Carbon tetrachloride
241047
224889556
2008-07-10T21:26:33Z
Braitman
1660125
/* Uses */
{{Chembox new
| ImageFileL1 = Carbon Tetrachloride.svg
| ImageSizeL1 =
| ImageFileR1 = Carbon-tetrachloride-3D-vdW.png
| ImageSizeR1 =
| IUPACName = Carbon tetrachloride<br/>Tetrachloromethane
| OtherNames = Benziform, Carbon chloride, Methane tetrachloride, Perchloromethane, Carbon tet, Benzinoform, Tetraform, Tetrasol, Freon 10, Halon 104, UN 1846
| Section1 = {{Chembox Identifiers
| CASNo = 56-23-5
| EINECS = 200-262-8
| PubChem = 5943
| SMILES = C(Cl)(Cl)(Cl)Cl
| InChI = 1/CCl4/c2-1(3,4)5
| RTECS = FG4900000
| ChEBI = 27385
| KEGG = C07561
}}
| Section2 = {{Chembox Properties
| Formula = CCl<sub>4</sub>
| MolarMass = 153.82 g/mol
| Appearance = Colorless liquid
| Density = 1.5842 g/cm<sup>3</sup>, liquid<br>
1.831 g.cm<sup>-3</sup> at -186 °C (solid)<br>
1.809 g.cm<sup>-3</sup> at -80 °C (solid)<br>
| MeltingPt = -22.92 °C (250 K)
| BoilingPt = 76.72 °C (350 K)
| Solubility = 785 - 800 mg/L at 25 °C<!--Ullmann's-->
| LogP = 2.64
| VaporPressure = 11.94 kPa at 20 °C
| HenryConstant = 365 kJ.mol<sup>-1</sup> at 24.8 °C
}}
| Section3 = {{Chembox Structure
| CrystalStruct = [[Monoclinic]]
| Coordination =
| MolShape = [[Tetrahedron|Tetrahedral]]
}}
| Section4 = {{Chembox Hazards
| EUClass = Toxic ('''T'''), [[Carcinogen|Carc. Cat. 2B]], Dangerous for the environment ('''N''')
| MainHazards =
| NFPA-H = 3
| NFPA-F = 0
| NFPA-R = 0
| NFPA-O =
| RPhrases = {{R23/24/25}}, {{R40}}, {{R48/23}}, {{R59}}, {{R52/53}}
| SPhrases = {{S1/2}}, {{S23}}, {{S36/37}}, {{S45}}, {{S59}}, {{S61}}
| FlashPt = Not flammable
| Autoignition =
}}
}}
'''Carbon tetrachloride''', also known by many other names (see Table) is the [[chemical compound]] with the [[chemical formula|formula]] CCl<sub>4</sub>. It is a [[reagent]] in [[organic synthesis|synthetic]] chemistry and was formerly widely used in [[fire extinguisher]]s and as a precursor to [[refrigeration|refrigerant]]s. It is a colorless liquid with a "sweet" smell that can be detected at low levels.
Both carbon tetrachloride and tetrachloromethane are acceptable names under [[IUPAC nomenclature]]. Colloquially, it is called "carbon tet".
==History and synthesis==
The production of carbon tetrachloride has steeply declined since the 1980s due to environmental concerns and the decreased demand for [[haloalkane|CFC]]s, which were derived from carbon tetrachloride. In 1992, production in the U.S.-Europe-Japan was estimated at 720,000,000 kg.<ref name=Ross>Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.</ref>
Carbon tetrachloride was originally synthesised in 1839 by reaction of chloroform with chlorine, from the french chemist [[Henri Victor Regnault]],<ref>{{cite journal
| journal =Annalen der Pharmacie
| volume = 30
| issue = 3
| year = 1839
| title = Ueber die Chlorverbindungen des Kohlenstoffs, C2Cl2 und CCl2
| author = V. Regnault
| doi = 10.1002/jlac.18390300310
| pages =350
}}</ref> but now it is mainly synthesized from methane:
:[[methane|CH<sub>4</sub>]] + 4 Cl<sub>2</sub> → CCl<sub>4</sub> + 4[[hydrogen chloride|HCl]]
The production often utilizes by-products of other [[chlorination]] reactions, such as the syntheses of [[dichloromethane]] and [[chloroform]]. Higher chlorocarbons are also subjected to "chlorinolysis:"
:[[Hexachloroethane|C<sub>2</sub>Cl<sub>6</sub>]] + Cl<sub>2</sub> → 2 CCl<sub>4</sub>
Prior to the 1950s, carbon tetrachloride was manufactured by the chlorination of [[carbon disulfide]] at 105 to 130 °C:
:CS<sub>2</sub> + 3[[chlorine|Cl<sub>2</sub>]] → CCl<sub>4</sub> + [[Disulfur dichloride|S<sub>2</sub>Cl<sub>2</sub>]]<ref name=Ross/>
==Properties==
In the carbon tetrachloride [[molecule]], four [[chlorine]] [[atom]]s are positioned symmetrically as corners in a [[tetrahedron|tetrahedral]] configuration joined to a [[carbon]] atom, in the center, by single [[covalent bond]]s. Because of this symmetrical geometry, the molecule has no net [[dipole moment]]; that is, CCl<sub>4</sub> is non-polar. As a [[solvent]], it is well suited to dissolving other non-polar compounds, fats and oils. It is somewhat [[Volatility (chemistry)|volatile]], giving off [[vapor]]s having a smell characteristic of other chlorinated solvents, somewhat similar to the [[tetrachloroethylene]] smell reminiscent of [[dry cleaner]]s' shops.
