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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 1/CCl4/c2-1(3,4)5
Properties
Molecular formula CCl4
Molar mass 153. 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 They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each Chemical substance commercially available in the KEGG ( Kyoto Encyclopedia of Genes and Genomes) is a collection of Online databases dealing with Genomes Enzymatic pathways and biological chemicals ChEBI (meaning "Chemical Entities of Biological Interest" or "Chemistry at the EBI " is a database of molecular entities focused on 'small' chemical Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference The IUPAC International Chemical Identifier ( InChI, pronounced "INchee" is a textual Identifier for Chemical substances designed to provide a A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 82 g/mol
Appearance Colorless liquid
Density 1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 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. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 92 °C (250 K)
Boiling point

76. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid 72 °C (350 K)
Solubility in water 785 - 800 mg/L at 25 °C
log P 2. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. In the fields of organic and Medicinal chemistry, a partition (P or distribution coefficient (D is 64
Vapor pressure 11. Vapor pressure (also known as equilibrium vapor pressure or saturation vapor pressure) is the Pressure of a Vapor in equilibrium 94 kPa at 20 °C
kH 365 kJ. Henry's Law may sometimes refer to Lenz's Law In Chemistry, Henry's law is one of the Gas laws, formulated by William Henry. 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 (S1/2), S23, S36/37, S45, S59, S61
Flash point Not flammable
Supplementary data page
Structure and
properties		 n, εr, etc. 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 A crystal system is described by three vectors. Molecular geometry or molecular structure is the three- Dimensional arrangement of the Atoms that constitute a Molecule. A tetrahedron (plural tetrahedra) is a Polyhedron composed of four triangular faces three of which meet at each vertex. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance This page provides supplementary chemical data on Carbon 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 The term carcinogen refers to any substance Radionuclide or radiation that is an agent directly involved in the promotion of Cancer or in the fatation of its propagation Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning 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. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning 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. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning 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. 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 in air This page provides supplementary chemical data on Carbon This page provides supplementary chemical data on Carbon 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 Measurement The relative static permittivity εr can be measured for static Electric fields as follows first the Capacitance of a test
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. This page provides supplementary chemical data on Carbon This page provides supplementary chemical data on Carbon Ultraviolet-visible spectroscopy or ultraviolet-visible spectrophotometry ( UV/ VIS) involves the Spectroscopy of Photons in the UV-visible Infrared spectroscopy (IR spectroscopy is the subset of Spectroscopy that deals with the Infrared region of the Electromagnetic spectrum. Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is the name given to a technique which exploits the magnetic properties of certain nuclei Mass spectrometry is an analytical technique that identifies the chemical composition of a compound or sample based on the Mass-to-charge ratio of charged particles In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes It is a reagent in synthetic chemistry and was formerly widely used in fire extinguishers and as a precursor to refrigerants. A reagent or reactant is a substance or compound consumed during a Chemical reaction. Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic A fire extinguisher is an Active fire protection device used to extinguish or control small fires often in emergency situations Refrigeration is the process of removing Heat from an enclosed space or from a substance and moving it to a place where it is unobjectionable 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. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general Colloquially, it is called "carbon tet".

Contents

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 720,000,000 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 chlorination reactions, such as the syntheses of dichloromethane and chloroform. Henri Victor Regnault ( July 21, 1810 – January 19, 1878) was a French chemist and physicist best known for his careful measurements Methane is a Chemical compound with the molecular formula. It is the simplest Alkane, and the principal component of Natural gas. 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 Dichloromethane ( DCM) or methylene chloride is the Chemical compound with the formula CH2Cl2 Chloroform, also known as trichloromethane and methyl trichloride, is a Chemical compound with formula C[[Hydrogen H]] Cl 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:

CS2 + 3Cl2 → CCl4 + S2Cl2[1]

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. Hexachloroethane, also known as perchloroethane (PCA C2[[chlorine Cl6]], is a colorless solid at room temperature which is used by the Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and Disulfur dichloride is the Chemical compound with the formula S2Cl2 In Chemistry, a molecule is defined as a sufficiently stable electrically neutral group of at least two Atoms in a definite arrangement held together by Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and History See also Atomic theory, Atomism The concept that matter is composed of discrete units and cannot be divided into arbitrarily tiny A tetrahedron (plural tetrahedra) is a Polyhedron composed of four triangular faces three of which meet at each vertex. Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 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. A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. 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. Volatility in the context of Chemistry, Physics and Thermodynamics is a measure of the tendency of a substance to Vaporize. A vapor or vapour (see Spelling differences) is a substance in the Gas phase at a Temperature lower than its Critical temperature Tetrachloroethylene, also known under its systematic name tetrachloroethene and as perchloroethylene, perchloroethene, perc, and PCE Dry cleaning is any cleaning process for Clothing and Textiles using an organic Solvent rather than Water.

