1,1,1-Trichloroethane
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{{Chembox new
| Name = 1,1,1-Trichloroethane
| ImageFile = 1,1,1-trichloroethane-2D-skeletal.png
| ImageSize = 140px
| ImageName = Skeletal formula of 1,1,1-trichloroethane
| ImageFile1 = 1,1,1-trichloroethane-3D-vdW.png
| ImageSize1 = 140px
| ImageName1 = Space-filling model of 1,1,1-trichloroethane
| IUPACName = 1,1,1-trichloroethane
| OtherNames = methyl chloroform, chlorothene
| Section1 = {{Chembox Identifiers
| SMILES = CC(Cl)(Cl)Cl
| CASNo = 71-55-6
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>2</sub>H<sub>3</sub>Cl<sub>3</sub> or CH<sub>3</sub>CCl<sub>3</sub>
| MolarMass = 133.4 g/mol
| Appearance = Colorless liquid
| Density = 1.32 g/cm³, liquid
| Solubility = insoluble in water
| MeltingPt = -33 °C (240 K)
| BoilingPt = 74 °C (347 K)
}}
| Section7 = {{Chembox Hazards
| MainHazards = Irritant to the upper respiratory tract. Causes severe irritation and swelling to eyes.
| NFPA-H = 3
| NFPA-F = 1
| NFPA-R = 1
| RPhrases = {{R19}} {{R20}} {{R40}} {{R59}} {{R66}}
| SPhrases = {{S9}} {{S16}} {{S24}} {{S25}} {{S46}} {{S59}} {{S61}}
}}
| Section8 = {{Chembox Related
| OtherAnions =
| OtherCations =
| Function =
| OtherFunctn =
| OtherCpds =
}}
}}
The [[chemical compound]] '''1,1,1-trichloroethane''' is a [[chlorine|chlorinated]] [[hydrocarbon]] that was until recently widely used as an industrial [[solvent]]. Other names for it include '''methyl chloroform''', '''chlorothene''', and the trade names '''Solvent 111''' and '''Genklene''' (used by [[Imperial Chemical Industries|ICI]]).
1,1,1-trichloroethane was first produced by the [[France|French]] [[chemist]] [[Henri Victor Regnault]] in 1840. It was produced in large quantities by the chemical industry beginning in the mid-1950s and continuing through 1995. Today, it is banned by the [[Montreal Protocol]].
==Production==
Industrially, 1,1,1-trichloroethane is usually produced in a two-step process from [[vinyl chloride]]. In the first step, vinyl chloride reacts with [[hydrochloric acid|hydrogen chloride]] at 20-50 °C to produce [[1,1-Dichloroethane|1,1-dichloroethane]]. This reaction is [[catalyst|catalyzed]] by one of [[aluminium chloride]], [[iron(III) chloride]], or [[zinc chloride]]. Its [[chemical equation]] is
:[[vinyl chloride|CH<sub>2</sub>=CHCl]] + [[hydrochloric acid|HCl]] → [[1,1-Dichloroethane|CH<sub>3</sub>CHCl<sub>2</sub>]]
The 1,1-dichloroethane is then converted to 1,1,1-trichloroethane by reaction with [[chlorine]] under [[ultraviolet]] irradiation
:[[1,1-Dichloroethane|CH<sub>3</sub>CHCl<sub>2</sub>]] + [[chlorine|Cl<sub>2</sub>]] → CH<sub>3</sub>CCl<sub>3</sub> + [[hydrochloric acid|HCl]]
This reaction proceeds at 80-90% yield, and the hydrogen chloride byproduct can be recycled to the first step in the process. The major side-product is the related compound [[1,1,2-Trichloroethane|1,1,2-trichloroethane]], from which the 1,1,1-trichloroethane can be separated by [[distillation]].