Solid tetrachloromethane has 2 [[Allotropy|allotropes]]: crystaline II below -47.5 °C (225.6 K) and crystaline I above -47.5 °C.<ref>[http://webbook.nist.gov/cgi/cbook.cgi?ID=C56235&Units=SI&Mask=4#Thermo-Phase Carbon tetrachloride<!-- Bot generated title -->]</ref>
At -47.3 °C it has [[Monoclinic crystal system|monoclinic]] crystal structure with space group ''C2/c'' and [[lattice constants]] ''a'' = 20.3, ''b'' = 11.6, ''c'' = 19.9 (.10<sup>-1</sup> nm), β = 111°.<ref name="chtas">F. Brezina, J. Mollin, R. Pastorek, Z. Sindelar. ''Chemicke tabulky anorganickych sloucenin'' (''Chemical tables of inorganic compounds''). SNTL, 1986.</ref>
==Uses==
In the early 20th century, carbon tetrachloride was widely used as a [[dry cleaning]] [[solvent]], as a [[refrigerant]], and in [[fire extinguisher]]s<ref>{{cite journal| title= 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|author= Doherty R. E.|issue= 1|year= 2000| pages= 69–81| doi=10.1006/enfo.2000.0010| journal= Environmental Forensics| volume= 1}}</ref>. 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]].
One specialty use of "carbon tet" was by stamp collectors to reveal watermarks on the backs of postage stamps. 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.
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, and is widely used in scientific research to evaluate hepatoprotective agents 7,8
====Reactivity====
Carbon tetrachloride has practically no [[flammable|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|''N''-bromosuccinimide]].
In [[organic chemistry]], carbon tetrachloride serves as a source of chlorine in the [[Appel reaction]].
====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.{{Fact|date=May 2008}} It is sometimes useful as a solvent for [[infrared spectroscopy]] because there are no significant absorption bands > 1600 cm<sup>-1</sup>. 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<ref>[http://www.cem.msu.edu/~reusch/VirtualText/Spectrpy/nmr/nmr1.htm Introduction to Nuclear Magnetic Resonance Spectroscopy], [[Michigan State University]]</ref>. Its use has been largely superseded by deuterated solvents, which offer superior solvating properties and allow for deuterium lock by the spectrometer. Use of carbon tetrachloride in determination of oil has been replaced by various other solvents<ref>Use of Ozone Depleting Substances in Laboratories. TemaNord 516/2003. [http://www.norden.org/pub/ebook/2003-516.pdf]</ref>.
==Safety==
Exposure to high concentrations of carbon tetrachloride (including [[vapor]]) can affect the [[central nervous system]], degenerate the liver<ref>{{cite journal
| author = WF Seifert, A Bosma, A Brouwer, HF Hendriks, PJ
| title = Vitamin A deficiency potentiates carbon tetrachloride-induced liver fibrosis in rats
| journal = Hepatology
| volume = 19
| pages = 193–201
| year = 1994
| issue = 1 }}</ref> and kidneys<ref>{{cite journal
| author = Liu KX, Kato Y, Yamazaki M, Higuchi O, Nakamura T, Sugiyama Y.
| title = Decrease in the hepatic clearance of hepatocyte growth factor in carbon tetrachloride-intoxicated rats
| journal = Hepatology
| volume = 17
| pages = 651–60
| year = 1993
| doi = 10.1002/hep.1840170420
| issue = 4
}}</ref> and may result (after prolonged exposure) in [[coma]] and even [[death]]<ref>{{cite journal
| title = Mechanism of Carbon-tetrachloride Toxicity
| author = Recknagel R.O., Glende E.A., Dolak J.A., Waller R.L.
| journal = Pharmacology Therapeutics
| issue = 43
| pages = 139–154
| year = 1989
| doi = 10.1016/0163-7258(89)90050-8
| volume = 43
}}</ref>. Chronic exposure to carbon tetrachloride can cause [[Hepatotoxicity|liver]]<ref>{{cite journal
| author = Recknagel RO
| title = Carbon tetrachloride Hepatotoxicity
| journal = Pharmacological Reviews
| volume = 19
| issue = 2
| pages = 145
| year = 1967 }}</ref><ref> {{cite journal
| author = Masuda Y
| title = Learning toxicology from carbon tetrachloride-induced hepatotoxicity
| journal = Yakugaku Zasshi -Journal of the Pharmaceutical Society of Japan
| volume = 126
| issue =10
| pages = 885–899
| year = 2006
| doi = 10.1248/yakushi.126.885}}</ref> and [[Nephrotoxicity|kidney damage]] and could result in [[cancer]]<ref>{{cite journal
| author = Rood AS, McGavran PD, Aavenson JW, et al.
| title = Stochastic estimates of exposure and cancer risk from carbon tetrachloride released to the air from the Rocky Flats Plant
| journal = Risk Analysis
| volume = 21
| issue =4
| pages = 675–695
| year = 2001
| doi = 10.1111/0272-4332.214143
}}</ref> More information can be found in [[Material safety data sheet]]s.
