationoftheenergeticenergeticNTO/TZTNcocrystal.
AsmentionedinTable5,thecocrystalmeltsat156.
6℃andincreasescomparingwithTZTN,whatisattributedtothehydrogenbondinginthestructure.
Itsexothermicpeakshiftstolowertemperaturewithtwocontinuoussharpexothermicprocessat177.
5℃and197.
9℃,respectively,whatindicatessomechangesinthecrystalphase.
ThedetonationvelocityanddetonationpressureofNTO/TZTNcocrystalare7458km·s-1and23.
5GPa,respectively,alittlelowerthanthoseofNTO.
Thecocrystalpresentsacrystallographicdensityof1.
665g·cm-3,whichishigherthanTZTN,butlowerthanthatofNTO.
Inanotherresearchwork,ZhaoandYang[16]haveusedthedensityfunctionaltheory(DFT)tostudytheeffectofhydrostaticpressureof0-80GPaonthegeometricalandelectronicstructuresoftheenergeticNTO/TZTNcocrystal.
Ithasbeenrevealedthattheincreasingofpressurecontributedtotheincreaseofinteractionforcegradually.
Thestabilityofsuchcocrystalhasbeenimprovedbytheformationoffiveandeightmemberedringsduringexternalcompression.
At4GPa,thetransformationfromHbondO(1)…H(3)tocovalentbondcontributedtotheformationoftheeightmemberedring.
Inaddition,anewcovalentbondisgeneratedbetweenN(2)andH(4)atoms.
After8GPa,thecovalentbondbetweenO(1)andH(3)atoms,N(4)andH(2)atomsintensifiedthethermalstabilityofthecocrystalsystemsignificantly.
Inadditiontothecurrentmethodwidelyemployedfortheformationofcocrystalssuchassolutioncocrystallization,mechanochemicalmethodsandultrasounds,arelativelynewmethod,whichistheresonantacousticmixing,hasbeenrecentlyutilized[122].
Thislatterisrevealedtobesafe,simple,scalableandissupportedbyacommercialplatformofRAMmixersavailablethroughtheResodynCorporation.
ThisapproachwasefficientlyappliedtoprepareNTO/4,4biperidine(BP)cocrystal,whereadropofwaterisrequiredotherwiseasaltisformed[123].
SpontaneouscrystallizationfromsolutionatroomtemperaturewasreportedbyLloyd,whichproducesacocrystalofNTO/BPin1∶1molarratios[124].
ItwasexhibitedthatthecrystalstructuredensityanddetonationvelocityofthecocrystalarelowerthanthoseofNTO.
Thecocrystaldisplayedasharpexothermicpeakat217℃.
Asharpendothermicpeakwasalsoobserved,whichisattributedtothemeltingofthedecompositionproducts.
InthepaperofHang,anovelenergeticcocrystalconsistedofCL20/NTOwithdifferentmolarratioswasestablishedthroughsubstitutionmethod[97].
Thegeometricstructuresandthepropertieswereoptimizedbasedonthemoleculardynamicsmethod.
Theauthorsrevealedthatthecocrystalformedwiththemolarratioin2∶1,1∶1or1∶2showedhigherstability,lowermechanicalsensitivityandbettersafetyincomparisontoCL20.
Thedetonationpropertiesandperformancesofthecocrystalsaredeclined,buttheystilldisplayedexcellentenergydensity.
5NTODerivativesTheacidicnatureofNTOallowstheformationTable5PropertiesofNTO,TZTNandtheircocrystalsampledensity/g·cm-3heatofformation/kJ·mol-1detonationvelocity/m·s-1detonationpressure/GPaexothermicpick/℃NTO1.
93-6.
3844633279TZTN1.
577499.
2727221.
6197.
1HMX--910037.
76281NTO/TZTN1.
665481.
4745823.
5177.
5,197.
9NTO/HMX1.
92-873035.
14282.
5338CHINESEJOURNALOFENERGETICMATERIALS含能材料2019年第27卷第4期(326-347)5Nitro1,2,4triazole3one:AReviewofRecentAdvancesofalargenumberofsaltswithmetals,aliphaticandaromaticsamines(Fig.
