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Trichlorofluoromethane, also called freon-11, CFC-11, or R-11, is a
chlorofluorocarbon Chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) are fully or partly Halogenation, halogenated hydrocarbons that contain carbon (C), hydrogen (H), chlorine (Cl), and fluorine (F). They are produced as volatility (chemistry), volat ...
(CFC). It is a colorless, faintly ethereal, and sweetish-smelling liquid that boils around room temperature. CFC-11 is a Class 1
ozone Ozone () (or trioxygen) is an Inorganic compound, inorganic molecule with the chemical formula . It is a pale blue gas with a distinctively pungent smell. It is an allotrope of oxygen that is much less stable than the diatomic allotrope , break ...
-depleting substance which damages Earth's protective stratospheric ozone layer. 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 A refrigerant is a working fluid used in the cooling, heating, or reverse cooling/heating cycles of air conditioning systems and heat pumps, where they undergo a repeated phase transition from a liquid to a gas and back again. Refrigerants are ...
. 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 R-12 or 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 . The replacement,
dichloromethane Dichloromethane (DCM, methylene chloride, or methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with ...
, boiling point , 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.


Production

Trichlorofluoromethane can be obtained by reacting
carbon tetrachloride Carbon tetrachloride, also known by many other names (such as carbon tet for short and tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC), is a chemical compound with the chemical formula CCl4. It is a n ...
with
hydrogen fluoride Hydrogen fluoride (fluorane) is an Inorganic chemistry, inorganic compound with chemical formula . It is a very poisonous, colorless gas or liquid that dissolves in water to yield hydrofluoric acid. It is the principal industrial source of fluori ...
at 435 °C and 70 atm, producing a mixture of trichlorofluoromethane, tetrafluoromethane and
dichlorodifluoromethane Dichlorodifluoromethane (R-12) is a colorless gas popularly known by the genericized brand name Freon (as Freon-12). It is a chlorofluorocarbon halomethane (CFC) used as a refrigerant and aerosol spray propellant. In compliance with the Montreal ...
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: : Trichlorofluoromethane is also formed as one of the byproducts when
graphite Graphite () is a Crystallinity, crystalline allotrope (form) of the element carbon. It consists of many stacked Layered materials, layers of graphene, typically in excess of hundreds of layers. Graphite occurs naturally and is the most stable ...
reacts with chlorine and hydrogen fluoride at 500 °C. Sodium hexafluorosilicate under pressure at 270 °C, titanium(IV) fluoride, chlorine trifluoride,
cobalt(III) fluoride Cobalt(III) fluoride is the inorganic compound with the formula . Hydrates are also known. The anhydrous compound is a hygroscopic brown solid. It is used to synthesize organofluorine compounds. The related cobalt(III) chloride is also known b ...
, iodine pentafluoride, and bromine trifluoride are also suitable fluorinating agents for carbon tetrachloride. : : Trichlorofluoromethane was included in the production moratorium in the
Montreal Protocol The Montreal Protocol on Substances That Deplete the Ozone Layer is an international treaty designed to protect the ozone layer by phasing out the production of numerous substances that are responsible for ozone depletion. It was agreed on 16 ...
of 1987. It is assigned an
ozone depletion potential The ozone depletion potential (ODP) of a chemical compound is the relative amount of degradation to the ozone layer it can cause, with trichlorofluoromethane (R-11 or CFC-11) being fixed at an ODP of 1.0. Chlorodifluoromethane (R-22), for examp ...
of 1.0, and U.S. production was ended on January 1, 1996.


Regulatory challenges

In 2018, the atmospheric concentration of CFC-11 was noted by researchers to be declining more slowly than expected, and it subsequently emerged that it remains in widespread use as a
blowing agent A blowing agent is a substance which is capable of producing a cellular structure via a foaming process in a variety of materials that undergo hardening or phase transition, such as polymers, plastics, and metals. They are typically applied whe ...
for polyurethane foam insulation in the construction industry of
China China, officially the People's Republic of China (PRC), is a country in East Asia. With population of China, a population exceeding 1.4 billion, it is the list of countries by population (United Nations), second-most populous country after ...
. 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. In 2022, the
European Commission The European Commission (EC) is the primary Executive (government), executive arm of the European Union (EU). It operates as a cabinet government, with a number of European Commissioner, members of the Commission (directorial system, informall ...
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.


Dangers

R11, like most
chlorofluorocarbons Chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) are fully or partly halogenated hydrocarbons that contain carbon (C), hydrogen (H), chlorine (Cl), and fluorine (F). They are produced as volatile derivatives of methane, ethane, ...
, forms phosgene gas when exposed to a naked flame.


Use in Planetary Astrophysics

Because trichlorofluoromethane is one of the easiest to detect
chlorofluorocarbons Chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) are fully or partly halogenated hydrocarbons that contain carbon (C), hydrogen (H), chlorine (Cl), and fluorine (F). They are produced as volatile derivatives of methane, ethane, ...
produced by anthropogenic activity, it has been used in attempting to detect industrial pollution in the atmospheres of earth-like exoplanets.


Gallery

File:CFC-11 mm.png, CFC-11 measured by the Advanced Global Atmospheric Gases Experiment
AGAGE
in the lower atmosphere (
troposphere The troposphere is the lowest layer of the atmosphere of Earth. It contains 80% of the total mass of the Atmosphere, planetary atmosphere and 99% of the total mass of water vapor and aerosols, and is where most weather phenomena occur. From the ...
) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in 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


See also

*
List of refrigerants This is a list of refrigerants, sorted by their ASHRAE-designated numbers, commonly known as R numbers. Many modern refrigerants are human-made halogenated gases, especially fluorinated gases and chlorinated gases, that are frequently referred ...
* IPCC list of greenhouse gases


References


External links


CFC-11 NOAA/ESRL Global measurements

Public health goal for trichlorofluoromethane in drinking water

Names at webbook.nist.gov


* *
Phase change data at webbook.nist.gov





materialsproject.org
{{fluorine compounds Halomethanes Chlorofluorocarbons Refrigerants Greenhouse gases Ozone-depleting chemical substances Chlorofluoroalkanes