Dutch liquid, Dutch oil
|Jmol 3D model||Interactive image|
|Molar mass||98.95 g·mol−1|
|Odor||characteristic, pleasant chloroform-like odor|
|Density||1.253 g/cm3, liquid|
|Melting point||−35 °C (−31 °F; 238 K)|
|Boiling point||84 °C (183 °F; 357 K)|
|0.87 g/100 mL (20 °C)|
|Viscosity||0.84 mPa·s at 20 °C|
|Main hazards||Toxic, flammable, carcinogenic|
|Safety data sheet||See: data page|
|R-phrases||R11 R45 R36/37/38|
|Flash point||13 °C (55 °F; 286 K)|
|Lethal dose or concentration (LD, LC):|
LC50 (median concentration)
|3000 ppm (guinea pig, 7 hr)
1000 ppm (rat, 7 hr)
LCLo (lowest published)
|1217 ppm (mouse, 2 hr)
1000 ppm (rat, 4 hr)
3000 ppm (rabbit, 7 hr)
|US health exposure limits (NIOSH):|
|TWA 50 ppm C 100 ppm 200 ppm [5-minute maximum peak in any 3 hours]|
|Ca TWA 1 ppm (4 mg/m3) ST 2 ppm (8 mg/m3)|
IDLH (Immediate danger)
|Ca [50 ppm]|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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.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 (b.p. 70.5 °C) and other chlorocarbons.
In 1794, physician Jan Rudolph Deiman, merchant Adriaan Paets van Troostwijk, chemist Anthoni Lauwerenburg, and botanist Nicolaas Bondt, under the name of Gezelschap der Hollandsche Scheikundigen (Dutch: Society of Dutch Chemists), were the first to produce 1,2-dichloroethane from olefiant gas (oil-making gas, ethylene) and chlorine gas. 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.
Nearly 20 million tons of 1,2-dichloroethane are produced in the United States, Western Europe, and Japan. Production is primarily achieved through the iron(III) chloride-catalysed reaction of ethene (ethylene) and chlorine.
- H2C=CH2 + Cl2 → ClCH2-CH2Cl
- 2 H2C=CH2 + 4 HCl + O2 → 2 ClCH2-CH2Cl + 2 H2O
In principle, it can be prepared by the chlorination of ethane and, less directly, from ethanol.
Vinyl chloride monomer (VCM) production
Approximately 80% of the world's production of 1,2-dichloroethane is used in the production of vinyl chloride monomer (VCM, chloroethene) with hydrogen chloride as a byproduct. VCM is the precursor to polyvinyl chloride.
- Cl-CH2-CH2-Cl → H2C=CH-Cl + HCl
The hydrogen chloride can be re-used in the production of more 1,2-dichloroethane via the oxychlorination route described above.
As a good polar aprotic solvent, 1,2-dichloroethane could be used as degreaser and paint remover but is now banned from use due to its toxicity and possible carcinogenity. As a useful 'building block' reagent, it is used as an intermediate in the production of various organic compounds such as ethylenediamine. In the laboratory it is occasionally used as a source of chlorine, with elimination of ethene and chloride.
1,2-Dichloroethane is toxic (especially by inhalation due to its high vapour pressure), highly flammable, 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. 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. 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 metal and, when moist, with zinc and iron.
- "NIOSH Pocket Guide to Chemical Hazards #0271". National Institute for Occupational Safety and Health (NIOSH).
- "Ethylene dichloride". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
- "ATSDR - Toxic Substances - 1,2-Dichloroethane". www.atsdr.cdc.gov. Retrieved 2015-09-23.
- 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
- 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.
- J.A. Field & R. Sierra-Alvarez (2004). "Biodegradability of chlorinated solvents and related chlorinated aliphatic compounds". Rev. Environ. Sci. Biotechnol. 3 (3): 185–254. doi:10.1007/s11157-004-4733-8.
- Seyferth, D. (2003). "The Rise and Fall of Tetraethyllead. 2". Organometallics. 22 (25): 5154–5178. doi:10.1021/om030621b.
- "1,2-Dichoroethane MSDS." Mallinckrodt Chemicals. 19 May 2008. Web. <http://hazard.com/msds/mf/baker/baker/files/d2440.htm>.
- 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.
- Toxic Christmas: Plastic Ornaments May Pollute Your Air
- 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. doi:10.1111/j.1745-6592.2009.01267.x.
- Gezelschap der Hollandsche Scheikundigen
- ChemicalLand compound database
- 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
- CDC - NIOSH Pocket Guide to Chemical Hazards