Solid tetrachloromethane has 2 allotropes: crystaline II below -47. Allotropy (Gr allos, other and tropos, manner is a behavior exhibited by certain Chemical elements these elements can exist in two or more different 5 °C (225. 6 K) and crystaline 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. In Crystallography, the monoclinic Crystal system is one of the 7 lattice Point groups A crystal system is described by three vectors. The Lattice Constant refers to the constant distance between Unit cells in a Crystal lattice. 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 solvent, as a refrigerant, and in fire extinguishers[5]. Dry cleaning is any cleaning process for Clothing and Textiles using an organic Solvent rather than Water. A solvent is a liquid or gas 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 A fire extinguisher is an Active fire protection device used to extinguish or control small fires often in emergency situations 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. Tetrachloroethylene, also known under its systematic name tetrachloroethene and as perchloroethylene, perchloroethene, perc, and PCE Year 1940 ( MCMXL) was a Leap year starting on Monday (link will display the full 1940 calendar of the Gregorian calendar. 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. A pesticide is a substance or mixture of substances used to kill a pest. Year 1970 ( MCMLXX) was a Common year starting on Thursday (link shows full calendar of the Gregorian calendar. The United States of America —commonly referred to as the

Prior to the Montreal Protocol, large quantities of carbon tetrachloride were used to produce the freon refrigerants R-11 (trichlorofluoromethane) and R-12 (dichlorodifluoromethane). For other similarly-named agreements see Montreal Convention (disambiguation. Freon is DuPont 's trade name for its odorless colorless nonflammable and noncorrosive Chlorofluorocarbon and Hydrochlorofluorocarbon Refrigerants Trichlorofluoromethane also called freon-11, CFC-11, or R-11, is a Chlorofluorocarbon. Dichlorodifluoromethane ( R-12) usually sold under the Brand name Freon-12, is a Chlorofluorocarbon Halomethane, commonly known However, these refrigerants are now believed to play a role in ozone depletion and have been phased out. 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 Earth's Carbon tetrachloride is still used to manufacture less destructive refrigerants.

Carbon tetrachloride has also been used in the detection of neutrinos. Neutrinos are Elementary particles that travel close to the Speed of light, lack an Electric charge, are able to pass through ordinary matter almost 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 flammability at lower temperatures. Flammability is the ease with which a substance will ignite causing Fire or Combustion. Under high temperatures in air, it forms poisonous phosgene. Phosgene is the Chemical compound with the formula COCl2 This colorless gas gained infamy as a Chemical weapon during World War I

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 or NBS is a Chemical reagent which is used in Radical substitution and Electrophilic addition reactions

In organic chemistry, carbon tetrachloride serves as a source of chlorine in the Appel reaction. Organic chemistry is a discipline within Chemistry which involves the scientific study of the structure properties composition reactions, and preparation The Appel reaction is an Organic reaction that converts an Alcohol into an Alkyl Chloride using Triphenylphosphine and Carbon

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. A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. It is sometimes useful as a solvent for infrared spectroscopy because there are no significant absorption bands > 1600 cm-1. Infrared spectroscopy (IR spectroscopy is the subset of Spectroscopy that deals with the Infrared region of the Electromagnetic spectrum. Because carbon tetrachloride does not have any hydrogen atoms, it was historically used in proton NMR spectroscopy. Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is the name given to a technique which exploits the magnetic properties of certain nuclei 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. Use of carbon tetrachloride in determination of oil has been replaced by various other solvents[7].

