Dichlorodifluoromethane (R-12) is a colorless gas usually sold under the
brand name
A brand is a name, term, design, symbol or any other feature that distinguishes one seller's good or service from those of other sellers. Brands are used in business, marketing, and advertising for recognition and, importantly, to create a ...
Freon-12, and a
chlorofluorocarbon
Chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) are fully or partly halogenated hydrocarbons that contain carbon (C), hydrogen (H), chlorine (Cl), and fluorine (F), produced as volatile derivatives of methane, ethane, and pro ...
halomethane Halomethane compounds are derivatives of methane () with one or more of the hydrogen atoms replaced with halogen atoms ( F, Cl, Br, or I). Halomethanes are both naturally occurring, especially in marine environments, and human-made, most notably ...
(CFC) used as a
refrigerant
A refrigerant is a working fluid used in the refrigeration cycle of air conditioning systems and heat pumps where in most cases they undergo a repeated phase transition from a liquid to a gas and back again. Refrigerants are heavily regulate ...
and
aerosol spray propellant. Complying with the
Montreal Protocol
The Montreal Protocol is an international treaty
A treaty is a formal, legally binding written agreement between actors in international law. It is usually made by and between sovereign states, but can include international organization ...
, its manufacture was banned in developed countries (non-article 5 countries) in 1996, and 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 absorbs most of the Sun's ultraviolet radiation. It contains a high concentration of ozone (O3) in relation to other parts of the atmosphere, although still small in rel ...
.
Its only allowed usage is as
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 solub ...
in many
organic
Organic may refer to:
* Organic, of or relating to an organism, a living entity
* Organic, of or relating to an anatomical organ
Chemistry
* Organic matter, matter that has come from a once-living organism, is capable of decay or is the product o ...
solvents
A solvent (s) (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 ...
. R-12 cylinders are colored
white
White is the lightness, lightest color and is achromatic (having no hue). It is the color of objects such as snow, chalk, and milk, and is the opposite of black. White objects fully diffuse reflection, reflect and scattering, scatter all the ...
.
Preparation
It can be prepared by reacting
carbon tetrachloride
Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVACR) is an organic compound with the chemi ...
with
hydrogen fluoride in the presence of a
catalytic
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycl ...
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 subst ...
:
:CCl
4 + 2HF
→ CCl
2F
2 + 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 ...
(CCl
3F),
chlorotrifluoromethane
Chlorotrifluoromethane, R-13, CFC-13, or Freon 13, is a non-flammable, non-corrosive chlorofluorocarbon (CFC) and also a mixed halomethane. It is a man-made substance used primarily as a refrigerant. When released into the environment, CFC-13 h ...
(CClF
3) and
tetrafluoromethane
Tetrafluoromethane, also known as carbon tetrafluoride or R-14, is the simplest perfluorocarbon ( C F4). As its IUPAC name indicates, tetrafluoromethane is the perfluorinated counterpart to the hydrocarbon methane. It can also be classified as a h ...
(CF
4).
History
Charles (Boss) Kettering, 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
Albert Leon Henne (1901–1967) was an American chemist known for his work on refrigerants.Goldwhite, Harold (2021) Midgley Introduces Dichlorodifluoromethane as a Refrigerant Gas. ''Salem Press Encyclopedia''
Henne was born in Brussels, Belgium ...
, and Robert McNary. From 1930 to 1935, they developed dichlorodifluoromethane (CCl
2F
2 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 ...
(CCl
3F 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 ...
(CHClF
2 or R22),
trichlorotrifluoroethane Trichlorotrifluoroethane may refer to:
* 1,1,1-Trichloro-2,2,2-trifluoroethane
* 1,1,2-Trichloro-1,2,2-trifluoroethane
1,1,2-Trichloro-1,2,2-trifluoroethane, also called trichlorotrifluoroethane or CFC-113, is a chlorofluorocarbon. It has the form ...
(CCl
2FCClF
2 or R113), and
dichlorotetrafluoroethane
1,2-Dichlorotetrafluoroethane, or R-114, also known as cryofluorane (INN), is a chlorofluorocarbon (CFC) with the molecular formula ClFCCFCl. Its primary use has been as a refrigerant. It is a non-flammable gas with a sweetish, chloroform-like ...
(CClF
2CClF
2 or R114), through
Kinetic Chemicals
Polytetrafluoroethylene (PTFE) is a synthetic fluoropolymer of tetrafluoroethylene that has numerous applications. It is one of the best-known and widely applied PFAS. The commonly known brand name of PTFE-based composition is Teflon by Chemou ...
which was a joint venture between
DuPont and
General Motors.
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 which works by causing rel ...
, 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 s ...
. A different propellant known as
hydrofluoroalkane
Organofluorine chemistry describes the chemistry of the organofluorines, organic compounds that contain the carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, re ...
, or HFA, which was not known to harm the environment, was chosen to replace it.
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, Freon 134a, Forane 134a, Genetron 134a, Green Gas, Florasol 134a, Suva 134a, or HFC-134a) is a hydrofluorocarbon (HFC) and haloalkane refrigerant with thermodynamic properties ...
(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 started using R-134a instead of R-12 in 1992–1994. 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 which has a global warming potential 3,400 times that of carbon dioxide) is required in some jurisdictions. The United States does not require automobile owners to retrofit their systems; however, taxes on ozone-depleting chemicals coupled with the relative scarcity of the original refrigerants on the open market make retrofitting the only economical option. Retrofitment requires 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. Another replacement for R-12 is the highly flammable, but truly drop-in
HC-12a HC-12a, also called ES-12a, OZ-12a, DURACOOL 12a and Hydrocarbon Blend B, is a "drop-in" replacement refrigerant for Freon-12 and to a lesser extent, R-134a. HC-12a is a mixture of hydrocarbons, specifically propane (R-290) and isobutane (R-600a), ...
, whose flammability has led to injuries and deaths.
Dangers
Aside from its immense environmental impacts, R12, like most chlorofluoroalkanes, forms
phosgene
Phosgene is the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. Phosgene is a valued and important industrial building block, es ...
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 first and lowest layer of the atmosphere of the Earth, and contains 75% of the total mass of the planetary atmosphere, 99% of the total mass of water vapour and aerosols, and is where most weather phenomena occur. From ...
) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in parts-per-trillion
In science and engineering, the parts-per notation is a set of pseudo-units to describe small values of miscellaneous dimensionless quantities, e.g. mole fraction or mass fraction. Since these fractions are quantity-per-quantity measures, they ...
.
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
Ozone depletion
Greenhouse gases
Refrigerants