- Carbon tetrachloride
Carbon tetrachloride Identifiers CAS number PubChem ChemSpider UNII EC number UN number 1846 KEGG ChEBI ChEMBL RTECS number FG4900000 Jmol-3D images Image 1 Properties Molecular formula CCl4 Molar mass 153.82 g mol−1 Appearance colourless liquid
Density 1.5867 g cm−3 (liquid)
1.831 g cm−3 at −186 °C (solid)
1.809 g cm−3 at −80 °C (solid)
-22.92 °C, 250 K, -9 °F
76.72 °C, 350 K, 170 °F
Solubility in water 785–800 mg/L at 25 °C Solubility soluble in alcohol, ether, chloroform, benzene log P 2.64 Vapor pressure 11.94 kPa at 20 °C Refractive index (nD) 1.4601 Structure Crystal structure Monoclinic Molecular shape Tetrahedral Hazards MSDS External MSDS EU Index 602-008-00-5 EU classification Carc. Cat. 3
Dangerous for the environment (N)
R-phrases , , , , S-phrases , , , , , NFPA 704 Flash point Not flammable Autoignition
982 °C LD50 2350 mg/kg Related compounds Other cations Silicon tetrachloride
Related chloromethanes Chloromethane
Related compounds Tetrafluoromethane
Supplementary data page Structure and
n, εr, etc. Thermodynamic
Solid, liquid, gas
Spectral data UV, IR, NMR, MS (what is: /?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Carbon tetrachloride, also known by many other names (the most notable being carbon tet in the cleaning industry, and 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.
History and synthesis
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.
- CH4 + 4 Cl2 → CCl4 + 4 HCl
- C2Cl6 + Cl2 → 2 CCl4
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.
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 1910, The Pyrene Manufacturing Company of Delaware filed a patent for a 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.) In 1911, they patented a small, portable extinguisher that used the chemical. This consisted of a brass bottle with an integrated handpump that was used to expel a jet of liquid toward the fire. As the container was unpressurized, it could be easily refilled after use. Carbon tetrachloride was suitable for liquid and electrical fires and the extinguisers were often fitted to motor vehicles.
One specialty use of carbon tetrachloride was in Stamp collecting, to reveal Watermarks on postage stamps without damaging them. 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 seen.
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 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 (these conditions are known as Wohl-Ziegler Bromination).
It is used as a solvent in synthetic chemistry research, but, because of its adverse health effects, it is no longer commonly used, and in general chemists 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, such as tetrachloroethylene.
Exposure to high concentrations of carbon tetrachloride (including vapor) can affect the central nervous system, degenerate the liver and kidneys and may result (after prolonged exposure) in coma and even death. Chronic exposure to carbon tetrachloride can cause liver 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).
Like many other volatile substances, carbon tetrachloride is prone to misuse by inhalation, due to its possible depressant and/or dissociative effect upon the central nervous system. Use of carbon tetrachloride in this manner presents serious health risks, and may result in toxic effects described above.
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.
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- Environmental health criteria for carbon tetrachloride
- Carbon tetrachloride MSDS at Hazardous Chemical Database
- MSDS at Oxford University
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Halomethanes Monosubstituted Disubstituted Trisubstituted Inorganic carbon compounds
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Look at other dictionaries:
carbon tetrachloride — n a colorless nonflammable toxic carcinogenic liquid CCl4 that has an odor resembling that of chloroform and is used as a solvent and a refrigerant called also tetrachloromethane * * * a pungent volatile fluid used as a dry cleaner. When inhaled… … Medical dictionary
carbon tetrachloride — n. a nonflammable, colorless, poisonous liquid, CCl4, used in making refrigerants, as a solvent for fats and oils, etc … English World dictionary
carbon tetrachloride — a colorless, nonflammable, vaporous, toxic liquid, CCl4, usually produced by the reaction of chlorine with carbon disulfide, methane, or other carbon containing compounds: used mainly as a refrigerant, fire extinguisher, cleaning fluid, solvent,… … Universalium
carbon tetrachloride — An extremely toxic solvent, possibly causing liver cancer and severe liver damage, even from small exposures. Exposure to carbon tetrachloride can be fatal by skin absorption or inhalation … Glossary of Art Terms
carbon tetrachloride — tetrachlormetanas statusas T sritis chemija formulė CCl₄ atitikmenys: angl. carbon tetrachloride; tetrachloromethane rus. тетрахлорметан; четыреххлористый углерод ryšiai: sinonimas – anglies tetrachloridas … Chemijos terminų aiškinamasis žodynas
carbon tetrachloride — noun a colorless nonflammable liquid used as a solvent for fats and oils; because of its toxicity its use as a cleaning fluid or fire extinguisher has declined (Freq. 19) • Syn: ↑carbon tet, ↑tetrachloromethane, ↑perchloromethane • Hypernyms:… … Useful english dictionary
carbon tetrachloride — Synonyms and related words: Foamite, acid, automatic sprinkler, carbon tet, carbon dioxide foam, deck gun, deluge set, extinguisher, fire apparatus, fire engine, fire hose, fire hydrant, fireplug, foam, foam extinguisher, hook and ladder, ladder… … Moby Thesaurus
carbon tetrachloride — noun Date: 1866 a colorless nonflammable toxic liquid CCl4 that has an odor resembling that of chloroform and is used as a solvent and a refrigerant … New Collegiate Dictionary
carbon tetrachloride — noun The halogenated hydrocarbon tetrachloromethane; a toxic, non inflammable liquid, used as a solvent, in dry cleaning and in fire extinguishers … Wiktionary
carbon tetrachloride — noun a colourless toxic volatile liquid used as a solvent. [CCl4.] … English new terms dictionary