Tetrachloro-1,1-difluoroethane

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Tetrachloro-1,1-difluoroethane
1,1,1,2-Tetrachloro-2,2-difluoroethane.png
1,1,1,2-Tetrachloro-2,2-difluoroethane-3D-balls.png
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.850 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-934-0
PubChem CID
RTECS number
  • KI1425000
UNII
UN number 1078
  • InChI=1S/C2Cl4F2/c3-1(4,5)2(6,7)8
    Key: SLGOCMATMKJJCE-UHFFFAOYSA-N
  • C(C(Cl)(Cl)Cl)(F)(F)Cl
Properties
C2Cl4F2
Molar mass 203.82 g·mol−1
Density 1.65 g/mL [1]
Melting point 40.6 °C (105.1 °F; 313.8 K) [2]
Boiling point 91 °C (196 °F; 364 K) [2]
Related compounds
Related compounds
CFC-112
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetrachloro-1,1-difluoroethane or 1,1,1,2-tetrachloro-2,2-difluoroethane, Freon 112a, R-112a, or CFC-112a is an asymmetric chlorofluorocarbon isomer of tetrachloro-1,1-difluoroethane with formula CClF2CCl3. It contains ethane substituted by four chlorine atoms and two fluorine atoms. With a boiling point of 91.5°C it is the freon with second highest boiling point.

Contents

Tetrachlorodifluoroethane as made is a mixture of the symmetrical and asymmetric isomers. [3]

Preparation

Tetrachloro-1,1-difluoroethane can be prepared in 40% yield by reacting 1,1,2-trichloro-1,2,2-trifluoroethane (freon 113) with aluminium chloride at 60°C. [2]

It can also be made in a reaction with hydrogen fluoride with hexachloroethane or tetrachloroethane with extra chlorine. This reaction occurs with an aluminium fluoride catalyst at 400°C. unsymmetrical trichlorotrifluoroethane (CCl2FCClF2) is also produced along with other chlorofluorocarbons. Separation of the symmetrical and unsymmetrical isomer is difficult. [4]

Properties

Tetrachloro-1,1-difluoroethane is non-combustible.

It has a critical pressure of 4.83 MPa and a critical temperature of 279.2°. At the critical point the density is 0.754 g/cc. [5]

Tetrachloro-1,1-difluoroethane in liquid form is miscible with perfluorocarbons. [6]

Reactions

Tetrachloro-1,1-difluoroethane reacts with zinc in ethanol at 60°C to yield unsymmetrical dichlordifluoroethylene (CCl2=CF2). [7]

Use

Tetrachlorodifluoroethane (mixture of isomers) has been used as a veterinary medicine to treat parasites ( Fasciola hepatica ). [8]

Atmosphere

Tetrachloro-1,1-difluoroethane was first detected in air collected from Cape Grim, Tasmania in the Cape Grim Air Archive, and later from air bubbles in snow from Greenland. The substance made its first appearance around 1965, and increased in level until around 2000. [9] In 2000 Earth's atmosphere contained 0.08 parts per trillion of Freon 112a. [10] Level slightly declined to 0.07 ppt by 2012. [9] Estimated lifetime in the stratosphere is 44 years. [10] By 2014 3,600 tons of Freon 112a had been put into the atmosphere. [9] As of 2023, levels have been rising in the Earth's atmosphere. [11]

As a greenhouse gas its radiative efficiency is 0.25 Wm−2ppb−1. [10]

Related Research Articles

<span class="mw-page-title-main">Chlorofluorocarbon</span> Class of organic compounds commonly used as refrigerants

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 propane.

<span class="mw-page-title-main">Thomas Midgley Jr.</span> American chemist and engineer (1889–1944)

Thomas Midgley Jr. was an American mechanical and chemical engineer. He played a major role in developing leaded gasoline and some of the first chlorofluorocarbons (CFCs), better known in the United States by the brand name Freon; both products were later banned from common use due to their harmful impact on human health and the environment. He was granted more than 100 patents over the course of his career.