A somewhat smaller amount of 1,1,1-trichloroethane is produced from the reaction of [[vinylidene chloride]] and hydrogen chloride in the presence of an iron(III) chloride catalyst:
:[[vinylidene chloride|CH<sub>2</sub>=CCl<sub>2</sub>]] + [[hydrochloric acid|HCl]] → CH<sub>3</sub>CCl<sub>3</sub>
==Uses==
1,1,1-trichloroethane is an excellent solvent for many [[organic chemistry|organic]] materials and also one of the least toxic of the chlorinated [[hydrocarbon]]s. Prior to the Montreal Protocol, it was used for cleaning [[metal]] parts and [[circuit board]]s, as a [[photoresist]] [[solvent]] in the [[electronics]] industry, as an [[Aerosol spray|aerosol]] propellant, as a [[cutting fluid]] additive, and as a solvent for [[ink]]s, [[paint]]s, [[adhesive]]s, and other coatings. It was also very effective at safely removing [[PVC]] from copper and silver coins that had been stored in PVC containers for several years.
It was also the standard cleaner for photographic film (movie/slide/negatives, etc).
It had the property of being able to clean almost anything off film, without softening or otherwise damaging the emulsion.
Other commonly available solvents damage emulsion, and thus are not suitable for this application.
The standard replacement, Forane 141 is much less effective, and tends to leave a residue.
Many applications for 1,1,1-trichloroethane (including film cleaning) were previously done with [[carbon tetrachloride]], which was banned in 1970.
The Montreal Protocol targeted 1,1,1-trichloroethane as one of those compounds responsible for [[ozone depletion]] and banned its use beginning in [[1996]]. Since then, its manufacture and use has been phased out throughout most of the world.
1,1,1-trichloroethane is generally considered as a non-polar solvent, but since all three electronegative chlorine atoms lie on the same side of the molecule, it is slightly polar, making it a good solvent for organic matters that do not dissolve into totally non-polar substances such as [[hexane]]. 1,1,1-trichloroethane in laboratory analytics has been replaced by other solvents<ref>Use of Ozone Depleting Substances in Laboratories. TemaNord 516/2003. [http://www.norden.org/pub/ebook/2003-516.pdf]</ref>.
==Safety==
Although not as [[toxicity|toxic]] as many similar compounds, inhaled or ingested 1,1,1-trichloroethane does act as a [[central nervous system]] [[depressant]] and can cause effects similar to those of [[intoxication]], including [[dizziness]], confusion, and in sufficiently high concentrations, [[unconsciousness]] and [[death]].
Prolonged [[skin]] contact with the [[liquid]] can result in the removal of [[fat]]s from the [[skin]], resulting in chronic skin irritation.
Studies on [[laboratory animal]]s have shown that 1,1,1-trichloroethane is not retained in the body for long periods of time. However, chronic exposure has been linked to abnormalities in the [[liver]], [[kidney]]s, and [[heart]]. [[Pregnancy|Pregnant]] women should avoid exposure, as the compound has been linked to [[birth defect]]s in laboratory animals (see [[teratogenesis]]).
The substance is deadly to [[insects]].
==Cultural references==
It is referenced in [[Chuck Palahniuk]]'s novel "[[Choke (novel)|Choke]]" as the substance the protagonist's mother inhales in order to forget everything she knows.
==References==
{{Unreferenced|date=September 2007}}
<references/>
==Further reading==
{{citationstyle}}
Agency for Toxic Substances and Disease Registry (ATSDR). 2006. Toxicological Profile for 1,1,1-Trichloroethane. [http://www.atsdr.cdc.gov/toxprofiles/tp70.html link]
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 2 - Trichloroethylene and 1,1,1-Trichloroethane. Journal of Environmental Forensics (2000) 1, 83-93. [http://www.informaworld.com/smpp/content?content=10.1006/enfo.2000.0011 link]
{{DEFAULTSORT:Trichloroethane, 1,1,1-}}
[[Category:Greenhouse gases]]
[[Category:Hazardous air pollutants]]
[[Category:Organochlorides]]
[[Category:Halogenated solvents]]
[[de:1,1,1-Trichlorethan]]
[[it:1,1,1-tricloroetano]]
[[ja:トリクロロエタン]]
[[no:Trikloretan]]
[[fi:1,1,1-trikloorietaani]]
[[zh:1,1,1-三氯乙烷]]