Carbon tetrachloride

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Carbon tetrachloride

IUPAC name[hide]
Tetrachloromethane

Other names[hide]
1,1,1,1-Tetrachloromethane, Benziform, Benzinoform, Carbon
chloride, Carbon tet, Freon 10, Halon 104, Methane
tetrachloride, Perchloromethane, Tetraform, Tetrasol

Identifiers

CAS number 56-23-5 

PubChem 5943

ChemSpider 5730 

UNII CL2T97X0V0 

EC number 200-262-8

UN number 1846

KEGG C07561

ChEBI 27385

RTECS number FG4900000

SMILES
[show]
 InChI
[show]

Properties

Molecular formula CCl4

Molar mass 153.82 g/mol

colourless liquid
Appearance
ether-like odor

1.5867 g/cm3, liquid

Density
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 785–800 mg/L at 25 °C
soluble in alcohol, ether,
Solubility
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
Carc. Cat. 3
EU classification Toxic (T)
Dangerous for the environment (N)
R23/24/25, R40, R48/23, R59,
R-phrases
R52/53
S-phrases (S1/2), S23, S36/37, S45, S59, S61
NFPA 704
 0
3
0
Flash point Not flammable
Autoignition
982 °C
temperature
LD50 2350 mg/kg
Related compounds
Silicon tetrachloride
Germanium tetrachloride
Other cations
Tin tetrachloride
Lead tetrachloride
Chloromethane
Related chloromethanes Dichloromethane
Chloroform
Tetrafluoromethane
Related compounds Tetrabromomethane
Tetraiodomethane
Supplementary data page
Structure and
n, εr, etc.
properties
Thermodynamic Phase behaviour
data Solid, liquid, gas
Spectral data UV, IR, NMR, MS
   (what is this?)  (verify)
Except where noted otherwise, data are given for materials in
their standard state (at 25 °C, 100 kPa)
Infobox references

Carbon tetrachloride, also known by many other names (notably, carbon tet in the
cleaning industry, and as 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.

Contents
[hide]
  1 History and synthesis
 2 Properties
 3 Uses
o 3.1 Reactivity
o 3.2 Solvent
 4 Safety
 5 References
 6 External links

[edit] 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.[1]

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

CH4 + 4 Cl2 → CCl4 + 4 HCl

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:"

C2Cl6 + Cl2 → 2 CCl4

Prior to the 1950s, carbon tetrachloride was manufactured by the chlorination of carbon
disulfide at 105 to 130 °C:[1]

CS2 + 3Cl2 → CCl4 + S2Cl2

[edit] Properties
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 having a smell characteristic of other chlorinated
solvents, somewhat similar to the tetrachloroethylene smell reminiscent of dry cleaners'
shops.
Solid tetrachloromethane has 2 polymorphs: crystalline II below -47.5 °C (225.6 K) and
crystalline I above -47.5 °C.[3]

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°.[4] 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.

[edit] Uses

A brass, Pyrene carbon-tetrachloride, fire extinguisher.

In the 20th century, carbon tetrachloride was widely used as a dry cleaning solvent, as a
refrigerant, and in lava lamps.[5]

In 1910, The Pyrene Manufacturing Company of Delaware filed a patent for a device using
carbon tetrachloride to extinguish fires.[6] 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. A carbon tetrachloride fire extinguisher was patented in 1911, taking the
form of a brass bottle with a hand pump to expel a jet of liquid.[7] Such extinguishers were
commonly used until the mid-20th century.

One specialty use of carbon tetrachloride was by stamp collectors to reveal watermarks on
the backs of postage stamps without damaging the stamp. 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.

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 is one of the most potent hepatotoxins (toxic to the liver), and is
widely used in scientific research to evaluate hepatoprotective agents.[8][9]

[edit] Reactivity

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.

In organic chemistry, carbon tetrachloride serves as a source of chlorine in the Appel

reaction.

[edit] 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 replace it with other
solvents.[citation needed] 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.[10] Its use has been
largely superseded by deuterated solvents. Use of carbon tetrachloride in determination of
oil has been replaced by various other solvents[8].

[edit] Safety
Time-series of atmospheric concentrations of CCl4 (Walker et al., 2000).

Exposure to high concentrations of carbon tetrachloride (including vapor) can affect the
central nervous system, degenerate the liver[9] and kidneys[11] and may result (after
prolonged exposure) in coma and even death.[12] Chronic exposure to carbon tetrachloride
can cause liver[13][14] and kidney damage and could result in cancer.[15] More information can
be found in Material safety data sheets.[16]

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).[17]

Carbon tetrachloride is also both ozone-depleting[18] and a greenhouse gas.[19] However,

since 1992[20] 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[21]

