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Hydrazine
FromWikipedia,thefreeencyclopedia

Hydrazine(systematicallynamed
diazaneor
tetrahydridodinitrogen(NN))is
aninorganiccompoundwiththe

Hydrazine

chemicalformulaH2NNH2(also
writtenN2H4).Itisacolourless
flammableliquidwithanammonia
likeodor.Hydrazineishighlytoxic
anddangerouslyunstableunless
handledinsolution.Asof2000,
approximately120,000tonsof
hydrazinehydrate(corresponding
toa64%solutionofhydrazinein
waterbyweight)were
manufacturedworldwideper
year.[8]Hydrazineismainlyusedas
afoamingagentinpreparing
polymerfoams,butsignificant
applicationsalsoincludeitsusesas
aprecursortopolymerization
catalystsandpharmaceuticals.
Additionally,hydrazineisusedin
variousrocketfuelsandtoprepare
thegasprecursorsusedinairbags.
Hydrazineisusedwithinboth
nuclearandconventionalelectrical
powerplantsteamcyclesasan
oxygenscavengertocontrol
concentrationsofdissolvedoxygen
inanefforttoreducecorrosion.

Hydrazinehydrate
Names
SystematicIUPACname
Hydrazine[2]

Contents
1Molecularstructureand
properties
2Synthesisandproduction
2.1Oxidationby
chloroaminefrom
hypochloriteon
ammonia
2.2Oxidationofurea
byhypochlorite

https://en.wikipedia.org/wiki/Hydrazine

Othernames
Diamine[1]
Diazane[2]
Identifiers
CASRegistry
Number

302012

3DMet

B00770

Beilstein
Reference

878137

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byhypochlorite
2.3Oxidationby
chloroaminefrom
hypochloriteon
ammoniainpresence
ofacetone
2.4Oxidationby
oxaziridinefrom
peroxideon
ammonia
3Applications
3.1Precursorto
pesticidesand
pharmaceuticals
4Hydrazineinbiology
5Organicchemistry
5.1Hydrazone
formation
5.2WolffKishner
reduction
5.3Heterocyclic
chemistry
5.4Sulfonation
5.5Deprotectionof
phthalimides
5.6Reducingagent
5.7Hydrazinium
salts
6Otherindustrialuses
6.1Rocketfuel
6.2Fuelcells
6.3Gunpropellant
7Hazards
8History
9Seealso
10References
11Externallinks

Molecularstructure
andproperties
Hydrazineformsamonohydrate
thatisdenser(1.032g/cm3)than
theanhydrousmaterial.
Hydrazinecanariseviacouplinga
pairofammoniamoleculesby
removalofonehydrogenper
https://en.wikipedia.org/wiki/Hydrazine

ChEBI

CHEBI:15571

ChEMBL

ChEMBL1237174

ChemSpider

8960

ECnumber

2061149

GmelinReference 190
InChI

Jmol3Dimages

Image(http://chemapps.stolaf.edu/jmol/jmol.php?
model=NN)

KEGG

C05361

MeSH

Hydrazine

PubChem

9321

RTECSnumber

MU7175000

SMILES

UNII

27RFH0GB4R

UNnumber

2029
Properties

Chemicalformula N H
2 4
Molarmass

32.0452gmol1

Appearance

Colourless,fuming,oilyliquid[3]

Odor

ammonialike[3]

Density

1.021gcm3

Meltingpoint

2C35F275K

Boilingpoint

114C237F387K

Solubilityinwater miscible[3]
logP

0.67

Vaporpressure

1kP(at30.7C)

Acidity(pKa)

8.10[4]

Basicity(pKb)

5.90

Refractiveindex
(nD)

1.46044(at22C)

Viscosity

0.876cP
Structure

Molecularshape

TriangularpyramidalatN

Dipolemoment

1.85D[5]
Thermochemistry

Stdmolar

121.52JK1mol1
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molecule.EachH2NNsubunitis

entropy(So298)

pyramidalinshape.TheNNsingle
bonddistanceis1.45(145pm),
andthemoleculeadoptsagauche
conformation.[9]Therotational
barrieristwicethatofethane.
Thesestructuralproperties
resemblethoseofgaseous
hydrogenperoxide,whichadoptsa
"skewed"anticlinalconformation,
andalsoexperiencesastrong
rotationalbarrier.

