1,2-Dichloroethane

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1,2-Dichloroethane

General
Systematic name	1,2-dichloroethane
Other names	Ethylene dichloride Ethane dichloride Dutch liquid, Dutch oil Freon 150
Molecular formula	C₂H₄Cl₂
SMILES	ClCCCl
Molar mass	98.96 g/mol
Appearance	Colourless liquid with characteristic odour
CAS number	[107-06-2]
Properties
Density and phase	1.253 g/cm³, liquid
Solubility in water	0.87 g/100 ml (20 °C)
Melting point	-35 °C (238 K)
Boiling point	83.5–84.0 °C (357 K)
Viscosity	0.84 mPa·s at 20 °C
Structure
Molecular shape	?
Dipole moment	5.24 D
Hazards
MSDS	External MSDS
Main hazards	toxic, flammable, corrosive
NFPA 704	3 2 0
Flash point	17 °C
R/S statement	R: R11, R45, R36/37/38 S: S45, S53
RTECS number	KI0525000
Supplementary data page
Structure and properties	n, ε_r, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related haloalkanes	methyl chloride methylene chloride 1,1,1-trichloroethane
Related compounds	ethylene chlorine vinyl chloride polyvinyl chloride
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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. 1,2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds, and as a solvent.

1 History
2 Chemistry
3 Production
4 Uses
- 4.1 Vinyl chloride monomer (VCM) production
- 4.2 Other uses
5 Safety
6 External links, References

[edit] 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.

[edit] Chemistry

1,2-Dichloroethane has chemical formula C₂H₄Cl₂.

Cf. 1,1-Dichloroethane (ethylidene dichloride).

[edit] Production

1,2-dichloroethane is primarily produced by 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

[edit] Uses

[edit] 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, chloroethen), 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).

[edit] Other uses

As a good apolar aprotic solvent, 1,2-dichloroethane is used as degreaser, paint remover. As an active building reagent, it is used as intermediate various organic compounds. And historically, it was used as anti-knock additive in leaded fuels.