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1,2-Dichloroethane
From Wikipedia, the free encyclopedia

The chemical compound 1,2-dichloroethane, commonly 1,2-Dichloroethane

known by its old name of ethylene dichloride (EDC), is
a chlorinated hydrocarbon, mainly used to produce vinyl
chloride monomer (VCM, chloroethene), the major
precursor for PVC production. It is a colourless liquid
with a chloroform-like odour. 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.[1]

Contents
IUPAC name
1 History
1,2-dichloroethane
2 Production
Other names
3 Uses
Ethylene dichloride
3.1 Vinyl chloride monomer (VCM) Ethane dichloride
production Dutch liquid, Dutch oil
3.2 Other uses Freon 150
Identifiers
4 Safety
CAS number 107-06-2
5 References
ChemSpider 10
6 External links
RTECS number KI0525000
SMILES
ClCCCl
History Properties
Molecular formula C2H4Cl2
In 1794, physician Jan Rudolph Deiman, merchant
Molar mass 98.96 g/mol
Adriaan Paets van Troostwijk, chemist Anthoni
Appearance Colourless liquid with
Lauwerenburg, and botanist Nicolaas Bondt, under the
characteristic odour
name of Gezelschap der Hollandsche Scheikundigen
Density 1.253 g/cm³, liquid
(Dutch: Society of Dutch Chemists), were the first to
Melting point
produce 1,2-dichloroethane from olefiant gas (oil-making -35 °C (238 K)
gas, ethylene) and chlorine gas. Although the Gezelschap
in practice did not do much in-depth scientific research, Boiling point
they and their publications were highly regarded. Part of 83.5–84.0 °C (357 K)
that acknowledgement is that 1,2-dichloroethane has been
Solubility in water 0.87 g/100 ml (20 °C)
called "Dutch oil" in old chemistry.
Viscosity 0.84 mPa·s at 20 °C
Structure
Production Dipole moment 1.80 D
Hazards
Nearly 20 million tons of 1,2-dichloroethane are produced
MSDS External MSDS
in the United States, Western Europe, and Japan.[2] R-phrases R11, R45, R36/37/38
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R-phrases R11, R45, R36/37/38
Production is primarily achieved through the iron(III)
S-phrases S45, S53
chloride-catalysed reaction of ethene (ethylene) and
NFPA 704
chlorine. 0
3 2
H2C=CH2 + Cl2 → ClCH2-CH2Cl COR

1,2-dichloroethane is also generated by the copper(II) Flash point 13 °C

chloride-catalysed "oxychlorination" of ethylene: Related compounds
H2C=CH2 + 2 HCl + ½ O 2 → ClCH2-CH2Cl + Related haloalkanes methyl chloride
methylene chloride
H2O 1,1,1-trichloroethane
Related compounds ethylene
In principle, it can be prepared by the chlorination of chlorine
ethane and, less directly, from ethanol. vinyl chloride
polyvinyl chloride
Uses Supplementary data page
Structure and n, εr, etc.
Vinyl chloride monomer (VCM) production properties
Thermodynamic Phase behaviour
data Solid, liquid, gas
With approximately 80% of the world's consumption of
Spectral data UV, IR, NMR, MS
1,2-dichloroethane, the major use of 1,2-dichloroethane is
in the production of vinyl chloride monomer (VCM, (what is this?) (verify)
(http://en.wikipedia.org/w/index.php?title=1,2-
chloroethene) with hydrogen chloride as a byproduct.
Dichloroethane&diff=cur&oldid=322196266)
VCM is the precursor to polyvinyl chloride. Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Cl-CH2-CH2-Cl → H2C=CH-Cl + HCl
Infobox references
The hydrogen chloride can be re-used in the production of more 1,2-dichloroethane via the oxychlorination
route described above.

Other uses

As a good apolar aprotic solvent, 1,2-dichloroethane is used as degreaser and paint remover. 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.

Via several steps, 1,2-dichloroethane is a precursor to 1,1,1-trichloroethane, which is used in dry cleaning.
Historically, 1,2-dichloroethane was used as an anti-knock additive in leaded fuels.

Safety
1,2-dichloroethane is toxic (especially by inhalation due to its high vapour pressure), corrosive, highly
flammable,[3] 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.[4] Substitutes are recommended and will vary according to application. 1,3-dioxolane and
toluene are possible substitutes as solvents. Dichloroethane is unstable in the presence of aluminium metal and,
when moist, with zinc and iron. Molded plastic consumer products (e.g., toys and holiday decorations) are
known to release 1,2-dichloroethane over time.

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References
1. ^ 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.
http://dx.doi.org/10.1002/14356007.a06_233.pub2
2. ^ J.A. Field & R. Sierra-Alvarez (2004). "Biodegradability of chlorinated solvents and related chlorinated
aliphatic compounds". Rev. Environ. Sci. Biotechnol. 3: 185–254. doi:10.1007/s11157-004-4733-8
(http://dx.doi.org/10.1007%2Fs11157-004-4733-8) .
3. ^ "1,2-Dichoroethane MSDS." Mallinckrodt Chemicals. 19 May 2008. Web.
<http://www.jtbaker.com/msds/englishhtml/D2440.htm>.
4. ^ S. De Wildeman & W. Verstraete (25 Mar., 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 (http://dx.doi.org/10.1007%2Fs00253-002-1174-6) .
PMID 12655450 (http://www.ncbi.nlm.nih.gov/pubmed/12655450) .

External links
Gezelschap der Hollandsche Scheikundigen (http://www.scholarly-societies.org/history/1790ghs.html)
ChemicalLand compound database
(http://www.chemicalland21.com/arokorhi/industrialchem/organic/ETHYLENE%20DICHLORIDE.htm)
Environmental Chemistry compound database
(http://environmentalchemistry.com/yogi/chemicals/cn/Ethylene%A0Dichloride.html)
Merck Chemicals database (http://chemdat.merck.de/pls/pi03/web2.search_page2?
text=100955&lang=4)
National Pollutant Inventory - 1,2 Dichlorethane Fact Sheet (http://www.npi.gov.au/database/substance-
info/profiles/33.html)
Locating and estimating air emissions from sources of ethylene dichloride, EPA report EPA-450/4-84-
007d, March 1984 (http://www.epa.gov/ttn/chief/le/ethyldi.pdf)

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