Carbon tetrachloride

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Carbon tetrachloride
Structural formula of tetrachloride Tetrachlormethan.svg
Structural formula of tetrachloride
Space-filling model carbon tetrachloride Carbon-tetrachloride-3D-vdW.png
Space-filling model carbon tetrachloride
Carbon tetrachloride.JPG
Names
Preferred IUPAC name
Tetrachloromethane
Other names
Benziform
benzinoform
carbon chloride gas [1]
carbon tet.
Freon-10
Refrigerant-10
Halon-104
methane tetrachloride
methyl tetrachloride
perchloromethane, PCM
Tetraform
Tetrasol
TCM, trematocide
Identifiers
3D model (JSmol)
1098295
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.239 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-262-8
2347
KEGG
PubChem CID
RTECS number
  • FG4900000
UNII
UN number 1846
  • InChI=1S/CCl4/c2-1(3,4)5 Yes check.svgY
    Key: VZGDMQKNWNREIO-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/CCl4/c2-1(3,4)5
    Key: VZGDMQKNWNREIO-UHFFFAOYAV
  • ClC(Cl)(Cl)Cl
Properties
CCl4
Molar mass 153.81 g/mol
AppearanceColourless liquid
Odor Sweet, chloroform-like odor
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)
Melting point −22.92 °C (−9.26 °F; 250.23 K)
Boiling point 76.72 °C (170.10 °F; 349.87 K)
  • 0.097 g/100mL (0 °C)
  • 0.081 g/100mL (25 °C)
Solubility Soluble in alcohol, ether, chloroform, benzene, naphtha, CS2, formic acid
log P 2.64
Vapor pressure 11.94 kPa at 20 °C
2.76×10−2 atm·m3/mol
−66.60×10−6 cm3/mol
Thermal conductivity 0.1036 W/m·K (300 K) [2]
1.4607
Viscosity 0.86 mPa·s [3]
0 D
Structure
Monoclinic
Tetragonal
Tetrahedral
0 D
Thermochemistry
132.6 J/mol·K
Std molar
entropy
(S298)
214.39 J/mol·K
−95.6 kJ/mol
−87.34 kJ/mol [4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
potential occupational carcinogen
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H301, H302, H311, H331, H351, H372, H412, H420
P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P314, P321, P322, P330, P361, P363, P403+P233, P405, P501, P502
NFPA 704 (fire diamond)
3
0
0
982 °C (1,800 °F; 1,255 K)
Lethal dose or concentration (LD, LC):
250 mg/kg
  • 5400 ppm (mammal)
  • 8000 ppm (rat, 4 hr)
  • 9526 ppm (mouse, 8 hr) [5]
  • 1000 ppm (human)
  • 20,000 ppm (guinea pig, 2 hr)
  • 38,110 ppm (cat, 2 hr)
  • 50,000 ppm (human, 5 min)
  • 14,620 ppm (dog, 8 hr) [5]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 10 ppm C 25 ppm 200 ppm (5-minute maximum peak in any 4 hours) [6]
REL (Recommended)
Ca ST 2 ppm (12.6 mg/m3) [60-minute] [6]
IDLH (Immediate danger)
200 ppm [6]
Safety data sheet (SDS) ICSC 0024
Related compounds
Other anions
Carbon tetrafluoride
Carbon tetrabromide
Carbon tetraiodide
Other cations
Silicon tetrachloride
Germanium tetrachloride
Tin tetrachloride
Lead tetrachloride
Related chloromethanes
Chloromethane
Dichloromethane
Chloroform
Supplementary data page
Carbon tetrachloride (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVACR) is an organochlorine chemical compound with the chemical formula CCl4. It is a colourless liquid with a "sweet" smell that can be detected at low levels. It is practically incombustible at lower temperatures. It was formerly widely used in fire extinguishers, as a precursor to refrigerants and as a cleaning agent, but has since been phased out because of environmental and safety concerns. Exposure to high concentrations of carbon tetrachloride (including vapor) can affect the central nervous system and degenerate the liver and kidneys. Prolonged exposure can be fatal.

Contents

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 symmetric 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 such as 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.

Solid tetrachloromethane has two polymorphs: crystalline II below 47.5 °C (225.6 K) and crystalline I above 47.5 °C. [7] 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°. [8]

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.