Stdenthalpyof
formation
(fHo298)

Hydrazinehasbasic(alkali)
chemicalpropertiescomparableto
thoseofammonia:

GHShazard
statements

H226,H301,H311,H314,H317,H331,H350,H410

GHS
precautionary
statements

P201,P261,P273,P280,P301+310,P305+351+338

EUIndex

007008003

N2H4+H2O[N2H5]++
OH
withthevalues:[10]

50.63kJmol1

Hazards
Safetydatasheet
GHSpictograms

ICSC0281
(http://www.inchem.org/documents/icsc/icsc/eics0281.htm)

GHSsignalword DANGER

EUclassification

T+

N [6]

Rphrases

R45,R10,R23/24/25,R34,R43,R50/53

Kb=1.3x106

Sphrases

S53,S45,S60,S61

pKa=8.1

NFPA704

(forammoniaKb=1.78x105)
Hydrazineisdifficultto
diprotonate:[11]
[N2H5]++H2O[N2H6]2+
+OHKb=8.4x1016
Theheatofcombustionof
hydrazineinoxygen(air)is1.941x
107J/kg(9345BTU/lb).[12]

Synthesisand
production
Differentrouteshavebeen
developedovertheyears:[8]thekey
stepisthecreationofthenitrogen
nitrogensinglebond.IntheOlin
Raschigprocess,chlorinebased
https://en.wikipedia.org/wiki/Hydrazine

Flashpoint

52C(126F325K)

Autoignition
temperature

24to270C(75to518F297to543K)

Explosivelimits

1.899.99%

Lethaldoseorconcentration(LD,LC):
LD50(Median 5960mg/kg(oralinrats,mice)[7]
dose)
UShealthexposurelimits(NIOSH):
PEL
(Permissible)

TWA1ppm(1.3mg/m3)[skin][3]

REL
CaC0.03ppm(0.04mg/m3)[2hour][3]
(Recommended)
IDLH
(Immediate
danger

Ca[50ppm][3]

Relatedcompounds
Otheranions

tetrafluorohydrazine
hydrogenperoxide
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oxidantsoxidizesammoniawithout
thepresenceofketone.Inthe
peroxideprocess,hydrogen
peroxideoxidizesammoniainthe
presenceofketone.Insteadof
carbonnitrogendoublebondin
imine,ureaprovidesaminegroups
bondedtocarbonylforoxidation.

Oxidationbychloroamine
fromhypochloriteon
ammonia

diphosphane
diphosphorustetraiodide
Othercations

organichydrazines

RelatedBinary
azanes

Ammonia
triazane

Related
compounds

diazene
triazene
tetrazene
diphosphene

Exceptwhereotherwisenoted,dataaregivenformaterialsintheirstandard
state(at25C[77F],100kPa).

HydrazineisproducedintheOlin
verify(whatis: / ?)
Raschigprocessfromsodium
Infoboxreferences
hypochlorite(theactiveingredient
inmanybleaches)andammonia,a
processannouncedin1907.Thismethodreliesonthereactionofchloraminewithammoniatocreatethe
nitrogennitrogensinglebondaswellasahydrogenchloridebyproduct:[13]
NH2Cl+NH3H2NNH2+HCl

Oxidationofureabyhypochlorite
RelatedtotheRaschingprocess,ureacanbeoxidizedinsteadofammonia.Againsodiumhypochlorite
servesastheoxidant.Thenetreactionisshown:[14]
(H2N)2C=O+NaOCl+2NaOHN2H4+H2O+NaCl+Na2CO3
TheprocessgeneratessignificantbyproductsandismainlypracticedinAsia.[8]

