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1,2-Dichloroethane
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<h2 id="history">History</h2> <p>In 1794, physician <a href="/facts/Jan_Rudolph_Deiman/YxKHH3Q0">Jan Rudolph Deiman</a>, merchant <a href="/facts/Adriaan_Paets_van_Troostwijk/VJuHKdMl">Adriaan Paets van Troostwijk</a>, chemist Anthoni Lauwerenburg, and botanist Nicolaas Bondt, under the name of Society of Dutch Chemists (<a href="/facts/Dutch_language/yIB5lbsx">Dutch</a>: <i>Gezelschap der Hollandsche Scheikundigen</i>), were the first to produce 1,2-dichloroethane from olefiant gas (oil-making gas, <a href="/facts/Ethylene/QMNBYLYn">ethylene</a>) and <a href="/facts/Chlorine/y27UwYBM">chlorine</a> gas.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> Although the <i>Gezelschap</i> 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. </p> <h2 id="production">Production</h2> <p>Nearly 20 million tons of 1,2-dichloroethane are produced annually in the <a href="/facts/United_States/P0sCdLe5">United States</a>, <a href="/facts/Western_Europe/YmWlV59w">Western Europe</a>, and <a href="/facts/Japan/U5mz0SRT">Japan</a>.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> Production is primarily achieved through the <a href="/facts/Iron(III)_chloride/a51pulq1">iron(III) chloride</a>-<a href="/facts/Catalysis/LPBS7TQC">catalysed reaction</a> of ethylene and chlorine: </p> H2C=CH2 (g) + Cl2 (g) → ClC2H4Cl (l) (<a href="/facts/Standard_enthalpy_of_reaction/u5pffxVM">Δ<i>H</i>⊖r</a> = −218 kJ/mol) <p>1,2-dichloroethane is also generated by the <a href="/facts/Copper(II)_chloride/saTjsWXT">copper(II) chloride</a>-catalysed <a href="/facts/Oxychlorination/repqpsoS">oxychlorination</a> of ethylene: </p> H2C=CH2 + 2 HCl + 1/2 O2 → ClC2H4Cl + H2O <h2 id="uses">Uses</h2> <h3>Vinyl chloride production</h3> <p>Approximately 95% of the world's production of 1,2-dichloroethane is used in the production of <a href="/facts/Vinyl_chloride/UNGUdwTK">vinyl chloride</a> <a href="/facts/Monomer/Gw3CltMb">monomer</a> (VCM) with <a href="/facts/Hydrogen_chloride/7Wzkhomd">hydrogen chloride</a> as a byproduct. VCM is the precursor to <a href="/facts/Polyvinyl_chloride/9VkegJvr">polyvinyl chloride</a>. </p> ClC2H4Cl → H2C=CHCl + HCl <p>The hydrogen chloride can be re-used in the production of more 1,2-dichloroethane via the <a href="/facts/Oxychlorination/repqpsoS">oxychlorination</a> route described above.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p> <h3>Other uses</h3> <p>1,2-Dichloroethane has been used as degreaser and paint remover but this use has phased out due to its <a href="/facts/Toxicity/qa96rs60">toxicity</a>. As a useful 'building block' reagent, it is used as an intermediate in the production of diverse organic compounds such as <a href="/facts/Ethylenediamine/VDX8VfFv">ethylenediamine</a> and higher <a href="/facts/Ethyleneamines/XV22uWQf">ethyleneamines</a>.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> In the laboratory it is occasionally used as a source of <a href="/facts/Chlorine/y27UwYBM">chlorine</a>, with elimination of ethene and chloride. </p><p>Via several steps, 1,2-dichloroethane is a precursor to <a href="/facts/1,1,1-trichloroethane/lL4G6CaC">1,1,1-trichloroethane</a>. Historically, before leaded petrol was phased out, chloroethanes were used as an additive in petrol to prevent lead buildup in engines.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> </p> <h2 id="safety">Safety</h2> <p>1,2-Dichloroethane is highly <a href="/facts/Flammable/1QexTQ4T">flammable</a><a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a> and releases <a href="/facts/Hydrochloric_acid/HqItJlUT">hydrochloric acid</a> when combusted: </p> ClC2H4Cl + 5/2 O2 → 2 CO2 + H2O + 2 HCl <p>It is also <a href="/facts/Toxic/qa96rs60">toxic</a> (especially by inhalation due to its high <a href="/facts/Vapour_pressure/whrEr96T">vapour pressure</a>) and possibly <a href="/facts/Carcinogen/soH8Y9CE">carcinogenic</a>. Its high <a href="/facts/Solubility/kLE9h3Jb">solubility</a> and 50-year <a href="/facts/Half-life/kGVH8BAB">half-life</a> in <a href="/facts/Anoxic_waters/vLdveWX0">anoxic</a> <a href="/facts/Aquifer/UwG6ksdG">aquifers</a> make it a perennial pollutant and health risk that is very expensive to treat conventionally, requiring a method of <a href="/facts/Bioremediation/zft68Ez9">bioremediation</a>.<a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a> 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 <a href="/facts/China/lTjIXY5p">China</a> that released 1,2-dichloroethane into homes at levels high enough to produce cancer risk.