1,1-Dichloroethylene, commonly called vinylidene chloride or 1,1-DCE, is an organochloride with the molecular formula . 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 clingwrap, Saran, for food, but this application has been phased out.
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 is a base-catalyzed reaction which uses either NaOH or Ca(OH) with temperature ca. 100 °C.[1]
ClCHCHCl + NaOH → ClC=CH + NaCl + HOThe gas phase reaction, without the base, would be more desirable but is less selective.[2]
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 (SiO) films.
See main article: 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.
The health effects from exposure to vinylidene chloride are primarily on the central nervous system, including symptoms of sedation, inebriation, convulsions, spasms, and unconsciousness at high concentrations.[3]
International Agency for Research on Cancer has put vinylidene chloride in Class 2B, meaning possibly carcinogenic to humans. National Institute for Occupational Safety and Health considers vinylidene chloride a potential occupational carcinogen.[4]