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| − | {{Chembox new
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| − | | Name = Chloroethane
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| − | | ImageFileL1 = Chloroethane-skeletal.png
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| − | | ImageSizeL1 = 100px
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| − | | ImageFileR1 = Chloroethane-2D.png
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| − | | ImageSizeR1 = 100px
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| − | | ImageFile2 = Chloroethane-3D-vdW.png
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| − | | ImageSize2 = 150px
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| − | | IUPACName = Chloroethane
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| − | | OtherNames = Ethyl chloride<br />Monochloroethane<br />Chlorene<br />Muriatic ether<br />EtCl<br />[[UN number|UN 1037]]
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| − | | Section1 = {{Chembox Identifiers
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| − | | SMILES = CCCl
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| − | | CASNo = 75-00-3
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| − | | PubChem = 6337
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| − | | RTECS = KH7525000
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| − | }}
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| − | | Section2 = {{Chembox Properties
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| − | | Formula = C<sub>2</sub>H<sub>5</sub>Cl
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| − | | MolarMass = 64.51 g mol<sup>−1</sup>
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| − | | Appearance = colourless gas
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| − | | Density = 0.92 g cm<sup>−3</sup>, liquid
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| − | | Solubility = 0.6 g/100 ml (?°C)
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| − | | MeltingPt = −139°C (134 K)
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| − | | BoilingPt = 12.3°C (285.4 K)
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| − | | pKa =
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| − | | pKb =
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| − | | Viscosity = ? [[Poise|cP]] at ?°C
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| − | }}
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| − | | Section3 = {{Chembox Structure
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| − | | Dipole = 2.06 [[Debye|D]]
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| − | }}
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| − | | Section7 = {{Chembox Hazards
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| − | | ExternalMSDS =
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| − | | MainHazards = Flammable
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| − | | NFPA-H = 2
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| − | | NFPA-F = 4
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| − | | NFPA-R = 2
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| − | | FlashPt = −50°C (closed cup)
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| − | | RPhrases = {{R12}}, {{R40}}, {{R52}}, {{R53}}
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| − | | SPhrases = {{S9}}, {{S16}}, {{S33}}, {{S36}}, {{S37}}, {{S61}}
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| − | }}
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| − | | Section8 = {{Chembox Related
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| − | | Function = [[haloalkanes]]
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| − | | OtherFunctn =
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| − | [[1,1-Dichloroethane|1,1-dichloroethane]]<br />
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| − | [[1,2-Dichloroethane|1,2-dichloroethane]]<br />
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| − | [[1,1,1-Trichloroethane|1,1,1-trichloroethane]]<br />
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| − | [[1,1,2-Trichloroethane|1,1,2-trichloroethane]]<br />
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| − | [[bromoethane]]<br />
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| − | [[chloromethane]]}}
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| − | }}
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| − | '''Chloroethane''' or '''monochloroethane''', commonly known by its old name '''ethyl chloride''', is a [[chemical compound]] once widely used in producing [[tetra-ethyl lead]], a [[gasoline]] additive. It is a colorless, flammable gas or refrigerated liquid with a faintly sweet odor.
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| − | ==Production==
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| − | Ethyl chloride is produced by [[chemical reaction|reacting]] [[ethylene]] and [[hydrogen chloride]] over an [[aluminium chloride]] [[catalyst]] at temperatures ranging from 130-250°C. Under these conditions, ethyl chloride is produced according to the [[chemical equation]].
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| − |
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| − | :[[ethylene|C<sub>2</sub>H<sub>4</sub>]] + [[hydrochloric acid|HCl]] → C<sub>2</sub>H<sub>5</sub>Cl
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| − | At various times in the past, ethyl chloride has also been produced from [[ethanol]] and [[hydrochloric acid]], or from [[ethane]] and [[chlorine]], but these routes are no longer economical. Some ethyl chloride is generated as a byproduct of [[polyvinyl chloride]] production. Should demand for ethyl chloride continue to fall to the point where making it for its own sake is not economical, this may become the leading source of the chemical.
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| − | ==Uses==
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| − | Beginning in 1922 and continuing through most of the 20th century, the major use of ethyl chloride was to produce [[tetraethyl lead]] (TEL), an [[anti-knock additive]] for [[gasoline]]. However, due to growing awareness of [[air pollution]], TEL has been or is being phased out in most of the industrialized world, and the demand for ethyl chloride has fallen sharply.
