View source for Chloroethane

{{short description|Chemical compound commonly known as ethyl chloride}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 443517203
| Name = Chloroethane
| ImageFileL1 = Chloroethane-skeletal.svg
| ImageSizeL1 = 100px
| ImageClassL1 = skin-invert
| ImageNameL1 = Skeletal formula of chloroethane
| ImageFileR1 = Chloroethane-2D.svg
| ImageSizeR1 = 100px
| ImageClassR1 = skin-invert
| ImageNameR1 = Skeletal formula of chloroethane with stereo bonds
| ImageFile2 = Chloroethane-3D-vdW.png
| ImageClass2 = bg-transparent
| ImageSize2 = 150px
| ImageName2 = Ball-and-stick model of chloroethane
| PIN = Chloroethane
| OtherNames = Ethyl chloride, Monochloroethane, Chlorene, Muriatic ether, EtCl, [[UN number|UN 1037]], Hydrochloric Ether, Chelen, Kelene<ref>Helbing, H. (1895). Modern materia medica for pharmacists, medical men, and students. USA: Lehn & Fink.</ref>
|Section1={{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 47554
| SMILES = ClCC
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6097
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 46U771ERWK
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D04088
| InChI = 1/C2H5Cl/c1-2-3/h2H2,1H3
| InChIKey = HRYZWHHZPQKTII-UHFFFAOYAJ
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 46058
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H5Cl/c1-2-3/h2H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HRYZWHHZPQKTII-UHFFFAOYSA-N
| CASNo = 75-00-3
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 6337
| RTECS = KH7525000
  }}
|Section2={{Chembox Properties
| C=2 | H=5 | Cl=1
| Appearance = Colorless gas
| Density = 0.921 g/cm<sup>3</sup> (0-4 °C)<ref name=sigma>{{Sigma-Aldrich|id=295310|name=Chloroethane|accessdate=2014-05-26}}</ref><br> 0.8898 g/cm<sup>3</sup> (25 °C)
| Odor = Pungent, ethereal<ref name=pubchem>{{PubChemLink|6337}}</ref>
| Solubility = 0.447 g/100 mL (0 °C)<br> 0.574 g/100 mL (20 °C)<ref name=epa /><ref name=chemister />
| SolubleOther = Soluble in [[ethanol|alcohol]], [[diethyl ether|ether]]<ref name=mts>{{cite web|url=https://www.mathesongas.com/pdfs/msds/MAT08880.pdf|title=Material Safety Data Sheet|website=www.mathesongas.com|publisher=Matheson Tri-Gas, Inc.|access-date=2014-05-26}}</ref>
| Solubility1 = 48.3 g/100 g (21 °C)<ref name=chemister />
| Solvent1 = ethanol
| MeltingPtC = −138.7
| BoilingPtC = 12.27
| BoilingPt_notes = <br> decomposes at 510&nbsp;°C<ref name=chemister>{{Cite web | url=http://chemister.ru/Database/properties-en.php?dbid=1&id=1545 |title = Chloroethane}}</ref>
| pKa = 
| pKb = 
| Viscosity = 0.279 cP (10 °C)<ref name=pubchem />
| RefractIndex = 1.3676 (20 °C)<br> 1.001 (25 °C)<ref name=pubchem />
| VaporPressure = 8.4 kPa (-40 °C)<br> 62.3 kPa (0 °C)<ref name=nist>{{nist|name=Ethyl chloride|id=C75003|accessdate=2014-05-26|mask=FFFF|units=SI}}</ref><br> 134.6 kPa (20 °C)<ref name=pubchem />
| HenryConstant = 11.1 L·atm/mol (24 °C)<ref name=pubchem />
  }}
|Section5={{Chembox Thermochemistry
| HeatCapacity = 104.3 J/mol·K<ref name=chemister />
| Entropy = 275.7 J/mol·K<ref name=chemister />
| DeltaHf = −137 kJ/mol<ref name=chemister /><ref name=nist />
| DeltaGf = −59.3 kJ/mol<ref name=chemister />
}}
|Section3={{Chembox Structure
| Dipole = 2.06 [[Debye|D]]
  }}
|Section6={{Chembox Pharmacology
| ATCCode_prefix = N01
| ATCCode_suffix = BX01
}}
|Section7={{Chembox Hazards
| ExternalSDS = 
| GHSPictograms = {{GHS02}}{{GHS08}}<ref name="sigma" />
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|220|351|412}}<ref name="sigma" />
| PPhrases = {{P-phrases|210|273|281|410+403}}<ref name="sigma" />
| MainHazards = Flammable
| NFPA-H = 2
| NFPA-F = 4
| NFPA-R = 2
| FlashPtC = −43
| FlashPt_notes = <br> open cup<ref name=epa>{{cite web|url=https://nepis.epa.gov/Exe/ZyNET.exe/00002EZG.txt?ZyActionD=ZyDocument&Client=EPA&Index=1986%20Thru%201990&Docs=&Query=&Time=&EndTime=&SearchMethod=1&TocRestrict=n&Toc=&TocEntry=&QField=&QFieldYear=&QFieldMonth=&QFieldDay=&UseQField=&IntQFieldOp=0&ExtQFieldOp=0&XmlQuery=&File=D%3A%5CZYFILES%5CINDEX%20DATA%5C86THRU90%5CTXT%5C00000001%5C00002EZG.txt&User=ANONYMOUS&Password=anonymous&SortMethod=h%7C-&MaximumDocuments=1&FuzzyDegree=0&ImageQuality=r75g8/r75g8/x150y150g16/i425&Display=p%7Cf&DefSeekPage=x&SearchBack=ZyActionL&Back=ZyActionS&BackDesc=Results%20page&MaximumPages=1&ZyEntry=6|title=Summary of Emissions Associated with Sources of Ethyl Chloride|website=nepis.epa.gov|publisher=National Service Center for Environmental Publications (NSCEP)|access-date=2014-05-26}}</ref><br> {{convert|-50|C|F K}}<br> closed cup<ref name="sigma" /><ref name=mts />
| AutoignitionPtC = 494 to 519
| AutoignitionPt_ref = <ref name=chemister /><ref name=mts />
| PEL = TWA 1000 ppm (2600 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0267}}</ref>
| ExploLimits = 3.8%-15.4%<ref name=PGCH/>
| IDLH = 3800 ppm<ref name=PGCH/>
| REL = Handle with caution in the workplace.<ref name=PGCH/>
| LC50 = 59,701 ppm (rat, 2 hr)<br/>54,478 ppm (mouse, 2 hr)<br/><ref name=IDLH>{{IDLH|75003|Ethyl chloride}}</ref>
| LCLo = 40,000 ppm (guinea pig, 45 min)<ref name=IDLH/>
  }}
|Section8={{Chembox Legal status
| legal_AU = 
| legal_BR = B1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_US = 
| legal_UK = 
| legal_UN = 
}}
|Section9={{Chembox Related
| OtherFunction_label = [[haloalkanes]]
| OtherFunction =
[[1,1-Dichloroethane|1,1-dichloroethane]]<br />
[[1,2-Dichloroethane|1,2-dichloroethane]]<br />
[[1,1,1-Trichloroethane|1,1,1-trichloroethane]]<br />
[[1,1,2-Trichloroethane|1,1,2-trichloroethane]]<br />
[[bromoethane]]<br />
[[chloromethane]]}}
}}

