1,1-Dichloroethylene

changed changed 477202178 1,1-Dichloroethylene 1,1-Dichloroethene.svg Structural formula 1,1-Dichloroethene-3D-balls.png Ball-and-stick model 1,1-Dichloroethene 1,1-Dichloroethylene1,1-DCEVinylidene chlorideVinylidene dichlorideAsymmetrical dichloroethene correct chemspider 6126 6366 changed EBI 34031 75-35-4 correct CAS correct FDA 21SK105J9D ClC(Cl)=C correct kegg C14039 changed chemspider 1S/C2H2Cl2/c1-2(3)4/h1H2 changed chemspider LGXVIGDEPROXKC-UHFFFAOYSA-N C2H2Cl2 96.94 g/mol 1.213 g/cm3 -122 32 1.3 D 2,240mg/L (25°C) 500 mmHg (20°C) −49.2·10−6 cm3/mol Planar C2v 2 4 2 -22.8 Ca [N.D.]0661 Ca none 6.5–15.5% 200 ppm (rat, 4.1 hr)98 ppm (mouse, 22–23 hr)1,000 ppm (rat, 2.4 hr)https://cfpub.epa.gov/ncea/iris/iris_documents/documents/toxreviews/0039tr.pdf https://web.archive.org/web/20161221084730/https://cfpub.epa.gov/ncea/iris/iris_documents/documents/toxreviews/0039tr.pdf dead December 21, 2016 United States Environmental Protection Agency June 2002 Washington, D.C. Toxicological Review of 1,1-Dichloroethylene 1500 mg/kg (rat)194 mg/kg (mouse) 1,1-Dichloroethylene, commonly called vinylidene chloride or 1,1-DCE, is an organochloride with the molecular formula CCl2CH2. 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. 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 is a base-catalyzed reaction which uses either NaOH or Ca(OH)2 with temperature ca. 100 °C.Course CEIC2004 Industrial Chemistry for Engineers. Chemistry Lecture Notes, UNSW Cl2CHCH2Cl + NaOH → Cl2C=CH2 + NaCl + H2O The gas phase reaction, without the base, would be more desirable but is less selective.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. 10.1002/14356007.a06_233.pub2. 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 polyvinylidene chloride As with many other alkenes or substituted 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. Accordingly, SC Johnson changed their formulation of Saran Wrap in 2004 to a form of polyethylene.Burke Michael 2015-04-25 CEO explains why SC Johnson hobbled Saran Wrap https://journaltimes.com/business/local/ceo-explains-why-sc-johnson-hobbled-saran-wrap/article_55000b9a-88cb-5786-a36e-3835f1d820ce.html 2024-09-18 Journal Times en Safety 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.epa.gov 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.CDC - NIOSH Pocket Guide to Chemical Hazards See also 1,2-Dichloroethene Dichloroethane References External links Agency for Toxic Substances and Disease Registry: 1,1-Dichloroethene Category:Chloroalkenes Category:Halogenated solvents Category:Vinylidene compounds Category:Haloethenes