3)[69].
ThepreparationofNTOsaltsinvolvessimpleacidbasereaction.
TherearemanyreportsintheliteratureabouttheionizationofNTO.
ThetwohydrogensitesinNTOmoleculeatpositionsN(2)andN(4)(Table2)canbeionizedtoformdifferentderivativesofNTObychangingthenatureofthesolution.
Ithasbeenshownthatthehydrogenatposition2ismoreacidicthanthatatposition4[19,72].
Severalworkshavebeenperformeduntilnow,whereahugenumberofNTOderivativeshavebeenreported[17,71-73,79,125-126].
ThepioneeringworksonNTOderivativeshavebeencarriedoutbyChipenetal.
andthencompletedbyaresearchgroupfromUSdepartmentofthearmyandtheUSdepartmentofenergy[29].
Commonly,thepreparationofaminesaltsofNTOwasachievedbymixingthehotaqueoussolutionofNTOwithasolutionofcorrespondingbase.
Leeetal.
havesynthetizedsevenaminosaltsofNTOhydrazine(HNTO),ammonia(ANTO),ethylenediamine(ENTO),guanidine(GuNTO),aminoguanidine(AGuNTO),diaminoguanidine(DAGuNTO),triaminoguanidine(TAGuNTO)[70,127].
Furthermore,ithasbeendemonstratedthatANTOandENTOappearedaspotentialcandidatestobeusedasexplosives[128].
Recently,Singhhasdeeplyreviewedthepreparation,characterization,thermolysisandapplicationofmorethan50NTOsalts[19].
Varioussaltsareconsideredinsensitiveandhighlyenergeticinnature,inadditiontootherprominentfeaturesandpotentialapplications.
Saltswithhighnitrogencationssuchashydrazineandtriaminoguanidine,aresuggestedasconstituentsofgunpropellants[127].
Saltswithmetalshavebeenassessedasballisticmodifiersandcatalystsforsolidrocketpropellants[129-130].
OtherinterestingaminobasedsaltsofNTO,thathavealsobeenwellcharacterized,aredimethylamine(DMNTO),3,3dinitroazetidine(DNAZNTO),and2azidoethylamine(AANTO)[125-126,131-132].
AnotherderivativeofNTOhasbeenobtainedbynitrationusingfumingnitricacidandaceticanhydride,whichisthe2,4dihydro2,4,5trinitro3H1,2,4triazol3one(DTNTO).
Inthiscase,theNHgroupofNTOissubstitutedbyNO2.
IthasbeenfoundthatthisnewderivativeismoresensitivethanNTO,buthaspositiveoxygenbalancewhichisanattractivefeaturefromthepointofviewofitsapplicationasanecofriendlyoxidizerinpropellantformulations[133].
Duringthepastfewyears,newNTOsaltshavebeeninvestigatedaswell(Fig.
3).
Energeticsaltscontainingeitherenergeticsubstitutedtriazoliumortetrazoliumcationsand3nitro1,2,4triazolate5oneanionshavebeensynthesizedandcharacterizedbyShreeve′sgroup[71].
3Amino1,2,4triazolium3nitro1,2,4triazolate5one,1amino1,2,4triazolium3nitro1,2,4triazolate5one,4amino1,2,4triazolium3nitro1,2,4triazolate5one,methyl5aminotetrazolium,and3Nitro1,2,4triazolate5oneareformedbyusingNTOassubstrate.
TheseenergeticsaltsexhibitedgoodpropertiesinFig.
3AcompilationofNTOderivativesreportedinliterature.
SCZNTO:semicarbazidiumNTO;NCGuNTO:NcarbamoylguanidiumNTO;TTABTZNTO:4,40,5,50tetraamino3,30bi1,2,4triazoliumNTO;TATATNTO:3,6,7triamino7H[1,2,4]triazolo[5,1c][1,2,4]triazol2iumNTO;DATTZNTO:1,5diamino1,2,4tetrazoliumNTO;TATZNTO:3,4,5triamino1,2,4triazoliumNTO;XATNTZO:XAmino1,2,4triazolium3Nitro1,2,4triazolate5one;Methyl5ATTNTZO:Methyl5Amino1,2,4tetrazolium3Nitro1,2,4triazolate5one;NPTNPTO:5nitro2picryl(2,4,6trinitrophenyl)2,4dihydro3H1,2,4triazol3one;NDPDTNPTO:5nitro2,4dipicryl(di2,4,6trinitrophenyl)2,4dihydro3H1,2,4triazol3one[69]339www.