History and synthesis

Carbon tetrachloride was originally synthesized by Michael Faraday who named it "protochloride of carbon" in 1820 via decomposition of hexachloroethane ("perchloride of carbon") which he synthesized by chlorination of ethylene [9] 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: [10]

CS2 + 3Cl2 → CCl4 + S2Cl2

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. [10]

Safety

Carbon tetrachloride is one of the most potent hepatotoxins (toxic to the liver), so much so that it is widely used in scientific research to evaluate hepatoprotective agents. [11] [12] Exposure to high concentrations of carbon tetrachloride (including vapor) can affect the central nervous system and degenerate the liver [12] and kidneys, [13] and prolonged exposure may lead to coma or death. [14] Chronic exposure to carbon tetrachloride can cause liver [15] [16] and kidney damage and could result in cancer. [17] See safety data sheets. [18]

The effects of carbon tetrachloride on human health and the environment have been assessed under REACH in 2012 in the context of the substance evaluation by France. [19]

In 2008, a study of common cleaning products found the presence of carbon tetrachloride in "very high concentrations" (up to 101 mg/m3) as a result of manufacturers' mixing of surfactants or soap with sodium hypochlorite (bleach). [20]

Carbon tetrachloride is also both ozone-depleting [21] and a greenhouse gas. [22] However, since 1992 [23] its atmospheric concentrations have been in decline for the reasons described above (see atmospheric concentration graphs in the gallery). CCl4 has an atmospheric lifetime of 85 years. [24]

At high temperatures in air, it decomposes or burns to produce poisonous phosgene.

Toxicological studies

Carbon tetrachloride is a suspected human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. [25] The World Health Organization reports carbon tetrachloride can induce hepatocellular carcinomas (hepatomas) in mice and rats. The doses inducing hepatic tumours are higher than those inducing cell toxicity. [26] The International Agency for Research on Cancer (IARC) classified this compound in Group 2B, "possibly carcinogenic to humans". [27]

Uses

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

Carbon tetrachloride made from heavy chlorine-37 has been used in the detection of neutrinos.

One specialty use of carbon tetrachloride is in stamp collecting, to reveal watermarks on postage stamps without damaging them. A small amount of the liquid is placed on the back of a stamp, sitting in a black glass or obsidian tray. The letters or design of the watermark can then be seen clearly.

Historical uses

Carbon tetrachloride was widely used as a dry cleaning solvent, as a refrigerant, and in lava lamps. [28] In the last case, carbon tetrachloride is a key ingredient that adds weight to the otherwise buoyant wax.

Solvent

It once was a popular solvent in organic chemistry, but, because of its adverse health effects, it is rarely used today. [11] It is sometimes useful as a solvent for infrared spectroscopy, because there are no significant absorption bands above 1600 cm−1. Because carbon tetrachloride does not have any hydrogen atoms, it was historically used in proton NMR spectroscopy. In addition to being toxic, its dissolving power is low. [29] Its use in NMR spectroscopy 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. [11] Because it has no C–H bonds, carbon tetrachloride does not easily undergo free-radical reactions. 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).

Fire suppression

A brass Pyrene carbon tetrachloride fire extinguisher Carbon tetrachloride 1930s fire extinguisher.jpg
A brass Pyrene carbon tetrachloride fire extinguisher
A Red Comet brand glass globe ("fire grenade") containing carbon tetrachloride Snohomish - Blackman House Museum - Comet fire extinguisher 02A.jpg
A Red Comet brand glass globe ("fire grenade") containing carbon tetrachloride

In 1910, the Pyrene Manufacturing Company of Delaware filed a patent to use carbon tetrachloride to extinguish fires. [30] The liquid was vaporized by the heat of combustion and extinguished flames, an early form of gaseous fire suppression. At the time it was believed the gas simply displaced oxygen in the area near the fire, but later research found that the gas actually inhibits the chemical chain reaction of the combustion process. [ citation needed ]

In 1911, Pyrene patented a small, portable extinguisher that used the chemical. [31] The extinguisher consisted of a brass bottle with an integrated hand-pump that was used to expel a jet of liquid toward the fire. As the container was unpressurized, it could easily be refilled after use. [32] Carbon tetrachloride was suitable for liquid and electrical fires and the extinguishers were often carried on aircraft or motor vehicles. However as early as 1920, there were reports of fatalities caused by the chemical when used to fight a fire in a confined space. [33]

