Carbon tetrachloride

1.831 g·cm−3 at −186 °C (solid)1.809 g·cm−3 at −80 °C (solid)Carbon tetrachloride, also known by many other names (the most notable being 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 chemical formula CCl4. It is a colourless liquid with a 'sweet' smell that can be detected at low levels. It has practically no flammability at lower temperatures. It was formerly widely used in fire extinguishers, as a precursor to refrigerants and as a cleaning agent, but has since been phased out because of toxicity and safety concerns. Exposure to high concentrations of carbon tetrachloride (including vapor) can affect the central nervous system, degenerate the liver and kidneys. Prolonged exposure can be fatal. Carbon tetrachloride, also known by many other names (the most notable being 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 chemical formula CCl4. It is a colourless liquid with a 'sweet' smell that can be detected at low levels. It has practically no flammability at lower temperatures. It was formerly widely used in fire extinguishers, as a precursor to refrigerants and as a cleaning agent, but has since been phased out because of toxicity and safety concerns. Exposure to high concentrations of carbon tetrachloride (including vapor) can affect the central nervous system, degenerate the liver and kidneys. Prolonged exposure can be fatal. Carbon tetrachloride was originally synthesized by the French chemist Henri Victor Regnault in 1839 by the reaction of chloroform with chlorine, but now it is mainly produced from methane: 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': Prior to the 1950s, carbon tetrachloride was manufactured by the chlorination of carbon disulfide at 105 to 130 °C: 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. 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 with a smell characteristic of other chlorinated solvents, somewhat similar to the tetrachloroethylene smell reminiscent of dry cleaners' shops. Solid tetrachloromethane has two 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°. With a specific gravity greater than 1, carbon tetrachloride will be present as a dense nonaqueous phase liquid if sufficient quantities are spilled in the environment. In organic chemistry, carbon tetrachloride serves as a source of chlorine in the Appel reaction.