Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 1,1,1-Trichloroethane: Difference between pages

{{Short description|Solvent, now banned for ozone depletion}}

| verifiedrevid = 477201594

| Name = 1,1,1-Trichloroethane

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageFile =

| ImageSizeL1 = 140px

| ImageNameL1 = Skeletal formula of 1,1,1-trichloroethane

| ImageFileR1 = 1,1,1-trichloroethane-3D-vdW.png

| ImageSizeR1 = 120px

| ImageNameR1 = Space-filling model of 1,1,1-trichloroethane

| ImageFileL2= 1,1,1-Trichlorethan.svg

| ImageSizeL2 = 140px

| ImageFileR2 = 1,1,1-trichloroethane-3D-balls.png

| ImageSizeR2 = 120px

| PIN = 1,1,1-Trichloroethane

| OtherNames = 1,1,1-TCA, Methyl chloroform, Chlorothene, Solvent 111, R-140a, Genklene, monochlorethylidene chloride (archaic)

| SystematicName =

| CASNo = 71-55-6

| CASNo_Ref = {{cascite|correct|CAS}}

| IUPHAR_ligand = 5482

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 16080

| EC_number = 200-756-3

| Gmelin = 82076

| RTECS = KJ2975000

| UNNumber = 2831

| SMILES = ClC(Cl)(Cl)C

}}

| Formula = C{{sub|2}}H{{sub|3}}Cl{{sub|3}} or CH{{sub|3}}CCl{{sub|3}}

| MolarMass = 133.40 g/mol

| Appearance = Colorless liquid

| Odor = mild, chloroform-like<ref name=PGCH/>

| Density = 1.32 g/cm{{sup|3}}

| Solubility = 0.4% (20°C)<ref name=PGCH/><br/>0.480 g/litre at 20 °C<ref>{{cite web |url=http://www.inchem.org/documents/ehc/ehc/ehc136.htm |title=International Programme On Chemical Safety, Environmental Health Criteria 136 |date=1990 |publisher=World Health Organization, Geneva |access-date=2017-12-25}}</ref>

| MeltingPtC = -33

| BoilingPtC = 74

| VaporPressure = 100 mmHg (20°C)<ref name=PGCH/>

| RefractIndex = 1.437<ref>Timmermans, Jean, Physico-chemical constants of pure organic compounds (1950), [https://archive.org/details/physicochemicalc0001timm/page/242/mode/1up p. 242]</ref>

}}

| Section3 =

| Section4 =

| Section5 =

| Section6 =

| MainHazards = Ozone layer impact. Irritant to the upper respiratory tract. Causes severe irritation and swelling to eyes.

| NFPA-H = 2

| NFPA-F = 1

| NFPA-R = 0

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|332|420}}

| PPhrases = {{P-phrases|261|271|304+312|304+340|312|502}}

| PEL = TWA 350 ppm (1900 mg/m{{sup|3}})<ref name=PGCH>{{PGCH|0404}}</ref>

| ExploLimits = 7.5%-12.5%<ref name=PGCH/>

| REL = C 350 ppm (1900 mg/m{{sup|3}}) [15-minute]<ref name=PGCH/>

| IDLH = 700 ppm<ref name=PGCH/>

| LC50 = 3911 ppm (mouse, 2 hr)<br/>18000 ppm (rat, 4 hr)<ref name=IDLH>{{IDLH|71556|Methyl chloroform}}</ref>

| LD50 = 9600 mg/kg (oral, rat)<br/>6000 mg/kg (oral, mouse)<br/>5660 mg/kg (oral, rabbit)<ref name=IDLH/>

}}

| OtherAnions =

| OtherCations =

| Function =

| OtherFunctn =

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}}

The [[organic compound]] '''1,1,1-trichloroethane''', also known as '''methyl chloroform''' and '''chlorothene''', is a [[chloroalkane]] with the chemical formula CH₃CCl₃. It is an isomer of [[1,1,2-trichloroethane]]. This colorless, sweet-smelling liquid was once produced industrially in large quantities for use as a [[solvent]].<ref>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. Torkelson, Eckhard Löser, Klaus K. Beutel, Trevor Mann "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a06_233.pub2}}.</ref> It is regulated by the [[Montreal Protocol]] as an ozone-depleting substance and its use is being rapidly phased out.

