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Revision as of 13:58, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 456915252 of page Trichlorofluoromethane for the Chem/Drugbox validation project (updated: '').  Latest revision as of 10:35, 6 December 2024 edit Yeaggermiester (talk | contribs)47 edits →Use in Planetary Astrophysics: clarification that industrial pollution has never been detected in the atmosphere of an earthlike exoplanet, therefore it hasn't been used to detect said industrial pollution. Maybe there is a better way to phrase the whole sentence than my revision, but this revision more accurately reflects what is in the linked article than the previous 
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{{Short description|A type of chlorofluorocarbon}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{update|date=October 2023}}
{{chembox {{chembox
| Verifiedfields = changed | Watchedfields = changed
| verifiedrevid = 418313616 | verifiedrevid = 470613490
| ImageFileL1_Ref = {{chemboximage|correct|??}} | ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1 = Trichlorofluoromethane-2D.svg | ImageFileL1 = Trichlorofluoromethane-2D.svg
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| ImageFileR1 = Trichlorofluoromethane-3D-vdW.png | ImageFileR1 = Trichlorofluoromethane-3D-vdW.png
| ImageSizeR1 = | ImageSizeR1 =
| PIN = Trichloro(fluoro)methane <!-- Parentheses are used according to Subsection P-16.5.1.3 of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->
| IUPACName = Trichlorofluoromethane
| OtherNames = Trichloro(fluoro)methane, Fluorotrichloromethane, Fluorochloroform, Freon 11, CFC 11, R 11, Arcton 9, Freon 11A, Freon 11B, Freon HE, Freon MF | OtherNames = Trichlorofluoromethane<br />Fluorotrichloromethane<br />Fluorochloroform<br />Freon 11<br />CFC 11<br />R 11<br />Arcton 9<br />Freon 11A<br />Freon 11B<br />Freon HE<br />Freon MF
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6149 | ChemSpiderID = 6149
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
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| SMILES1 = ClC(Cl)(Cl)F | SMILES1 = ClC(Cl)(Cl)F
| CASNo = 75-69-4 | CASNo = 75-69-4
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| EINECS = 200-892-3 | EINECS = 200-892-3
| PubChem = 6389 | PubChem = 6389
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 48236 | ChEBI = 48236
| SMILES = C(F)(Cl)(Cl)Cl | SMILES = C(F)(Cl)(Cl)Cl
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 990TYB331R | UNII = 990TYB331R
| InChI = 1/CCl3F/c2-1(3,4)5 | InChI = 1/CCl3F/c2-1(3,4)5
| RTECS = TB6125000 | RTECS = PB6125000
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=1 | Cl=3 | F=1
| Formula = CCl<sub>3</sub>F
⚫ | Appearance = Colorless liquid/gas
| MolarMass = 137.37 g/mol
| Odor = nearly odorless<ref name=PGCH/>
⚫ | Appearance = Colorless liquid/gas
| Density = 1.494 g/cm<sup>3</sup> | Density = 1.494 g/cm<sup>3</sup>
| MeltingPt = -110.48 °C | MeltingPtC = -110.48
| BoilingPt = 23.77 °C | BoilingPtC = 23.77
| Solubility = 1.1 g/l at 20 °C | Solubility = 1.1 g/L (at 20 °C)
| LogP = 2.53 | LogP = 2.53
| VaporPressure = 89 kPa at 20 °C<br/>131 kPa at 30 °C | VaporPressure = 89 kPa at 20 °C<br/>131 kPa at 30 °C
| ThermalConductivity = {{nowrap|1=0.0079 W m<sup>−1</sup> K<sup>−1</sup>}} (gas&nbsp;at 300&nbsp;K, ignoring pressure&nbsp;dependence)<ref>Touloukian, Y.S., Liley, P.E., and Saxena, S.C. Thermophysical properties of matter - the TPRC data series. Volume 3. Thermal conductivity - nonmetallic liquids and gases. Data book. 1970.</ref>{{Verify source|date=January 2022}}
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
⚫ | MainHazards =
| EUIndex = Not listed
⚫ | FlashPt = Non-flammable
⚫ | MainHazards = Ozone depletor
| GHSSignalWord = warning
⚫ | FlashPt = Non-flammable
| GHSPictograms = {{GHS07}}
| RPhrases =
| HPhrases = {{HPhrases|H420}}
| SPhrases =
| PPhrases = {{PPhrases|P502}}
| GHS_ref = <ref>{{GESTIS|ZVG=30930}}</ref>
| PEL = TWA 1000 ppm (5600 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0290}}</ref>
| IDLH = 2000 ppm<ref name=PGCH/>
| REL = C 1000 ppm (5600 mg/m<sup>3</sup>)<ref name=PGCH/>
| LCLo = 26,200 ppm (rat, 4 hr)<br/>100,000 ppm (rat, 20 min)<br/>100,000 ppm (rat, 2 hr)<ref>{{IDLH|75694|Fluorotrichloromethane}}</ref>
}} }}
}} }}