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4,2019(326-347)SabrinaHanafi,DjalalTrache,SlimaneAbdous,ZineddineBensalem,AbderrahmaneMezrouacludingrelativelyhighdensities,highpositiveheatofformationandmoderatedetonationproperties,becausebothcationandanionhavethehighestnitrogencontentwhichinturnenhancedthedensityandthedetonationcharacteristics.
Themelamine3nitro1,2,4triazol5onesalt(MNTO)wassynthesizedandcharacterizedbyNajafietal.
[134].
IthasbeenfoundthatitpossessesacriticaltemperatureofthermalexplosionhigherthanthatofNTO.
In2011,theyfurtherperformedastudyonthermalbehaviorofMNTO.
ItrevealsthatMNTOcouldbeusedinvariousapplicationswhichrequireshighinsensitivity,thermalstability,andnitrogencontent[135].
Wallaceetal.
havereportedthesynthesisofnewazoandazoxycompoundsviaelectrochemicalreductionofnitrotriazolesinaqueousmediausingnitrotriazolone(NTO)andnitrotriazole(NTr)asrepresentativesubstrates.
ReductionofNTOproducesmainlysolidazoxytriazolone(AZTO),withazotriazolone(azoTO)andaminotriazolone(ATO)asminorproducts[136].
Thesecompounds,whichexhibitedgreaterthermalstabilitythanNTO,havebeenshowntobeofinterestasnewgreenhighnitrogencompoundsforuseasinsensitivehighexplosives[137].
Beforethat,Croninetal.
hadreportedontheformationofAZTObyelectrochemicalreductionofnitrotriazolone(NTO)inacidicaqueoussolution[138].
Inanotherwork,Renetal.
havesynthesizedanioniccompound(3ATz)+(NTO)-bythereactionof3amino1,2,4triazole(3ATz)withNTOinethanol[125].
Theobtainedproducthasagoodoxygenbalance,ahigherchemicalstabilityandconsistencytobeemployedinpropellantandexplosiveformulations.
MonopicrylanddipicrylderivativesofNTO(5nitro2picryl(2,4,6trinitrophenyl)2,4dihydro3H1,2,4triazol3oneand5nitro2,4dipicryl(di2,4,6trinitrophenyl)2,4dihydro3H1,2,4triazol3one)havebeensynthesizedbythetreatmentofNTOwithpicrylfluoridein1methyl2pyrrolidinone(NMP)atroomtemperature[139].
Inref.
[140],authorshaveinvestigatedthetheoreticalinvestigationoftwoclassesofNTOpicrylderivativesincluding12constitutionalisomers.
Ithasbeenrevealedthatallconstitutionalisomersareendothermicinnature,andhavehigherdetonationperformancethanNTO.
Becauseofthelackofdetonationdataofseveralaminesalts(HNTO,ANTO,GuNTO,AGuNTO,DAGuNTO,TAGuNTO),Zhang[73]haverecentlysynthesizedandcharacterizedtheselatterinadditiontosixnewsalts,whichareNcarbamoylguanidinium,semicarbazidium,1,5diamino1,2,4tetrazolium,3,4,5triamino1,2,4triazolium,3,6,7triamino7H[1,2,4]triazolo[5,1c][1,2,4]triazol2ium,and4,40,5,50tetraamino3,30bi1,2,4triazolium.
ThereportedresultsshowedthatalltheenergeticsaltsexceptTAGuNTOexhibitedexcellentthermalstabilitieswithdecompositiontemperaturesupto200℃.
Moreover,theyhaveestablishedthatHNTOhadexcellentpropertiessuchasthedetonationvelocityof9575m·s-1,whichiscomparabletothatofCL20,andthefrictionsensitivityof360Nwithadecompositiontemperatureof203℃.