Oxidationbychloroaminefromhypochloriteonammoniainpresenceofacetone
TheBayerKetazineProcessisthepredecessortotheperoxideprocess.Itemployssodiumhypochloriteas
oxidantinsteadofhydrogenperoxide.Likeallhypochloritebasedroutes,thismethodsuffersfromthefact
thatitproducesanequivalentofsaltforeachequivalentofhydrazine.[8]

Oxidationbyoxaziridinefromperoxideonammonia
Hydrazinecanbesynthesizedfromammoniaandhydrogenperoxideintheperoxideprocess(sometimes
calledPechineyUgineKuhlmannprocess,theAtofinaPCUKcycle,orketazineprocess).[8]Thenet
reactionfollows:[15]
2NH3+H2O2H2NNH2+2H2O

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Inthisroute,hydrazineisproducedinseveralstepsfromammonia,hydrogenperoxide,andaketonesuch
asacetoneormethylethylketone.Theketoneandammoniafirstcondensetogivetheimine,whichis
oxidisedbyhydrogenperoxidetotheoxaziridine,athreememberedringcontainingcarbon,oxygen,and
nitrogen.Next,theoxaziridinegivesthehydrazonebytreatmentwithammonia,aprocesscreatingthe
nitrogennitrogensinglebond.Thishydrazonecondenseswithonemoreequivalentofketonetheresulting
azineishydrolyzedtogivehydrazineandregeneratetheketone.UnliketheOlinRaschigProcess,this
approachdoesnotproduceasaltasabyproduct.[16]

Applications
Themajorityuseofhydrazineisasaprecursortoblowingagents.Specificcompoundsinclude
azodicarbonamideandazobisisobutyronitrile,whichyield100200mLofgaspergramofprecursor.Ina
relatedapplication,sodiumazide,thegasformingagentinairbags,isproducedfromhydrazinebyreaction
withsodiumnitrite.[8]
Hydrazineisalsousedasapropellantonboardspacevehicles,andtobothreducetheconcentrationof
dissolvedoxygeninandcontrolpHofwaterusedinlargeindustrialboilers.TheF16fighterjetuses
hydrazinetofueltheaircraft'semergencypowerunit.

Precursortopesticidesandpharmaceuticals
Hydrazineisausefulbuildingblockinorganicsynthesisofpharmaceuticalsandpesticides.Oneexampleis
3amino1,2,4triazoleandanotherismaleichydrazide.Theantituberculardrugisoniazidispreparedfrom
hydrazine.

Hydrazineinbiology
Hydrazineistheintermediateintheanaerobicoxidationofammonia(anammox)process.[17]Itisproduced
bysomeyeastsandtheopenoceanbacteriumanammox(Brocadiaanammoxidans).[18]Thefalsemorel
producesthepoisongyromitrinwhichisanorganicderivativeofhydrazinethatisconvertedto
monomethylhydrazinebymetabolicprocesses.Eventhemostpopularedible"button"mushroomAgaricus
bisporusproducesorganichydrazinederivatives,includingagaritine,ahydrazinederivativeofanamino
acid,andgyromitrin.[19][20]

Organicchemistry
Hydrazinesarepartofmanyorganicsyntheses,oftenthoseofpracticalsignificanceinpharmaceuticals,
suchastheantituberculosismedicationisoniazidandtheantifungalfluconazole,aswellasintextiledyes
andinphotography.[8]

Hydrazoneformation
Illustrativeofthecondensationofhydrazinewithasimplecarbonylisitsreactionwithpropanonetogive
thediisopropylidenehydrazine(acetoneazine).Thelatterreactsfurtherwithhydrazinetoyieldthe
hydrazone:[21]
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2(CH3)2CO+N2H42H2O+[(CH3)2C=N]2
[(CH3)2C=N]2+N2H42(CH3)2C=NNH2
ThepropanoneazineisanintermediateintheAtofinaPCUKprocess.Directalkylationofhydrazineswith
alkylhalidesinthepresenceofbaseyieldsalkylsubstitutedhydrazines,butthereactionistypically
inefficientduetopoorcontrolonlevelofsubstitution(sameasinordinaryamines).Thereductionof
hydrazonestohydrazinespresentacleanwaytoproduce1,1dialkylatedhydrazines.
Inarelatedreaction,2cyanopyridinesreactwithhydrazinetoformamidehydrazides,whichcanbe
convertedusing1,2diketonesintotriazines.

