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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 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.
, 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.
1,2-Dichloroethane has chemical formula 242
Cf. 1,1-Dichloroethane (ethylidene dichloride).
Every year 17.5 million tons of 1,2-dichloroethane are produced in the United States
, Western Europe
. This is primarily achieved through the iron(III) chloride
catalysed reaction of ethene
(ethylene) and chlorine
- H2C=CH2 + Cl2 → Cl-CH2-CH2-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.
- H2C=CH2 + 2 HCl + ½ O2 → Cl-CH2-CH2-Cl + H2O
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-CH2-CH2-Cl → H2C=CH-Cl + HCl
The hydrogen chloride can be re-used in the production process, in the formation of more 1,2-dichloroethane (see Production).
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. 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.
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
Substitutes are recommended and will vary according to application. 1,3-dioxolane and toluene are possible substitutes as solvents.