Carbon tetrachloride - wikipedia Carbon tetrachloride For the chemokine, see CCL4. Carbon tetrachloride Names IUPAC name Carbon tetrachloride, Tetrachloromethane Other names Benziform, Benzinoform, Carbon chloride, Carbon tet, Freon - 10, Refrigerant - 10, Halon - 104, Methane tetrachloride, Methyl tetrachloride, Perchloromethane, Tetraform, Tetrasol Identifiers CAS Number 56 - 23 - 5 3D model ( JSmol ) Interactive image ChEBI CHEBI : 27385 ChemSpider 5730 ECHA InfoCard 100.000. 239 EC Number 200 - 262 - 8 KEGG C07561 PubChem CID 5943 RTECS number FG4900000 UNII CL2T97X0V0 UN number 1846 InChI InChI = 1S / CCl4 / c2 - 1 ( 3, 4 ) 5 Key : VZGDMQKNWNREIO - UHFFFAOYSA - N InChI = 1 / CCl4 / c2 - 1 ( 3, 4 ) 5 Key : VZGDMQKNWNREIO - UHFFFAOYAV SMILES ClC ( Cl ) ( Cl ) Cl Properties Chemical formula CCl Molar mass 153.81 g mol Appearance colourless liquid Odor ether - like odor Density 1.5867 g cm ( liquid ) 1.831 g cm at − 186 ° C ( solid ) 1.809 g cm 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 ) Solubility in water 0.097 g / 100 mL ( 0 ° C ) 0.081 g / 100 mL ( 25 ° C ) Solubility soluble in alcohol, ether, chloroform, benzene, naphtha, CS, formic acid log P 2.64 Vapor pressure 11.94 kPa at 20 ° C Henry 's law constant ( k ) 2.76 x10 atm - cu m / mol Magnetic susceptibility ( χ ) - 66.60 10 cm / mol Refractive index ( n ) 1.4607 Dipole moment 0 D Structure Crystal structure Monoclinic Coordination geometry Tetragonal Molecular shape Tetrahedral Dipole moment 0 D Thermochemistry Specific heat capacity ( C ) 132.6 J / mol K Std molar entropy ( S ) 214.42 J / mol K Std enthalpy of formation ( Δ H ) - 139.3 kJ / mol Gibbs free energy ( Δ G  ̊ ) - 686 kJ / mol Hazards Safety data sheet See : data page ICSC 0024 EU classification ( DSD ) ( outdated ) R - phrases ( outdated ) R23 / 24 / 25, R40, R48 / 23, R59, R52 / 53 S - phrases ( outdated ) ( S1 / 2 ), S23, S36 / 37, S45, S59, S61 NFPA 704 0 0 Flash point < 982 ° C Autoignition temperature 982 ° C ( 1,800 ° F ; 1,255 K ) Lethal dose or concentration ( LD, LC ) : LD ( median dose ) 2350 mg / kg LC ( median concentration ) 5400 ppm ( mammal ) 8000 ppm ( rat, 4 hr ) 9526 ppm ( mouse, 8 hr ) LC ( lowest published ) 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 ) US health exposure limits ( NIOSH ) : PEL ( Permissible ) TWA 10 ppm C 25 ppm 200 ppm ( 5 - minute maximum peak in any 4 hours ) REL ( Recommended ) Ca ST 2 ppm ( 12.6 mg / m ) ( 60 - minute ) IDLH ( Immediate danger ) 200 ppm Related compounds Other cations Silicon tetrachloride Germanium tetrachloride Tin tetrachloride Lead tetrachloride Related chloromethanes Chloromethane Dichloromethane Chloroform Related compounds Tetrafluoromethane Tetrabromomethane Tetraiodomethane Supplementary data page Structure and properties Refractive index ( n ), Dielectric constant ( ε ), etc. Thermodynamic data Phase behaviour solid -- liquid -- gas Spectral data UV, IR, NMR, MS Except where otherwise noted, data are given for materials in their standard state ( at 25 ° C ( 77 ° F ), 100 kPa ). Y verify ( what is ? ) Infobox references Carbon tetrachloride, also known by many other names ( the most notable being tetrachloromethane, also recognized by the IUPAC, carbon tet in the cleaning industry, Halon - 104 in firefighting, and Refrigerant - 10 in HVACR ) is an organic compound with the chemical formula CCl. 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. It has practically no flammability at lower temperatures. Contents 1 History and synthesis 2 Properties 3 Uses 3.1 Historic uses 3.1. 1 Lava Lamps 3.1. 2 Solvent 3.1. 3 Fire suppression 3.1. 4 Niche 3.2 Intoxicant 4 Safety 5 References 6 External links History and synthesis Carbon tetrachloride was originally synthesized by the French chemist Henri Victor Regnault in 1839 by the reaction of chloroform with chlorine, but now it is mainly produced from methane : CH + 4 Cl → CCl + 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 '' : C Cl + Cl → 2 CCl Prior to the 1950s, carbon tetrachloride was manufactured by the chlorination of carbon disulfide at 105 to 130 ° C : CS + 3 Cl → CCl + S Cl 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. 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, CCl 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 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. 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 nm ), β = 111 °. 