In the first half of the 20th century, another common fire extinguisher was a single-use, sealed glass globe known as a "fire grenade", filled with either carbon tetrachloride or salt water. The bulb could be thrown at the base of the flames to quench the fire. The carbon tetrachloride type could also be installed in a spring-loaded wall fixture with a solder-based restraint. When the solder melted by high heat, the spring would either break the globe or launch it out of the bracket, allowing the extinguishing agent to be automatically dispersed into the fire. [34]

A well-known brand of fire grenade was the "Red Comet", which was variously manufactured with other fire-fighting equipment in the Denver, Colorado area by the Red Comet Manufacturing Company from its founding in 1919 until manufacturing operations were closed in the early 1980s. [35]

Refrigerants

Prior to the Montreal Protocol, large quantities of carbon tetrachloride were used to produce the chlorofluorocarbon refrigerants R-11 (trichlorofluoromethane) and R-12 (dichlorodifluoromethane). However, these refrigerants play a role in ozone depletion and have been phased out. Carbon tetrachloride is still used to manufacture less destructive refrigerants.

Fumigant

Carbon tetrachloride was widely used as a fumigant to kill insect pests in stored grain. [36] It was employed in a mixture known as 80/20, that was 80% carbon tetrachloride and 20% Carbon disulfide. [37] The United States Environmental Protection Agency banned its use in 1985. [38]

Related Research Articles

<span class="mw-page-title-main">Phosgene</span> Toxic gaseous compound (COCl2)

Phosgene is the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. It can be thought of as formaldehyde with the hydrogen atoms replaced by chlorine atoms. Phosgene is a valued and important industrial building block, especially for the production of precursors of polyurethanes and polycarbonate plastics.

<span class="mw-page-title-main">Chlorofluorocarbon</span> Class of organic compounds commonly used as refrigerants

Chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) are fully or partly halogenated hydrocarbons that contain carbon (C), hydrogen (H), chlorine (Cl), and fluorine (F), produced as volatile derivatives of methane, ethane, and propane. They are also commonly known by the DuPont brand name Freon.

Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene, and abbreviations such as "perc" (or "PERC"), and "PCE", is a chlorocarbon with the formula Cl2C=CCl2. It is a colorless liquid widely used for dry cleaning of fabrics, hence it is sometimes called "dry-cleaning fluid". It also has its uses as an effective automotive brake cleaner. It has a sweet odor, similar to the smell of chloroform, detectable by most people at a concentration of 1 part per million (1 ppm). Worldwide production was about 1 million metric tons (980,000 long tons; 1,100,000 short tons) in 1985.

<span class="mw-page-title-main">Carbon disulfide</span> Neurotoxic compound with formula S=C=S

Carbon disulfide is an inorganic compound with the chemical formula CS2 and structure S=C=S. It is a colorless liquid, which is used as a building block in organic synthesis. It has a pleasant, ether- or chloroform-like odor, but commercial samples are usually yellowish and are typically contaminated with foul-smelling impurities.

Bromotrifluoromethane, commonly known as Halon 1301, R13B1, Halon 13B1 or BTM, is an organic halide with the chemical formula CBrF3. It is used for gaseous fire suppression as a far less toxic alternative to bromochloromethane.

<span class="mw-page-title-main">Dichloromethane</span> Chemical compound

Dichloromethane is an organochlorine compound with the formula CH2Cl2. This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents.

Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula CH3Cl. One of the haloalkanes, it is a colorless, odorless, flammable gas. Methyl chloride is a crucial reagent in industrial chemistry, although it is rarely present in consumer products, and was formerly utilized as a refrigerant.

<span class="mw-page-title-main">1,1,1-Trichloroethane</span> Chemical compound

The organic compound 1,1,1-trichloroethane, also known as methyl chloroform, is a chloroalkane with the chemical formula CH3CCl3. It is an isomer of 1,1,2-trichloroethane. This colorless, sweet-smelling liquid was once produced industrially in large quantities for use as a solvent. It is regulated by the Montreal Protocol as an ozone-depleting substance and its use is being rapidly phased out.

<span class="mw-page-title-main">Trichloroethylene</span> Chemical compound

The chemical compound trichloroethylene is a halocarbon with the formula C2HCl3, commonly used as an industrial solvent. It is a clear, colourless non-flammable liquid with a chloroform-like sweet smell. It should not be confused with the similar 1,1,1-trichloroethane, which is commonly known as chlorothene.

