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1,1,1-Trichloroethane

From Wikipedia, the free encyclopedia
Solvent, now banned for ozone depletion

1,1,1-Trichloroethane
Skeletal formula of 1,1,1-trichloroethane
Skeletal formula of 1,1,1-trichloroethane
Space-filling model of 1,1,1-trichloroethane
Space-filling model of 1,1,1-trichloroethane
Names
Preferred IUPAC name
1,1,1-Trichloroethane
Other names
  • 1,1,1-TCA
  • Methyl chloroform
  • Chlorothene
  • Solvent 111
  • R-140a
  • Genklene
  • monochlorethylidene chloride (archaic)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.000.688Edit this at Wikidata
EC Number
  • 200-756-3
82076
KEGG
RTECS number
  • KJ2975000
UNII
UN number2831
  • InChI=1S/C2H3Cl3/c1-2(3,4)5/h1H3 checkY
    Key: UOCLXMDMGBRAIB-UHFFFAOYSA-N checkY
  • InChI=1/C2H3Cl3/c1-2(3,4)5/h1H3
    Key: UOCLXMDMGBRAIB-UHFFFAOYAP
  • ClC(Cl)(Cl)C
Properties
C2H3Cl3 orCH3CCl3
Molar mass133.40 g·mol−1
AppearanceColourless liquid
Odormild, chloroform-like[1]
Density
  • 1.37 g/cm3 (0 °C (32 °F; 273 K))
  • 1.35 g/cm3 (15 °C (59 °F; 288 K))
  • 1.32 g/cm3 (30 °C (86 °F; 303 K))[2]
Melting point−33 °C (−27 °F; 240 K)[5]
Boiling point74–76 °C (165–169 °F; 347–349 K)[5]
  • 0.480 g/L (20 °C (68 °F; 293 K))[3]
  • reacts slowly producing hydrochloric acid[4]
logP2.49 (20 °C (68 °F; 293 K))[5]
Vapor pressure100 mmHg (13 kPa) (20 °C (68 °F; 293 K))[1]
1.437 D[2]
Viscosity0.86 cP (20 °C (68 °F; 293 K))[4]
Hazards
GHS labelling:[5]
GHS07: Exclamation markGHS08: Health hazard
Danger
H332,H350,H402,H420
P201,P202,P261,P271,P273,P280,P304+P340+P312,P308+P313,P405,P501,P502
NFPA 704 (fire diamond)
537 °C; 998 °F; 810 K[5]
Explosive limits7.5%–15%[5]
350 ppm (1,4-dioxane:20 ppm, danger of cutaneous absorption) (TWA), 450 ppm (STEL), 350 ppm (1900 mg/m3) (C)
Lethal dose or concentration (LD, LC):
  • 1,1,1-TCA:
  • 9600 mg/kg (oral, rat)
  • 6000 mg/kg (oral, mouse)
  • 5660 mg/kg (oral, rabbit)[6]
  • 1,4-dioxane (stabilizer):
  • 7600 μL/kg (skin, rabbit)[4]
  • 3911 mg/kg (mouse, 2 hr)
  • 18,000 ppm (rat, 4 hr)[6]
NIOSH (US health exposure limits):
PEL (Permissible)
  • 350 ppm (1900 mg/m3, TWA)[1]
  • 1,4-dioxane:100 ppm (360 mg/m3, TWA, skin)[5]
REL (Recommended)
  • 350 ppm (1900 mg/m3, C)[1]
  • 1,4-dioxane:1 ppm (3.6 mg/m3, C, potential carcinogen, skin absorption)[5]
IDLH (Immediate danger)
700 ppm[1]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

1,1,1-Trichloroethane, also known asmethyl chloroform andchlorothene, is achloroalkane with the chemical formulaCH3CCl3. It is an isomer of1,1,2-trichloroethane. A colourless and sweet-smelling liquid, it was once produced industrially in large quantities for use as asolvent.[7] It is regulated by theMontreal Protocol as an ozone-depleting substance, and as such, use has declined since 1996. Trichloroethane should not be confused with the similar-soundingtrichloroethene which is also commonly used as a solvent.

