Carbon tetrachloride



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)

Melting point

-22.92 °C (250 K)

Boiling point

76.72 °C (350 K)

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
0
3
0
 
R-phrases R23/24/25, R40, R48/23, R59, R52/53
S-phrases S61
Flash point Non flammable
Supplementary data page
Structure and
properties 		εr, etc.
Thermodynamic
data 		Phase behaviour
Solid, liquid, gas
Spectral data 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 refrigerants. 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".

Production

The production of carbon tetrachloride has steeply declined since the 1980's 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 720,000,000 kg.[1]

Carbon tetrachloride was originally synthesised in 1839 by reaction of chloroform with chlorine, from the french chemist Henri Victor Regnault,[2] but now it is mainly synthesized from methane:

CH4 + 4 Cl2 → CCl4 + 4HCl

The production often utilizes by-products of other chloroform. Higher chlorocarbons are also subjected to "chlorinolysis:"

C2Cl6 + Cl2 → 2 CCl4

Prior to the 1950's, carbon tetrachloride was manufactured by the chlorination of carbon disulfide at 105 to 130 °C:

CS2 + 3S2Cl2[1]

Properties

In the carbon tetrachloride tetrachloroethylene smell reminiscent of dry cleaners' shops.

Solid tetrachloromethane has 2 allotropes: crystaline II below -47.5 °C (225.6 K) and crystaline I above -47.5 °C.[3]

At -47.3 °C it has lattice constants a = 20.3, b = 11.6, c = 19.9 (.10-1 nm), β = 111°.[4]

Uses

In the early 20th century, carbon tetrachloride was widely used as a dry cleaning 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 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 widly used in scientific research to evaluate hepatoprotective agents 7,8

Reactivity

Carbon tetrachloride has practically no 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 Appel reaction.

As a solvent

It is used as a NMR spectroscopy. However, carbon tetrachloride is toxic, and its dissolving power is low[6]. Its use has been largely superseded by deuterated solvents, which offer superior solvating properties and allow for deuterium lock by the spectrometer.

Safety

Exposure to high concentrations of carbon tetrachloride (including Material safety data sheets.

Carbon tetrachloride is also both ozone-depleting[13] and a greenhouse gas[14]. However, since 1992[15] its atmospheric concentrations have been in decline for the reasons described above (see also the atmospheric time-series figure).

 

See also

  • Dutch standards

References

  1. ^ a b 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.
  2. ^ V. Regnault (1839). "Ueber die Chlorverbindungen des Kohlenstoffs, C2Cl2 und CCl2". Annalen der Pharmacie 30 (3). doi:10.1002/jlac.18390300310.
  3. ^ http://webbook.nist.gov/cgi/cbook.cgi?ID=C56235&Units=SI&Mask=4#Thermo-Phase
  4. ^ F. Brezina, J. Mollin, R. Pastorek, Z. Sindelar. Chemicke tabulky anorganickych sloucenin (Chemical tables of inorganic compounds). SNTL, 1986.
  5. ^ 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.
  6. ^ Introduction to Nuclear Magnetic Resonance Spectroscopy, Michigan State University
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ Recknagel RO (1967). "Carbon tetrachloride Hepatotoxicity". Pharmacological Reviews 19 (2): 145.
  11. ^ Masuda Y (2006). "Learning toxicology from carbon tetrachloride-induced hepatotoxicity". Yakugaku Zasshi -Journal of the Pharmaceutical Society of Japan 126 (10): 885-899.
  12. ^ 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.
  13. ^ Fraser P. (1997). "Chemistry of stratospheric ozone and ozone depletion". Australian Meteorological Magazine 46 (3): 185-193.
  14. ^ Evans WFJ, Puckrin E (1996). "A measurement of the greenhouse radiation associated with carbon tetrachloride (CCl4)". Geophysical Research Letters 23 (14): 1769-1772.
  15. ^ 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.
 
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