==Production==

1,1,1-Trichloroethane was first reported by [[Henri Victor Regnault]] in 1840. Industrially, it is usually produced in a two-step process from [[vinyl chloride]]. In the first step, vinyl chloride reacts with [[hydrogen chloride]] at 20-50&nbsp;°C to produce [[1,1-Dichloroethane|1,1-dichloroethane]]:

:CH{{sub|2}}=CHCl + HCl → CH{{sub|3}}CHCl{{sub|2}}

This reaction is [[catalyst|catalyzed]] by a variety of [[Lewis acids and bases|Lewis acids]], mainly [[aluminium chloride]], [[iron(III) chloride]], or [[zinc chloride]]. The 1,1-dichloroethane is then converted to 1,1,1-trichloroethane by reaction with [[chlorine]] under [[ultraviolet]] irradiation:

:CH{{sub|3}}CHCl{{sub|2}} + Cl{{sub|2}} → CH{{sub|3}}CCl{{sub|3}} + 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 [[1,1-dichloroethene]] and [[hydrogen chloride]] in the presence of an [[iron(III) chloride]] catalyst:

:CH{{sub|2}}=CCl{{sub|2}} + HCl → CH{{sub|3}}CCl{{sub|3}}

1,1,1-Trichloroethane is sold with stabilizers because it is unstable with respect to dehydrochlorination and attacks some metals. Stabilizers comprise up to 8% of the formulation, including acid scavengers (epoxides, amines) and [[chelating agents|complexants]].

==Uses==

1,1,1-Trichloroethane is an excellent solvent for many [[organic compound]]s and also one of the least toxic of the [[chlorinated hydrocarbon]]s. It is generally considered non-[[chemical polarity|polar]], but owing to the good [[polarizability]] of the chlorine atoms, it is a superior solvent for organic compounds that do not dissolve well in hydrocarbons such as [[hexane]]. Prior to the Montreal Protocol, it was widely 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 inks, paints, [[adhesive]]s, and other coatings. 1,1,1-Trichloroethane was used to [[Dry cleaning|dry-clean]] [[leather]] and [[suede]]. <ref>Morrison, R. D., Murphy, B. L. (2013). Chlorinated Solvents: A Forensic Evaluation. UK Royal Society of Chemistry. Page 203</ref> 1,1,1-Trichloroethane is also used as an [[insecticide|insecticidal]] [[fumigation|fumigant]].

It was also the standard cleaner for photographic film (movie/slide/negatives, etc.). Other commonly available solvents damage emulsion and base ([[acetone]] will severely damage triacetate base on most films), and thus are not suitable for this application. The standard replacement, [[1,1-Dichloro-1-fluoroethane|Forane 141]] is much less effective, and tends to leave a residue. 1,1,1-Trichloroethane was used as a thinner in [[correction fluid]] products such as [[liquid paper]]. Many of its applications previously used [[carbon tetrachloride]] (which was banned in US consumer products in 1970). In turn, 1,1,1-trichloroethane itself is now being replaced by other solvents in the laboratory.<ref>[http://www.norden.org/pub/ebook/2003-516.pdf Use of Ozone Depleting Substances in Laboratories. TemaNord 516/2003] {{webarchive|url=https://web.archive.org/web/20080227052412/http://www.norden.org/pub/ebook/2003-516.pdf |date=2008-02-27}}</ref>

===Anaesthetic research===

1,1,1-Trichloroethane was one of the volatile organochlorides that have been tried as alternatives to [[chloroform]] in anaesthesia.<ref>The American Practitioner 1881-01: Volume 23, [https://archive.org/details/sim_american-practitioner_1881-01_23/page/28/mode/1up?q=%22methyl+chloroform%22 page 28]</ref>

In the 1880s, it was found to be a safe and strong substitute for chloroform<ref>''Methyl-Chloroform'' (1887) in Saint Louis Medical and Surgical Journal, [https://archive.org/details/saintlouismedic08unkngoog/page/n127/mode/1up?q=%22methyl+chloroform%22 page 121]</ref> but its production was expensive and difficult.<ref>''An introduction to modern therapeutics'' (1892), Brunton, T. Lauder, [https://archive.org/details/b20406204/page/121/mode/1up?q=%22methyl+chloroform%22 page 122]</ref>