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. Uses In organic chemistry, carbon tetrachloride serves as a source of chlorine in the Appel reaction. Historic uses 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. Carbon tetrachloride has also been used in the detection of neutrinos. Lava lamps Carbon tetrachloride is a key ingredient in lava lamps, as it 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. It is sometimes useful as a solvent for infrared spectroscopy, because there are no significant absorption bands > 1600 cm. 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. Its use 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. 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 In 1910, the Pyrene Manufacturing Company of Delaware filed a patent to use carbon tetrachloride to extinguish fires. 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. In 1911, Pyrene patented a small, portable extinguisher that used the chemical. The extinguisher consisted of a brass bottle with an integrated handpump that was used to expel a jet of liquid toward the fire. As the container was unpressurized, it could easily be refilled after use. Carbon tetrachloride was suitable for liquid and electrical fires and the extinguishers were often carried on aircraft or motor vehicles. 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. A well - known brand 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. A Red Comet brand, glass globe `` fire grenade '' Niche Carbon tetrachloride was widely used as a dry cleaning solvent, as a refrigerant, and in lava lamps. 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 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 seen. Intoxicant Like many other volatile substances, carbon tetrachloride is prone to misuse by inhalation, due to its possible depressant and / or dissociative effect upon the central nervous system. Use of carbon tetrachloride in this manner presents serious health risks, and may result in toxic effects described below. Safety Time - series of atmospheric concentrations of CCl ( Walker et al., 2000 ). 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. Exposure to high concentrations of carbon tetrachloride ( including vapor ) can affect the central nervous system, degenerate the liver and kidneys, and prolonged exposure may lead to coma or death. Chronic exposure to carbon tetrachloride can cause liver and kidney damage and could result in cancer. See safety data sheets. 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. Thereafter, further information has been requested from the registrants. Later this decision was reversed. In 2008, a study of common cleaning products found the presence of carbon tetrachloride in `` very high concentrations '' ( up to 101 mg / m ) as a result of manufacturers ' mixing of surfactants or soap with sodium hypochlorite ( bleach ). Carbon tetrachloride is also both ozone - depleting and a greenhouse gas. However, since 1992 its atmospheric concentrations have been in decline for the reasons described above ( see also the atmospheric time - series figure ). CCl has an atmospheric lifetime of 85 years. Under high temperatures in air, it forms poisonous phosgene. References ^ Jump up to : `` NIOSH Pocket Guide to Chemical Hazards # 0107 ''. National Institute for Occupational Safety and Health ( NIOSH ). ^ Jump up to : `` Carbon tetrachloride ''. Immediately Dangerous to Life and Health Concentrations ( IDLH ). National Institute for Occupational Safety and Health ( NIOSH ). Jump up ^ V. Regnault ( 1839 ) `` Sur les chlorures de carbone CCl et CCl '' ( On the chlorides of carbon CCl and CCl ), Annales de Chimie et de Physique, vol. 70, pages 104 - 107. Reprinted in German as : V. Regnault ( 1839 ). `` Ueber die Chlorverbindungen des Kohlenstoffs, C2Cl2 und CCl2 ''. Annalen der Pharmacie. 30 ( 3 ) : 350 -- 352. doi : 10.1002 / jlac. 18390300310. ^ Jump up to : 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 Jump up ^ Carbon tetrachloride Jump up ^ F. Brezina, J. Mollin, R. Pastorek, Z. Sindelar. Chemicke tabulky anorganickych sloucenin ( Chemical tables of inorganic compounds ). SNTL, 1986. ^ Jump up to : Use of Ozone Depleting Substances in Laboratories. TemaNord 516 / 2003. Archived February 27, 2008, at the Wayback Machine. Jump up ^ W. Reusch. `` Introduction to Nuclear Magnetic Resonance Spectroscopy ''. Virtual Textbook of Organic Chemistry. Michigan State University. Archived from the original on August 31, 2006. Jump up ^ U.S. Patent 1,010,870, filed April 5, 1910. Jump up ^ U.S. Patent 1,105,263, filed Jan 7, 1911. Jump up ^ `` Pyrene Fire Extinguishers ''. Vintage Fire Extinguishers. Archived from the original on 25 March 2010. Retrieved 23 December 2009. Jump up ^ `` Red Comet Manufacturing Company ''. City of Littleton, CO. Retrieved 30 September 2016. Jump up ^ 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. ^ Jump up to : 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. Jump up ^ 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. Jump up ^ 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. Jump up ^ Recknagel RO ( June 1967 ). `` Carbon tetrachloride hepatotoxicity ''. Pharmacol. Rev. 19 ( 2 ) : 145 -- 208. PMID 4859860. Jump up ^ Masuda Y ( October 2006 ). `` ( Learning toxicology from carbon tetrachloride - induced hepatotoxicity ) ''. Yakugaku Zasshi ( in Japanese ). 