Freon is a registered trademark of the Chemours Company and generic descriptor for a number of halocarbon products. They are stable, nonflammable, low toxicity gases or liquids which have generally been used as refrigerants and as aerosol propellants. These include chlorofluorocarbons and hydrofluorocarbons, both of which cause ozone depletion and contribute to global warming. 'Freon' is the brand name for the refrigerants R-12, R-13B1, R-22, R-410A, R-502, and R-503 manufactured by The Chemours Company, and so is not used to label all refrigerants of this type. They emit a strong smell similar to acetone.

<span class="mw-page-title-main">Refrigerant</span> Substance in a refrigeration cycle

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 regulated due to their toxicity, flammability and the contribution of CFC and HCFC refrigerants to ozone depletion and that of HFC refrigerants to climate change.

<span class="mw-page-title-main">Halomethane</span> Halogen compounds derived from methane

Halomethane compounds are derivatives of methane with one or more of the hydrogen atoms replaced with halogen atoms. Halomethanes are both naturally occurring, especially in marine environments, and human-made, most notably as refrigerants, solvents, propellants, and fumigants. Many, including the chlorofluorocarbons, have attracted wide attention because they become active when exposed to ultraviolet light found at high altitudes and destroy the Earth's protective ozone layer.

<span class="mw-page-title-main">Hydrofluorocarbon</span> Synthetic organic compounds

Hydrofluorocarbons (HFCs) are man-made organic compounds that contain fluorine and hydrogen atoms, and are the most common type of organofluorine compounds. Most are gases at room temperature and pressure. They are frequently used in air conditioning and as refrigerants; R-134a (1,1,1,2-tetrafluoroethane) is one of the most commonly used HFC refrigerants. In order to aid the recovery of the stratospheric ozone layer, HFCs were adopted to replace the more potent chlorofluorocarbons (CFCs), which were phased out from use by the Montreal Protocol, and hydrochlorofluorocarbons (HCFCs) which are presently being phased out. HFCs replaced older chlorofluorocarbons such as R-12 and hydrochlorofluorocarbons such as R-21. HFCs are also used in insulating foams, aerosol propellants, as solvents and for fire protection.

<span class="mw-page-title-main">Fluoromethane</span> Chemical compound

Fluoromethane, also known as methyl fluoride, Freon 41, Halocarbon-41 and HFC-41, is a non-toxic, liquefiable, and flammable gas at standard temperature and pressure. It is made of carbon, hydrogen, and fluorine. The name stems from the fact that it is methane (CH4) with a fluorine atom substituted for one of the hydrogen atoms. It is used in semiconductor manufacturing processes as an etching gas in plasma etch reactors.

Dichlorodifluoromethane (R-12) is a colorless gas usually sold under the brand name Freon-12, and a chlorofluorocarbon halomethane (CFC) used as a refrigerant and aerosol spray propellant. In compliance with the Montreal Protocol, its manufacture was banned in developed countries in 1996, and in developing countries in 2010 out of concerns about its damaging effect on the ozone layer. Its only allowed usage is as a fire retardant in submarines and aircraft. It is soluble in many organic solvents. R-12 cylinders are colored white.

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 which damages Earth's protective stratospheric ozone layer.

<span class="mw-page-title-main">1,1-Difluoroethane</span> Chemical compound

1,1-Difluoroethane, or DFE, is an organofluorine compound with the chemical formula C2H4F2. This colorless gas is used as a refrigerant, where it is often listed as R-152a (refrigerant-152a) or HFC-152a (hydrofluorocarbon-152a). It is also used as a propellant for aerosol sprays and in gas duster products. As an alternative to chlorofluorocarbons, it has an ozone depletion potential of zero, a lower global warming potential (124) and a shorter atmospheric lifetime (1.4 years).