In 1880, 1,1,1-Trichloroethane was suggested as an anaesthetic. It was first referred to as "methyl-chloroform" in the same year. At the time, the narcotic effects of [[chloral hydrate]] were owed to a hypothetical metabolic pathway to chloroform in "alkaline blood". Trichloroethane was studied for its structural similarity to chloral and potential anaesthetic effects. However, trichloroethane did not exhibit any conversion to chloroform in laboratory experiments. The [[1,1,2-trichloroethane]] isomer, which lacked a [[trichloromethyl group]], exhibited anaesthetic effects even stronger than the 1,1,1 isomer.<ref>''On Two New Anaesthetics'' (1880), The American Journal of Pharmacy 1881-03: Vol 53, [https://archive.org/details/sim_american-journal-of-pharmacy-and-the-sciences_1881-03_53/page/119/mode/1up?q=%22methyl+chloroform%22 pages 119–120]</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 [[ethanol]] [[Substance intoxication|intoxication]], including [[dizziness]], confusion, and, in sufficiently high concentrations, [[unconsciousness]] and death.<ref>[http://www.atsdr.cdc.gov/toxprofiles/tp70.html Toxicological Profile for 1,1,1-Trichloroethane] {{Webarchive|url=https://web.archive.org/web/20080509103329/http://www.atsdr.cdc.gov/toxprofiles/tp70.html |date=2008-05-09 }}, Agency for Toxic Substances and Disease Registry (ATSDR). 2006</ref> Fatal poisonings and illnesses linked to [[inhalant abuse|intentional inhalation]] of trichloroethane have been reported.<ref>{{cite journal

|title = Sudden Death in Adolescents Resulting From the Inhalation of Typewriter Correction Fluid

|journal = JAMA: The Journal of the American Medical Association

|volume = 253

|issue = 11

|pages = 1604–1606

|date = 15 March 1985

|pmid = 3974043

|url = http://jama.ama-assn.org/cgi/content/short/253/11/1604

|quote = We describe four cases of sudden death in adolescents associated with recreational sniffing of typewriter correction fluid occurring during the period 1979 through mid-1984.

|archive-url = https://archive.today/20130223191954/http://jama.ama-assn.org/cgi/content/short/253/11/1604

|archive-date = 2013-02-23

|url-status = live

|access-date = 2010-01-05

|last1 = King

|first1 = Gregory S.

|last2 = Smialek

|first2 = John E.

|last3 = Troutman

|first3 = William G.

|doi = 10.1001/jama.253.11.1604

}}</ref><ref>{{cite journal

|title=Fatal cerebral oedema following trichloroethane abuse

|journal=Journal of the Royal Society of Medicine

|volume=83

|issue=8

|pages=533–534

|date=August 1990

|pmid=2231588

|pmc=1292788

|last1=D'costa

|first1=DF

|last2=Gunasekera

|first2=NP

|doi=10.1177/014107689008300823

}}</ref><ref>{{cite journal

|title = Fatal inhalation of 1,1,1-trichloroethane

|url = https://archive.org/details/sim_forensic-science-international_1997-06-06_87_2/page/161

|journal = Forensic Science International

|volume = 87

|issue = 2

|pages = 161–165

|date = 6 June 1997

|pmid = 9237378

|doi = 10.1016/S0379-0738(97)00040-6

|last1 = Winekab

|first1 = Charles L.

|last2 = Wahba

|first2 = Wagdy W.

|last3 = Huston

|first3 = Robert

|last4 = Rozin

|first4 = Leon

|quote = A 13-year-old male was found dead in the woods subsequent to 1,1,1-trichloroethane (TCE) inhalation.