ItisalsofoundcompatiblewithmostofpotentialEMs,whatmakingHNTOahighlypromisingenergeticmaterialforcompositeexplosivesandpropellants.
Morerecently,SzalahavesynthesizedtwonewsaltsofNTO,whicharethe2methylimidazole(2MeIm·NTO)andImidazole(Im·NTO)bydissolvingNTOinDMSOandheatingthesolutionto40℃forimidazoleand50℃for2methylimidazole[79].
Theyhavereportedthatbothsaltsarestableupto200℃andpresentlowersensitivityformechanicalstimulithanTNT.
DetonationvelocityandpressurearesimilartothoseofTNTandmuchlowerthanthatestimatedforNTO.
Furthermore,2MeIm·NTOhasmethylgroupwiththreeprotonswhicharrangesthemoleculesincrystalbetterthantheparentimidazole.
NewlydescribedNTOimidazolesaltsmayhaveloweraciditythanappropriatecocrystals.
6NTObasedFormulationsResearchersareexploringdifferentapproachestofulfilltheincreasingrequirementsofEMsthatim340CHINESEJOURNALOFENERGETICMATERIALS含能材料2019年第27卷第4期(326-347)5Nitro1,2,4triazole3one:AReviewofRecentAdvancesparthighperformance,enhancedmechanicalproperties,prolongedlifetime,lessvulnerability,andnegligibleenvironmentaleffectsduringmanufacturing,processing,handling,transport,storage,usageanddisposal[2,8].
Effortsarebeingmadeallovertheworldtodevelopmodern/furisticEMsbasedsystemsmeetingthepreviouslymentionedchallenges.
Safetyaspectsofhighenergymaterialsareoneofthekeyfactorsofresearchactivitiesinthisfield.
Thus,compoundswithhighenergycombinedwithlesssensitivityaresoughtfor.
Luckily,theNTOissuchacomponentwithperformancescomparabletothatofRDXandinsensitivitycomparabletothatofTATB.
Itsthermalstabilityisalsohighanddecomposesexothermicallyataround272℃[18].
NTOiscurrentlywidelyemployedinseveralformulationssuchasexplosivefillings:meltcast,castcuredplasticbondedexplosives(PBX)andpressedPBX,gasgeneratorsforautomobileinflatorairbagssystems,etc.
[2,18-19,21,76,79,82,110,141].
ThesaltderivativesofNTOarealsofoundinsensitiveandaretestedforseveralexplosiveformulations,ingredientofgunpropellants,modifierandcatalystforrocketpropellant[19,73,79].
Nevertheless,despitethenumberofpreparationmethodsandcharacteristicsofseveralNTOsaltsexistingintheopenliterature,thereportsontheapplicationsoftheseEMsareeithermeagerlyaccessibleorhiddeninclassifiedreports.
NTObasedexplosiveformulationshavebeenconsideredforavarietyofapplications.
SmithandCliffhavereviewedtheformulationscontainingNTOdevelopedbyUK,SwissandNorwegian,GermanandCanadianandthatperformedatSNPE(French)[21,142].
Mukundanetal.
haveprovedthatNTObasedpressesandcastcuredexplosiveformulationsexhibitedsuperiormechanicalandthermalproperties,andmoreimportantlytheyareinsensitive[41].
NTOhasbeenusedinPBXbasedonsiliconrubberandithasbeenrevealedthatitsactivationenergyandonsettemperaturearerelativelyhigh(267.
0℃),whichrevealsbetterthermalstabilitythanotherPBXs[143].
TheSociétéNationaledesPoudresetExplosifs(SNPE),France,hasreportedB2214basedonaninertbinder,HMXandNTO(12%and72%respectively)formissilewarhead.
ItwasdemonstratedthatthisformulationislesssensitiveandmoreefficientthatCompositionB(Hexol60/40)[2].
Baudinetal.
havestudiedtheshocktodetonationtransition(SDT)anditsmodelingforcastcuredPBXcontainingHMX,RDXandNTOandtheyhavecomparedittopressedone[144].
