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1,1-Dichloroethene

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Title: 1,1-Dichloroethene  
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1,1-Dichloroethene

1,1-Dichloroethene
Structural formula Ball-and-stick model
Identifiers
CAS number  YesY
PubChem
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEBI  N
Jmol-3D images Image 1
Properties
Molecular formula C2H2Cl2
Molar mass 96.94 g/mol
Density 1.213 g/cm3
Melting point −122 °C (−188 °F; 151 K)
Boiling point 32 °C (90 °F; 305 K)
Dipole moment 1.3 D
Hazards
NFPA 704
4
2
2
Flash point −22.8 °C (−9.0 °F; 250.4 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/N?)

1,1-Dichloroethene, commonly called 1,1-dichloroethylene or 1,1-DCE, is an organochloride with the molecular formula C2H2Cl2. It is a colorless liquid with a sharp odor. Like most chlorocarbons, it is poorly soluble in water, but soluble in organic solvents. 1,1-DCE was the precursor to the original cling-wrap for food, but this application has been phased out.

Contents

  • Production 1
  • Applications 2
    • Polyvinylidene chloride 2.1
  • Safety 3
  • See also 4
  • References 5
  • External links 6

Production

1,1-DCE is produced by dehydrochlorination of 1,1,2-trichloroethane, a relatively unwanted byproduct in the production of 1,1,1-trichloroethane and 1,2-dichloroethane. The conversion involves a base-catalyzed reaction:

Cl2CHCH2Cl + NaOH → Cl2C=CH2 + NaCl + H2O

The gas phase reaction, without the base, would be more desirable but is less selective.[1]

Applications

1,1-DCE is mainly used as a comonomer in the polymerization of vinyl chloride, acrylonitrile, and acrylates. It is also used in semiconductor device fabrication for growing high purity silicon dioxide (SiO2) films.

Polyvinylidene chloride

As with many other alkenes, 1,1-DCE can be polymerised to form polyvinylidene chloride. A very widely used product, cling wrap, or Saran was made from this polymer. During the 1990s research suggested that, in common with many chlorinated carbon compounds, Saran posed a possible danger to health by leaching, especially on exposure to food in microwave ovens. Since 2004, therefore cling wrap's formulation has changed to a form of polyethylene.

Safety

The health effects from exposure to 1,1-DCE are primarily on the central nervous system, including symptoms of sedation, inebriation, convulsions, spasms, and unconsciousness at high concentrations.[2] 1,1-DCE is considered a potential occupational carcinogen by the National Institute for Occupational Safety and Health .[3]

See also

References

  1. ^ 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.
  2. ^ epa.gov
  3. ^ CDC - NIOSH Pocket Guide to Chemical Hazards

External links

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