1/27/2017 MethaneWikipedia

Methane
FromWikipedia,thefreeencyclopedia

Methane(US/men/orUK/mien/)isachemicalcompoundwiththechemicalformulaCH4(one Methane
atomofcarbonandfouratomsofhydrogen).Itisagroup14hydrideandthesimplestalkane,andisthe
mainconstituentofnaturalgas.TherelativeabundanceofmethaneonEarthmakesitanattractivefuel,
thoughcapturingandstoringitposeschallengesduetoitsgaseousstateundernormalconditionsfor
temperatureandpressure.

Naturalmethaneisfoundbothbelowgroundandundertheseafloor.Whenitreachesthesurfaceand
theatmosphere,itisknownasatmosphericmethane.[5]TheEarth'satmosphericmethaneconcentration
hasincreasedbyabout150%since1750,anditaccountsfor20%ofthetotalradiativeforcingfromall
ofthelonglivedandgloballymixedgreenhousegases(thesegasesdon'tincludewatervaporwhichis
byfarthelargestcomponentofthegreenhouseeffect).[6]

Contents
Names
1 History PreferredIUPACname
2 Propertiesandbonding
3 Chemicalreactions Methane[1]
3.1 Acidbasereactions SystematicIUPACname
3.2 Combustion Carbane(neverrecommended[1])
3.3 Reactionswithhalogens
4 Uses Othernames
4.1 Fuel MarshGas
4.1.1 Naturalgas NaturalGas
4.1.2 Liquefiednaturalgas Carbontetrahydride
4.1.3 Liquidmethanerocketfuel Hydrogencarbide
4.2 Chemicalfeedstock
5 Production Identifiers
5.1 Biologicalroutes CASNumber 74828(http://www.commonc
5.2 Industrialroutes hemistry.org/ChemicalDetail.as
5.2.1 Powertomethane
px?ref=74828)
5.2.2 Laboratorysynthesis
5.2.3 OnMars 3Dmodel(Jmol) Interactiveimage(http://chema
6 Occurrence pps.stolaf.edu/jmol/jmol.php?m
6.1 Alternativesources odel=C)
6.2 Atmosphericmethane
3DMet B01450(http://www.3dmet.dn
6.3 Clathrates
7 Anaerobicoxidationofmethane a.affrc.go.jp/cgi/show_data.ph
8 Safety p?acc=B01450)
9 Extraterrestrialmethane BeilsteinReference 1718732
10 Seealso
ChEBI CHEBI:16183(https://www.eb
11 Notes
12 References i.ac.uk/chebi/searchId.do?chebi
13 Externallinks Id=16183)
ChEMBL ChEMBL17564(https://www.e
bi.ac.uk/chembldb/index.php/co
History mpound/inspect/ChEMBL1756
4)
InNovember1776,methanewasfirstscientificallyidentifiedbyItalianphysicistAlessandroVoltain ChemSpider 291(http://www.chemspider.co
themarshesofLakeMaggiorestraddlingItalyandSwitzerland.Voltawasinspiredtosearchforthe
m/ChemicalStructure.291.htm
substanceafterreadingapaperwrittenbyBenjaminFranklinabout"flammableair".[7]Voltacollected
l)
thegasrisingfromthemarsh,andby1778hadisolatedthepuregas.[8]Healsodemonstratedthatthe
ECHAInfoCard 100.000.739(https://echa.europ
gascouldbeignitedwithanelectricspark.[8]
a.eu/substanceinformation//su
Thename"methane"wascoinedin1866bytheGermanchemistAugustWilhelmvonHofmann.[9]The bstanceinfo/100.000.739)
namewasderivedfrommethanol. ECNumber 2008127
GmelinReference 59
Propertiesandbonding KEGG C01438(http://www.kegg.jp/en
try/C01438)
MethaneisatetrahedralmoleculewithfourequivalentCHbonds.Itselectronicstructureisdescribed
MeSH Methane(https://www.nlm.nih.
byfourbondingmolecularorbitals(MOs)resultingfromtheoverlapofthevalenceorbitalsonCandH.
gov/cgi/mesh/2014/MB_cgi?mo
ThelowestenergyMOistheresultoftheoverlapofthe2sorbitaloncarbonwiththeinphase
combinationofthe1sorbitalsonthefourhydrogenatoms.Abovethisenergylevelisatriply de=&term=Methane)

https://en.wikipedia.org/wiki/Methane 1/11
1/27/2017 MethaneWikipedia
degeneratesetofMOsthatinvolveoverlapofthe2porbitalsoncarbonwithvariouslinear PubChem 297(https://pubchem.ncbi.nlm.
combinationsofthe1sorbitalsonhydrogen.Theresulting"threeoverone"bondingschemeis nih.gov/compound/297)
consistentwithphotoelectronspectroscopicmeasurements. RTECSnumber PA1490000
UNnumber 1971
Atroomtemperatureandstandardpressure,methaneisacolorless,odorlessgas.[10]Thefamiliarsmell
ofnaturalgasasusedinhomesisachievedbytheadditionofanodorant,usuallyblendscontainingtert InChI
butylthiol,asasafetymeasure.Methanehasaboilingpointof161C(257.8F)atapressureofone SMILES
atmosphere.[11]Asagasitisflammableoverarangeofconcentrations(5.417%)inairatstandard Properties
pressure.
Chemicalformula CH4

