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Dichlorodifluoromethane (R-12) is a colorless gas popularly known by the genericized brand name Freon (as Freon-12). It 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 ...
halomethane Halomethane compounds are derivatives of methane () with one or more of the hydrogen atoms replaced with halogen atoms (Fluorine, F, Chlorine, Cl, Bromine, Br, or Iodine, I). Halomethanes are both naturally occurring, especially in marine environm ...
(CFC) 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 ...
and aerosol spray propellant. In compliance with 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 ...
, its manufacture was banned in developed countries (non-article 5 countries) in 1996, and in developing countries (Article 5 countries) in 2010 out of concerns about its damaging effect on the
ozone layer The ozone layer or ozone shield is a region of Earth's stratosphere that absorption (electromagnetic radiation), absorbs most of the Sun's ultraviolet radiation. It contains a high concentration of ozone (O3) in relation to other parts of the a ...
. Its only allowed usage is as a
fire retardant A fire retardant is a substance that is used to slow down or stop the spread of fire or reduce its intensity. This is commonly accomplished by chemical reactions that reduce the flammability of fuels or delay their combustion. Fire retardants ...
in submarines and aircraft. It is
soluble In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solubi ...
in many organic
solvents A solvent (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ...
. R-12 cylinders are colored white.


Preparation

It can be prepared 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 ...
in the presence of a
catalytic Catalysis () is the increase in reaction rate, rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst ...
amount of
antimony pentachloride Antimony pentachloride is a chemical compound with the formula SbCl5. It is a colourless oil, but typical samples are yellowish due to dissolved chlorine. Owing to its tendency to hydrolyse to hydrochloric acid, SbCl5 is a highly corrosive subs ...
: :CCl4 + 2HF CCl2F2 + 2HCl This reaction can also produce
trichlorofluoromethane 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. CFC-11 is a Class 1 ozone-depleting substance w ...
(CCl3F), chlorotrifluoromethane (CClF3) and tetrafluoromethane (CF4).


History

Charles F. Kettering Charles Franklin Kettering (August 29, 1876 – November 25, 1958) sometimes known as Charles Fredrick Kettering was an American inventor, engineer, businessman, and the holder of 186 patents. For the list of patents issued to Kettering, see, Le ...
, vice president of General Motors Research Corporation, was seeking a refrigerant replacement that would be colorless, odorless, tasteless, nontoxic, and nonflammable. He assembled a team that included Thomas Midgley Jr., Albert Leon Henne, and Robert McNary. From 1930 to 1935, they developed dichlorodifluoromethane (CCl2F2 or R12),
trichlorofluoromethane 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. CFC-11 is a Class 1 ozone-depleting substance w ...
(CCl3F or R11),
chlorodifluoromethane Chlorodifluoromethane or difluoromonochloromethane is a hydrochlorofluorocarbon (HCFC). This colorless gas is better known as HCFC-22, or R-22, or . It was commonly used as a propellant and refrigerant. These applications were phased out under ...
(CHClF2 or R22), trichlorotrifluoroethane (CCl2FCClF2 or R113), and dichlorotetrafluoroethane (CClF2CClF2 or R114), through Kinetic Chemicals which was a joint venture between
DuPont Dupont, DuPont, Du Pont, duPont, or du Pont may refer to: People * Dupont (surname) Dupont, also spelled as DuPont, duPont, Du Pont, or du Pont is a French surname meaning "of the bridge", historically indicating that the holder of the surname re ...
and
General Motors General Motors Company (GM) is an American Multinational corporation, multinational Automotive industry, automotive manufacturing company headquartered in Detroit, Michigan, United States. The company is most known for owning and manufacturing f ...
.


Use as an aerosol

The use of chlorofluorocarbons as aerosols in medicine, such as USP-approved
salbutamol Salbutamol, also known as albuterol and sold under the brand name Ventolin among others, is a medication that opens up the medium and large airways in the lungs. It is a short-acting β2 adrenergic receptor agonist that causes relaxation of ...
, has been phased out by the
U.S. Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...
. A different propellant known as
hydrofluoroalkane Organofluorine chemistry describes the chemistry of organofluorine compounds, organic compounds that contain a carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from Lipophobicity, oil and hydrophobe, water repell ...
, or HFA, which was not known to harm the environment, was chosen to replace it. That being said it still listed on the FDA's approved food additive list.


Environmental Effects

R-12 has the highest ozone depletion potential among chlorocarbons due to the presence of 2 chlorine atoms in the molecule. R-12 also has intense global warming potential (GWP) with the 20yr, 100yr and 500yr GWP being 11400, 11200 and 5100 times greater than .


Retrofitting

R-12 was used in most refrigeration and vehicle air conditioning applications prior to 1994 before being replaced by
1,1,1,2-tetrafluoroethane 1,1,1,2-Tetrafluoroethane (also known as norflurane ( INN), R-134a, Klea 134a, Freon 134a, Forane 134a, Genetron 134a, Green Gas, Florasol 134a, Suva 134a, HFA-134a, or HFC-134a) is a hydrofluorocarbon (HFC) and haloalkane refrigerant with th ...
(R-134a), which has an insignificant
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 ...
. Automobile manufacturers began phasing in R-134a around 1993. When older units leak or require repair involving removal of the refrigerant,
retrofit Retrofitting is the addition of new technology or features to older systems. Retrofits can happen for a number of reasons, for example with big capital expenditures like naval vessels, military equipment or manufacturing plants, businesses or go ...
ment to a refrigerant other than R-12 (most commonly R-134a) is required in some jurisdictions. The United States does not require such conversion. Retrofitment requires a system flush and a new filter/dryer or accumulator, and may also involve the installation of new seals and/or hoses made of materials compatible with the refrigerant being installed. Mineral oil used with R-12 is not compatible with R-134a. Some oils designed for conversion to R-134a are advertised as compatible with residual R-12 mineral oil. Illegal replacements for R-12 include highly flammable hydrocarbon blends such as HC-12a, the flammability of which has caused injuries and deaths.


Dangers

Aside from its environmental impacts, R12, like most chlorofluoroalkanes, forms
phosgene Phosgene is an organic chemical compound with the formula . It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of chemically as the double acyl chloride analog of ...
gas when exposed to a naked flame.


Properties

Table of thermal and physical properties of saturated liquid refrigerant 12:


Gallery

File:Monthly means of CFC-12.png, CFC-12 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 f12 global.png, Hemispheric and global mean CFC-12 concentrations (NOAA/ESRL) Image:AYool CFC-12 history.png, Time-series of atmospheric concentrations of CFC-12 (Walker ''et al.'', 2000) File:GLODAP sea-surf CFC12 AYool.png, 1990s sea surface CFC-12 concentration File:GLODAP invt CFC12 AYool.png, 1990s CFC-12 oceanic vertical inventory File:CFC-12 CFC-11 H-1211 SF6 vertical profiles Fairbanks Alaska 1976.png, CFC-12, CFC-11, H-1211 and SF6 vertical profiles


References


External links


NOAA/ESRL CFC-12 global measurements
*






IR absorption spectra


{{Authority control Halomethanes Chlorofluorocarbons Greenhouse gases Ozone-depleting chemical substances Refrigerants Belgian inventions Chlorofluoroalkanes