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Carbon tetrachloride, also known by many other names (notably, carbon tet in the cleaning industry, and as a Halon or Freon in HVAC, see Table for others) is the organic compound with the formula CCl4. It was formerly widely used in fire extinguishers, as a precursor to refrigerants, and as a cleaning agent. It is a colourless liquid with a "sweet" smell that can be detected at low levels.
Both carbon tetrachloride and tetrachloromethane are acceptable names under IUPAC nomenclature.
The production of carbon tetrachloride has steeply declined since the 1980s due to environmental concerns and the decreased demand for CFCs, which were derived from carbon tetrachloride. In 1992, production in the U.S.-Europe-Japan was estimated at 720,000 tonnes.
Carbon tetrachloride was originally synthesised by the French chemist Henri Victor Regnault in 1839 by the reaction of chloroform with chlorine, but now it is mainly produced from methane:
CH4 + 4 Cl2 → CCl4 + 4 HCl
The production often utilizes by-products of other chlorination reactions, such as from the syntheses of dichloromethane and chloroform. Higher chlorocarbons are also subjected to "chlorinolysis:"
C2Cl6 + Cl2 → 2 CCl4
Prior to the 1950s, carbon tetrachloride was manufactured by the chlorination of carbon disulfide at 105 to 130 °C:
In the carbon tetrachloride molecule, four chlorine atoms are positioned symmetrically as corners in a tetrahedral configuration joined to a central carbon atom by single covalent bonds. Because of this symmetrical geometry, CCl4 is non-polar. Methane gas has the same structure, making carbon tetrachloride a halomethane. As a solvent, it is well suited to dissolving other non-polar compounds, fats and oils. It can also dissolve iodine. It is somewhat volatile, giving off vapors having a smell characteristic of other chlorinated solvents, somewhat similar to the tetrachloroethylene smell reminiscent of dry cleaners' shops.
Solid tetrachloromethane has 2 polymorphs: crystalline II below -47.5 °C (225.6 K) and crystalline I above -47.5 °C.
At -47.3 °C it has monoclinic crystal structure with space group C2/c and lattice constants a = 20.3, b = 11.6, c = 19.9 (.10−1 nm), β = 111°.
In the 20th century, carbon tetrachloride was widely used as a dry cleaning solvent, as a refrigerant, and in lava lamps.
In 1910, The Pyrene Manufacturing Company of Delaware filed a patent for a device using carbon tetrachloride to extinguish fires. The liquid vaporized and extinguished the flames by inhibiting the chemical chain reaction of the combustion process. It was an early 20th century presupposition that the fire suppression ability of carbon tetrachloride relied on oxygen removal. A carbon tetrachloride fire extinguisher was patented in 1911, taking the form of a brass bottle with a hand pump to expel a jet of liquid.Such extinguishers were commonly used until the mid-20th century.
One specialty use of carbon tetrachloride was by stamp collectors to reveal watermarks on the backs of postage stamps without damaging the stamp. A small amount of the liquid was placed on the back of a stamp sitting in a black glass or obsidian tray. The letters or design of the watermark could then be clearly detected.
However, once it became apparent that carbon tetrachloride exposure had severe adverse health effects, safer alternatives such as tetrachloroethylene were found for these applications, and its use in these roles declined from about 1940 onward. The fact that high temperatures cause it to react to produce phosgene made it especially hazardous when used against fires. This reaction also caused a rapid depletion of oxygen. Carbon tetrachloride persisted as a pesticide to kill insects in stored grain, but in 1970, it was banned in consumer products in the United States.
Prior to the Montreal Protocol, large quantities of carbon tetrachloride were used to produce the freon refrigerants R-11 (trichlorofluoromethane) and R-12 (dichlorodifluoromethane). However, these refrigerants are now believed to play a role in ozone depletion and have been phased out. Carbon tetrachloride is still used to manufacture less destructive refrigerants. Carbon tetrachloride has also been used in the detection of neutrinos.
Carbon tetrachloride is one of the most potent hepatotoxins (toxic to the liver), and is widely used in scientific research to evaluate hepatoprotective agents.
Carbon tetrachloride has practically no flammability at lower temperatures. Under high temperatures in air, it forms poisonous phosgene.
Because it has no C-H bonds, carbon tetrachloride does not easily undergo free-radical reactions. Hence, it is a useful solvent for halogenations either by the elemental halogen, or by a halogenation reagent such as N-bromosuccinimide.
In organic chemistry, carbon tetrachloride serves as a source of chlorine in the Appel reaction.
It is used as a solvent in synthetic chemistry research, but because of its adverse health effects, it is no longer commonly used, and chemists generally try to replace it with other solvents. It is sometimes useful as a solvent for infrared spectroscopy, because there are no significant absorption bands > 1600 cm−1. Because carbon tetrachloride does not have any hydrogen atoms, it was historically used in proton NMR spectroscopy. However, carbon tetrachloride is toxic, and its dissolving power is low. Its use has been largely superseded by deuterated solvents. Use of carbon tetrachloride in determination of oil has been replaced by various other solvents
Exposure to high concentrations of carbon tetrachloride (including vapor) can affect the central nervous system, degenerate the liverand kidneys and may result (after prolonged exposure) in coma and even death. Chronic exposure to carbon tetrachloride can cause liver[13][14] and kidney damage and could result in cancer. More information can be found in Material safety data sheets.
In 2008, a study of common cleaning products found the presence of carbon tetrachloride in "very high concentrations" (up to 101 mg m−3) as a result of manufacturers' mixing of surfactants or soap with sodium hypochlorite (bleach).
Carbon tetrachloride is also both ozone-depleting and a greenhouse gas. However, since 1992 its atmospheric concentrations have been in decline for the reasons described above (see also the atmospheric time-series figure). CCl4 has an atmospheric lifetime of 85 years
http://en.wikipedia.org/wiki/Carbon_tetrachloride
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