1,1,1-Trichloroethane

Solvent, now banned for ozone depletion May 2024 May 2024 477201594 1,1,1-Trichloroethane correct ?? 1,1,1-trichloroethane-2D-skeletal.png 140px skin-invert Skeletal formula of 1,1,1-trichloroethane 1,1,1-trichloroethane-3D-vdW.png bg-transparent 120px Space-filling model of 1,1,1-trichloroethane 1,1,1-Trichlorethan.svg 140px skin-invert 1,1,1-trichloroethane-3D-balls.png bg-transparent 120px 1,1,1-Trichloroethane 1,1,1-TCA Methyl chloroform Chlorothene Solvent 111 R-140a Genklene monochlorethylidene chloride (archaic) 71-55-6 correct CAS 5482 correct chemspider correct EBI 36015 correct EBI 16080 6042 200-756-3 82076 6278 KJ2975000 2831 correct FDA 113C650IR1 correct kegg C18246 1/C2H3Cl3/c1-2(3,4)5/h1H3 UOCLXMDMGBRAIB-UHFFFAOYAP ClC(Cl)(Cl)C correct chemspider 1S/C2H3Cl3/c1-2(3,4)5/h1H3 correct chemspider UOCLXMDMGBRAIB-UHFFFAOYSA-N C2H3Cl3 or CH3CCl3 2 3 3 Colourless liquid mild, chloroform-like 1.37068 2 g/cm3 (0 C F K) 1.34587 2 g/cm3 (15 C F K) 1.32096 2 g/cm3 (30 C F K) 0.480 g/L (20 C F K)http://www.inchem.org/documents/ehc/ehc/ehc136.htm International Programme On Chemical Safety, Environmental Health Criteria 136 1990 World Health Organization, Geneva 2017-12-25 reacts slowly producing hydrochloric acid -33 74-76 2.49 (20 C F K) 100 mmHg kPa (20 C F K) 1.437 DPhysico-chemical constants of pure organic compounds Timmermans Jean Jean Timmermans Elsevier 1 1 January 1950 https://archive.org/details/physicochemicalc0001timm/page/242/mode/1up registration 242 978-0444405715 0.86 cP (20 C F K) T54704 1,1,1-trichloroethane 6 January 2026 07 08 Danger 332 350 402 420 201 202 261 271 273 280 304+340+312 308+313 405 501 502 2 1 0 - Material Safety Data Sheet - 1,1,1-Trichloroethane https://southwest.tn.edu/ehs/msds/1-10/111%20Trichloroethane.pdf southwest.tn.edu Fisher Scientific 5 January 2026 2-4 4 March 2013 998 7.5 – 15 % 3911 mg/kg (mouse, 2 hr) 18000 ppm commas (rat, 4 hr)71556 Methyl chloroform 1,1,1-TCA: 9600 mg/kg (oral, rat) 6000 mg/kg (oral, mouse) 5660 mg/kg (oral, rabbit) 1,4-dioxane (stabilizer): 7600 μL/kg (skin, rabbit) 350 ppm (1,4-dioxane: 20 ppm, danger of cutaneous absorption) 450 ppm 350 ppm (1900 mg/m3) 350 ppm (1900 mg/m3, TWA)0404 1,4-dioxane: 100 ppm (360 mg/m3, TWA, skin) 350 ppm (1900 mg/m3, C) 1,4-dioxane: 1 ppm (3.6 mg/m3, C, potential carcinogen, skin absorption) 700 ppm 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. A colourless and sweet-smelling liquid, it was once produced industrially in large quantities for use as a solvent.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 10.1002/14356007.a06_233.pub2. It is regulated by the Montreal Protocol as an ozone-depleting substance, and as such, use has declined since 1996. Trichloroethane should not be confused with the similar-sounding trichloroethene which is also commonly used as a solvent. 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 C to produce 1,1-dichloroethane:January 2026 H2C\dCHCl + HCl -> CH3CHCl2 This reaction is catalyzed by a variety of 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:January 2026 CH3CHCl2 + Cl2 -> CH3CCl3 + 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, from which the 1,1,1-trichloroethane can be separated by distillation.January 2026 A somewhat smaller amount is produced from the reaction of 1,1-dichloroethene and hydrogen chloride in the presence of an iron(III) chloride catalyst:January 2026 CH2\dCCl2 + 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) and complexants. One discontinued product contained only 1,4-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. Uses 1,1,1-Trichloroethane is an excellent solvent for many organic compounds and one of the least toxic of the chlorinated hydrocarbons. It is generally considered non-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 boards, as a photoresist solvent in the electronics industry, as an aerosol propellant, as a cutting fluid additive, and as a solvent for inks, paints, adhesives, and other coatings.January 2026 It was used to dry-clean leather and suede. Use in dry-cleaning remained until the 1980s. It was used as an insecticidal fumigant.Morrison Robert D. Murphy Brian Chlorinated solvents: a forensic evaluation 2013 RSC Publishing Cambridge Chapter 6: Methyl Chloroform (1,1,1-TCA) 10.1039/9781849737265-00186 978-1-84973-196-6 It was also the standard cleaner for photographic 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.January 2026 It was also 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.http://www.norden.org/pub/ebook/2003-516.pdf dead Use of