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Revision as of 12:37, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 468696256 of page Tetrafluoromethane for the Chem/Drugbox validation project (updated: '').		Latest revision as of 21:11, 11 July 2024 edit JWBE (talk | contribs)Extended confirmed users10,128 editsm →External links
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 444218716
			| verifiedrevid = 470603964
	| ImageFileL1_Ref = {{chemboximage|correct|??}}		| ImageFileL1_Ref = {{chemboximage|correct|??}}
			| ImageSize2 =
	| ImageFileL1 = Carbon-tetrafluoride-2D-dimensions.png
	| ImageSizeL1 = 150		| ImageFile =
	| ImageFileR1 = Carbon-tetrafluoride-3D-balls-B.png		| ImageFileL1 = Carbon-tetrafluoride-2D-dimensions.png
	| ImageSizeR1 = 110px		| ImageSizeL1 =
	| IUPACName = Tetrafluoromethane<br/>Carbon tetrafluoride		| ImageFileR1 = Carbon-tetrafluoride-3D-balls-B.png
			| ImageFile2 = Carbon Tetrafluoride.png
	| OtherNames = Carbon tetrafluoride, Perfluoromethane, Tetrafluorocarbon, Freon 14, Halon 14, Arcton 0, CFC 14, PFC 14, R 14, UN 1982
			| IUPACName = Tetrafluoromethane<br/>Carbon tetrafluoride
	| Section1 = {{Chembox Identifiers
			| OtherNames = Carbon tetrafluoride, Perfluoromethane, Tetrafluorocarbon, Freon 14, Halon 14, Arcton 0, CFC 14, PFC 14, R 14, UN 1982
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| Section1 = {{Chembox Identifiers
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 6153		| ChemSpiderID = 6153
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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	| StdInChIKey = TXEYQDLBPFQVAA-UHFFFAOYSA-N		| StdInChIKey = TXEYQDLBPFQVAA-UHFFFAOYSA-N
	| CASNo = 75-73-0		| CASNo = 75-73-0
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| EINECS = 200-896-5		| EINECS = 200-896-5
	| PubChem = 6393		| PubChem = 6393
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 94WG9QG0JN		| UNII = 94WG9QG0JN
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 38825		| ChEBI = 38825
	| SMILES = FC(F)(F)F		| SMILES = FC(F)(F)F
	| InChI = 1/CF4/c2-1(3,4)5		| InChI = 1/CF4/c2-1(3,4)5
	| RTECS = FG4920000		| RTECS = FG4920000
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
	| Formula = CF<sub>4</sub>		| Formula = CF<sub>4</sub>
	| MolarMass = 88.0043 g/mol		| MolarMass = 88.0043 g/mol
	| Appearance = Colorless odorless gas		| Appearance = Colorless gas
	| Density = 3.72 g/l, gas (15 °C)		| Odor = odorless
			| Density = 3.72 g/L, gas (15 °C)
	| MeltingPt = -183.6 °C (89.6 K)		| MeltingPtC = -183.6
	| BoilingPt = -127.8 °C (145.4 K)		| BoilingPtC = -127.8
			| CriticalTP = {{convert|&minus;45.55|C|F K|1}}, {{convert|36.91|atm|kPa psi|1}}<ref>{{cite book|url=https://api.pageplace.de/preview/DT0400.9781000102574_A40413991/preview-9781000102574_A40413991.pdf|last1=Lide|first1=David R.|last2=Kehiaian|first2=Henry V.|title=CRC Handbook of Thermophysical and Themochemical Data|year=1994|page=31|publisher=CRC Press}}</ref>
	| Solubility = 0.005%<sub>V</sub> at 20 °C<br/>0.0038%<sub>V</sub> at 25 °C
	| VaporPressure = 3.65 MPa at 15 °C<br/>106.5 kPa at -127 °C		| Solubility = 0.005%<sub>V</sub> at 20 °C<br/>0.0038%<sub>V</sub> at 25 °C
			| SolubleOther = soluble in ], ]