126 ( 10 ) : 885 -- 99. doi : 10.1248 / yakushi. 126.885. PMID 17016019. Jump up ^ 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. Jump up ^ Material Safety Data Sheet, Carbon tetrachloride at Fisher Scientific Jump up ^ http://echa.europa.eu/information-on-chemicals/evaluation/community-rolling-action-plan/corap-table/-/substance-rev/3080/term Jump up ^ Odabasi M ( 2008 ). `` Halogenated Volatile Organic Compounds from the Use of Chlorine - Bleach - Containing Household Products ''. Environmental Science & Technology. 42 ( 5 ) : 1445 -- 51. Bibcode : 2008EnST... 42.1445 O. doi : 10.1021 / es702355u. Jump up ^ Fraser P. ( 1997 ). `` Chemistry of stratospheric ozone and ozone depletion ''. Australian Meteorological Magazine. 46 ( 3 ) : 185 -- 193. Jump up ^ Evans WFJ, Puckrin E ( 1996 ). `` A measurement of the greenhouse radiation associated with carbon tetrachloride ( CCl ) ''. Geophysical Research Letters. 23 ( 14 ) : 1769 -- 72. Bibcode : 1996GeoRL... 23.1769 E. doi : 10.1029 / 96GL01258. Jump up ^ 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. Bibcode : 2000JGR... 10514285W. doi : 10.1029 / 1999JC900273. Jump up ^ The Atlas of Climate Change ( 2006 ) by Kirstin Dow and Thomas E. Downing ISBN 978 - 0 - 520 - 25558 - 6 External links International Chemical Safety Card 0024 `` NIOSH Pocket Guide to Chemical Hazards # 0107 ''. National Institute for Occupational Safety and Health ( NIOSH ). `` Carbon Tetrachloride ( Group 2B ) ''. International Agency for Research on Cancer ( IARC ) -- Summaries & Evaluations. 71 : 401. 1999. IARC Monograph : `` Carbon Tetrachloride '' Toxicological profile for carbon tetrachloride Environmental health criteria for carbon tetrachloride Carbon tetrachloride MSDS at Hazardous Chemical Database Substance profile at ntp.niehs.nih.gov ChemSub Online : Carbon tetrachloride Halomethanes Monosubstituted CH F CH Cl CH Br CH I Disubstituted CH F CH ClF CH BrF CH FI CH Cl CH BrCl CH ClI CH Br CH BrI CH I Trisubstituted CHF CHClF CHBrF CHF I CHCl F C * HBrClF C * HClFI CHBr F C * HBrFI CHFI CHCl CHBrCl CHCl I CHBr Cl C * HBrClI CHClI CHBr CHBr I CHBrI CHI Tetrasubstituted CF CClF CBrF CF I CCl F CBrClF CClF I CBr F CBrF I CF I CCl F CBrCl F CCl FI CBr ClF C * BrClFI CClFI CBr F CBr FI CBrFI CFI CCl CBrCl CCl I CBr Cl CBrCl I CCl I CBr Cl CBr ClI CBrClI CClI CBr CBr I CBr I CBrI CI CAt * Chiral compound. Inorganic compounds of carbon and related ions Compounds CBr CCl CF CF CI CO CO CO COS CS CS CSe SiC Carbon ions Carbides ( : C ≡ C : ), ( : : C : : ), ( : C = C = C : ) Cyanides ( : C ≡ N : ) Cyanates ( : O-C ≡ N : ) Thiocyanates ( : S-C ≡ N : ) Fulminates ( : C ≡ N-O : ) Thiofulminates ( : C ≡ N-S : ) Oxides and related Oxides Metal carbonyls Carbonic acid Bicarbonates Carbonates LCCN : sh85020127 GND : 4184864 - 0 NDL : 00576051 Retrieved from `` https://en.wikipedia.org/w/index.php?title=Carbon_tetrachloride&oldid=821176465 '' Categories : Chloroalkanes Halomethanes Inorganic carbon compounds Nonmetal halides Chlorides Greenhouse gases Hazardous air pollutants Organochloride insecticides Refrigerants Halogenated solvents IARC Group 2B carcinogens Inorganic solvents Dry cleaning Hepatotoxins Hidden categories : Webarchive template wayback links CS1 Japanese - language sources ( ja ) ECHA InfoCard ID from Wikidata Chembox having DSD data Chemical articles having a data page Articles containing unverified chemical infoboxes Wikipedia articles with LCCN identifiers Wikipedia articles with GND identifiers Talk Contents About Wikipedia تۆرکجه Català Čeština Dansk Deutsch Eesti Español Esperanto فارسی Français 한국어 Հայերեն Hrvatski Bahasa Indonesia Italiano Latviešu Lëtzebuergesch Lietuvių Magyar Nederlands 日本 語 Polski Português Română Русский Simple English Slovenčina Slovenščina Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska தமிழ் తెలుగు ไทย Türkçe Українська Tiếng Việt 中文 Edit links This page was last edited on 18 January 2018, at 21 : 31. 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Question: how many atoms of chlorine (cl) are in the carbon tetrachloride molecule (ccl4)
Answer: four