[edit] References
1. ^ a b Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-
Ludwig Dreher, Ernst Langer, Heinz Jaerts, 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 Industrial Chemistry,
2006 Wiley-VCH, Weinheim.doi:10.1002/14356007.a06_233.pub2
2. ^ V. Regnault (1839). "Ueber die Chlorverbindungen des Kohlenstoffs, C2Cl2 und CCl2".
Annalen der Pharmacie 30 (3): 350. doi:10.1002/jlac.18390300310.
3. ^ Carbon tetrachloride
4. ^ F. Brezina, J. Mollin, R. Pastorek, Z. Sindelar. Chemicke tabulky anorganickych
sloucenin (Chemical tables of inorganic compounds). SNTL, 1986.
5. ^ Doherty RE (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". Environmental
Forensics 1 (1): 69–81. doi:10.1006/enfo.2000.0010.
6. ^ U.S. Patent 1,010,870, filed April 5, 1910.
7. ^ U.S. Patent 1,105,263
8. ^ a b Use of Ozone Depleting Substances in Laboratories. TemaNord 516/2003.
 9. ^ a b Seifert WF, Bosma A, Brouwer A, et al (January 1994). "Vitamin A deficiency
potentiates carbon tetrachloride-induced liver fibrosis in rats". Hepatology 19 (1): 193–201.
doi:10.1002/hep.1840190129. PMID 8276355.
10. ^ W. Reusch. "Introduction to Nuclear Magnetic Resonance Spectroscopy". Virtual
Textbook of Organic Chemistry. Michigan State University.
http://www.cem.msu.edu/~reusch/VirtualText/Spectrpy/nmr/nmr1.htm.
11. ^ Liu KX, Kato Y, Yamazaki M, Higuchi O, Nakamura T, Sugiyama Y (April 1993).
"Decrease in the hepatic clearance of hepatocyte growth factor in carbon tetrachloride-
intoxicated rats". Hepatology 17 (4): 651–60. doi:10.1002/hep.1840170420.
PMID 8477970.
12. ^ Recknagel R.O., Glende E.A., Dolak J.A., Waller R.L. (1989). "Mechanism of Carbon-
tetrachloride Toxicity". Pharmacology Therapeutics 43 (43): 139–154. doi:10.1016/0163-
7258(89)90050-8.
13. ^ Recknagel RO (June 1967). "Carbon tetrachloride hepatotoxicity". Pharmacol. Rev. 19
(2): 145–208. PMID 4859860. http://pharmrev.aspetjournals.org/cgi/pmidlookup?
view=long&pmid=4859860.
14. ^ Masuda Y (October 2006). "[Learning toxicology from carbon tetrachloride-induced
hepatotoxicity"] (in Japanese) ([dead link]). Yakugaku Zasshi 126 (10): 885–99.
doi:10.1248/yakushi.126.885. PMID 17016019.
http://joi.jlc.jst.go.jp/JST.JSTAGE/yakushi/126.885?from=PubMed&lang=en.
15. ^ Rood AS, McGavran PD, Aanenson JW, Till JE (August 2001). "Stochastic estimates of
exposure and cancer risk from carbon tetrachloride released to the air from the rocky flats
plant". Risk Anal. 21 (4): 675–95. doi:10.1111/0272-4332.214143. PMID 11726020.
16. ^ Material Safety Data Sheet, Carbon tetrachloride at Fisher Scientific
17. ^ Odabasi M (2008). "Halogenated Volatile Organic Compounds from the Use of Chlorine-
Bleach-Containing Household Products". Environmental Science & Technology 42 (5):
1445–51. doi:10.1021/es702355u.
18. ^ Fraser P. (1997). "Chemistry of stratospheric ozone and ozone depletion". Australian
Meteorological Magazine 46 (3): 185–193.
19. ^ Evans WFJ, Puckrin E (1996). "A measurement of the greenhouse radiation associated
with carbon tetrachloride (CCl4)". Geophysical Research Letters 23 (14): 1769–72.
doi:10.1029/96GL01258.
20. ^ 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: 14285–96.
doi:10.1029/1999JC900273.
21. ^ The Atlas of Climate Change (2006) by Kirstin Dow and Thomas E. Downing ISBN 978-
0-520-25558-6

[edit] External links

 International Chemical Safety Card 0024
 NIOSH Pocket Guide to Chemical Hazards 0107
 "Carbon Tetrachloride (Group 2B)". International Agency for Research on Cancer
(IARC) – Summaries & Evaluations 71: 401. 1999.
http://www.inchem.org/documents/iarc/vol71/011-carbontetrac.html.
 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
 Egli C, Tschan T, Scholtz R, Cook AM, Leisinger T (November 1988).
"Transformation of tetrachloromethane to dichloromethane and carbon dioxide by
Acetobacterium woodii". Appl. Environ. Microbiol. 54 (11): 2819–24.
PMID 3145712. PMC 204379. http://aem.asm.org/cgi/pmidlookup?
view=long&pmid=3145712.|
 Picardal FW, Arnold RG, Couch H, Little AM, Smith ME (November 1993).
"Involvement of cytochromes in the anaerobic biotransformation of
tetrachloromethane by Shewanella putrefaciens 200". Appl. Environ. Microbiol. 59
(11): 3763–70. PMID 8285682. PMC 182529. http://aem.asm.org/cgi/pmidlookup?
view=long&pmid=8285682.
 Substance profile at ntp.niehs.nih.gov

[show]
v • d • e
Halomethanes

[show]
v • d • e
  Inorganic carbon compounds
Retrieved from "http://en.wikipedia.org/wiki/Carbon_tetrachloride"
Categories: Organochlorides | Halomethanes | Inorganic carbon compounds | Nonmetal
halides | Chlorides | Aerosol propellants | Greenhouse gases | Hazardous air pollutants |
Organochloride insecticides | Refrigerants | Halogenated solvents | IARC Group 2B
carcinogens | Inorganic solvents
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