	| RefractIndex = 1.113
			| VaporPressure = 106.5 kPa at −127 °C
	}}
			| HenryConstant = 5.15 atm-cu m/mole
	| Section3 = {{Chembox Structure
			| RefractIndex = 1.0004823<ref>{{cite journal|last=Abjean|first=R.|author2=A. Bideau-Mehu |author3=Y. Guern |title=Refractive index of carbon tetrafluoride (CF4) in the 300-140 nm wavelength range|journal=Nuclear Instruments and Methods in Physics Research Section A: Accelerators, Spectrometers, Detectors and Associated Equipment|date=15 July 1990|volume=292|issue=3|pages=593–594|doi=10.1016/0168-9002(90)90178-9|bibcode=1990NIMPA.292..593A}}</ref>
	| CrystalStruct =
			| Viscosity = 17.32 μPa·s<ref name="Kestin1971">{{cite journal |title=Reference values of the viscosity of twelve gases at 25°C |journal= Transactions of the Faraday Society|year=1971|last1=Kestin|first1=J.|last2=Ro|first2=S.T.|last3=Wakeham|first3=W.A.|volume=67|pages= 2308–2313|doi=10.1039/TF9716702308 }}</ref>
	| Coordination =
			}}
	| MolShape = Tetrahedral
			| Section3 = {{Chembox Structure
	}}
			| CrystalStruct =
	| Section3 = {{Chembox Hazards
			| Coordination = Tetragonal
	| ExternalMSDS =
			| MolShape = Tetrahedral
	| EUIndex = Not listed
	| RPhrases =		| Dipole = 0 D
			}}
	| SPhrases =
			| Section4 = {{Chembox Hazards
	| NFPA-H = 1
			| ExternalSDS =
	| NFPA-F = 0
			|MainHazards = Simple asphyxiant and greenhouse gas
	| NFPA-R = 0
	| NFPA-O =		| NFPA-H = 1
			| NFPA-F = 0
	| FlashPt = Non-flammable
			| NFPA-R = 0
	| Autoignition = 1100 °C
			| NFPA-S = SA
	}}
			| FlashPt = Non-flammable
	| Section8 = {{Chembox Related
			}}
	| Function = fluoromethanes
			| Section8 = {{Chembox Related
	| OtherFunctn = ]<br/>]<br/>]
			| OtherFunction_label = fluoromethanes
	| OtherCpds = ]<br/>]<br/>]
	| OtherCations = ]<br/>]<br/>]<br/>]		| OtherFunction = ]<br/>]<br/>]
			| OtherCompounds =
			| OtherAnions = ]<br/>]<br/>]
			| OtherCations = ]<br/>]<br/>]<br/>]
	}}		}}
	}}		}}
			'''Tetrafluoromethane''', also known as '''carbon tetrafluoride''' or R-14, is the simplest ] (]]<sub>4</sub>). As its IUPAC name indicates, tetrafluoromethane is the perfluorinated counterpart to the hydrocarbon ]. It can also be classified as a ] or ]. Tetrafluoromethane is a useful ] but also a potent ].<ref name="Ull"/> It has a very high bond strength due to the nature of the ].
			==Bonding==
			Because of the multiple carbon–fluorine bonds, and the high ] of ], the carbon in tetrafluoromethane has a significant positive ] which strengthens and shortens the four carbon–fluorine bonds by providing additional ] character. Carbon–fluorine bonds are the strongest single bonds in ].<ref name=hagan>{{cite journal |author=O'Hagan D |title=Understanding organofluorine chemistry and in cations. An introduction to the C–F bond |journal=Chemical Society Reviews |volume=37 |issue=2 |pages=308–19 |date=February 2008 |pmid=18197347 |doi=10.1039/b711844a }}</ref> Additionally, they strengthen as more carbon–fluorine bonds are added to the same carbon. In the one-carbon ]s represented by molecules of ], ], ], and tetrafluoromethane, the carbon–fluorine bonds are strongest in tetrafluoromethane.<ref name="Lemal2004">{{Cite journal
			| last = Lemal | first = D.M.
