Adverts

Open Access Articles- Top Results for 1,2-Dichloroethane

1,2-Dichloroethane

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. colspan=2 class="borderless" border=0 align=center #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.
1,2-Dichloroethane

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-

colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Names

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-

IUPAC name
1,2-Dichloroethane
Other names
Ethylene dichloride
Ethane dichloride
Dutch liquid, Dutch oil
Freon 150
colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Identifiers#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-



107-06-2 7pxY ChEBI CHEBI:27789 7pxN ChEMBL ChEMBL16370 7pxN ChemSpider 13837650 7pxN Jmol-3D images Image KEGG C06752 7pxY PubChem Template:Chembox PubChem/format RTECS number KI0525000 Template:Chembox UNII colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Properties

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-

C2H4Cl2 Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1 Appearance Colorless liquid Odor characteristic, pleasant chloroform-like odor[1] Density 1.253 g/cm3, liquid Melting point Script error: No such module "convert". Boiling point Script error: No such module "convert". 0.87 g/100 mL (20 °C) Viscosity 0.84 mPa·s at 20 °C colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Structure

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-





Dipole moment 1.80 D colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Hazards

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.- #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. SDS #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. External SDS #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-

Main hazards Toxic, flammable, carcinogenic R-phrases R11 R45 R36/37/38 S-phrases S45 S53 NFPA 704

Error: Must specify an image in the first line.

3
3
0
Flash point Script error: No such module "convert". Explosive limits 6.2%-16%[1] US health exposure limits (NIOSH):

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. style="padding-left:0.5em;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. TWA 50 ppm C 100 ppm 200 ppm [5-minute maximum peak in any 3 hours][1] #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. style="padding-left:0.5em;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Ca TWA 1 ppm (4 mg/m3) ST 2 ppm (8 mg/m3)[1] #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. style="padding-left:0.5em;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Ca [50 ppm][1] #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-

colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Related compounds

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-


Related haloalkanes
Methyl chloride
Methylene chloride
1,1,1-Trichloroethane
Related compounds
Ethylene
Chlorine
Vinyl chloride colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Supplementary data page#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.- #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Refractive index (n),
Dielectric constantr), etc. #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.
Thermodynamic
data

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Phase behaviour
solid–liquid–gas #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. UV, IR, NMR, MS #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 14pxN verify (what is10pxY/10pxN?) 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.[2]

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.[3] 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.[4] 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

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.

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.

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 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.[5]

Safety

1,2-Dichloroethane is toxic (especially by inhalation due to its high vapour pressure), highly flammable,[6] 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.[7] 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.[8][9] 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.

References

  1. 1.0 1.1 1.2 1.3 1.4 "NIOSH Pocket Guide to Chemical Hazards #0271". National Institute for Occupational Safety and Health (NIOSH). 
  2. Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, Trevor Mann "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a06_233.pub2
  3. Deimann, van Troostwyk, Bondt and Louwrenburgh (1795) "Ueber die Gasarten, welche man aus Verbindungen von starker Vitriolsäure und Alkohol erhält" (On the types of gases which one obtains from combinations of strong vitriolic acid and alcohol), Chemische Annalen … , 2 : 195-205, 310-316, 430-440. The production and characterization of 1,2-dichloroethane appear on pages 200-202. The investigators were trying to detect the presence of carbon (Kohl) in ethylene (Luft, literally, "air") by adding chlorine (zündend Salzgas, literally, "burning gas from salt"). Instead of the expected soot, an oil (Oehl) formed.
  4. J.A. Field & R. Sierra-Alvarez (2004). "Biodegradability of chlorinated solvents and related chlorinated aliphatic compounds". Rev. Environ. Sci. Biotechnol. 3 (3): 185–254. doi:10.1007/s11157-004-4733-8. 
  5. Seyferth, D. (2003). "The Rise and Fall of Tetraethyllead. 2". Organometallics 22 (25): 5154–5178. doi:10.1021/om030621b. 
  6. "1,2-Dichoroethane MSDS." Mallinckrodt Chemicals. 19 May 2008. Web. <http://hazard.com/msds/mf/baker/baker/files/d2440.htm>.
  7. S. De Wildeman & W. Verstraete (25 March 2003). "The quest for microbial reductive dechlorination of C2 to C4 chloroalkanes is warranted". Appl. Microbiol. Biotechnol. 61 (2): 94–102. PMID 12655450. doi:10.1007/s00253-002-1174-6. 
  8. Toxic Christmas: Plastic Ornaments May Pollute Your Air
  9. Doucette, WJ and Hall, AJ and Gorder, KA (Winter 2010). "Emissions of 1, 2-Dichloroethane from Holiday Decorations as a Source of Indoor Air Contamination". Ground Water Monitoring & Remediation 30 (1): 67–73. doi:10.1111/j.1745-6592.2009.01267.x. 

External links

Lua error in Module:Authority_control at line 346: attempt to index field 'wikibase' (a nil value).