Carbon tetrachloride
IUPAC name	Carbon tetrachloride Tetrachloromethane
Other names	Benziform, Carbon chloride, Methane tetrachloride, Perchloromethane, Carbon tet, Benzinoform, Tetraform, Tetrasol, Freon 10, Halon 104, UN 1846
Identifiers
CAS number	[56-23-5]
PubChem	5943
EINECS number	200-262-8
KEGG	C07561
ChEBI	27385
RTECS number	FG4900000
SMILES	C(Cl)(Cl)(Cl)Cl
InChI	InChI=1/CCl4/c2-1(3,4)5
Properties
Molecular formula	CCl4
Molar mass	153.82 g/mol
Appearance	Colorless liquid
Density	1.5842 g/cm3, liquid 1.831 g.cm-3 at -186 °C (solid) 1.809 g.cm-3 at -80 °C (solid) Image File history File links en: Molecular Structure of Carbon tetrachloride, also called Tetrachloromethane sk: Tetrachlórmetán H Padleckas created this image file on May 19, 2005 especially for use in the article Carbon tetrachloride in Wikipedia. ... Image File history File links Size of this preview: 612 × 600 pixelsFull resolution (1100 × 1078 pixel, file size: 167 KB, MIME type: image/png) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... PubChem is a database of chemical molecules. ... The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981. ... KEGG PATHWAY Database is one of the important databases in bioinformatics. ... ChEBI (meaning Chemical Entities of Biological Interest, or Chemistry at the EBI) is a database of molecular entities focused on small chemical compounds. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... The IUPAC International Chemical Identifier (InChI), developed by IUPAC and NIST, is a digital equivalent of the IUPAC name for any particular covalent compound. ... This article or section does not cite any references or sources. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is...
Melting point	-22.92 °C (250 K) The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ...
Boiling point	76.72 °C (350 K) Italic text This article is about the boiling point of liquids. ...
Solubility in water	8 mg/l at 20 °C
log P	2.64
Vapor pressure	11.94 kPa at 20 °C
kH	365 kJ.mol-1 at 24.8 °C
Structure
Crystal structure	Monoclinic
Molecular shape	Tetrahedral
Hazards
MSDS	External MSDS
EU classification	Toxic (T), Carc. Cat. 2B, Dangerous for the environment (N)
NFPA 704	Solubility refers to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... A partition coefficient is a measure of differential solubility of a compound in two solvents. ... In chemistry and physics, Vapor pressure is the pressure of a vapor in equilibrium with its non-vapor phases. ... In chemistry, Henrys law is one of the gas laws, formulated by William Henry. ... Enargite crystals In mineralogy and crystallography, a crystal structure is a unique arrangement of atoms in a crystal. ... In crystallography, the monoclinic crystal system is one of the 7 lattice point groups. ... four sp³ orbitals three sp² orbitals In chemistry, hybridisation or hybridization (see also spelling differences) is the concept of mixing atomic orbitals to form new hybrid orbitals suitable for the qualitative description of atomic bonding properties. ... A tetrahedron (plural: tetrahedra) is a polyhedron composed of four triangular faces, three of which meet at each vertex. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... This page provides supplementary chemical data on carbon tetrachloride. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main European Union law concerning chemical safety. ... The hazard symbol for carcinogenic chemicals in the Globally Harmonized System. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... 0 3 0
R-phrases	R23/24/25, R40, R48/23, R59, R52/53
S-phrases	(S1/2), S23, S36/37, S45, S59, S61
Flash point	Non flammable
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Carbon tetrachloride, also known by many other names (see Table) is the chemical compound with the formula CCl₄. It is a reagent in synthetic chemistry and was formerly widely used in fire extinguishers and as a precursor to refrigerants. It is a colorless liquid with a "sweet" smell that can be detected at low levels. R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... This page provides supplementary chemical data on carbon tetrachloride. ... This page provides supplementary chemical data on carbon tetrachloride. ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... This page provides supplementary chemical data on carbon tetrachloride. ... This page provides supplementary chemical data on carbon tetrachloride. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... Infrared spectroscopy (IR Spectroscopy) is the subset of spectroscopy that deals with the IR region of the EM spectrum. ... It has been suggested that NMR Data Processing be merged into this article or section. ... Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or informally, mass-spec and MS) is an analytical technique used to measure the mass-to-charge ratio of ions. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... This article or section does not cite any references or sources. ... A reagent or reactant is any substance used in a chemical reaction. ... Organic synthesis is the construction of organic molecules via chemical processes. ... Fire extinguisher A fire extinguisher is a device used to put out a fire, often in an emergency situation. ... Refrigeration is the process of removing heat from an enclosed space, or from a substance, and rejecting it elsewhere for the primary purpose of lowering the temperature of the enclosed space or substance and then maintaining that lower temperature. ...