Solidmethaneexistsinseveralmodifications.Presentlynineareknown.[12]Coolingmethaneatnormal Molarmass 16.04gmol1

pressureresultsintheformationofmethaneI.Thissubstancecrystallizesinthecubicsystem(space Appearance Colorlessgas
groupFm3m).ThepositionsofthehydrogenatomsarenotfixedinmethaneI,i.e.methanemolecules
Odor Odorless
mayrotatefreely.Therefore,itisaplasticcrystal.[13]
Density 0.656g/L(gas,25C,1atm)
0.716g/L(gas,0C,1atm)
Chemicalreactions
0.42262gcm3
Theprimarychemicalreactionsofmethanearecombustion,steamreformingtosyngas,and (liquid,162C)[2]
halogenation.Ingeneral,methanereactionsaredifficulttocontrol.Partialoxidationtomethanol,for Meltingpoint 182.5C296.4F90.7K
example,ischallengingbecausethereactiontypicallyprogressesallthewaytocarbondioxideand Boilingpoint 161.49C258.68F
waterevenwithaninsufficientsupplyofoxygen.Theenzymemethanemonooxygenaseproduces
111.66K
methanolfrommethane,butcannotbeusedforindustrialscalereactions.[14]
Solubilityinwater 22.7mgL1
Acidbasereactions Solubility solubleinethanol,diethyl
ether,benzene,toluene,
Likeotherhydrocarbons,methaneisaveryweakacid.ItspKainDMSOisestimatedtobe56.[15]It methanol,acetone
cannotbedeprotonatedinsolution,buttheconjugatebasewithmethyllithiumisknown. logP 1.09
Henry'slaw 14nmolPa1kg1
Avarietyofpositiveionsderivedfrommethanehavebeenobserved,mostlyasunstablespeciesinlow
constant(kH)
pressuregasmixtures.TheseincludemetheniumormethylcationCH+ +
3 ,methanecationCH4 ,and
+ Magnetic 12.2106cm3/mol
methaniumorprotonatedmethaneCH5 .Someofthesehavebeendetectedinouterspace.Methanium
susceptibility()
canalsobeproducedasdilutedsolutionsfrommethanewithsuperacids.Cationswithhighercharge,
Structure
suchasCH2+ 3+
6 andCH7 ,havebeenstudiedtheoreticallyandconjecturedtobestable.
[16]
Pointgroup Td
DespitethestrengthofitsCHbonds,thereisintenseinterestincatalyststhatfacilitateCHbond Molecularshape Tetrahedron
activationinmethane(andotherlowernumberedalkanes).[17] Dipolemoment 0D
Thermochemistry
Combustion
Specific 35.69JK1mol1
heatcapacity(C)
Methane'sheatofcombustionis55.5MJ/kg.[18]Combustionofmethaneisamultiplestepreaction.The
Stdmolar 186.25JK1mol1
followingequationsarepartoftheprocess,withthenetresultbeing:
entropy(So298)
CH4+2O2CO2+2H2O(H=891kJ/mol(atstandardconditions)) Stdenthalpyof 74.87kJmol1
formation(fHo298)
1.CH4+M*CH3+H+M Stdenthalpyof 891.1to890.3kJmol1
2.CH4+O2CH3+HO2 combustion
3.CH4+HO2CH3+2OH (cHo298)
4.CH4+OHCH3+H2O Hazards[3]
5.O2+HO+OH Safetydatasheet See:datapage
6.CH4+OCH3+OH
GHSpictograms
7.CH3+O2CH2O+OH
8.CH2O+OCHO+OH
9.CH2O+OHCHO+H2O GHSsignalword DANGER
10.CH2O+HCHO+H2 GHShazard H220
statements
11.CHO+OCO+OH
12.CHO+OHCO+H2O GHSprecautionary P210
statements
13.CHO+HCO+H2
EUclassification
14.H2+OH+OH (DSD) F+
15.H2+OHH+H2O
Rphrases R12
16.CO+OHCO2+H
Sphrases (S2),S16,S33
17.H+OH+MH2O+M*
NFPA704
18.H+H+MH2+M* 4
19.H+O2+MHO2+M* 2 0

https://en.wikipedia.org/wiki/Methane 2/11