TheyhaverevealedthatacastcuredPBXisnotporousincontrarytoapressedPBXandthehotspotsaremainlylocatedatthegrainbinderinterfaceincaseofcastcuredPBX,leadingtoadifferentburningbehaviorduringshocktodetonationtransition.
Moreover,ithasbeenrevealedthatcastcuredPBXcontainingHMX,RDXandNTOdoesnotexhibitanydesensitizationwhensubmittedtodoubleshockwaves.
Morerecently,Zeman′sgrouphasreportedanewPBXbasedoncis1,3,4,6tetranitrooctahydroimidazo[4,5d]imidazole(BCHMX)andNTO,bonedbypolydimethylsiloxanebinder(44/44/12massfraction).
TheseresearchersrevealedthatthisinsensitiveformulationappearedasagoodcandidateforLOVAexplosiveswithhighdetonationparameters,goodthermalstabilityandbettermechanicalproperties[76].
Inanotherwork,Tappanetal.
havepreparedaformulationsbasedon3,3′Diamino4,4′Azoxyfurazan(DAAF)andNTOtoevaluatetheirdetonationperformance.
Theobtainedproductpresentedbetterpropertiessuchasasmallerfailurediameter,lowershocksensitivity,higherdensityanddetonationpressure[141].
Belaadaetal.
havepreparedameltcastcompositionbasedonNTOandFOX7[145].
Theobtainedcompositionexhibitedgoodrheologicalfeaturesandthecastingprocessmaybeperformedatatemperaturerangeof85-90℃.
Thesensitivitiestoimpact,shockwave,jetattackandfastheatingdeterminedwerelowerthanthoseofTNT.
Itisindicatedthatsuchcompositionispromisingasamainchargefillingdestinedforinsensitivemunitions.
Intherecentyears,TNThasbeensubstitutedbyNTOinIMX101formulation,whichcontained43.
5%2,4dinitroanisole(DNAN),19.
7%NTO,341www.
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4,2019(326-347)SabrinaHanafi,DjalalTrache,SlimaneAbdous,ZineddineBensalem,AbderrahmaneMezrouaand36.
8%nitroguanidine,andhasbeenqualifiedforusebyU.
S.
NationalServiceAuthority[146].
OtherformulationssuchasIMX104(OSX7,DNAN/NTO/RDX)andPAX48(OSX8,DNAN/NTO/HMX)havebeenreported,whereNTOwasrevealedasalternativetoreplaceRDXinlargecalibermunitions,andconsideredsaferfortroopsduetotheirlowerlikelihoodforunintendedexplosions[67,147].
AnumberofNTOsaltswereconsideredforexplosiveformulations[19].
Recentstudiesconcludedthatsomesaltsarelikelytoshowinterestingpropertiessuchasdecompositiontemperature,densities,detonationpressureanddetonationvelocities[73,79].
Furthermore,inadditiontothelowenvironmentalimpact,theyareconsideredmorecompatiblewithmostofthecommonlyemployedorpotentialenergeticcompoundssuchasTNT,CL20,TNAZ,TKX50,Al,ammoniumperchlorate,etc.
Therefore,suchsaltsarepromisingcandidatesforuseinfuturecompositeexplosivesandpropellants.
Ontheotherhand,variousNTOsaltshavebeentestedinpropellantcompositionsasballisticmodifiers.
Singhetal.
haveassessedtheeffectofNTOascatalystsforHTPB/APpropellants.
Verypromisingresultshavebeenachieved[130,148].
SomeauthorshavealsodemonstratedthepotentialofNTOtosubstituteAP(heatofformationof-296.
0kJ·mol-1)incompositesolidpropellantssinceNTOpresentshigherheatofformation(-276.
56J·mol-1)anditscombustionisenvironmentallyfriendly[19].
However,itisworthytonotethatmuchworkisneededtobedoneontheeffectsofthesesaltsontheprocessingparameters,stabilityandaging,beforeitsrealusage.
Inaddition,varioustheoreticalcalculationsshouldbeexperimentallyvalidatedtochecktheeffectofsuchcomponentsonthetotalenergyaswellasspecificimpulse.