Carbon tetrachloride is also both [[ozone depletion|ozone-depleting]]<ref>{{cite journal
| author = Fraser P.
| title = Chemistry of stratospheric ozone and ozone depletion
| journal = Australian Meteorological Magazine
| volume = 46
| issue =3
| pages = 185–193
| year = 1997 }}</ref> and a [[greenhouse gas]]<ref>{{cite journal
| author = Evans WFJ, Puckrin E
| title = A measurement of the greenhouse radiation associated with carbon tetrachloride (CCl<sub>4</sub>)
| journal = Geophysical Research Letters
| volume = 23
| issue = 14
| pages = 1769–1772
| year = 1996
| doi = 10.1029/96GL01258}}</ref>. However, since 1992<ref>{{cite journal
| author = Walker, S. J., R. F. Weiss & P. K. Salameh
| year = 2000
| title = Reconstructed histories of the annual mean atmospheric mole fractions for the halocarbons CFC-11, CFC-12, CFC-113 and carbon tetrachloride
| journal = Journal of Geophysical Research
| volume =105
| pages = 14285–14296
| doi = 10.1029/1999JC900273
}}</ref> its atmospheric concentrations have been in decline for the reasons described above (see also the atmospheric time-series figure).
[[Image:AYool CCl4 history.png|thumb|225px|right|Time-series of atmospheric concentrations of CCl<sub>4</sub> (Walker ''et al.'', 2000).]]
==See also==
* [[Haloalkane]]
* [[Halomethane]]
* [[Chloromethane]]
* [[Dichloromethane]]
* [[Chloroform]]
* [[Tetrafluoromethane]]
* [[Tetrabromomethane]]
* [[Carbon tetraiodide]] (Tetraiodomethane)
* [[Dutch standards]]
==References==
<references/>
==External links==
*{{ICSC|0024|00}}
*{{PGCH|0107}}
*[http://www.inchem.org/documents/iarc/vol71/011-carbontetrac.html IARC Summaries & Evaluations Vol. 71 (1999)]
*[http://monographs.iarc.fr/ENG/Monographs/vol71/volume71.pdf IARC Monograph: "Carbon Tetrachloride"]
*[http://www.atsdr.cdc.gov/toxprofiles/tp30.pdf Toxicological profile for carbon tetrachloride]
*[http://www.inchem.org/documents/ehc/ehc/ehc208.htm Environmental health criteria for carbon tetrachloride]
*[http://ull.chemistry.uakron.edu/erd/Chemicals/7000/6256.html Carbon tetrachloride MSDS at Hazardous Chemical Database]
*[http://ptcl.chem.ox.ac.uk/MSDS/CA/carbon_tetrachloride.html MSDS at Oxford University]
*[http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=204379 Transformation of tetrachloromethane to dichloromethane and carbon dioxide by Acetobacterium woodii]
*[http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=182529 Involvement of cytochromes in the anaerobic biotransformation of tetrachloromethane by Shewanella putrefaciens 200]
*[http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s029carb.pdf Substance profile at ntp.niehs.nih.gov]
[[Category:Organochlorides]]
[[Category:Halomethanes]]
[[Category:Inorganic carbon compounds]]
[[Category:Nonmetal halides]]
[[Category:Chlorides]]
[[Category:Aerosol propellants]]
[[Category:Greenhouse gases]]
[[Category:Hazardous air pollutants]]
[[Category:Organochloride insecticides]]
[[Category:Refrigerants]]
[[Category:Halogenated solvents]]
[[Category:IARC Group 2B carcinogens]]
[[cs:Tetrachlormethan]]
[[da:Tetraklorkulstof]]
[[de:Tetrachlormethan]]
[[es:Tetracloruro de carbono]]
[[fr:Tétrachlorure de carbone]]
[[ko:사염화 탄소]]
[[id:Karbon tetraklorida]]
[[it:Tetracloruro di carbonio]]
[[lv:Tetrahlorogleklis]]
[[lt:Anglies tetrachloridas]]
[[hu:Szén-tetraklorid]]
[[nl:Tetrachloormethaan]]
[[ja:四塩化炭素]]
[[pl:Czterochlorek węgla]]
[[pt:Tetracloreto de carbono]]
[[ru:Тетрахлорметан]]
[[sk:Tetrachlórmetán]]
[[fi:Hiilitetrakloridi]]
[[sv:Koltetraklorid]]
[[vi:Cacbon tetraclorua]]
[[uk:Тетрахлорметан]]
[[zh:四氯化碳]]