Production

[edit]

1,1,1-Trichloroethane was first reported byHenri Victor Regnault in 1840. Industrially, it is usually produced in a two-step process fromvinyl chloride. In the first step, vinyl chloride reacts withhydrogen chloride at 20–50 °C (68–122 °F) to produce1,1-dichloroethane:[citation needed]

H2C=CHCl + HCl → CH3CHCl2

This reaction iscatalyzed by a variety ofLewis acids, mainlyaluminium chloride,iron(III) chloride, orzinc chloride. The 1,1-dichloroethane is then converted to 1,1,1-trichloroethane by reaction withchlorine underultraviolet irradiation:[citation needed]

CH3CHCl2 + Cl2 → CH3CCl3 + HCl

This reaction proceeds at80%–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, from which the 1,1,1-trichloroethane can be separated bydistillation.[citation needed]

A somewhat smaller amount is produced from the reaction of1,1-dichloroethene and hydrogen chloride in the presence of an iron(III) chloride catalyst:[citation needed]

CH2=CCl2 + HCl → CH3CCl3

It 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) andcomplexants. One discontinued product contained only1,4-dioxane (2%±1%), while another chemical supplier included 2.5% 1,4-dioxane, 0.47% 1,2-butylene oxide, and 0.35%nitromethane as stabilizers.[4][5]

Uses

[edit]

1,1,1-Trichloroethane is an excellent solvent for manyorganic compounds and also one of the least toxic of thechlorinated hydrocarbons. It is generally considerednon-polar, but owing to the goodpolarizability of the chlorine atoms, it is a superior solvent for organic compounds that do not dissolve well in hydrocarbons such ashexane. Prior to the Montreal Protocol, it was widely used for cleaning metal parts and circuit boards, as aphotoresist solvent in the electronics industry, as an aerosol propellant, as acutting fluid additive, and as a solvent for inks, paints, adhesives, and other coatings.[citation needed]

It was used todry-clean leather and suede and it was one of the components ofDow Chemical's "Dowclene" dry cleaning fluid among with tetrachloroethylene, first marketed in the late 1930s. Use in dry-cleaning remained until the 1980s, meanwhile tetrachloroethylene is still widely used. It is also used as aninsecticidalfumigant.[8]

It was also the standard cleaner forphotographic film. Other commonly available solvents damage emulsion and base (acetone will dissolve triacetate base on most films), and thus are not suitable for this application. The standard replacement,Forane 141 is much less effective, and tends to leave a residue.[citation needed] It was also used as a thinner incorrection fluid products such asliquid paper.

Many of its applications previously usedcarbon 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.[9] Phase-out of 1,1,1-Trichloroethane due to ozone depletion lead to a resurgence of the use oftrichloroethylene in metal degreasing.[8]

Methyl chloroform was also used as a veterinaryanthelmintic.[citation needed]

Early anaesthetic research

[edit]
🛈This section maylendundue weight to an essentially "trivia question" usage of this chemical that never actually went anywhere outside of discussions between doctors that ended in the late 1800s, and deserves maybe one citation and a one-liner. Pleasehelp improve it by rewriting it tocreate a more balanced presentation. Discuss andresolve this issue before removing this message.(January 2026)

1,1,1-Trichloroethane was one of the volatile organochlorides that have been tried as alternatives tochloroform in anaesthesia.[10]In the 1880s, it was found to be a safe and strong substitute for chloroform but its production was too expensive and difficult for the era.[11][12]

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 ofchloral 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. The1,1,2-Trichloroethane (vinyl trichloride) isomer, which lacked atrichloromethyl group, exhibited anaesthetic effects even stronger than the 1,1,1 isomer.[13]

Safety

[edit]

Although not astoxic as many similar compounds, inhaled or ingested 1,1,1-trichloroethane acts as acentral nervous systemdepressant and can cause decrease in reaction times and dexterity as well as impaired balance and abnormalEEG at lower concentrations, throat irritation, and in sufficiently high concentrations, death.[14]

TheInternational Agency for Research on Cancer places 1,1,1-trichloroethane inGroup 2A as a probablecarcinogen.[15]

Atmospheric concentration

[edit]
CH3CCl3 measured by the Advanced Global Atmospheric Gases Experiment[16] in the lower atmosphere (troposphere) at stations around the world. Abundances are given as pollution free monthly mean mole fractions inparts-per-trillion.
1,1,1-Trichloroethane timeseries at various latitudes.

1,1,1-Trichloroethane is a fairly potentgreenhouse gas with a 100-yearglobal warming potential of 169 relative tocarbon dioxide.[17] This is nonetheless less than a tenth that ofcarbon tetrachloride — which it replaced as a solvent — due to its relatively shortatmospheric lifetime of about 5 years.[18]

The Montreal Protocol targeted 1,1,1-trichloroethane as a compound responsible forozone depletion and banned its use beginning in 1996. Since then, its manufacture and use have been phased out throughout most of the world, and its atmospheric concentration has declined substantially.[18]

See also

[edit]