'''Chloroethane''', commonly known as '''ethyl chloride''', is a [[chemical compound]] with [[chemical formula]] CH<sub>3</sub>CH<sub>2</sub>Cl, once widely used in producing [[tetraethyllead]], a [[gasoline]] additive. It is a colorless, flammable gas or refrigerated liquid with a faintly sweet odor.<ref name=Ross/>

Ethyl chloride was first synthesized by [[Basil Valentine]] by reacting [[ethanol]] and [[hydrochloric acid]] in 1440.<ref name=Ross/> Glauber made it in 1648 by reacting ethanol and [[zinc chloride]].<ref name=Ross/>

==Production==
Chloroethane is produced by [[hydrochlorination]] of [[ethylene]]:<ref name=Ross>{{Ullmann | last1 = Rossberg | first1 = M. | last2 = Lendle | first2 = W. | last3 = Pfleiderer | first3 = G. | last4 = Tögel | first4 = A. | last5 = Dreher | first5 = E. L. | last6 = Langer | first6 = E. | last7 = Rassaerts | first7 = H. | last8 = Kleinschmidt | first8 = P. | last9 = Strack | first9 = H. | last10 = Cook | first10 = R. | last11 = Beck | first11 = U. | last12 = Lipper | first12 = K.-A. | last13 = Torkelson | first13 = T.R.| last14 = Löser | first14 = E. | last15 = Beutel | first15 = K.K. | last16 = Mann | first16 = T. | title= Chlorinated Hydrocarbons| year = 2006 | isbn = 3527306730 | doi=10.1002/14356007.a06_233.pub2 | pmc = }}</ref>
:C<sub>2</sub>H<sub>4</sub> + HCl → C<sub>2</sub>H<sub>5</sub>Cl