WolffKishnerreduction
HydrazineisusedintheWolffKishnerreduction,areactionthattransformsthecarbonylgroupofaketone
intoamethylenebridge(oranaldehydeintoamethylgroup)viaahydrazoneintermediate.Theproduction
ofthehighlystabledinitrogenfromthehydrazinederivativehelpstodrivethereaction.

Heterocyclicchemistry
Beingbifunctional,withtwoamines,hydrazineisakeybuildingblockforthepreparationofmany
heterocycliccompoundsviacondensationwitharangeofdifunctionalelectrophiles.With2,4
pentanedione,itcondensestogivethe3,5dimethylpyrazole.[22]IntheEinhornBrunnerreactionhydrazines
reactwithimidestogivetriazoles.

Sulfonation
Beingagoodnucleophile,N2H4canattacksulfonylhalidesandacylhalides.[23]Thetosylhydrazinealso
formshydrazonesupontreatmentwithcarbonyls.

Deprotectionofphthalimides
HydrazineisusedtocleaveNalkylatedphthalimidederivatives.Thisscissionreactionallowsphthalimide
aniontobeusedasamineprecursorintheGabrielsynthesis.[24]

Reducingagent
Hydrazineisaconvenientreductantbecausethebyproductsaretypicallynitrogengasandwater.Thus,it
isusedasanantioxidant,anoxygenscavenger,andacorrosioninhibitorinwaterboilersandheating
systems.Itisalsousedtoreducemetalsaltsandoxidestothepuremetalsinelectrolessnickelplatingand
plutoniumextractionfromnuclearreactorwaste.Somecolourphotographicprocessesalsouseaweak
solutionofhydrazineasastabilizingwash,asitscavengesdyecouplerandunreactedsilverhalides.
Hydrazineisthemostcommonandeffectivereducingagentusedtoconvertgrapheneoxide(GO)to
reducedgrapheneoxide(rGO)viahydrothermaltreatment.[25]

Hydraziniumsalts
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Hydrazineisconvertedtosolidsaltsbytreatmentwithmineralacids.Acommonsaltishydrazinesulfate,
[N2H5]HSO4,calledhydraziniumsulfate.[26]Hydrazinesulfatewasinvestigatedasatreatmentofcancer
inducedcachexia,butprovedineffective.[27]
Hydrazineazide(N5H5),thesaltofhydrazineandhydrazoicacid,wasofscientificinterest,becauseofits
+

highnitrogencontentandexplosiveproperties.Structurally,itis[N2H5] [N3] .Itdecomposesexplosively

intohydrazine,ammoniaandnitrogengas:[28]
12N5H53N2H4+16NH3+19N2
ReactionofN5H5withsulfuricacidgivesquantitativeyieldsofpurehydrazinesulfateandhydrazoic
acid.[29]

Otherindustrialuses
Hydrazineisusedinmanyprocessesincluding:productionofspandexfibers,asapolymerizationcatalyst
infuelcells,solderfluxesandphotographicdevelopers,asachainextenderinurethanepolymerizations,
andheatstabilizers.Inaddition,asemiconductordepositiontechniqueusinghydrazinehasrecentlybeen
demonstrated,withpossibleapplicationtothemanufactureofthinfilmtransistorsusedinliquidcrystal
displays.Hydrazineina70%hydrazine,30%watersolutionisusedtopowertheEPU(emergencypower
unit)ontheLockheedF16FightingFalconfighterplane.TheexplosiveAstroliteismadebycombining
hydrazinewithammoniumnitrate.
Hydrazineisoftenusedasanoxygenscavengerandcorrosioninhibitorinboilerwatertreatment.However
duetothetoxicityandcertainundesiredeffectsthispracticeisdiscouraged.

