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Revision as of 12:38, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 448301930 of page Fluoroform for the Chem/Drugbox validation project (updated: 'ChEBI').		Latest revision as of 18:52, 25 April 2024 edit Arjayay (talk | contribs)Autopatrolled, Extended confirmed users, Page movers, Pending changes reviewers, Rollbackers626,476 editsm Sp
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			{{Redirect|CHF3|the Transport Canada LID|Westlock (Hnatko Farms) Aerodrome}}
	{{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
			| Verifiedfields = changed
	| verifiedrevid = 443823636
			| Watchedfields = changed
			| verifiedrevid = 461102015
	| ImageFileL1 = Fluoroform.svg		| ImageFileL1 = Fluoroform.svg
	| ImageFileR1 = Fluoroform-3D-vdW.png		| ImageFileR1 = Fluoroform-3D-vdW.png
	| IUPACName = Trifluoromethane		| IUPACName = Trifluoromethane
	| OtherNames = Fluoroform, Carbon trifluoride, Methyl trifluoride, Fluoryl, Freon 23, Arcton 1, HFC 23, R-23, ], UN 1984		| OtherNames = Fluoroform, carbon trifluoride,{{cn|date=August 2023}} methyl trifluoride, Fluoryl, Freon 23, Arcton 1
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| Abbreviations = HFC 23, R-23, ], UN 1984
	| ChemSpiderID = 21106179		| ChemSpiderID = 21106179
	| InChIKey = XPDWGBQVDMORPB-UHFFFAOYAM		| InChIKey = XPDWGBQVDMORPB-UHFFFAOYAM
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	| StdInChIKey = XPDWGBQVDMORPB-UHFFFAOYSA-N		| StdInChIKey = XPDWGBQVDMORPB-UHFFFAOYSA-N
	| CASNo = 75-46-7		| CASNo = 75-46-7
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| EINECS = 200-872-4		| EINECS = 200-872-4
	| PubChem = 6373		| PubChem = 6373
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = ZJ51L9A260		| UNII = ZJ51L9A260
	| SMILES = FC(F)F		| SMILES = FC(F)F
	| InChI = 1/CHF3/c2-1(3)4/h1H		| InChI = 1/CHF3/c2-1(3)4/h1H
	| RTECS = PB6900000		| RTECS = PB6900000
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|changed|EBI}}
	| ChEBI = 41550		| ChEBI = 24073
			}}
			|Section2={{Chembox Properties
			| C=1|H=1|F=3
			| Appearance = Colorless gas
			| MeltingPtC = −155.2
			| BoilingPtC = −82.1
			| Solubility = 1 g/l
			| SolubleOther = Soluble
			| Solvent = organic solvents
			| VaporPressure = 4.38 MPa at 20 °C
			| HenryConstant = 0.013 mol·kg<sup>−1</sup>·bar<sup>−1</sup>
			| pKa = 25–28
			| Density = 2.946 kg/m<sup>3</sup> (gas, 1 bar, 15 °C)
			}}
			|Section3={{Chembox Structure
			| CrystalStruct =
			| Coordination =
			| MolShape = ]
			}}
			|Section7={{Chembox Hazards
			| MainHazards = Nervous system depression
			| GHSPictograms = {{GHS04}}
			| GHSSignalWord = Warning
			| HPhrases = {{HPhrases|H280}}
			| PPhrases = {{PPhrases|P403}}
			| GHS_ref = <ref>GHS: </ref>
			| NFPA-H = 2
			| NFPA-F = 0
			| NFPA-R = 0
			| NFPA-S =
			| FlashPt = Non-flammable
			| AutoignitionPt =
			}}
			|Section9 = {{Chembox Related
			|OtherFunction_label = chloromethanes
			|OtherCompounds = {{ubl|] {{chem2|CH3F}}|] {{chem2|CH2F2}}|] {{chem2|CF4}}|] {{chem2|CHCl3}}|] {{chem2|CHBr3}}|] {{chem2|CHI3}}|] {{chem2|CHF2Cl}}|] {{chem2|CHFCl2}}|] {{chem2|CHCl2Br}}|] {{chem2|CHClBr2}}|] {{chem2|CHF2Br}}|] {{chem2|CHFBr2}}|] {{chem2|CDCl3}}}}
	}}		}}
	| Section2 = {{Chembox Properties