References

[edit]
  1. ^abcdeNIOSH Pocket Guide to Chemical Hazards."#0404".National Institute for Occupational Safety and Health (NIOSH).
  2. ^abTimmermans, Jean.Physico-chemical constants of pure organic compounds (1 ed.). Elsevier. p. 242.ISBN 978-0444405715.
  3. ^"International Programme On Chemical Safety, Environmental Health Criteria 136". World Health Organization, Geneva. 1990. Retrieved25 December 2017.
  4. ^abcde"Material Safety Data Sheet - 1,1,1-Trichloroethane"(PDF).southwest.tn.edu. Fisher Scientific. 4 March 2013. pp. 2–4. Retrieved5 January 2026.
  5. ^abcdefghiSigma-Aldrich Co.,1,1,1-trichloroethane. Retrieved on 6 January 2026.
  6. ^ab"Methyl chloroform".Immediately Dangerous to Life or Health Concentrations.National Institute for Occupational Safety and Health.
  7. ^Rossberg, Manfred; Lendle, Wilhelm; Pfleiderer, Gerhard; Tögel, Adolf; Ernst Langer, Eberhard-Ludwig Dreher; Rassaerts, Heinz; Kleinschmidt, Peter; Strack, Heinz; Cook, Richard; Beck, Uwe; Lipper, Karl-August; Torkelson, Theodore R.; Löser, Eckhard; Beutel, Klaus K.; Mann, Trevor. "Chlorinated Hydrocarbons".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.doi:10.1002/14356007.a06_233.pub2.ISBN 978-3-527-30673-2..
  8. ^abMorrison, Robert D.; Murphy, Brian (2013). "Chapter 6: Methyl Chloroform (1,1,1-TCA)".Chlorinated solvents: a forensic evaluation. Cambridge: RSC Publishing.doi:10.1039/9781849737265-00186.ISBN 978-1-84973-196-6.
  9. ^"Use of Ozone Depleting Substances in Laboratories"(PDF). TemaNord. 516/2003. Archived fromthe original(PDF) on 27 February 2008.[page needed]
  10. ^"Foreign Correspondence".The American Practitioner.23: 28. January 1881 [15 December 1880].
  11. ^James, Frank L.; Ohmann-Dumesnil, A. H., eds. (August 1887)."Editorial Department - Surgery - Methyl Chloroform".Saint Louis Medical and Surgical Journal.53: 121.ISSN 1077-663X.OCLC 11254212. Retrieved6 January 2026.
  12. ^Brunton, T. Lauder (1892) [20 June 1889]. "Lecture III: Control and Cure of Disease".An introduction to modern therapeutics: being the Croonian Lectures on the relationship between chemical structure and physiological action in relation to the prevention, control, and cure of disease delivered before the Royal College of Physicians in London, June 1889. London; New York: Macmillian. p. 122.OCLC 969481521.OL 25611933M.
  13. ^Sadtler, Samuel P. (March 1881) [1880]."On Two New Anaesthetics".The American Journal of Pharmacy.53. Philadelphia College of Pharmacy: Philadelphia College of Pharmacy:119–120.ISSN 0730-7780.
  14. ^"Toxicological Profile for 1,1,1-Trichloroethane"(PDF). U.S. Department of Health and Human Services - Agency for Toxic Substances and Disease Registry. March 2024 [December 1990]. p. 3.
  15. ^IARC.1,1,1-Trichloroethane and Four Other Industrial Chemicals.ISBN 978-92-832-0197-7.
  16. ^Chen, Gao."AGAGE - Advanced Global Atmospheric Gases Experiment".www-air.larc.nasa.gov. NASA. Retrieved6 January 2026.
  17. ^Hodnebrog, ø.; Aamaas, B.; Fuglestvedt, J. S.; Marston, G.; Myhre, G.; Nielsen, C. J.; Sandstad, M.; Shine, K. P.; Wallington, T. J. (September 2020)."Updated Global Warming Potentials and Radiative Efficiencies of Halocarbons and Other Weak Atmospheric Absorbers".Reviews of Geophysics.58 (3).Bibcode:2020RvGeo..5800691H.doi:10.1029/2019RG000691.PMC 7518032.PMID 33015672.
  18. ^abStocker, T.F.; D. Qin, G.-K.; Plattner, M.; Tignor, S.K.; Allen, J.; Boschung, A.; Nauels, Y.; Xia, V. Bex; Midgley, P.M., eds. (2013). "Chapter 8, Table 8.A.1".Climate Change 2013: The Physical Science Basis. Contribution of Working Group I to the Fifth Assessment Report of the Intergovernmental Panel on Climate Change.IPCC (Report). Cambridge, United Kingdom and New York, NY, USA: Cambridge University Press. p. 733.
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