Rocketfuel
HydrazinewasfirstusedasarocketfuelduringWorldWarIIfortheMesserschmittMe163B(thefirst
rocketpoweredfighterplane),underthecodenameBStoff(hydrazinehydrate).Whenmixedwith
methanol(MStoff)andwateritwascalledCStoff.[30]
Hydrazineisalsousedasalowpowermonopropellantforthemaneuveringthrustersofspacecraft,andwas
usedtopowertheSpaceShuttle'sauxiliarypowerunits(APUs).Inaddition,monopropellanthydrazine
fueledrocketenginesareoftenusedinterminaldescentofspacecraft.Suchengineswereusedonthe
Vikingprogramlandersinthe1970saswellasthePhoenixlanderandCuriosityroverwhichlandedon
MarsinMay2008andAugust2012,respectively.
Inallhydrazinemonopropellantengines,thehydrazineispassedbyacatalystsuchasiridiummetal
supportedbyhighsurfaceareaalumina(aluminiumoxide)orcarbonnanofibers,[31]ormorerecently
molybdenumnitrideonalumina,[32]whichcausesittodecomposeintoammonia,nitrogengas,and
hydrogengasaccordingtothefollowingreactions:[33]
1. 3N2H44NH3+N2
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2. N2H4N2+2H2
3. 4NH3+N2H43N2+8H2
Reactions1and2areextremelyexothermic(thecatalystchambercanreach800Cinamatterof
milliseconds,[31])andtheyproducelargevolumesofhotgasfromasmallvolumeofliquid,[32]making
hydrazineafairlyefficientthrusterpropellantwithavacuumspecificimpulseofabout220seconds.[34]
Reaction3isendothermicandsoreducesthetemperatureoftheproducts,butalsoproducesagreater
numberofmolecules.ThecatalyststructureaffectstheproportionoftheNH3thatisdissociatedinReaction
3ahighertemperatureisdesirableforrocketthrusters,whilemoremoleculesaredesirablewhenthe
reactionsareintendedtoproducegreaterquantitiesofgas.
Othervariantsofhydrazinethatareusedasrocketfuelaremonomethylhydrazine,(CH3)NH(NH2)(also
knownasMMH),andunsymmetricaldimethylhydrazine,(CH3)2N(NH2)(alsoknownasUDMH).These
derivativesareusedintwocomponentrocketfuels,oftentogetherwithnitrogentetroxide,N2O4,
sometimesknownasdinitrogentetroxide.Thesereactionsareextremelyexothermic,andtheburningisalso
hypergolic,whichmeansthatitstartswithoutanyexternalignition
source.[35]
Thereareongoingeffortstoreplacehydrazinealongwithother
highlytoxicsubstancesfromtheaerospaceindustry.Promising
alternativesincludehydroxylammoniumnitrate,2
Dimethylaminoethylazide(DMAZ)[36]andenergeticionic
liquids.[37]

Fuelcells
TheItaliancatalystmanufacturerActahasproposedusinghydrazine
asanalternativetohydrogeninfuelcells.Thechiefbenefitofusing
hydrazineisthatitcanproduceover200mW/cm2morethana
similarhydrogencellwithouttheneedtouseexpensiveplatinum
catalysts.[38]Asthefuelisliquidatroomtemperature,itcanbe
handledandstoredmoreeasilythanhydrogen.Bystoringthe
hydrazineinatankfullofadoublebondedcarbonoxygen
Anhydroushydrazinebeingloaded
carbonyl,thefuelreactsandformsasafesolidcalledhydrazone.By
intotheMESSENGERspaceprobe.
thenflushingthetankwithwarmwater,theliquidhydrazinehydrate
Notethesafetysuitthetechnicianis
isreleased.Hydrazinehasahigherelectromotiveforceof1.56V
wearing
comparedto1.23Vforhydrogen.Hydrazinebreaksdowninthe
celltoformnitrogenandhydrogenwhichbondswithoxygen,
releasingwater.[38]HydrazinewasusedinfuelcellsmanufacturedbyAllisChalmersCorp.,includingsome
thatprovidedelectricpowerinspacesatellitesinthe1960s.