	| Formula = CHF<sub>3</sub>
	| MolarMass = 70.01 g/mol
	| Appearance = Colorless gas
	| MeltingPt = -155.2 °C (117.95 K)
	| BoilingPt = -82.1°C (191.05 K)
	| Solubility = 1 g/l
	| SolubleOther = Soluble
	| Solvent = organic solvents
	| VaporPressure = 4.38 MPa at 20 °C
	| HenryConstant = 0.013 mol.kg<sup>-1</sup>.bar<sup>-1</sup>
	| pKa = 25 - 28
	}}
	| Section3 = {{Chembox Structure
	| CrystalStruct =
	| Coordination =
	| MolShape = ]
	}}
	| Section3 = {{Chembox Hazards
	| MainHazards = Nervous system depression
	| SPhrases = {{S38}}
	| NFPA-H = 2
	| NFPA-F = 0
	| NFPA-R = 0
	| NFPA-O =
	| FlashPt = Non-flammable
	| Autoignition =
	}}
	}}		}}
			'''Fluoroform''', or '''trifluoromethane''', is the ] with the formula {{chem2|CHF3}}. It is a ] as well as being a part of the ], a class of compounds with the formula {{chem2|CHX3}} (X = ]) with C<sub>3v</sub> ]. Fluoroform is used in diverse applications in ]. It is not an ] but is a ].<ref name=SynLett>{{cite journal|journal=Synlett|year=2015|volume=26|issue=13|pages=1911–1912|doi=10.1055/s-0034-1380924|title=Fluoroform (CHF3)|author=ShivaKumar Kyasa|doi-access=free}}</ref>
			== Synthesis ==
			About 20 million kg per year are produced industrially as both a by-product of and precursor to the manufacture of ].<ref name=SynLett/> It is produced by reaction of ] with ]:<ref name=Ullmann>{{Ullmann|author=G. Siegemund|author2=W. Schwertfeger|author3=A. Feiring|author4= B. Smart|author5=F. Behr|author6= H. Vogel|author7=B. McKusick|title=Fluorine Compounds, Organic|year=2005|doi=10.1002/14356007.a11_349}}</ref>
			:{{chem2|CHCl3 + 3 HF → CHF3 + 3 HCl}}
			It is also generated biologically in small amounts apparently by ] of ].<ref>Kirschner, E., Chemical and Engineering News 1994, 8.</ref>
			===Historical===
			Fluoroform was first obtained by ] in the violent reaction of ] with dry ] in 1894.<ref>{{cite journal|title = Recherches sur quelques fluorures organiques de la série grasse|author = Meslans M. M.
			|journal = ]|year = 1894|volume = 7|issue = 1|pages = 346–423|url = http://gallica.bnf.fr/ark:/12148/bpt6k34901c/f344.table}}</ref> The reaction was improved by ] by substitution of silver fluoride by a mixture of ] and ].<ref name="JACS_1937">{{cite journal|title = Fluoroform|author = Henne A. L.|journal = ]|year = 1937|volume = 59|issue = 7|pages = 1200–1202|doi = 10.1021/ja01286a012}}</ref> The exchange reaction works with iodoform and ], and the exchange of the first two ] atoms by fluorine is vigorous. By changing to a two step process, first forming a ] in the reaction of ] with bromoform and finishing the reaction with mercury fluoride the first efficient synthesis method was found by Henne.<ref name="JACS_1937"/>
			== Industrial applications ==
			{{chem2|CHF3}} is used in the ] ] in ] of ] and ]. Known as R-23 or HFC-23, it was also a useful ], sometimes as a replacement for ] (CFC-13) and is a byproduct of its manufacture.
			When used as a fire suppressant, the fluoroform carries the ] trade name, FE-13. {{chem2|CHF3}} is recommended for this application because of its low toxicity, its low reactivity, and its high density. HFC-23 has been used in the past as a replacement for ](CFC-13B1) in ]s as a total flooding ] agent.