Both carbon tetrachloride and tetrachloromethane are acceptable names under IUPAC nomenclature, depending on whether it is seen as an inorganic or an organic compound. Colloquially, it is called "carbon tet". IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... Inorganic chemistry is the branch of chemistry concerned with the properties and reactions of inorganic compounds. ... Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting of primarily carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ...

Production

Carbon tetrachloride was originally synthesised in 1839 by reaction of chloroform with chlorine, but the most common synthesis is now chlorination of carbon disulfide at 105 to 130 °C: Chlorination is the process of adding the element chlorine to water as a method of water purification to make it fit for human consumption as drinking water. ... Carbon disulfide is a colorless liquid with the formula CS2. ...

CS₂ + 3Cl₂ → CCl₄ + S₂Cl₂

CCl₄ can also be prepared from methane via the reaction: General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... Disulfur dichloride is S2Cl2. ...

CH₄ + 4 Cl₂ → CCl₄ + 4HCl

It is also a byproduct in the synthesis of dichloromethane and chloroform. Methane is a chemical compound with the molecular formula CH4. ... R-phrases , S-phrases , , , , Flash point non-flammable Supplementary data page Structure and properties n, εr, etc. ... Dichloromethane or Methylene chloride is a chemical compound widely used as a solvent for organic materials. ... R-phrases , , , S-phrases , Flash point Non-flammable U.S. Permissible exposure limit (PEL) 50 ppm (240 mg/m3) (OSHA) Supplementary data page Structure and properties n, εr, etc. ...

Properties

In the carbon tetrachloride molecule, four chlorine atoms are positioned symmetrically as corners in a tetrahedral configuration joined to a carbon atom, in the center, by single covalent bonds. Because of this symmetrical geometry, the molecule has no net dipole moment; that is, CCl₄ is non-polar. As a solvent, it is well suited to dissolving other non-polar compounds, fats and oils. 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. In science, a molecule is a group of atoms in a definite arrangement held together by chemical bonds. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... Properties In chemistry and physics, an atom (Greek ἄτομος or átomos meaning indivisible) is the smallest particle still characterizing a chemical element. ... A tetrahedron (plural: tetrahedra) is a polyhedron composed of four triangular faces, three of which meet at each vertex. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... Covalent bonding is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms, or sometimes between atoms and other covalent bonds. ... This article is about the electromagnetic phenomenon. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... The ability of a liquid to evaporate quickly and at relatively low temperatures. ... Vapor (US English) or vapour (British English) is the gaseous state of matter. ... Tetrachloroethylene Cl2C=CCl2 is a manufactured chemical compound that is widely used for the dry cleaning of fabrics and for metal-degreasing. ... Dry cleaning is any cleaning process for clothing and textiles using a solvent other than water. ...

Solid tetrachloromethane has 2 allotropes - crystaline II below -47.5 °C (225.6 K) and crystaline I above -47.5 °C.^[1] This article is in need of attention from an expert on the subject. ...

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°.^[2] In crystallography, the monoclinic crystal system is one of the 7 lattice point groups. ... The lattice constant refers to the constant distance between unit cells in a crystal lattice. ...

Uses

In the early 20th century, carbon tetrachloride was widely used as a dry cleaning solvent, as a refrigerant, and in fire extinguishers^[3]. 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. 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. Dry cleaning is any cleaning process for clothing and textiles using an organic solvent other than water — generally known as dry cleaning fluid, and typically this is tetrachloroethylene. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... A refrigerant is a compound used in a heat cycle that undergoes a phase change from a gas to a liquid and back. ... Fire extinguisher A fire extinguisher is a device used to put out a fire, often in an emergency situation. ... Tetrachloroethylene Cl2C=CCl2 is a manufactured chemical compound that is widely used for the dry cleaning of fabrics and for metal-degreasing. ... This article or section does not cite any references or sources. ... A cropduster spreading pesticide. ... 1970 (MCMLXX) was a common year starting on Thursday. ...

