Everything about 1 2-dichloroethane totally explained
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The
chemical compound 1,2-dichloroethane, commonly known by its old name of
ethylene dichloride (
EDC), is a
chlorinated hydrocarbon, mainly used to produce
vinyl chloride monomer (VCM, chloroethene), the major 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.
History
In
1794, a group of four
Dutch friends under the name of
Gezelschap der Hollandsche Scheikundigen (Society of Dutch Chemists) consisted of physician
Jan Rudolph Deiman, merchant
Adriaan Paets van Troostwijk, chemist
Anthoni Lauwerenburg and botanist
Nicolaas Bondt. They were the first to produce 1,2-dichloroethane from olefiant gas (oil-making gas,
ethylene) and
chlorine gas. Although the
Gezelschap in practice didn't do much in-depth scientific research, they and their publications where highly regarded. Part of that acknowledgement is that 1,2-dichloroethane has been called
Dutch oil in old chemistry.
Chemistry
1,2-Dichloroethane has
chemical formula 242.
Cf. 1,1-Dichloroethane (ethylidene dichloride).
Production
Every year 17.5 million tons of 1,2-dichloroethane are produced in the
United States,
Western Europe and
Japan. This is primarily achieved through the
iron(III) chloride catalysed reaction of
ethene (ethylene) and
chlorine.
» H
2C=CH
2 + Cl
2 → Cl-CH
2-CH
2-Cl
In subsequent reactions, notably to
vinyl chloride (chloroethene),
hydrogen chloride is formed and re-used in a
copper(II) chloride catalysed reaction, to also produce 1,2-dichloroethane from ethene and
oxygen.
» H
2C=CH
2 + 2 HCl + ½ O
2 → Cl-CH
2-CH
2-Cl + H
2O
Uses
Vinyl chloride monomer (VCM) production
With approximately 80% of the world's consumption of 1,2-dichloroethane, the major application is in the production of vinyl chloride
monomer (VCM,
chloroethene), which is the precursor to
polyvinyl chloride under the formation of
hydrogen chloride.
» Cl-CH
2-CH
2-Cl → H
2C=CH-Cl + HCl
The hydrogen chloride can be re-used in the production process, in the formation of more 1,2-dichloroethane (see
Production).
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's used as an intermediate in the production of various organic compounds. It is also used as a reagent as an
electrophillic source of
chlorine, with elimination of ethene and chloride.
Historically, it 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, and possibly
carcinogenic. Its high solubility and 50-year
half-life in
anoxic aquifers make it a perennial pollutant and health risk that's very expensive to treat conventionally, requiring a method of
bioremediation.
Substitutes are recommended and will vary according to application.
1,3-dioxolane and
toluene are possible substitutes as solvents.
Further Information
Get more info on '1 2-dichloroethane'.
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