Halomethane compounds are derivatives of methane with one or more of the hydrogen atoms replaced with halogen atoms. Halomethanes are both naturally occurring, especially in marine environments, and human-made, most notably as refrigerants, solvents, propellants, and fumigants. Many, including the chlorofluorocarbons, have attracted wide attention because they become active when exposed to ultraviolet light found at high altitudes and destroy the Earth's protective ozone layer.

Dichlorodifluoromethane (R-12) is a colorless gas usually sold under the brand name Freon-12, and a chlorofluorocarbon halomethane (CFC) used as a refrigerant and aerosol spray propellant. Complying with the Montreal Protocol, its manufacture was banned in developed countries in 1996, and in developing countries in 2010 out of concerns about its damaging effect on the ozone layer. Its only allowed usage is as a fire retardant in submarines and aircraft. It is soluble in many organic solvents. R-12 cylinders are colored white.

Trichlorofluoromethane, also called freon-11, CFC-11, or R-11, is a chlorofluorocarbon (CFC). It is a colorless, faintly ethereal, and sweetish-smelling liquid that boils around room temperature. CFC-11 is a Class 1 ozone-depleting substance which damages Earth's protective stratospheric ozone layer.

<span class="mw-page-title-main">Carbon tetrafluoride</span> Chemical compound

Tetrafluoromethane, also known as carbon tetrafluoride or R-14, is the simplest perfluorocarbon (CF4). As its IUPAC name indicates, tetrafluoromethane is the perfluorinated counterpart to the hydrocarbon methane. It can also be classified as a haloalkane or halomethane. Tetrafluoromethane is a useful refrigerant but also a potent greenhouse gas. It has a very high bond strength due to the nature of the carbon–fluorine bond.

1,2-Dichlorotetrafluoroethane, or R-114, also known as cryofluorane (INN), is a chlorofluorocarbon (CFC) with the molecular formula ClF2CCF2Cl. Its primary use has been as a refrigerant. It is a non-flammable gas with a sweetish, chloroform-like odor with the critical point occurring at 145.6 °C and 3.26 MPa. When pressurized or cooled, it is a colorless liquid. It is listed on the Intergovernmental Panel on Climate Change's list of ozone depleting chemicals, and is classified as a Montreal Protocol Class I, group 1 ozone depleting substance.

Chlorotrifluoromethane, R-13, CFC-13, or Freon 13, is a non-flammable, non-corrosive chlorofluorocarbon (CFC) and also a mixed halomethane. It is a man-made substance used primarily as a refrigerant. When released into the environment, CFC-13 has a high ozone depletion potential, high global warming potential, and long atmospheric lifetime.

<span class="mw-page-title-main">Bromochloromethane</span> Chemical compound

Bromochloromethane or methylene bromochloride and Halon 1011 is a mixed halomethane. It is a heavy low-viscosity liquid with refractive index 1.4808.

<span class="mw-page-title-main">Hexachlorobutadiene</span> Chemical compound

Hexachlorobutadiene, Cl2C=C(Cl)C(Cl)=CCl2, is a colorless liquid at room temperature that has an odor similar to that of turpentine. It is a chlorinated aliphatic diene with niche applications but is most commonly used as a solvent for other chlorine-containing compounds.

1,1,2-Trichloro-1,2,2-trifluoroethane, also called trichlorotrifluoroethane or CFC-113, is a chlorofluorocarbon. It has the formula Cl2FC−CClF2. This colorless, volatile liquid is a versatile solvent.

<span class="mw-page-title-main">1,2-Dichloropropane</span> Chemical compound

1,2-Dichloropropane is an organic compound classified as a chlorocarbon. It is a colorless, flammable liquid with a sweet odor. it is obtained as a byproduct of the production of epichlorohydrin, which is produced on a large scale.

<span class="mw-page-title-main">Perchloromethyl mercaptan</span> Chemical compound

Perchloromethyl mercaptan is the organosulfur compound with the formula CCl3SCl. It is mainly used as an intermediate for the synthesis of dyes and fungicides (captan, folpet). It is a colorless oil, although commercial samples are yellowish. It is insoluble in water but soluble in organic solvents. It has a foul, unbearable, acrid odor. Perchloromethyl mercaptan is the original name. The systematic name is trichloromethanesulfenyl chloride, because the compound is a sulfenyl chloride, not a mercaptan.

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