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. The largest Antarctic ozone hole recorded as of September 2000 For other similarly-named agreements, see Montreal Protocol (disambiguation). ... Freon is a trade name for a group of chlorofluorocarbons used primarily as a refrigerant. ... R-11 redirects here, for the ballistic missile, see Scud. ... Disclaimer and references Dichlorodifluoromethane (R-12), usually sold under the brand name Freon-12, is a chlorofluorocarbon halomethane used as a refrigerant and aerosol spray propellant until its manufacture was discontinued in 1995, due to concerns about damage to the ozone layer. ... Global monthly average total ozone amount Ozone depletion describes two distinct, but related observations: a slow, steady decline of about 4 percent per decade in the total amount of ozone in Earths stratosphere since around 1980; and a much larger, but seasonal, decrease in stratospheric ozone over Earths...

Carbon tetrachloride has also been used in the detection of neutrinos. The neutrino is an elementary particle. ...

Reactivity

Carbon tetrachloride has practically no flammability at lower temperatures. Under high temperatures in air, it forms poisonous phosgene. Flammable or Flammability refers to the ease at which a substance will ignite, causing fire or combustion. ... Phosgene (also known as carbonyl chloride, COCl2) is a highly toxic gas or refrigerated liquid that was used as a chemical weapon in World War I. It has no color, but is detectable in air by its odor, which resembles moldy hay. ...

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. Flash point None R/S statement R: ? S: ? RTECS number  ? Supplementary data page Structure and properties n, εr, etc. ...

In organic chemistry, carbon tetrachloride serves as a source of chlorine in the Appel reaction. Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting of primarily carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... The Appel reaction is a chemical reaction that converts an alcohol into an alkyl chloride using triphenylphosphine and carbon tetrachloride. ...

As a solvent

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 substitute 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^[4]. Its use has been largely superseded by deuterated solvents, which offer superior solvating properties and allow for deuterium lock by the spectrometer. A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... Infrared spectroscopy (IR Spectroscopy) is the subset of spectroscopy that deals with the IR region of the EM spectrum. ... It has been suggested that NMR Data Processing be merged into this article or section. ...

Safety

Exposure to high concentrations of carbon tetrachloride (including vapor) can affect the central nervous system, degenerate the liver^[5] and kidneys^[6] and may result (after prolonged exposure) in coma and even death^[7]. Chronic exposure to carbon tetrachloride can cause liver^[8][9] and kidney damage and could result in cancer^[10] More information can be found in Material safety data sheets. Vapor (US English) or vapour (British English) is the gaseous state of matter. ... A diagram showing the CNS: 1. ... In medicine, a coma (from the Greek koma, meaning deep sleep) is a profound state of unconsciousness. ... This article or section does not adequately cite its references or sources. ... Hepatotoxicity (from hepatic toxicity) is chemical-driven liver damage. ... Nephrotoxicity is a poisonous effect of some substances, both toxins and medication, on the kidney. ... Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ...

Carbon tetrachloride is also both ozone-depleting^[11] and a greenhouse gas^[12]. However, since 1992^[13] its atmospheric concentrations have been in decline for the reasons described above (see also the atmospheric time-series figure). Global monthly average total ozone amount Ozone depletion describes two distinct, but related observations: a slow, steady decline of about 4 percent per decade in the total amount of ozone in Earths stratosphere since around 1980; and a much larger, but seasonal, decrease in stratospheric ozone over Earths... Top: Increasing atmospheric CO2 levels as measured in the atmosphere and ice cores. ...

Time-series of atmospheric concentrations of CCl₄ (Walker et al., 2000).

Image File history File links Size of this preview: 703 × 600 pixelsFull resolution (1700 × 1450 pixel, file size: 84 KB, MIME type: image/png) Time series of atmospheric concentrations of carbon tetrachloride from 1908 to 2003. ... Image File history File links Size of this preview: 703 × 600 pixelsFull resolution (1700 × 1450 pixel, file size: 84 KB, MIME type: image/png) Time series of atmospheric concentrations of carbon tetrachloride from 1908 to 2003. ...

