View source for Trichlorofluoromethane

{{Short description|A type of chlorofluorocarbon}}
{{update|date=May 2019}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 470613490
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1 = Trichlorofluoromethane-2D.svg
| ImageSizeL1 =
| ImageFileR1 = Trichlorofluoromethane-3D-vdW.png
| 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) -->
| 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
| data page pagename = none
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6149
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 348290
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/CCl3F/c2-1(3,4)5
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CYRMSUTZVYGINF-UHFFFAOYSA-N
| SMILES1 = ClC(Cl)(Cl)F
| CASNo = 75-69-4
| CASNo_Ref = {{cascite|correct|CAS}}
| EINECS = 200-892-3
| PubChem = 6389
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 48236
| SMILES = C(F)(Cl)(Cl)Cl
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 990TYB331R
| InChI = 1/CCl3F/c2-1(3,4)5
| RTECS = PB6125000
  }}
|Section2={{Chembox Properties
| C=1 | Cl=3 | F=1
| Appearance = Colorless liquid/gas
| Odor = nearly odorless<ref name=PGCH/>
| Density = 1.494 g/cm<sup>3</sup>
| MeltingPtC = -110.48
| BoilingPtC = 23.77
| Solubility = 1.1 g/L (at 20 °C)
| LogP = 2.53
| 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
| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0047.htm ICSC 0047]
| MainHazards = 
| FlashPt = Non-flammable
| GHSSignalWord = warning
| GHSPictograms = {{GHS07}}
| HPhrases = {{HPhrases|H420}}
| 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 [[chlorofluorocarbon]] (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 ozone-depleting substance which damages Earth's protective [[ozone layer|stratospheric ozone layer]].<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>

== Historical use ==
Trichlorofluoromethane was first widely used as a [[refrigerant]].  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 [[Dichlorodifluoromethane|R-12]] or [[Chlorodifluoromethane|R-22]].

Trichlorofluoromethane is used as a reference compound for [[fluorine-19 NMR]] studies.

Trichlorofluoromethane was formerly used in the [[drinking bird]] novelty, largely because it has a boiling point of {{convert|23.77|C|F}}. The replacement, [[dichloromethane]], 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}}</ref>

== Production moratorium ==
Trichlorofluoromethane was included in the production moratorium agreed in the [[Montreal Protocol]] of 1987.  It is assigned an  [[ozone depletion potential]] 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 |author=Montzka, S.A.; Dutton, G.S.; 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 [[blowing agent]] for [[polyurethane#Production|polyurethane foam insulation]] in the construction industry of [[China]].<ref>{{cite web |last1=McGrath |first1=Matt |title=China 'home foam' gas key to ozone mystery |url=https://www.bbc.co.uk/news/science-environment-44738952 |website=BBC News |access-date=9 July 2018 |date=9 July 2018}}</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 |url=https://news.mit.edu/2021/cfc-11-ozone-recovery-0210 |title=Reductions in CFC-11 emissions put ozone recovery back on track |author=Jennifer Chu |publisher=MIT News |date=2021-02-10}}</ref>

==Gallery==
<gallery class="center">
File:CFC-11 mm.png|thumb|CFC-11 measured by the Advanced Global Atmospheric Gases Experiment ([http://agage.mit.edu/ AGAGE]) in the lower atmosphere ([[troposphere]]) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in [[Parts-per notation|parts-per-trillion]].
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)
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==
* [[List of refrigerants]]
* [[IPCC list of greenhouse gases]]

==References==
{{Reflist}}

==External links==
* [http://www.esrl.noaa.gov/gmd/hats/combined/CFC11.html CFC-11 NOAA/ESRL Global measurements]
* [https://web.archive.org/web/20070624181441/http://www.oehha.ca.gov/water/phg/pdf/fc_11_c.pdf Public health goal for trichlorofluoromethane in drinking water]
* [http://webbook.nist.gov/cgi/cbook.cgi?ID=75-69-4&Units=SI Names at webbook.nist.gov]
* [http://www.speclab.com/compound/c75694.htm Data sheet at speclab.com]
* {{ICSC|0047|00}}
* {{PGCH|0290}}
* [http://webbook.nist.gov/cgi/cbook.cgi?ID=C75694&Units=SI&Mask=4#Thermo-Phase Phase change data at webbook.nist.gov]
* [http://www.chemnet.ru/rus/handbook/ivtan/221.html Thermochemistry data at chemnet.ru]
* [http://chemsub.online.fr/name/trichlorofluoromethane.html ChemSub Online: Trichlorofluoromethane - CFC-11]
* [https://materialsproject.org/materials/mp-23071/ materialsproject.org]

{{Halomethanes}}
{{fluorine compounds}}

[[Category:Halomethanes]]
[[Category:Chlorofluorocarbons]]
[[Category:Refrigerants]]
[[Category:Greenhouse gases]]