Gunpropellant

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Amixtureof63%hydrazine,32%hydrazinenitrateand5%waterisastandardpropellantforexperimental
bulkloadedliquidpropellantartillery.Thepropellantmixtureaboveisoneofthemostpredictableand
stable,withaflatpressureprofileduringfiring.Misfiresareusuallycausedbyinadequateignition.The
movementoftheshellafteramisignitioncausesalargebubblewithalargerignitionsurfacearea,andthe
greaterrateofgasproductioncausesveryhighpressure,sometimesincludingcatastrophictubefailures(i.e.
explosions).[39]

Hazards
Hydrazineishighlytoxic,anddangerouslyunstableintheanhydrousform.AccordingtotheU.S.
EnvironmentalProtectionAgency:
Symptomsofacute(shortterm)exposuretohighlevelsofhydrazinemayincludeirritationof
theeyes,nose,andthroat,dizziness,headache,nausea,pulmonaryedema,seizures,comain
humans.Acuteexposurecanalsodamagetheliver,kidneys,andcentralnervoussystem.The
liquidiscorrosiveandmayproducedermatitisfromskincontactinhumansandanimals.
Effectstothelungs,liver,spleen,andthyroidhavebeenreportedinanimalschronically
exposedtohydrazineviainhalation.Increasedincidencesoflung,nasalcavity,andliver
tumorshavebeenobservedinrodentsexposedtohydrazine.[40]
Limittestsforhydrazineinpharmaceuticalssuggestthatitshouldbeinthelowppmrange.[41]Hydrazine
mayalsocausesteatosis.[42]Atleastonehumanisknowntohavediedafter6monthsofsublethalexposure
tohydrazinehydrate.[43]
OnFebruary21,2008,theUnitedStatesgovernmentdestroyedthedisabledspysatelliteUSA193witha
sealaunchedmissile,reportedlyduetothepotentialdangerofahydrazinereleaseifitreenteredtheEarth's
atmosphereintact.[44]

History
Thename"hydrazine"wascoinedbyEmilFischerin1875hewastryingtoproduceorganiccompounds
thatconsistedofmonosubstitutedhydrazine.[45]By1887,TheodorCurtiushadproducedhydrazinesulfate
bytreatingorganicdiazideswithdilutesulfuricacidhowever,hewasunabletoobtainpurehydrazine,
despiterepeatedefforts.[46]PureanhydroushydrazinewasfirstpreparedbytheDutchchemistLobryde
Bruynin1895.[47]

Seealso
Diazene
Hydrazinesulfate
ListofStoffs
Nitrousoxidefuelblend
USA193
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(http://gallica.bnf.fr/ark:/12148/bpt6k907102/f818.image.langEN)(Ondiamide(hydrazine)),Berichteder
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47. See:
C.A.LobrydeBruyn(1894)"Surl'hydrazine(diamide)libre"(Onfreehydrazine(diamide)),Recueildes
TravauxChimiquesdesPaysBas,13(8):433440.
C.A.LobrydeBruyn(1895)"Surl'hydrated'hydrazine"(Onthehydrateofhydrazine),Recueildes
TravauxChimiquesdesPaysBas,14(3):8588.
C.A.LobrydeBruyn(1896)"L'hydrazinelibreI"(Freehydrazine,Part1),RecueildesTravaux
ChimiquesdesPaysBas,15(6):174184.

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