At various times in the past, chloroethane has also been produced from [[ethanol]] and [[hydrochloric acid]], from [[ethane]] and [[chlorine]], or from [[ethanol]] and [[phosphorus trichloride]], but these routes are no longer economical. Some chloroethane is generated as a byproduct of [[polyvinyl chloride]] production.
==Uses==
Chloroethane is an inexpensive ethylating agent. It reacts with [[aluminium]] metal to give [[ethylaluminium sesquichloride]], a precursor to polymers and other useful [[organoaluminium compound]]s.<ref name=UllmannAl>{{Ullmann|last1=Krause|first1=M.J.|last2=Orlandi|first2=F.|last3=Saurage|first3=A.T.|last4=Zietz, Jr.|first4=J.R.|title=Aluminum Compounds|year=2000|doi=10.1002/14356007.a01_543}}</ref> Chloroethane is used to convert [[cellulose]] to [[ethylcellulose]], a thickening agent and binder in [[paint]]s, [[cosmetics]], and similar products.

Like other chlorinated [[hydrocarbon]]s, chloroethane has been used as a [[refrigeration|refrigerant]], an [[aerosol spray#Aerosol propellants|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.

===Obsolete uses===
Beginning in 1922 and continuing through most of the 20th century, the major use of chloroethane was to produce [[tetraethyllead]] (TEL), an [[anti-knock additive]] for [[gasoline]]. TEL has been or is being phased out in most of the industrialized world, and the demand for chloroethane has fallen sharply.<ref name=Ross/> 

===Niche uses===
[[File:Bottle of Aethylum chloratum pro narcosi.JPG|thumb|Bottle of compressed EtCl for anaesthesia]]

Chloroethane has a low [[boiling point]], so when applied [[topically]], the heat absorbed by the boiling liquid produces a deep and rapid chill. When sprayed on the skin, this chill has a mild anesthetic effect, which can be useful when removing splinters or incising abscesses in a clinical setting. Chloroethane was standard equipment in casualty wards.{{when|date=December 2023}} It was commonly used to induce general anaesthesia before continuing with [[diethyl ether]], which has a much slower uptake.{{cn|date=December 2023}} In dentistry, chloroethane is used as one of the means of diagnosing a 'dead tooth', i.e., one in which the pulp has died. A small amount of the substance is placed on the suspect tooth using a cotton wad; if the tooth is still alive this should be sensed by the patient as mild discomfort that subsides when the wad is removed.{{cn|date=December 2023}}

Chloroethane is used to wind the [[Atmos clock]] (manufactured by Jaeger-LeCoultre). The clock gets the energy it needs to wind the mainspring from temperature changes in the environment and does not need to be wound manually. The mainspring is wound by the expansion and contraction of liquid and gaseous ethyl chloride in an internal hermetically sealed metal bellows.<ref> Wikipedia - [[Atmos clock]] </ref>

===Recreational drug===
Chloroethane is a recreational inhalant drug, although it should not be confused with a duster or canned air, which is composed of fluorinated low-weight hydrocarbons such as [[Carbon_tetrafluoride|tetrafluoromethane]], [[chlorodifluoromethane]] or another similar gas.

In [[Brazil]], it is a major component of a traditional (though illegal) drug taken during [[Brazilian Carnival|Carnaval]], known locally as "lança-perfume"<ref>{{Cite magazine | url=https://healthland.time.com/2010/12/02/whats-lanca-perfume-the-biggest-drug-in-rio-youve-never-heard-of/ |title = What's Lança-Perfume? The Drug from Rio's Bust You've Never Heard of|magazine = Time|last1 = Melnick|first1 = Meredith|date = 2 December 2010}}</ref> (lit. ''perfume launcher'' or ''sprayer'').