<span class="mw-page-title-main">Octafluorocyclobutane</span> Chemical compound

Octafluorocyclobutane, or perfluorocyclobutane, C4F8, is an organofluorine compound which enjoys several niche applications. Octafluorocyclobutane is a colourless gas and shipped as a liquefied gas. It is the perfluorinated analogue of cyclobutane whereby all C–H bonds are replaced with C–F bonds.

1,2-Dichlorotetrafluoroethane, or R-114, also known as cryofluorane (INN), is a chlorofluorocarbon (CFC) with the molecular formula ClF2CCF2Cl. Its primary use has been as a refrigerant. It is a non-flammable gas with a sweetish, chloroform-like odor with the critical point occurring at 145.6 °C and 3.26 MPa. When pressurized or cooled, it is a colorless liquid. It is listed on the Intergovernmental Panel on Climate Change's list of ozone depleting chemicals, and is classified as a Montreal Protocol Class I, group 1 ozone depleting substance.

Chlorotrifluoromethane, R-13, CFC-13, or Freon 13, is a non-flammable, non-corrosive, nontoxic 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 has a high ozone depletion potential, and long atmospheric lifetime. Only a few other greenhouse gases surpass CFC-13 in global warming potential (GWP). The IPCC AR5 reported that CFC-13's atmospheric lifetime was 640 years.

The Vienna Convention for the Protection of the Ozone Layer is a multilateral environmental agreement signed in 1985 that provided frameworks for international reductions in the production of chlorofluorocarbons due to their contribution to the destruction of the ozone layer, resulting in an increased threat of skin cancer.

1,1,2-Trichloro-1,2,2-trifluoroethane, also called trichlorotrifluoroethane or CFC-113, is a chlorofluorocarbon. It has the formula Cl2FC−CClF2. This colorless, volatile liquid is a versatile solvent.

<span class="mw-page-title-main">1-Chloro-1,1-difluoroethane</span> Chemical compound

1-Chloro-1,1-difluoroethane (HCFC-142b) is a haloalkane with the chemical formula CH3CClF2. It belongs to the hydrochlorofluorocarbon (HCFC) family of man-made compounds that contribute significantly to both ozone depletion and global warming when released into the environment. It is primarily used as a refrigerant where it is also known as R-142b and by trade names including Freon-142b.

1,2-Difluoroethane is a saturated hydrofluorocarbon containing an atom of fluorine attached to each of two carbons atoms. The formula can be written CH2FCH2F. It is an isomer of 1,1-difluoroethane. It has a HFC name of HFC-152 with no letter suffix. When cooled to cryogenic temperatures it can have different conformers, gauche and trans. In the liquid form these are about equally abundant and easily interconvert. As a gas it is mostly the gauche form.

<span class="mw-page-title-main">Tetrachloro-1,2-difluoroethane</span> Chemical compound

Tetrachloro-1,2-difluoroethane is a chlorofluorocarbon known as Freon 112, CFC-112 or R-112. It has a symmetrical structure CCl2FCCl2F and so can be called symmetrical tetrachlorodifluoroethane. "Symmetrical" may also be abbreviated to "s-" or "sym-". In contrast an asymmetrical isomer has formula CCl3CClF2.

<span class="mw-page-title-main">1,1-Dichlorotetrafluoroethane</span> Chemical compound

1,1-Dichlorotetrafluoroethane is a chlorofluorocarbon also known as CFC-114a or R114a by American Society of Heating, Refrigerating, and Air Conditioning Engineers. It has two chlorine atoms on one carbon atom and none on the other. It is one of two isomers of dichlorotetrafluoroethane, the other being 1,2-dichlorotetrafluoroethane, also known as CFC-114.

<span class="mw-page-title-main">2-Chloro-1,1-difluoroethylene</span> Chemical compound

2-Chloro-1,1-difluoroethene (also known as R 1122, u-HCFC-1122 or HCFO-1122) is a toxic unsaturated chlorofluorocarbon which can be written as CF2=CHCl. The HCFO portion of the name stands for hydrochlorofluoroolefin. Another constitutional isomer of it, 1-chloro-1,2-difluoroethylene, is known as HCFO-1122a.