			| year = 2004
			| title = Perspective on Fluorocarbon Chemistry
			| journal = ]
			| volume = 69
			| pages = 1–11
			| doi = 10.1021/jo0302556
			| pmid = 14703372
			| issue = 1
			}}</ref> This effect is due to the increased ] attractions between the fluorine atoms and the carbon because the carbon has a positive ] of 0.76.<ref name="Lemal2004"/>
			== Preparation ==
			Tetrafluoromethane is the product when any carbon compound, including carbon itself, is burned in an atmosphere of fluorine. With hydrocarbons, ] is a coproduct. It was first reported in 1926.<ref name="chemelem">{{Greenwood&Earnshaw}}</ref> It can also be prepared by the ] of ], ] or ] with ]. Commercially it is manufactured by the reaction of ] with ] or ]; it is also produced during the ] of metal ]s MF, MF<sub>2</sub> using a carbon electrode.
			Although it can be made from a myriad of precursors and fluorine, elemental fluorine is expensive and difficult to handle. Consequently, {{chem|CF|4}} is prepared on an industrial scale using ]:<ref name=Ull>{{Ullmann|first1=Günter |last1=Siegemund|first2=Werner|last2=Schwertfeger|first3=Andrew|last3= Feiring|first4=Bruce|last4=Smart|first5=Fred |last5=Behr|first6=Herward|last6=Vogel|first7=Blaine|last7=McKusick|title=Fluorine Compounds, Organic|year=2002|doi=10.1002/14356007.a11_349}}</ref>
			:CCl<sub>2</sub>F<sub>2</sub> + 2 HF → CF<sub>4</sub> + 2 HCl
			===Laboratory synthesis===
			Tetrafluoromethane and ] can be prepared in the laboratory by the reaction of ] with fluorine.
			: SiC + 4 F<sub>2</sub> → CF<sub>4</sub> + SiF<sub>4</sub>
			==Reactions==
			Tetrafluoromethane, like other fluorocarbons, is very stable due to the strength of its carbon–fluorine bonds. The bonds in tetrafluoromethane have a ] of 515 kJ⋅mol<sup>−1</sup>. As a result, it is inert to acids and hydroxides. However, it reacts explosively with ]s. ] or combustion of CF<sub>4</sub> produces toxic gases (] and ]) and in the presence of water will also yield ].
			It is very slightly soluble in water (about 20&nbsp;mg⋅L<sup>−1</sup>), but miscible with organic solvents.
			==Uses==
			Tetrafluoromethane is sometimes used as a low temperature ] (R-14). It is used in ] ] alone or in combination with ] as a ] for ], ], and ].<ref name=williams>K. Williams, K. Gupta, M. Wasilik. ''Etch Rates for Micromachining Processing – Part II'' J. Microelectromech. Syst., vol. 12, pp. 761–777, December 2003.</ref> It also has uses in neutron detectors.<ref>{{cite journal|title=Low efficiency 2-dimensional position-sensitive neutron detector for beam profile measurement|year=2005 |doi=10.1016/j.nima.2004.09.020|last1=Moon |first1=Myung-Kook |last2=Nam |first2=Uk-Won |last3=Lee |first3=Chang-Hee |last4=Em |first4=V.T. |last5=Choi |first5=Young-Hyun |last6=Cheon |first6=Jong-Kyu |last7=Kong |first7=Kyung-Nam |journal=Nuclear Instruments and Methods in Physics Research Section A: Accelerators, Spectrometers, Detectors and Associated Equipment |volume=538 |issue=1–3 |pages=592–596 |bibcode=2005NIMPA.538..592M }}</ref>
			== Environmental effects ==
			]
			) in the lower atmosphere (]) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in ].]]