Ozone Depleting Substances in Laboratories. TemaNord 516/2003 https://web.archive.org/web/20080227052412/http://www.norden.org/pub/ebook/2003-516.pdf 2008-02-27January 2026 Phase-out of 1,1,1-Trichloroethane due to ozone depletion lead to a resurgence of the use of trichloroethylene in metal degreasing. Methyl chloroform was also used as a veterinary anthelmintic.January 2026 Early anaesthetic research 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 January 2026 1,1,1-Trichloroethane was one of the volatile organochlorides that have been tried as alternatives to chloroform in anaesthesia.Foreign Correspondence The American Practitioner 23 https://archive.org/details/sim_american-practitioner_1881-01_23/page/28/mode/1up 28 15 December 1880 January 1881 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.James Frank L. Ohmann-Dumesnil A. H. Editorial Department - Surgery - Methyl Chloroform Saint Louis Medical and Surgical Journal August 1887 53 121 https://archive.org/details/saintlouismedic08unkngoog/page/n128/mode/1up 6 January 2026 11254212 1077-663XBrunton T. Lauder 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 20 June 1889 1892 Macmillian London; New York 122 https://archive.org/details/b20406204/page/122/mode/1up Lecture III: Control and Cure of Disease 969481521 OL25611933M 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 (vinyl trichloride) isomer, which lacked a trichloromethyl group, exhibited anaesthetic effects even stronger than the 1,1,1 isomer.Sadtler Samuel P. On Two New Anaesthetics 1880 The American Journal of Pharmacy March 1881 53 https://archive.org/details/sim_american-journal-of-pharmacy-and-the-sciences_1881-03_53/page/119/mode/1up 119-120 Philadelphia College of Pharmacy Philadelphia College of Pharmacy 0730-7780 Safety Although not as toxic as many similar compounds, inhaled or ingested 1,1,1-trichloroethane acts as a central nervous system depressant and can cause decrease in reaction times and dexterity as well as impaired balance and abnormal EEG at lower concentrations, throat irritation, and in sufficiently high concentrations, death.Toxicological Profile for 1,1,1-Trichloroethane https://www.atsdr.cdc.gov/ToxProfiles/tp70.pdf U.S. Department of Health and Human Services - Agency for Toxic Substances and Disease Registry 3 March 2024 December 1990 The International Agency for Research on Cancer places 1,1,1-trichloroethane in Group 2A as a probable carcinogen.IARC 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 1,1,1-Trichloroethane and Four Other Industrial Chemicals 978-92-832-0197-7 en Atmospheric concentration thumb|left|upright=1.2|CH3CCl3 measured by the Advanced Global Atmospheric Gases ExperimentChen Gao AGAGE - Advanced Global Atmospheric Gases Experiment https://www-air.larc.nasa.gov/missions/agage/ www-air.larc.nasa.gov NASA 6 January 2026 in the lower atmosphere (troposphere) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in parts-per-trillion. thumb|left|upright=1.0|1,1,1-Trichloroethane timeseries at various latitudes. 1,1,1-Trichloroethane is a fairly potent greenhouse gas with a 100-year global warming potential of 169 relative to carbon dioxide.Hodnebrog ø. Aamaas B. Fuglestvedt J. S. Marston G. Myhre G. Nielsen C. J. Sandstad M. Shine K. P. Wallington T. J. Updated Global Warming Potentials and Radiative Efficiencies of Halocarbons and Other Weak Atmospheric Absorbers Reviews of Geophysics September 2020 58 3 10.1029/2019RG000691 33015672 7518032 2020RvGeo..5800691H This is nonetheless less than a tenth that of carbon tetrachloride — which it replaced as a solvent — due to its relatively short atmospheric lifetime of about 5 years.Stocker, T.F. D. Qin, G.-K. Plattner, M. Tignor, S.K. Allen, J. Boschung, A. Nauels, Y. Xia, V. Bex Midgley, P.M. Cambridge, United Kingdom and New York, NY, USA IPCC 2013 Cambridge University Press https://www.ipcc.ch/report/ar5/wg1/ 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 733 The Montreal Protocol targeted 1,1,1-trichloroethane as a compound 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, and its atmospheric concentration has declined substantially. See also 1,1,2-Trichloro-1,2,2-trifluoroethane References 30em Category:5-HT3 agonists Category:Chloroalkanes Category:Dry cleaning Category:Excipients Category:GABAA receptor positive allosteric modulators Category:Glycine receptor agonists Category:Greenhouse gases Category:Halogenated solvents Category:Hypnotics Category:Ozone-depleting chemical substances Category:Sedatives Category:IARC Group 2A carcinogens Category:Haloethanes