			=== Organic chemistry ===
			Fluoroform is weakly acidic with a pK<sub>''a''</sub> = 25–28 and quite inert. Attempted deprotonation results in defluorination to generate {{chem2|F−}} and ] ({{chem2|CF2}}). Some organocopper and ]s have been developed as trifluoromethylation reagents.<ref>{{Cite journal|last1=Zanardi|first1=Alessandro|last2=Novikov|first2=Maxim A.|last3=Martin|first3=Eddy|last4=Benet-Buchholz|first4=Jordi|last5=Grushin|first5=Vladimir V.|date=2011-12-28|title=Direct Cupration of Fluoroform|journal=Journal of the American Chemical Society|volume=133|issue=51|pages=20901–20913|doi=10.1021/ja2081026|pmid=22136628|issn=0002-7863}}</ref>
			Fluoroform is a precursor of the Ruppert-Prakash reagent ], which is a source of the nucleophilic {{chem2|CF3−}} anion.<ref>Rozen, S.; Hagooly, A. "Fluoroform" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. {{doi| 10.1002/047084289X.rn00522}}</ref><ref>{{Cite journal|last1=Prakash|first1=G. K. Surya|last2=Jog|first2=Parag V.|last3=Batamack|first3=Patrice T. D.|last4=Olah|first4=George A.|date=2012-12-07|title=Taming of Fluoroform: Direct Nucleophilic Trifluoromethylation of Si, B, S, and C Centers|journal=Science|language=en|volume=338|issue=6112|pages=1324–1327|doi=10.1126/science.1227859|issn=0036-8075|pmid=23224551|bibcode=2012Sci...338.1324P|s2cid=206544170}}</ref>
			== Greenhouse gas ==
			) in the lower atmosphere (]) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in ].]]
			]
			{{chem2|CHF3}} is a potent ]. A ton of HFC-23 in the atmosphere has the same effect as 11,700 tons of carbon dioxide. This equivalency, also called a 100-yr ], is slightly larger at 14,800 for HFC-23.<ref name="Forster, P., V. Ramaswamy, P. Artaxo, T. Berntsen, R. Betts, D.W. Fahey, J. Haywood, J. Lean, D.C. Lowe, G. Myhre, J. Nganga, R. Prinn, G. Raga, M. Schulz and R. Van Dorland 2007">{{cite conference|title = Changes in Atmospheric Constituents and in Radiative Forcing.|book-title = Climate Change 2007: The Physical Science Basis. Contribution of Working Group I to the Fourth Assessment Report of the Intergovernmental Panel on Climate Change|url = http://www.ipcc.ch/pdf/assessment-report/ar4/wg1/ar4-wg1-chapter2.pdf|author = Forster, P.|author2 = V. Ramaswamy|author3 = P. Artaxo|author4 = T. Berntsen|author5 = R. Betts|author6 = D.W. Fahey|author7 = J. Haywood|author8 = J. Lean|author9 = D.C. Lowe|author10 = G. Myhre|author11 = J. Nganga|author12 = R. Prinn|author13 = G. Raga|author14 = M. Schulz|author15 = R. Van Dorland|name-list-style = amp|date = 2007 }}</ref>
			The atmospheric lifetime is 270 years.<ref name="Forster, P., V. Ramaswamy, P. Artaxo, T. Berntsen, R. Betts, D.W. Fahey, J. Haywood, J. Lean, D.C. Lowe, G. Myhre, J. Nganga, R. Prinn, G. Raga, M. Schulz and R. Van Dorland 2007"/>
			HFC-23 was the most abundant HFC in the global atmosphere until around 2001, when the global mean concentration of ] (1,1,1,2-tetrafluoroethane), the chemical now used extensively in automobile air conditioners, surpassed those of HFC-23. Global emissions of HFC-23 have in the past been dominated by the inadvertent production and release during the manufacture of the refrigerant ] (chlorodifluoromethane).
			Substantial decreases in HFC-23 emissions by developed countries were reported from the 1990s to the 2000s: from 6-8 Gg/yr in the 1990s to 2.8 Gg/yr in 2007.<ref>{{cite journal |doi=10.1029/2009GL041195|title=Recent increases in global HFC-23 emissions|year=2010|last1=Montzka|first1=S. A.|last2=Kuijpers|first2=L.|last3=Battle|first3=M. O.|last4=Aydin|first4=M.|last5=Verhulst|first5=K. R.|last6=Saltzman|first6=E. S.|last7=Fahey|first7=D. W.|journal=Geophysical Research Letters|volume=37|issue=2|pages=n/a|bibcode=2010GeoRL..37.2808M|s2cid=13583576 |url=https://escholarship.org/uc/item/3f31077f}}</ref>
			The ] Clean Development Mechanism ].
