出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/15 22:00:10」(JST)
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| Names | |||
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| IUPAC name
1,2-Dichloroethane
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| Other names
Ethylene dichloride
Ethane dichloride |
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| Identifiers | |||
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CAS Registry Number
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107-06-2 Y | ||
| ChEBI | CHEBI:27789 N | ||
| ChEMBL | ChEMBL16370 N | ||
| ChemSpider | 13837650 N | ||
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InChI
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| Jmol-3D images | Image | ||
| KEGG | C06752 Y | ||
| PubChem | 11 | ||
| RTECS number | KI0525000 | ||
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SMILES
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| UNII | 55163IJI47 Y | ||
| Properties | |||
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Chemical formula
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C2H4Cl2 | ||
| Molar mass | 98.95 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Odor | characteristic, pleasant chloroform-like odor[1] | ||
| Density | 1.253 g/cm3, liquid | ||
| Melting point | −35 °C (−31 °F; 238 K) | ||
| Boiling point | 84 °C (183 °F; 357 K) | ||
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Solubility in water
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0.87 g/100 mL (20 °C) | ||
| Viscosity | 0.84 mPa·s at 20 °C | ||
| Structure | |||
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Dipole moment
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1.80 D | ||
| Hazards | |||
| Main hazards | Toxic, flammable, carcinogenic | ||
| Safety data sheet | See: data page | ||
| R-phrases | R11 R45 R36/37/38 | ||
| S-phrases | S45 S53 | ||
| NFPA 704 |
3
3
0
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| Flash point | 13 °C (55 °F; 286 K) | ||
| Explosive limits | 6.2%-16%[1] | ||
| Lethal dose or concentration (LD, LC): | |||
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LC50 (Median concentration)
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3000 ppm (guinea pig, 7 hr) 1000 ppm (rat, 7 hr)[2] |
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LCLo (Lowest published)
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1217 ppm (mouse, 2 hr) 1000 ppm (rat, 4 hr) |
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| US health exposure limits (NIOSH): | |||
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PEL (Permissible)
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TWA 50 ppm C 100 ppm 200 ppm [5-minute maximum peak in any 3 hours][1] | ||
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REL (Recommended)
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Ca TWA 1 ppm (4 mg/m3) ST 2 ppm (8 mg/m3)[1] | ||
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IDLH (Immediate danger
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Ca [50 ppm][1] | ||
| Related compounds | |||
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Related haloalkanes
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Methyl chloride Methylene chloride |
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Related compounds
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Ethylene Chlorine |
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| Supplementary data page | |||
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Structure and
properties |
Refractive index (n), Dielectric constant (εr), etc. |
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Thermodynamic
data |
Phase behaviour solid–liquid–gas |
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Spectral data
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UV, IR, NMR, MS | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| N verify (what is: Y/N?) | |||
| Infobox references | |||
The chemical compound 1,2-dichloroethane (DCE) 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. It forms azeotropes with many other solvents, including water (b.p. 70.5 °C) and other chlorocarbons.[3]
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.[4] 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.
Nearly 20 million tons of 1,2-dichloroethane are produced in the United States, Western Europe, and Japan.[5] Production is primarily achieved through the iron(III) chloride-catalysed reaction of ethene (ethylene) and chlorine.
1,2-dichloroethane is also generated by the copper(II) chloride-catalysed "oxychlorination" of ethylene:
In principle, it can be prepared by the chlorination of ethane and, less directly, from ethanol.
With approximately 80% of the world's consumption of 1,2-dichloroethane, the major use of 1,2-dichloroethane is in the production of vinyl chloride monomer (VCM, chloroethene) with hydrogen chloride as a byproduct. VCM is the precursor to polyvinyl chloride.
The hydrogen chloride can be re-used in the production of more 1,2-dichloroethane via the oxychlorination route described above.
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 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.[6]
1,2-Dichloroethane is toxic (especially by inhalation due to its high vapour pressure), highly flammable,[7] and 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.[8] 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.[9][10] 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.
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| リンク元 | 「二塩化エチレン」「dichloroethane」 |
| 関連記事 | 「ethylene」「dichloride」 |