Gourt Home::Gourt :: 1,2-Dichloroethane
| 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 | * |
| 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 | |
| Flash point | 17 °C |
| R/S statement | R: , , S: , |
| RTECS number | KI0525000 |
| Supplementary data page | |
| Structure and properties | n, εr, 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) Chemical infobox | |
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
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
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, 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).
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.
Safety
It occurs as a toxic, corrosive, highly flammable, and possibly carcinogenic colorless liquid with a chloroform-like odor.
External links, References
- 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
IARC Group 2B carcinogens | Organochloride insecticides | Organochlorides | Plastics | Solvents
"1,2-Dichloroethane"