			Developing countries have become the largest producers of HCFC-23 in recent years according to data compiled by the Ozone Secretariat of the World Meteorological Organization.<ref>{{Cite web |url=http://ozone.unep.org/Data_Reporting/Data_Access/ |title=Data Access Centre |access-date=2010-04-03 |archive-url=https://web.archive.org/web/20110721233408/http://ozone.unep.org/Data_Reporting/Data_Access/ |archive-date=2011-07-21 |url-status=dead }}</ref><ref> August 8, 2012 New York Times</ref><ref></ref> Emissions of all HFCs are included in the UNFCCCs Kyoto Protocol. To mitigate its impact, {{chem2|CHF3}} can be destroyed with electric plasma arc technologies or by high temperature incineration.<ref>{{cite journal|author=Han, Wenfeng|author2=Li, Ying|author3=Tang, Haodong|author4=Liu, Huazhang
			|journal=Journal of Fluorine Chemistry|title=Treatment of the potent greenhouse gas, CHF<sub>3</sub>. An overview|year=2012|volume=140|page=7–16|doi=10.1016/j.jfluchem.2012.04.012}}</ref>
			== Additional physical properties ==
			{| class="wikitable"
			|-
			! Property
			! Value
			|-
			| ] (ρ) at -100&nbsp;°C (liquid)
			| 1.52 g/cm<sup>3</sup>
			|-
			| ] (ρ) at -82.1&nbsp;°C (liquid)
			| 1.431 g/cm<sup>3</sup>
			|-
			| ] (ρ) at -82.1&nbsp;°C (gas)
			| 4.57&nbsp;kg/m<sup>3</sup>
			|-
			| ] (ρ) at 0&nbsp;°C (gas)
			| 2.86&nbsp;kg/m<sup>3</sup>
			|-
			| ] (ρ) at 15&nbsp;°C (gas)
			| 2.99&nbsp;kg/m<sup>3</sup>
			|-
			| ]
			| 1.649 D
			|-
			| ] (p<sub>c</sub>)
			| 4.816 MPa (48.16 bar)
			|-
			| ] (T<sub>c</sub>)
			| 25.7&nbsp;°C (299 K)
			|-
			| ] (ρ<sub>c</sub>)
			| 7.52&nbsp;mol/l
			|-
			| ] (Z)
			| 0.9913
			|-
			| ] (ω)
			| 0.26414
			|-
			| ] (η) at 25&nbsp;°C
			| 14.4 μPa.s (0.0144 cP)
			|-
			| ] at constant volume (C<sub>V</sub>)
			| 51.577 J.mol<sup>−1</sup>.K<sup>−1</sup>
			|-
			| ] (l<sub>b</sub>)
			| 257.91 kJ.kg<sup>−1</sup>
			|}
			== References ==
			{{Reflist}}
			== Literature ==
			*{{cite journal|title = Fluorine Chemistry|author = McBee E. T.|journal = ]|year = 1947|volume = 39|issue = 3|pages = 236–237|doi = 10.1021/ie50447a002}}
			*{{cite journal|title = Growth of fluoroform (CHF<sub>3</sub>, HFC-23) in the background atmosphere|author1 = Oram D. E.|author2 = Sturges W. T.|author3 = Penkett S. A.|author4 = McCulloch A.|author5 = Fraser P. J.|journal = ]|year = 1998|volume = 25|issue = 1|pages = 236–237|doi = 10.1029/97GL03483|bibcode = 1998GeoRL..25...35O|doi-access = free}}
			*{{cite journal|title = Fluorocarbons in the global environment: a review of the important interactions with atmospheric chemistry and physics|author = McCulloch A.|journal = ]|year = 2003|volume = 123|issue = 1|pages = 21–29|doi = 10.1016/S0022-1139(03)00105-2}}
			== External links ==
			* {{ICSC|0577|05}}
			*
			*
			*
			{{Halomethanes}}
			{{fluorine compounds}}
			]
			]
			]
			]
			]
			]
			]