Safety

Exposure to high concentrations of carbon tetrachloride (including vapor) can affect the central nervous system, degenerate the liver[8] and kidneys[9] and may result (after prolonged exposure) in coma and even death[10]. A vapor or vapour (see Spelling differences) is a substance in the Gas phase at a Temperature lower than its Critical temperature In Vertebrates the central nervous system ( CNS) is the part of the Nervous system which is enclosed in the Meninges. In Medicine, a coma (from the Greek koma, meaning deep sleep is a profound state of Unconsciousness. Death is the termination of the biological functions that define living Organisms It refers both to a specific Chronic exposure to carbon tetrachloride can cause liver[11][12] and kidney damage and could result in cancer[13] More information can be found in Material safety data sheets. Drug metabolism in liver The human body identifies almost all drugs as foreign substances (i Nephrotoxicity (from Greek nephros "kidney" is a Poisonous effect of some substances both Toxic chemicals and Medication, on the Kidney Cancer (medical term Malignant Neoplasm) is a class of Diseases in which a group of cells display uncontrolled A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance

Carbon tetrachloride is also both ozone-depleting[14] and a greenhouse gas[15]. 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 Earth's Greenhouse gases are gaseous constituents of the atmosphere bothnatural and anthropogenic that absorb and emit radiation at specific wavelengths within the spectrum of thermal infrared However, since 1992[16] its atmospheric concentrations have been in decline for the reasons described above (see also the atmospheric time-series figure).

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

See also

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. The haloalkanes (also known as halogenoalkanes or alkyl halides) are a group of Chemical compounds consisting of Alkanes such as Methane Halomethane compounds are molecules of Methane ( C[[hydrogen H]]4 with one or more of the Hydrogen atoms replaced with Halogen atoms Chloromethane, also called Methyl chloride, R-40 or HCC 40 is a Chemical compound of the group of Organic compounds called Haloalkanes. Dichloromethane ( DCM) or methylene chloride is the Chemical compound with the formula CH2Cl2 Chloroform, also known as trichloromethane and methyl trichloride, is a Chemical compound with formula C[[Hydrogen H]] Cl Tetrafluoromethane, also known as carbon tetrafluoride, Freon-14 and R 14, is a Carbon Fluoride (CF4 Tetrabromomethane, CBr4 also known as carbon tetrabromide, is a Carbon Bromide. Carbon tetraiodide is CI4, a Tetrahalomethane. Being bright red it is a relatively rare example of a highly colored methane derivative Dutch Standards are environmental pollutant reference values used in Environmental remediation, investigation and cleanup 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): 350. doi:10.1002/jlac.18390300310. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
  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 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". Environmental Forensics 1 (1): 69 - 81. doi:10.1006/enfo.2000.0010. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
  6. ^ Introduction to Nuclear Magnetic Resonance Spectroscopy, Michigan State University
  7. ^ Use of Ozone Depleting Substances in Laboratories. Michigan State University ( MSU) is a co-educational public Research university in East Lansing, Michigan USA. TemaNord 516/2003. [1]
  8. ^ 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.  
  9. ^ 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. doi:10.1002/hep.1840170420. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
  10. ^ 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. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
  11. ^ Recknagel RO (1967). "Carbon tetrachloride Hepatotoxicity". Pharmacological Reviews 19 (2): 145.  
  12. ^ Masuda Y (2006). "Learning toxicology from carbon tetrachloride-induced hepatotoxicity". Yakugaku Zasshi -Journal of the Pharmaceutical Society of Japan 126 (10): 885-899.  
  13. ^ 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. doi:10.1111/0272-4332.214143. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
  14. ^ Fraser P. (1997). "Chemistry of stratospheric ozone and ozone depletion". Australian Meteorological Magazine 46 (3): 185-193.  
  15. ^ Evans WFJ, Puckrin E (1996). "A measurement of the greenhouse radiation associated with carbon tetrachloride (CCl4)". Geophysical Research Letters 23 (14): 1769-1772.  
  16. ^ 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. doi:10.1029/1999JC900273. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  

External links

The National Institute for Occupational Safety and Health (or NIOSH) is the United States federal agency responsible for conducting research and making recommendations

Dictionary

carbon tetrachloride

-noun

  1. (organic chemistry) The halogenated hydrocarbon tetrachloromethane; a toxic, non-inflammable liquid, used as a solvent, in dry cleaning and in fire extinguishers.
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