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| − | Like other chlorinated [[hydrocarbon]]s, ethyl chloride has been used as a [[refrigeration|refrigerant]], an [[aerosol spray#Propellant|aerosol spray propellant]], an [[anesthetic]], and a [[blowing agent]] for foam packaging. For a time it was used as a promoter chemical in the aluminium chloride catalyzed process to produce [[ethylbenzene]], the precursor for [[styrene]] monomer. At present though, it is not widely used in any of these roles.
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| − | The only remaining industrially important use of ethyl chloride is in treating [[cellulose]] to make [[ethylcellulose]], a thickening agent and binder in [[paint]]s, [[cosmetics]], and similar products.
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| − | Ethyl chloride is a prescription drug in the US, supplied as a liquid in a spray bottle propelled by its own vapor pressure. It acts as a mild topical anesthetic by its chilling effect when sprayed on skin, such as when removing splinters in a clinical setting. The heat absorbed by the boiling liquid on tissues produces a deep and rapid chill, but since the boiling point is well above the freezing point of water, it presents no danger of frostbite. The vapor is flammable and narcotic, which requires care.
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| − | Ethyl chloride is a narcotic inhalant drug, sometimes referred to as "Duster". Similar to [[Nitrite inhalants|poppers]], ethyl chloride is used as an inhalant (huffed) during sexual activity for an intense several-minute-long high that results in a prolonged orgasm. In [[Brazil]], it is a traditional (though illegal) drug taken during [[Carnaval]] parades, known as "lança-perfume".
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| − | ==Safety==
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| − | Ethyl chloride is the least toxic of the chloroethanes. Like other chlorinated hydrocarbons, it is a [[central nervous system]] [[depressant]], albeit a less potent one than many similar compounds. People breathing its vapors at less than 1% concentration in air usually experience no symptoms. At higher concentrations, victims usually exhibit symptoms similar to those of alcohol [[intoxication]]. Breathing its vapors at 15% or higher is often fatal.
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| − | Studies on the effects of chronic ethyl chloride exposure in animals have given inconsistent results, and there exist no data for its long-term effects on humans. Some studies have reported that prolonged exposure can produce [[liver]] or [[kidney]] damage, or [[uterus|uterine]] [[cancer]] in mice, but these data have been difficult to reproduce.
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| − | Recent information suggests carcinogenic potential; it has been designated as IARC category A3, ''Confirmed Animal Carcinogen with Unknown Relevance to Humans''. As a result, the State of California has incorporated it into [[Proposition 65]] as a known carcinogen. Nonetheless, it is still used in medicine as a [[local anesthetic]].
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| − | == See also ==
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| − | * [[Alkyl halide]]
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| − | * [[Ethane]]
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| − | * [[Ethylene]]
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| − | * [[Chlorine]]
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| − | * [[Organic chemistry]]
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| − | ==References==
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| − | * McMurry, John. 2004. ''Organic Chemistry'', 6th ed. Belmont, CA: Brooks/Cole. ISBN 0534420052
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| − | * Solomons, T.W. Graham, and Craig B. Fryhle. 2004. ''Organic Chemistry'', 8th ed. Hoboken, NJ: John Wiley. ISBN 0471417998
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| − | * Zumdahl, Steven S. 2005. ''Chemical Principles''. New York, NY: Houghton Mifflin. ISBN 0618372067
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| − | ==External links==
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| − | * [http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc01/icsc0132.htm 1-Chloroethane, International Chemical Safety Card 0132]. International Occupational Safety and Health Information Centre (CIS). Retrieved December 10, 2008.
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| − | * [http://www.cdc.gov/niosh/npg/npgd0267.html NIOSH Pocket Guide to Chemical Hazards: Ethyl chloride]. CDC, National Institute for Occupational Safety and Health. Retrieved December 10, 2008.
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| − | * [http://webbook.nist.gov/cgi/cbook.cgi?Name=chloroethane&Units=SI Ethyl chloride]. NIST Chemistry WebBook. Retrieved December 10, 2008.
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| − | * [http://www.npi.gov.au/database/substance-info/profiles/22.html Chloroethane (ethyl chloride) fact sheet]. National Pollutant Inventory. Retrieved December 10, 2008.
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| − | [[Category:Physical sciences]]
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| − | [[Category:Chemistry]]
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| − | [[Category:Environmental science]]
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| − | {{credit|250562654}}
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