1,2-Dichloroethane

August 2026 changed changed 477203605 1,2-Dichloroethane 1,2-dichloroethane.svg skin-invert-image 1,2-Dichloroethane 1,2-dichloroethane-3D-vdW.png bg-transparent 1,2-Dichloroethane 1,2-Dichloroethane Ethylene dichlorideEthylene chloride1,2-DCA1,2-DCE DCEStandard Abbreviations and Acronyms http://pubs.acs.org/paragonplus/submission/joceah/joceah_abbreviations.pdf Staff writer The Journal of Organic Chemistry DCE: 1,2-dichloroethane https://web.archive.org/web/20180801004052/http://pubs.acs.org/paragonplus/submission/joceah/joceah_abbreviations.pdf 2018-08-01 2025-07-19Ethane dichlorideDutch liquid, Dutch oilFreon 150 ClCCCl correct chemspider 1S/C2H4Cl2/c3-1-2-4/h1-2H2 correct chemspider WSLDOOZREJYCGB-UHFFFAOYSA-N B01041 107-06-2 correct chemspider 13837650 11 correct EBI 27789 correct EBI 16370 DB03733 203-458-1 49272 605264 correct CAS correct FDA 55163IJI47 KI0525000 correct kegg C06752 2 4 2 Colorless liquid characteristic, pleasant chloroform-like odor 1.253 g/cm3, liquid 0.87 g/100 mL (20 °C) −35 84 0.84 mPa·s at 20 °C 0.0 D Toxic, flammable, possibly carcinogenic 2 3 0 13 02 06 08 Danger 225 302 315 319 335 350 201 202 210 233 240 241 242 243 261 264 270 271 280 281 301+312 302+352 303+361+353 304+340 305+351+338 308+313 312 321 330 332+313 337+313 362 370+378 403+233 403+235 405 501 TWA 50 ppm C 100 ppm 200 ppm [5-minute maximum peak in any 3 hours]0271 6.2–16% Ca [50 ppm] Ca TWA 1 ppm (4 mg/m3) ST 2 ppm (8 mg/m3) 3000 ppm (guinea pig, 7 h)1000 ppm (rat, 7 h)107062 Ethylene dichloride 1217 ppm (mouse, 2 h)1000 ppm (rat, 4 h)3000 ppm (rabbit, 7 h) haloalkanes Methyl chlorideMethylene chloride1,1,1-Trichloroethane Ethylene1,1-DichloroethaneVinyl chloride The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl chloride, which is used to make polyvinyl chloride (PVC) pipes, furniture and automobile upholstery, wall coverings, housewares, and automobile parts. Toxic Substances – 1,2-Dichloroethane https://wwwn.cdc.gov/TSP/index.aspx?toxid=110 ATSDR 2015-09-23 1,2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds, and as a solvent. It forms azeotropes with many other solvents, including water (at a boiling point of 70.5 C F K or) and other chlorocarbons.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. 10.1002/14356007.a06_233.pub2. History In 1794, physician Jan Rudolph Deiman, merchant Adriaan Paets van Troostwijk, chemist Anthoni Lauwerenburg, and botanist Nicolaas Bondt, under the name of Society of Dutch Chemists (nl Gezelschap der Hollandsche Scheikundigen), were the first to produce 1,2-dichloroethane from olefiant gas (oil-making gas, ethylene) and chlorine gas.Deimann, van Troostwyk, Bondt and Louwrenburgh (1795) "Ueber die Gasarten, welche man aus Verbindungen von starker Vitriolsäure und Alkohol erhält" (On the types of gases which one obtains from combinations of strong vitriolic acid and alcohol), Chemische Annalen ... , 2 : 195-205, 310-316, 430-440. The production and characterization of 1,2-dichloroethane appear on pages 200-202. The investigators were trying to detect the presence of carbon (Kohl) in ethylene (Luft, literally, "air") by adding chlorine (zündend Salzgas, literally, "burning gas from salt"). Instead of the expected soot, an oil (Oehl) formed. Although the Gezelschap in practice did not do much in-depth scientific research, they and their publications were highly regarded. Part of that acknowledgement is that 1,2-dichloroethane was called "Dutch oil" in old chemistry. This is also the origin of the archaic term "olefiant gas" (oil-making gas) for ethylene, for in this reaction it is ethylene that makes the Dutch oil. "Olefiant gas" is the etymological origin of the modern term "olefins", the family of hydrocarbons of which ethylene is the first member. Production Nearly 20 million tons of 1,2-dichloroethane are produced annually in the United States, Western Europe, and Japan.J.A. Field R. Sierra-Alvarez amp 2004 Biodegradability of chlorinated solvents and related chlorinated aliphatic compounds Rev. Environ. Sci. Biotechnol. 