}}</ref><ref>{{cite journal

|title = Cardiac Effects of Inhaled Typewriter Correction Fluid

|journal = Annals of Internal Medicine

|volume = 110

|issue = 1

|pages = 91–92

|date = 1 January 1989

|pmid = 2908837

|url = http://www.annals.org/cgi/content/abstract/110/1/91-a

|archive-url = https://archive.today/20130414005033/http://www.annals.org/cgi/content/abstract/110/1/91-a

|archive-date = 2013-04-14

|url-status = live

|access-date = 2010-01-05

|doi = 10.7326/0003-4819-110-1-91_2

|last1 = Wodka

|first1 = Richard M.

|last2 = Jeong

|first2 = Erwin W. S.

}}</ref> The removal of the chemical from correction fluid commenced due to [[Proposition 65]] declaring it hazardous and toxic.<ref>{{cite news

|last = Paddock

|first = Richard C.

|title = Gillette Agrees to Remove Toxics From Its Paper Correction Fluid

|url = http://articles.latimes.com/1989-09-29/news/mn-252_1_liquid-paper-correction-fluid

|work = Los Angeles Times

|location = Sacramento

|date = 29 September 1989

|access-date = 5 January 2010

|archive-url = https://web.archive.org/web/20120715051020/http://articles.latimes.com/1989-09-29/news/mn-252_1_liquid-paper-correction-fluid

|archive-date = 15 July 2012

|url-status = live

}}</ref><ref>{{cite book

|last1=Estrin

|first1=Norman F.

|last2=Akerson

|first2=James M.

|title=Cosmetic regulation in a competitive environment

|publisher=[[Marcel Dekker]]

|year=2000

|isbn=0-8247-7516-3

|chapter-url=https://books.google.com/books?id=O8z3Nn9HzKIC&pg=PA138

|access-date=5 January 2010

|location=New York, New York

|page=138

|chapter=Proposition 65

|quote=Gillette agreed to reformulate the product so that it would not pose a risk requiring a Proposition 65 warning

}}</ref>

Prolonged skin contact with the liquid can result in the [[Defatting (medical)|removal of fats from the skin]], resulting in skin irritation.

The [[International Agency for Research on Cancer]] places 1,1,1-trichloroethane in [[IARC group 2A|Group 2A]] as a probable [[carcinogen]].<ref>{{Cite book |last=IARC |url=https://publications.iarc.fr/Book-And-Report-Series/Iarc-Monographs-On-The-Identification-Of-Carcinogenic-Hazards-To-Humans/1-1-1-Trichloroethane-And-Four-Other-Industrial-Chemicals-2022 |title=1,1,1-Trichloroethane and Four Other Industrial Chemicals |isbn=978-92-832-0197-7 |language=en}}</ref>

==Atmospheric concentration==

[[File:CH3CCl3 mm.png|thumb|left|upright=1.2|1,1,1-Trichloroethane (Methyl chloroform, CH₃CCl₃) measured by the Advanced Global Atmospheric Gases Experiment ([http://agage.mit.edu/ AGAGE]) in the lower atmosphere ([[troposphere]]) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in [[Parts-per notation|parts-per-trillion]].]]

[[File:BK MC.jpg|thumb|left|upright=1.0|1,1,1-Trichloroethane timeseries at various latitudes.]]

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 have been phased out throughout most of the world. Its atmospheric presence has declined rapidly due to its relatively short [[Greenhouse gas#Atmospheric lifetime|atmospheric lifetime]] of about 5 years.<ref>{{cite book |url=https://www.ipcc.ch/report/ar5/wg1/ |contribution= Chapter 8, Table 8.A.1 |title=AR5 Climate Change 2013: The Physical Science Basis |page=733}}</ref>

{{clear}}

==References==

{{Reflist|30em}}

==Further reading==

*{{cite journal |last1= Doherty |first1= R.E. |year= 2000 |title= 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= Environmental Forensics|volume= 1 |issue= 2|pages= 83–93 |doi=10.1006/enfo.2000.0011|bibcode= 2000EnvFo...1...83D |s2cid= 97370778 }}

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{{DEFAULTSORT:Trichloroethane, 1, 1, 1-}}

[[Category:Chloroalkanes]]

[[Category:Dry cleaning]]

[[Category:Excipients]]

[[Category:GABAA receptor positive allosteric modulators]]

[[Category:Glycine receptor agonists]]

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[[Category:Halogenated solvents]]

[[Category:Hazardous air pollutants]]

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