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1,2-Dichloroethane

Names
IUPAC name 1,2-Dichloroethane
Other names Ethylene dichloride 1,2-DCA DCE[1] Ethane dichloride Dutch liquid, Dutch oil Freon 150
Identifiers
CAS Number	107-06-2 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27789 N
ChEMBL	ChEMBL16370 N
ChemSpider	13837650 N
ECHA InfoCard	100.003.145
KEGG	C06752 Y
PubChem CID	11
RTECS number	KI0525000
UNII	55163IJI47 Y
InChI InChI=1S/C2H4Cl2/c3-1-2-4/h1-2H2 N Key: WSLDOOZREJYCGB-UHFFFAOYSA-N N
SMILES ClCCCl
Properties
Chemical formula	C2H4Cl2
Molar mass	98.95 g·mol−1
Appearance	Colorless liquid
Odor	characteristic, pleasant chloroform-like odor[2]
Density	1.253 g/cm3, liquid
Melting point	−35 °C (−31 °F; 238 K)
Boiling point	84 °C (183 °F; 357 K)
Solubility in water	0.87 g/100 mL (20 °C)
Viscosity	0.84 mPa·s at 20 °C
Structure
Dipole moment	1.80 D
Hazards
Main hazards	Toxic, flammable, carcinogenic
Safety data sheet	See: data page
R-phrases (outdated)	R11 R45 R36/37/38
S-phrases (outdated)	S45 S53
NFPA 704	3 3 0
Flash point	13 °C (55 °F; 286 K)
Explosive limits	6.2%-16%[2]
Lethal dose or concentration (LD, LC):
LC50 (median concentration)	3000 ppm (guinea pig, 7 hr) 1000 ppm (rat, 7 hr)[3]
LCLo (lowest published)	1217 ppm (mouse, 2 hr) 1000 ppm (rat, 4 hr) 3000 ppm (rabbit, 7 hr)[3]
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 50 ppm C 100 ppm 200 ppm [5-minute maximum peak in any 3 hours][2]
REL (Recommended)	Ca TWA 1 ppm (4 mg/m3) ST 2 ppm (8 mg/m3)[2]
IDLH (Immediate danger)	Ca [50 ppm][2]
Related compounds
Related haloalkanes	Methyl chloride Methylene chloride 1,1,1-Trichloroethane
Related compounds	Ethylene Chlorine Vinyl chloride
Supplementary data page
Structure and properties	Refractive index (n), Dielectric constant (εr), etc.
Thermodynamic data	Phase behaviour solid–liquid–gas
Spectral data	UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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.^[4]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.^[5]

History

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.^[6] 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.

Production

Nearly 20 million tons of 1,2-dichloroethane are produced in the United States, Western Europe, and Japan.^[7] Production is primarily achieved through the iron(III) chloride-catalysed reaction of ethene (ethylene) and chlorine.

H₂C=CH₂ + Cl₂ → ClCH₂−CH₂Cl

1,2-dichloroethane is also generated by the copper(II) chloride-catalysed oxychlorination of ethylene:

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.

Uses

Vinyl chloride monomer (VCM) production

Approximately 95% 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.
^[8]

Other uses

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.

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 to scavenge lead from cylinders and valves preventing buildup .^[9]

Safety

1,2-Dichloroethane is toxic (especially by inhalation due to its high vapour pressure), highly flammable,^[10] 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.^[11] 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.^[12][13]
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.^{[citation needed]}

References

External links

• 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