References

  1. "CDC - NIOSH Pocket Guide to Chemical Hazards - 1,1,1,2-Tetrachloro-2,2-difluoroethane". www.cdc.gov.
  2. 1 2 3 Miller, William T.; Fager, Edward W.; Griswald, Paul H. (February 1950). "The Rearrangement of Chlorofluorocarbons by Aluminum Chloride 1". Journal of the American Chemical Society. 72 (2): 705–707. doi:10.1021/ja01158a013.
  3. Gallagher, C. H.; Boray, J. C.; Koch, J. H. (June 1965). "Toxicity of Samples of Tetrachlorodifluoroethane". Australian Veterinary Journal. 41 (6): 167–172. doi:10.1111/j.1751-0813.1965.tb01814.x. PMID   14337687.
  4. Vecchio, M; Groppelli, G; Tatlow, J. C. (1 July 1974). "Studies on a vapour-phase process for the manufacture of chlorofluoroethanes". Journal of Fluorine Chemistry. 4 (2): 117–139. doi:10.1016/S0022-1139(00)82507-5.
  5. Bruno, Thomas J. (1990). Spectroscopic Library for Alternative Refrigerant Analysis. U.S. Department of Commerce, National Institute of Standards and Technology. p. 9.
  6. Fowler, R.; Buford III, W.; Hamilton, Jr., J.; Sweet, R.; Weber, C.; Kasper, J.; Litant, I. (March 1947). "Synthesis of Fluorocarbons". Industrial & Engineering Chemistry. 39 (3): 292–298. doi:10.1021/ie50447a612.
  7. Barr (Jr.), John T.; Gibson, J. D. (1950). The Preparation and Reactions of Substituted Polychloro 1,1-difluoroethanes. Carbide and Carbon Chemicals Division, Union Carbide and Carbon Corporation, K-25 Laboratory Division. p. 19.
  8. McKellar, Quintin A.; Kinabo, Ludovick D. B. (1 July 1991). "The pharmacology of flukicidal drugs". British Veterinary Journal. 147 (4): 306–321. doi:10.1016/0007-1935(91)90003-6. ISSN   0007-1935. PMID   1913127.
  9. 1 2 3 Laube, Johannes C.; Newland, Mike J.; Hogan, Christopher; Brenninkmeijer, Carl A. M.; Fraser, Paul J.; Martinerie, Patricia; Oram, David E.; Reeves, Claire E.; Röckmann, Thomas; Schwander, Jakob; Witrant, Emmanuel; Sturges, William T. (April 2014). "Newly detected ozone-depleting substances in the atmosphere" (PDF). Nature Geoscience. 7 (4): 266–269. Bibcode:2014NatGe...7..266L. doi:10.1038/ngeo2109. S2CID   140544959.
  10. 1 2 3 Davis, Maxine E.; Bernard, François; McGillen, Max R.; Fleming, Eric L.; Burkholder, James B. (1 July 2016). "UV and infrared absorption spectra, atmospheric lifetimes, and ozone depletion and global warming potentials for CCl2FCCl2F (CFC-112), CCl3CClF2 (CFC-112a), CCl3CF3 (CFC-113a), and CCl2FCF3; (CFC-114a)". Atmospheric Chemistry and Physics. 16 (12): 8043–8052. Bibcode:2016ACP....16.8043D. doi: 10.5194/acp-16-8043-2016 . hdl: 1983/df193a7b-14de-427c-a539-238701f9e3b3 . S2CID   102078043.
  11. Western, Luke M.; et al. (3 April 2023). "Global increase of ozone-depleting chlorofluorocarbons from 2010 to 2020". Nature Geoscience. 16 (4): 309–313. doi:10.1038/s41561-023-01147-w. hdl: 1983/9e103fef-e61c-49c7-a1a3-902540ec1d7c . S2CID   257941769.

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