<a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a><a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a> </p><p>Substitutes are recommended and will vary according to application. <a href="/facts/Dioxolane/E8sfNqTn">Dioxolane</a> and <a href="/facts/Toluene/Pzdt8dwD">toluene</a> are possible substitutes as solvents. <a href="/facts/Dichloroethane/1c08zyrP">Dichloroethane</a> is unstable in the presence of <a href="/facts/Aluminium/7wmR8jYE">aluminium</a> and, when moist, with <a href="/facts/Zinc/80b1qgk3">zinc</a> and <a href="/facts/Iron/QK1JYy8E">iron</a>. </p> <h2 id="external-links">External links</h2> <ul><li><a href="https://web.archive.org/web/20050908231559/http://www.scholarly-societies.org/history/1790ghs.html">Gezelschap der Hollandsche Scheikundigen</a></li> <li><a href="https://archive.today/20130102043336/http://www.chemicalland21.com/arokorhi/industrialchem/organic/ETHYLENE%20DICHLORIDE.htm">ChemicalLand compound database</a></li> <li><a href="http://environmentalchemistry.com/yogi/chemicals/cn/Ethylene%A0Dichloride.html">Environmental Chemistry compound database</a></li> <li><a href="https://web.archive.org/web/20080304085557/http://chemdat.merck.de/pls/pi03/web2.search_page2?text=100955&lang=4">Merck Chemicals database</a></li> <li><a href="https://web.archive.org/web/20060820040740/http://www.npi.gov.au/database/substance-info/profiles/33.html">National Pollutant Inventory – 1,2 Dichlorethane Fact Sheet</a></li> <li><a href="http://www.epa.gov/ttn/chief/le/ethyldi.pdf">Locating and estimating air emissions from sources of ethylene dichloride, EPA report EPA-450/4-84-007d, March 1984</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>"Toxic Substances – 1,2-Dichloroethane". ATSDR. Retrieved 23 September 2015. <a href="https://wwwn.cdc.gov/TSP/index.aspx?toxid=110" target="_blank">https://wwwn.cdc.gov/TSP/index.aspx?toxid=110</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>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. <a href="https://books.google.com/books?id=SFAyAQAAMAAJ&pg=PA173" target="_blank">https://books.google.com/books?id=SFAyAQAAMAAJ&pg=PA173</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>J.A. Field & R. Sierra-Alvarez (2004). "Biodegradability of chlorinated solvents and related chlorinated aliphatic compounds". Rev. Environ. Sci. Biotechnol. 3 (3): 185–254. Bibcode:2004RESBT...3..185F. doi:10.1007/s11157-004-4733-8. S2CID 36536985. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>"Ethylene Dichloride – Chemical Economics Handbook (CEH) – IHS Markit". ihs.com. Retrieved 8 April 2018. <a href="https://www.ihs.com/products/ethylene-dichloride-chemical-economics-handbook.html" target="_blank">https://www.ihs.com/products/ethylene-dichloride-chemical-economics-handbook.html</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Srivasan Sridhar; Richard G. Carter (2001). "Diamines and Higher Amines, Aliphatic". Kirk-Othmer Encyclopedia of Chemical Technology. New York: John Wiley. doi:10.1002/0471238961.0409011303011820.a01.pub2. ISBN 9780471238966. <a href="9780471238966" target="_blank">9780471238966</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Seyferth, D. (2003). "The Rise and Fall of Tetraethyllead. 2". Organometallics. 22 (25): 5154–5178. doi:10.1021/om030621b. <a href="/wiki/Organometallics" target="_blank">/wiki/Organometallics</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>"1,2-Dichoroethane MSDS." Mallinckrodt Chemicals. 19 May 2008. Web. <http://hazard.com/msds/mf/baker/baker/files/d2440.htm>. <a href="http://hazard.com/msds/mf/baker/baker/files/d2440.htm" target="_blank">http://hazard.com/msds/mf/baker/baker/files/d2440.htm</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>S. De Wildeman & W. Verstraete (25 March 2003). "The quest for microbial reductive dechlorination of C2 to C4 chloroalkanes is warranted". Appl. Microbiol. Biotechnol. 61 (2): 94–102. doi:10.1007/s00253-002-1174-6. PMID 12655450. S2CID 72921. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>"Toxic Christmas: Plastic Ornaments May Pollute Your Air". rodale.com. Archived from the original on 18 March 2012. Retrieved 8 April 2018. <a href="https://web.archive.org/web/20120318162835/http://www.rodale.com/plastic-christmas-ornaments?page=0,0" target="_blank">https://web.archive.org/web/20120318162835/http://www.rodale.com/plastic-christmas-ornaments?page=0,0</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>Doucette, WJ; Hall, AJ & Gorder, KA (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. Bibcode:2010GMRed..30a..67D. CiteSeerX 10.1.1.1013.1487. doi:10.1111/j.1745-6592.2009.01267.x. S2CID 96563330. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> </ol>