			]
			Tetrafluoromethane is a potent ] that contributes to the ]. It is very stable, has an ] of 50,000 years, and a high ] 6,500 times that of CO<sub>2</sub>.<ref>{{cite web |last1=Artaxo |first1=Paulo |last2=Berntsen |first2=Terje |last3=Betts |first3=Richard |last4=Fahey |first4=David W. |last5=Haywood |first5=James |last6=Lean |first6=Judith |author6-link=Judith Lean |last7=Lowe |first7=David C. |last8=Myhre |first8=Gunnar |last9=Nganga |first9=John |last10=Prinn |first10=Ronald |last11=Raga |first11=Graciela |last12=Schulz |first12=Michael |last13=van Dorland |first13=Robert |title=Changes in Atmospheric Constituents and in Radiative Forcing |url=https://www.ipcc.ch/site/assets/uploads/2018/02/ar4-wg1-chapter2-1.pdf |publisher=] |access-date=17 March 2021 |page=212 |date=February 2018}}</ref>
			Tetrafluoromethane is the most abundant ] in the atmosphere, where it is designated as PFC-14. Its atmospheric concentration is growing.<ref>{{Cite web |url=https://www.epa.gov/climate-indicators/climate-change-indicators-atmospheric-concentrations-greenhouse-gases |title=Climate change indicators - Atmospheric concentration of greenhouse gases - Figure 4 |date=27 June 2016 |publisher=] |access-date=2020-09-26}}</ref> As of 2019, the man-made gases ] and ] continue to contribute a stronger ] than PFC-14.<ref>{{Cite web |url=https://www.esrl.noaa.gov/gmd/aggi/aggi.html |title=The NOAA Annual Greenhouse Gas Index (AGGI) |publisher=] Global Monitoring Laboratory/Earth System Research Laboratories |author=Butler J. and Montzka S. |year=2020 }}</ref>
			Although structurally similar to ] (CFCs), tetrafluoromethane does not ]<ref>{{Cite journal |last=Cicerone |first=Ralph J. |date=1979-10-05 |title=Atmospheric Carbon Tetrafluoride: A Nearly Inert Gas |url=https://escholarship.org/content/qt5n81h9fs/qt5n81h9fs.pdf?t=obqs5d |journal=Science |language=en |volume=206 |issue=4414 |pages=59–61 |doi=10.1126/science.206.4414.59 |pmid=17812452 |bibcode=1979Sci...206...59C |s2cid=34911990 |issn=0036-8075}}</ref> because the carbon–fluorine bond is much stronger than that between carbon and chlorine.<ref>{{Cite web |title=Bond Energies |url=https://www2.chemistry.msu.edu/faculty/reusch/OrgPage/bndenrgy.htm |access-date=2023-01-15 |website=www2.chemistry.msu.edu}}</ref>
			Main industrial emissions of tetrafluoromethane besides ] are produced during production of ] using ]. CF<sub>4</sub> also is produced as product of the breakdown of more complex compounds such as ]s.<ref name="JubbMcGillen2015">{{cite journal|last1=Jubb|first1=Aaron M.|last2=McGillen|first2=Max R.|last3=Portmann|first3=Robert W.|last4=Daniel|first4=John S.|last5=Burkholder|first5=James B.|title=An atmospheric photochemical source of the persistent greenhouse gas CF4|journal=Geophysical Research Letters|volume=42|issue=21|year=2015|pages=9505–9511|issn=0094-8276|doi=10.1002/2015GL066193|bibcode=2015GeoRL..42.9505J|url=https://zenodo.org/record/1229070|doi-access=free}}</ref>
			== Health risks ==
			Due to its density, tetrafluoromethane can displace air, creating an ] hazard in inadequately ventilated areas. Otherwise, it is normally harmless due to its stability.
			== See also ==
			* ]
			* ]
			* ]
			== References ==
			{{reflist|30em}}
			== External links ==
			*{{ICSC|0575|05}}
			*
			* {{Webarchive|url=https://web.archive.org/web/20110721161453/http://encyclopedia.airliquide.com/Encyclopedia.asp?GasID=61 |date=2011-07-21 }}
			*
			*
			*
			*
			*
			{{Halomethanes}}
			{{Inorganic compounds of carbon}}
			{{fluorine compounds}}
			{{Authority control}}
			]
			]
			]
			]
			]