Theextensionoftheseinvestigationstoothercompositesolidpropellants,compositemodifieddoublebasepropellants,andexplosivesmaybeconsidered.
Furthermore,newformulationsbasedonNTOcocrystalswillcertainlybringnewinsightinthefield.
7ConclusionsThecurrentlydevelopedsubstitutesoftheconventionalEMssuchasNTOneedoptimizationtofullysatisfytherequirementsofidealhighEMs.
Thus,highperformingenergeticingredientswithbettersafetycharacteristicsareatoppriorityinternationallyandneedfurtherendeavortoreachtheiraim.
Inthepresentreport,comparativestrategiestoproduceNTOaswellasthemethodologiestomodifyitsparticlesmorphologyandsizehavebeeninvestigated.
IthasbeenfoundthatsomerecentsynthesismethodsareefficientandthepreparedNTOhadbetteryieldsthantheconventionalmethods.
TheuseofsphericalNTOisvitalinrealizinghighenergyformulationswithhighphysicochemicalpropertiesandbetterperformance.
TheexistingliteratureonnewerformofNTOincludingderivativesandcocrystalshasbeencollected.
VariousrecentNTOderivativespresenttremendousadvantagessuchashighperformance,betterstability,insensitivity,compatibilityandhighdensity,andaresufficientlyassessedindifferentpropellantandexplosiveformulations.
FurtherimprovementonthepropertiesofNTOhasbeenreachedbythepreparationofcocrystals,andsuchapproachprovidespromisingwaytotunetheNTOphysicochemicalfeaturesandperformance.
Forthenearfuture,energeticformulationscontainingNTO,itsderivativesorcocrystalsareexpectedtoadvancethestateoftheartofEMsfield.
NewNTOderivativesandcocrystalsbasedformulationswithimprovedsafetyandperformancefeatures,comparedwiththecorrespondingconventionalformulations,areveryinterestingandmayplayaprominentroleinthefutureofhighEMs,propellantsandweaponry.
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(责编:张琪)中国兵工学会火工烟火专业委员会第二十届学术年会征文通知为促进我国火工烟火行业的创新发展,紧跟世界火工烟火前沿技术和新兴技术发展趋势,加强科技人员间的学术交流与信息沟通,提高研究水平,经研究,定于2019年四季度召开中国兵工学会火工烟火专业委员会第二十届学术年会.
现将会议征文有关事项通知如下:一、征文内容1.
国内外火工品及相关药剂、烟火剂的基础理论和关键技术;2.
国内外火工品、爆破器材、烟火器材的发展动态、现状及趋势;3.
国内外火工品及相关药剂设计的新理论、新方法、新技术;4.
国内外火工品及相关药剂制造的新工艺、新材料、新设备;5.
火工品及相关药剂测试、分析、计量的新理论、新技术及新仪器;6.
火工品安全性、可靠性评估新理论、新方法、新技术;7.
火工烟火行业标准化的研究、标准探讨、经验交流、发展趋势;8.
信息技术在火工品及相关药剂管理、设计、仿真、试验、工艺、评估、数据库建设中的应用;9.
火工品机械化、自动化、智能化先进制造技术;10.
其它具有一定创新价值的技术、产品或具有较大意义的军民融合技术.
二、征文要求1.
研究成果具有较高的理论水平或应用价值;2.
论文未在国内外正式出版物上发表过,文责自负;3.
提交的论文为非密,须通过所在单位的保密审查;4.
论文格式按照科技论文标准规范,要求用Word2007以上版本软件排版;5.
论文格式及排序:题目,作者名,单位名,所在地,邮编,中文摘要,中文关键词,正文,参考文献,作者简介.
三、征文时间征文截至时间为2019年6月20日.
优秀论文将推荐到《火工品》期刊发表.
学术年会召开的具体时间和地点另行通知.
四、联系方式投稿邮箱:hgxh2005@163.
com联系地址:西安市99号信箱兵工学会邮编:710061联系人:王建华029-8533347013152441200.
中国兵工学会火工烟火专业委员会2019年3月18日读者·作者·编者347