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| Names | |||
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| Preferred IUPAC name 1,2-Dichloroethane | |||
| Other names Ethylene dichloride Ethylene chloride 1,2-DCA 1,2-DCE DCE[1] Ethane dichloride Dutch liquid, Dutch oil Freon 150 | |||
| Identifiers | |||
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3D model (JSmol) | |||
| 605264 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| DrugBank | |||
| ECHA InfoCard | 100.003.145 | ||
| EC Number |
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| 49272 | |||
| KEGG |
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| RTECS number |
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| UNII | |||
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| Properties | |||
| 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) | ||
| 0.87 g/100 mL (20 °C) | |||
| Viscosity | 0.84 mPa·s at 20 °C | ||
| Structure | |||
| 1.80 D | |||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | Toxic, flammable, possibly carcinogenic | ||
| GHS labelling: | |||
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| Danger | |||
| H225,H302,H315,H319,H335,H350 | |||
| P201,P202,P210,P233,P240,P241,P242,P243,P261,P264,P270,P271,P280,P281,P301+P312,P302+P352,P303+P361+P353,P304+P340,P305+P351+P338,P308+P313,P312,P321,P330,P332+P313,P337+P313,P362,P370+P378,P403+P233,P403+P235,P405,P501 | |||
| NFPA 704 (fire diamond) | |||
| 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 h) 1000 ppm (rat, 7 h)[3] | ||
LCLo (lowest published) | 1217 ppm (mouse, 2 h) 1000 ppm (rat, 4 h) 3000 ppm (rabbit, 7 h)[3] | ||
| NIOSH (US health exposure limits): | |||
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 | |||
Relatedhaloalkanes | Methyl chloride Methylene chloride 1,1,1-Trichloroethane | ||
Related compounds | Ethylene 1,1-Dichloroethane Vinyl chloride | ||
| Supplementary data page | |||
| 1,2-Dichloroethane (data page) | |||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Thechemical compound1,2-dichloroethane, commonly known asethylene dichloride (EDC), is achlorinated hydrocarbon. It is a colourlessliquid with achloroform-likeodour. The most common use of 1,2-dichloroethane is in the production ofvinyl chloride, which is used to makepolyvinyl 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 otherorganic chemical compounds, and as asolvent. It formsazeotropes with many othersolvents, including water (at a boiling point of 70.5 °C or 158.9 °F or 343.6 K) and otherchlorocarbons.[5]
In 1794, physicianJan Rudolph Deiman, merchantAdriaan Paets van Troostwijk, chemist Anthoni Lauwerenburg, and botanist Nicolaas Bondt, under the name of Society of Dutch Chemists (Dutch:Gezelschap der Hollandsche Scheikundigen), were the first to produce 1,2-dichloroethane from olefiant gas (oil-making gas,ethylene) andchlorine gas.[6] Although theGezelschap 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. This is also the origin of the archaic term "olefiant gas" (oil-making gas) for ethylene, for in this reaction it is ethylene that makes the Dutch oil. "Olefiant gas" is the etymological origin of the modern term "olefins", the family of hydrocarbons of which ethylene is the first member.
Nearly 20 million tons of 1,2-dichloroethane are produced annually in theUnited States,Western Europe, andJapan.[7] Production is primarily achieved through theiron(III) chloride-catalysed reaction of ethylene and chlorine:
1,2-dichloroethane is also generated by thecopper(II) chloride-catalysedoxychlorination of ethylene:
Approximately 95% of the world's production of 1,2-dichloroethane is used in the production ofvinyl chloridemonomer (VCM) withhydrogen chloride as a byproduct. VCM is the precursor topolyvinyl chloride.
The hydrogen chloride can be re-used in the production of more 1,2-dichloroethane via theoxychlorination route described above.[8]
1,2-Dichloroethane has been used as degreaser and paint remover but this use has phased out due to itstoxicity. As a useful 'building block' reagent, it is used as an intermediate in the production of diverse organic compounds such asethylenediamine and higherethyleneamines.[9] In the laboratory it is occasionally used as a source ofchlorine, with elimination of ethene and chloride.
Via several steps, 1,2-dichloroethane is a precursor to1,1,1-trichloroethane. Historically, before leaded petrol was phased out, chloroethanes were used as an additive in petrol to prevent lead buildup in engines.[10]
1,2-Dichloroethane is highlyflammable[11] and releaseshydrochloric acid when combusted:
It is alsotoxic (especially by inhalation due to its highvapour pressure) and possiblycarcinogenic. Its highsolubility and 50-yearhalf-life inanoxicaquifers make it a perennial pollutant and health risk that is very expensive to treat conventionally, requiring a method ofbioremediation.[12] 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) fromChina that released 1,2-dichloroethane into homes at levels high enough to produce cancer risk.[13][14]
Substitutes are recommended and will vary according to application.Dioxolane andtoluene are possible substitutes as solvents.Dichloroethane is unstable in the presence ofaluminium and, when moist, withzinc andiron.[citation needed]
DCE: 1,2-dichloroethane
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