See also

• Haloalkane
• Halomethane
• Chloromethane
• Dichloromethane
• Chloroform
• Tetrafluoromethane
• Tetrabromomethane
• Carbon tetraiodide (Tetraiodomethane)

• Dutch standards

Tetrafluoroethane (a haloalkane) is a clear liquid which boils well below room temperature (as seen here) and can be extracted from common canned air canisters by simply inverting them during use. ... Halomethane compounds are molecules of methane (CH4) with one or more of the hydrogen atoms replaced with halogen atoms. ... R-phrases , , S-phrases , , Flash point -46 °C Autoignition temperature 625 °C Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Chloromethane, also called Methyl chloride, or simply R-40 or HCC 40, is a chemical compound... Dichloromethane or Methylene chloride is a chemical compound widely used as a solvent for organic materials. ... R-phrases , , , S-phrases , Flash point Non-flammable U.S. Permissible exposure limit (PEL) 50 ppm (240 mg/m3) (OSHA) Supplementary data page Structure and properties n, εr, etc. ... Carbon tetrafluoride, CF4, is a carbon fluoride. ... Carbon tetrabromide, CBr4, is a carbon bromide. ... Carbon tetraiodide is CI4. ... Dutch Standard reference values for environmental investigation, clean up and remediation. ...

References

1. ^ http://webbook.nist.gov/cgi/cbook.cgi?ID=C56235&Units=SI&Mask=4#Thermo-Phase
2. ^ F. Brezina, J. Mollin, R. Pastorek, Z. Sindelar. Chemicke tabulky anorganickych sloucenin (Chemical tables of inorganic compounds). SNTL, 1986.
3. ^ Doherty R. E. (2000). "A History of the Production and Use of Carbon Tetrachloride, Tetrachloroethylene, Trichloroethylene and 1,1,1-Trichloroethane in the United States: Part 1--Historical Background; Carbon Tetrachloride and Tetrachloroethylene" (1): 69 - 81. DOI:10.1006/enfo.2000.0010. 
4. ^ Introduction to Nuclear Magnetic Resonance Spectroscopy, Michigan State University
5. ^ WF Seifert, A Bosma, A Brouwer, HF Hendriks, PJ (1994). "Vitamin A deficiency potentiates carbon tetrachloride-induced liver fibrosis in rats". Hepatology 19: 193-201. 
6. ^ Liu KX, Kato Y, Yamazaki M, Higuchi O, Nakamura T, Sugiyama Y. (1993). "Decrease in the hepatic clearance of hepatocyte growth factor in carbon tetrachloride-intoxicated rats". Hepatology 17: 651-60. 
7. ^ Recknagel R.O., Glende E.A., Dolak J.A., Waller R.L. (1989). "Mechanism of Carbon-tetrachloride Toxicity". Pharmacology Therapeutics (43): 139-154. DOI:10.1016/0163-7258(89)90050-8. 
8. ^ Recknagel RO (1967). "Carbon tetrachloride Hepatotoxicity". Pharmacological Reviews 19 (2): 145. 
9. ^ Masuda Y (2006). "Learning toxicology from carbon tetrachloride-induced hepatotoxicity". Yakugaku Zasshi -Journal of the Pharmaceutical Society of Japan 126 (10): 885-899. 
10. ^ Rood AS, McGavran PD, Aavenson JW, et al. (2001). "Stochastic estimates of exposure and cancer risk from carbon tetrachloride released to the air from the Rocky Flats Plant". Risk Analysis 21 (4): 675-695. 
11. ^ Fraser P. (1997). "Chemistry of stratospheric ozone and ozone depletion". Australian Meteorological Magazine 46 (3): 185-193. 
12. ^ Evans WFJ, Puckrin E (1996). "A measurement of the greenhouse radiation associated with carbon tetrachloride (CCl₄)". GeophysicalL Research Letters 23 (14): 1769-1772. 
13. ^ Walker, S. J., R. F. Weiss & P. K. Salameh (2000). "Reconstructed histories of the annual mean atmospheric mole fractions for the halocarbons CFC-11, CFC-12, CFC-113 and carbon tetrachloride". Journal of Geophysical Research 105: 14285—14296. 

A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Michigan State University (MSU) is a co-educational public research university in East Lansing, Michigan USA. Founded in 1855, it was the pioneer land-grant institution and served as a model for future land-grant colleges in the United States under the 1862 Morrill Act. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

External links

• International Chemical Safety Card 0024
• NIOSH Pocket Guide to Chemical Hazards 0107
• IARC Summaries & Evaluations Vol. 71 (1999)
• IARC Monograph: "Carbon Tetrachloride"
• Toxicological profile for carbon tetrachloride
• Environmental health criteria for carbon tetrachloride
• Carbon tetrachloride MSDS at Hazardous Chemical Database
• MSDS at Oxford University
• Transformation of tetrachloromethane to dichloromethane and carbon dioxide by Acetobacterium woodii
• Involvement of cytochromes in the anaerobic biotransformation of tetrachloromethane by Shewanella putrefaciens 200
• Substance profile at ntp.niehs.nih.gov