'''Trichlorofluoromethane,''' also called '''freon-11''', '''CFC-11''', or '''R-11''', is a ] (CFC). It is a colorless, faintly ethereal, and sweetish-smelling liquid that boils around room temperature.<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> CFC-11 is a Class 1 ]-depleting substance which damages Earth's protective ].<ref name=ods>{{cite web |url=https://www.epa.gov/ozone-layer-protection/international-treaties-and-cooperation-about-protection-stratospheric-ozone |title=International Treaties and Cooperation about the Protection of the Stratospheric Ozone Layer |date=15 July 2015 |publisher=U.S. Environmental Protection Agency |accessdate=2021-02-14}}</ref> R-11 is not flammable at ambient temperature and pressure but it can become very combustible if heated and ignited by a strong ignition source.

== Historical use ==
Trichlorofluoromethane was first widely used as a ]. Because of its high boiling point compared to most refrigerants, it can be used in systems with a low operating pressure, making the mechanical design of such systems less demanding than that of higher-pressure refrigerants ] or ].

Trichlorofluoromethane is used as a reference compound for ] studies.

Trichlorofluoromethane was formerly used in the ] novelty, largely because it has a boiling point of {{convert|23.77|C|F}}. The replacement, ], boiling point {{convert|39.6|C|F}}, requires a higher ambient temperature to work.

Prior to the knowledge of the ozone depletion potential of chlorine in refrigerants and other possible harmful effects on the environment, trichlorofluoromethane was sometimes used as a cleaning/rinsing agent for low-pressure systems.<ref>{{Cite news|url=https://hvacafe.com/r-10-r-11-r-12-gases/|title=R-10 ,R-11 ,R-12 GASES - ملتقى التبريد والتكييف HVACafe|date=2017-05-25|work=ملتقى التبريد والتكييف HVACafe|access-date=2018-05-18|language=ar-AR|archive-date=2018-05-18|archive-url=https://web.archive.org/web/20180518130157/https://hvacafe.com/r-10-r-11-r-12-gases/|url-status=dead}}</ref>

== Production ==
Trichlorofluoromethane can be obtained by reacting ] with ] at 435 °C and 70 atm, producing a mixture of trichlorofluoromethane, ] and ] in a ratio of 77:18:5. The reaction can also be carried out in the presence of ] or ]:<ref name="Katritzky_Gilchrist_Meth-Cohn_Rees">{{citation |author=Katritzky |first1=Alan R. |title=Comprehensive Organic Functional Group Transformations |date=1995 |pages=220 |url=https://books.google.com/books?id=YzBveZGm0GEC&pg=PA220 |publisher=] |isbn=978-0-08-042704-1 |last2=Gilchrist |first2=Thomas L. |last3=Meth-Cohn |first3=Otto |last4=Rees |first4=Charles Wayne |via=]}}<!-- auto-translated by Module:CS1 translator --></ref>
:<chem>CCl4 + HF -> CCl3F + CF4 + CCl2F2</chem>
Trichlorofluoromethane is also formed as one of the byproducts when ] reacts with chlorine and hydrogen fluoride at 500 °C.<ref name="Katritzky_Gilchrist_Meth-Cohn_Rees"/>

] under pressure at 270 °C, ], ], ], ], and ] are also suitable fluorinating agents for carbon tetrachloride.<ref name="Katritzky_Gilchrist_Meth-Cohn_Rees"/><ref name="DOI10.1039/JR9480002188">{{Cite journal |last1=Banks |first1=A.A. |last2=Emeléus |first2=H.J. |last3=Haszeldine |first3=R. N. |last4=Kerrigan |first4=V. |date=December 1948 |title=443. The reaction of bromine trifluoride and iodine pentafluoride with carbon tetrachloride, tetrabromide, and tetraiodide and with tetraiodoethylene. |journal=] |pages=2188–2190 |doi=10.1039/JR9480002188}}</ref>
:<chem>CCl4 + Na2SiF6 -> CCl3F + CCl2F2 + CCl3F + NaCl + SiF4</chem>
:<chem>CCl4 + BrF3 -> BrF + CCl2F2 + CCl3F</chem>

Trichlorofluoromethane was included in the production moratorium in the ] of 1987. It is assigned an ] of 1.0, and U.S. production was ended on January 1, 1996.<ref name=ods />

