Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Trichlorofluoromethane: Difference between pages

{{Short description|A type of chlorofluorocarbon}}

{{update|date=October 2023}}

| Watchedfields = changed

| verifiedrevid = 470613490

| 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}}

| CASNo_Ref = {{cascite|correct|CAS}}

| EINECS = 200-892-3

| PubChem = 6389

| ChEBI_Ref = {{ebicite|correct|EBI}}

| UNII_Ref = {{fdacite|correct|FDA}}

| 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/cm³

| 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⁻¹ K⁻¹}} (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/m³)<ref name=PGCH>{{PGCH|0290}}</ref>

| IDLH = 2000 ppm<ref name=PGCH/>

| REL = C 1000 ppm (5600 mg/m³)<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> 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 [[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|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 [[carbon tetrachloride]] with [[hydrogen fluoride]] at 435 °C and 70 atm, producing a mixture of trichlorofluoromethane, [[tetrafluoromethane]] and [[dichlorodifluoromethane]] in a ratio of 77:18:5. The reaction can also be carried out in the presence of [[antimony(III) chloride]] or [[antimony(V) chloride]]:<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=[[Elsevier]] |isbn=978-0-08-042704-1 |last2=Gilchrist |first2=Thomas L. |last3=Meth-Cohn |first3=Otto |last4=Rees |first4=Charles Wayne |via=[[Google Books]]}}<!-- auto-translated by Module:CS1 translator --></ref>

:<chem>CCl4 + HF -> CCl3F + CF4 + CCl2F2</chem>

Trichlorofluoromethane is also formed as one of the byproducts when [[graphite]] reacts with chlorine and hydrogen fluoride at 500 °C.<ref name="Katritzky_Gilchrist_Meth-Cohn_Rees"/>

[[Sodium hexafluorosilicate]] under pressure at 270 °C, [[titanium(IV) fluoride]], [[chlorine trifluoride]], [[cobalt(III) fluoride]], [[iodine pentafluoride]], and [[bromine trifluoride]] 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=[[Journal of the Chemical Society]] |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 [[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 |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 [[blowing agent]] for [[polyurethane#Production|polyurethane foam insulation]] in the construction industry of [[China]].<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=[[BBC News]]}}</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=[[MIT News]] |publisher=}}</ref> In 2022, the [[European Commission]] 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 [[Chlorofluorocarbon|chlorofluorocarbons]], forms [[Phosgene|phosgene gas]] 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>

==Gallery==

<gallery mode="center">

File:CFC-11 mm.png|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)

<!-- 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==

* [[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] {{Webarchive|url=https://web.archive.org/web/20070609215145/http://www.speclab.com/compound/c75694.htm |date=2007-06-09 }}

* {{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]]

[[Category:Ozone-depleting chemical substances]]