Abuse of chloroethane by inhaling the substance from commercial products (e.g., muscle sprays, cleaning solvents) has been reported intermittently. Cerebellar dysfunction is a common clinical feature of toxicity, but brain imaging studies are often unremarkable. Abusers can develop cardiac arrhythmias, some of which can be fatal.<ref>{{Cite journal |last=Tan |first=You-Jiang |last2=Khoo |first2=Shimona Q. X. |last3=Tan |first3=Youhong |date=2025-01-02 |title=Ethyl chloride poisoning from inhalational misuse: clinical features and outcomes |url=https://www.tandfonline.com/doi/full/10.1080/15563650.2024.2424460 |journal=Clinical Toxicology |language=en |volume=63 |issue=1 |pages=50–56 |doi=10.1080/15563650.2024.2424460 |issn=1556-3650|url-access=subscription }}</ref>

==Safety==
{{More citations needed section|date=December 2023}}
The vapor is flammable and narcotic, which requires care.{{cn|date=December 2023}}

Monochloroethane 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 concentrations of 3% to 5%, victims usually exhibit symptoms similar to those of [[alcohol intoxication]]. Breathing its vapors at >15% concentration is often fatal; most commercially available handheld containers contain 30% per volume of concentrated vapors that naturally disperse in the outside air.

If exposed to concentrations higher than 6% to 8% victims often exhibit shallow breathing, loss of consciousnesses, and depressed heart-rate. They can be roused with physical contact or loud noise. At this point removal from the area of exposure is advised to restore consciousness. The long-term effects of exposure over a period of 4 or more hours will cause side effects similar to alcoholic hang-over with [[dehydration]], dizziness, loss of clear vision and temporary loss of consciousness, which can last an hour or more. If no longer exposed to the gas, a victim will return to normal health quickly. This can be helped with intake of extra fluids, vitamins, and sugars.

Toxic over-exposure starts at 9% to 12% concentrations, the heart rate drops further, the victim may have more shallow breathing or stop all together, they do not respond to any outside stimulation and may begin to involuntarily gasp, belch or vomit, which can lead to [[Pulmonary aspiration|aspiration]] if the victim is not turned on their side. This constitutes a medical emergency and requires prompt action. It is advised to move the victim to clear air and administer forced breathing for them to purge the lungs of the toxic fumes. If the victim recovers quickly enough, hospitalization may not be required, but will require a medical examination to ensure that no organ damage has occurred.

At >12% concentration, the victim's heart, lungs and kidneys begin to fail. Immediate CPR followed by medical support measures may be required to prevent fatal kidney, lung and heart failure. Singer [[Darius Campbell Danesh]] died of "toxic effects of chloroethane" as well as suffocation.<ref>{{cite web | url=https://www.theguardian.com/music/2022/sep/10/darius-danesh-died-of-accidental-inhalation-of-chloroethane | title=Darius Campbell Danesh died of inhalation of chloroethane | website=[[TheGuardian.com]] | date=10 September 2022 }}</ref>

Studies on the effects of chronic ethyl chloride exposure in animals have given inconsistent results, and no data exists for its long-term effects on humans.

While chloroethane is not classified as [[carcinogen]]ic to humans specifically,<ref>[http://monographs.iarc.fr/ENG/Monographs/vol71/mono71-81.pdf Chloroethane], IARC</ref> it is still used in medicine as a [[local anesthetic]].<ref>{{Cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Chloroethane |title = Chloroethane}}</ref>

==References==
{{reflist}}

==External links==
{{Commons category|Chloroethane}}
*{{ICSC|0132|01}}
*{{PGCH|0267}}
*[[International Agency for Research on Cancer|IARC]] Monograph "[https://web.archive.org/web/20051012220805/http://www-cie.iarc.fr/htdocs/monographs/vol71/075-chlorethane.html Chloroethane.]"
*{{nist |id=C75003 |name=Ethyl chloride}}
*[https://web.archive.org/web/20050617092706/http://www.npi.gov.au/database/substance-info/profiles/22.html National Pollutant Inventory - Chloroethane]

{{Local anesthetics}}
{{General anesthetics}}
{{GABAAR PAMs}}

{{Authority control}}

[[Category:Chloroalkanes]]
[[Category:Local anesthetics]]
[[Category:General anesthetics]]
[[Category:IARC Group 3 carcinogens]]
[[Category:GABAA receptor positive allosteric modulators]]
[[Category:Muscle relaxants]]
[[Category:Inhalants]]
[[Category:Sweet-smelling chemicals]]