== Regulatory challenges ==
In 2018, the atmospheric concentration of CFC-11 was noted by researchers to be declining more slowly than expected,<ref>{{Cite journal |url=https://www.nature.com/articles/s41586-018-0106-2 |title=An unexpected and persistent increase in global emissions of ozone-depleting CFC-11 |vauthors=Montzka SA, Dutton GS, Yu P |display-authors=etal |journal=Nature |publisher=Springer Nature |issue=7705 |pages=413–417 |year=2018 |volume=557 |doi=10.1038/s41586-018-0106-2|pmid=29769666 |bibcode=2018Natur.557..413M |s2cid=21705434 |hdl=1983/fd5eaf00-34b1-4689-9f23-410a54182b61 |hdl-access=free }}</ref><ref>{{cite web |url=https://arstechnica.com/science/2018/05/it-seems-someone-is-producing-a-banned-ozone-depleting-chemical-again/ |title=It seems someone is producing a banned ozone-depleting chemical again |last=Johnson |first=Scott |date=5 May 2018 |website=Ars Technica |access-date=18 October 2018 |quote=Decline of CFC-11 has slowed in recent years, pointing to a renewed source}}</ref> and it subsequently emerged that it remains in widespread use as a ] for ] in the construction industry of ].<ref>{{cite web |last1=McGrath |first1=Matt |date=9 July 2018 |title=China 'home foam' gas key to ozone mystery |url=https://www.bbc.co.uk/news/science-environment-44738952 |access-date=9 July 2018 |website=]}}</ref> In 2021, researchers announced that emissions declined by 20,000 U.S. tons from 2018 to 2019, which mostly reversed the previous spike in emissions.<ref>{{cite web |author=Chu |first=Jennifer |date=2021-02-10 |title=Reductions in CFC-11 emissions put ozone recovery back on track |url=https://news.mit.edu/2021/cfc-11-ozone-recovery-0210 |website=] |publisher=}}</ref> In 2022, the ] announced an updated regulation that mandates the recovery and prevention of emissions of CFC-11 blowing agents from foam insulation in demolition waste, which is still emitted at significant scale.<ref>{{Cite web |date=2022-05-04 |title=Proposal for a regulation of the european parliament and the council on substances that deplete the ozone layer |url=https://climate.ec.europa.eu/system/files/2022-04/ods_proposal_en.pdf |access-date=24 November 2022 |website=European Commission |agency=European Commission-DG Environment}}</ref>

==Dangers==
R11, like most ], forms ] when exposed to a naked flame.<ref>{{cite web |last=Orr |first=Bryan |date=4 January 2021 |title=False Alarms: The Legacy of Phosgene Gas |url=https://hvacrschool.com/phosgene-gas/ |access-date=9 May 2022 |website=HVAC School}}</ref>

== Use in Planetary Astrophysics ==
Because trichlorofluoromethane is one of the easiest to detect ] produced by anthropogenic activity, it is has been used in attempting to detect industrial pollution in the atmospheres of earth-like exoplanets.<ref>{{Cite journal |last=Lin |first=Henry W. |last2=Abad |first2=Gonzalo Gonzalez |last3=Loeb |first3=Abraham |date=2014-08-12 |title=Detecting industrial pollution in the atmospheres of earth-like exoplanets |url=https://arxiv.org/abs/1406.3025 |journal=The Astrophysical Journal |volume=792 |issue=1 |pages=L7 |doi=10.1088/2041-8205/792/1/L7 |issn=2041-8213|arxiv=1406.3025 }}</ref>

==Gallery==
<gallery mode="center">
File:CFC-11 mm.png|CFC-11 measured by the Advanced Global Atmospheric Gases Experiment () in the lower atmosphere (]) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in ].
File:Hats_f11_global.png | Hemispheric and Global mean concentrations of CFC-11 (NOAA/ESRL)
Image:AYool CFC-11 history.png | Time-series of atmospheric concentrations of CFC-11 (Walker ''et al.'', 2000)
<!-- Deleted image removed: File:CFC11 inventory 0.png|CFC inventory of 2004 -->
File:GLODAP sea-surf CFC11 AYool.png | "Present day" (1990s) sea surface CFC-11 concentration
File:GLODAP invt CFC11 AYool.png | "Present day" (1990s) CFC-11 oceanic vertical inventory
</gallery>

==See also==
* ]
* ]

==References==
{{Reflist}}

==External links==
*
*
*
* {{Webarchive|url=https://web.archive.org/web/20070609215145/http://www.speclab.com/compound/c75694.htm |date=2007-06-09 }}
* {{ICSC|0047|00}}
* {{PGCH|0290}}
*
*
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*

{{Halomethanes}}
{{fluorine compounds}}

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