3 3 185–254 10.1007/s11157-004-4733-8 2004RESBT...3..185F 36536985 Production is primarily achieved through the iron(III) chloride-catalysed reaction of ethylene and chlorine: H2C\dCH2 (g) + Cl2 (g) -> ClC2H4Cl (l) (ΔH⊖r = −218 kJ/mol) 1,2-dichloroethane is also generated by the copper(II) chloride-catalysed oxychlorination of ethylene: H2C\dCH2 + 2 HCl + 1 2 O2 -> ClC2H4Cl + H2O Uses Vinyl chloride production Approximately 95% of the world's production of 1,2-dichloroethane is used in the production of vinyl chloride monomer (VCM) with hydrogen chloride as a byproduct. VCM is the precursor to polyvinyl chloride. ClC2H4Cl -> H2C\dCHCl + HCl The hydrogen chloride can be re-used in the production of more 1,2-dichloroethane via the oxychlorination route described above.https://www.ihs.com/products/ethylene-dichloride-chemical-economics-handbook.html Ethylene Dichloride – Chemical Economics Handbook (CEH) – IHS Markit ihs.com 8 April 2018 Other uses 1,2-Dichloroethane has been used as degreaser and paint remover but this use has phased out due to its toxicity. As a useful 'building block' reagent, it is used as an intermediate in the production of diverse organic compounds such as ethylenediamine and higher ethyleneamines. Diamines and Higher Amines, Aliphatic Srivasan Sridhar Richard G. Carter 10.1002/0471238961.0409011303011820.a01.pub2 2001 cs1 In the laboratory it is occasionally used as a source of chlorine, with elimination of ethene and chloride. Via several steps, 1,2-dichloroethane is a precursor to 1,1,1-trichloroethane. Historically, before leaded petrol was phased out, chloroethanes were used as an additive in petrol to prevent lead buildup in engines. Seyferth, D. The Rise and Fall of Tetraethyllead. 2 Organometallics 2003 22 25 5154–5178 10.1021/om030621b Safety 1,2-Dichloroethane is highly flammable"1,2-Dichoroethane MSDS." Mallinckrodt Chemicals. 19 May 2008. Web. <http://hazard.com/msds/mf/baker/baker/files/d2440.htm>. and releases hydrochloric acid when combusted: ClC2H4Cl + 5 2 O2 -> 2 CO2 + H2O + 2 HCl It is also toxic (especially by inhalation due to its high vapour pressure) and possibly carcinogenic. Its high solubility and 50-year half-life in anoxic aquifers make it a perennial pollutant and health risk that is very expensive to treat conventionally, requiring a method of bioremediation.S. De Wildeman W. Verstraete amp 25 March 2003 The quest for microbial reductive dechlorination of C2 to C4 chloroalkanes is warranted Appl. Microbiol. Biotechnol. 61 2 94–102 10.1007/s00253-002-1174-6 12655450 72921 While the chemical is not used in consumer products manufactured in the U.S., a case was reported in 2009 of molded plastic consumer products (toys and holiday decorations) from China that released 1,2-dichloroethane into homes at levels high enough to produce cancer risk.http://www.rodale.com/plastic-christmas-ornaments?page=0%2C0 Toxic Christmas: Plastic Ornaments May Pollute Your Air rodale.com 8 April 2018 https://web.archive.org/web/20120318162835/http://www.rodale.com/plastic-christmas-ornaments?page=0,0 18 March 2012 deadDoucette, WJ Hall, AJ Gorder, KA amp Winter 2010 Emissions of 1, 2-Dichloroethane from Holiday Decorations as a Source of Indoor Air Contamination Ground Water Monitoring & Remediation 30 1 67–73 10.1111/j.1745-6592.2009.01267.x 2010GMRed..30a..67D 96563330 Substitutes are recommended and will vary according to application. Dioxolane and toluene are possible substitutes as solvents. Dichloroethane is unstable in the presence of aluminium and, when moist, with zinc and iron.June 2016 References External links Gezelschap der Hollandsche Scheikundigen Environmental Chemistry compound database Merck Chemicals database National Pollutant Inventory – 1,2 Dichlorethane Fact Sheet Locating and estimating air emissions from sources of ethylene dichloride, EPA report EPA-450/4-84-007d, March 1984 Category:IARC Group 2B carcinogens Category:Organochloride insecticides Category:Chloroalkanes Category:Plastics Category:Halogenated solvents Category:Fuel additives Category:Haloethanes