1,1-dichloroethene
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | 1,1-dichloroethene | |||||||||||||||
other names |
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Molecular formula | C 2 H 2 Cl 2 | |||||||||||||||
Brief description |
colorless to yellowish flammable liquid with a sweetish odor |
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properties | ||||||||||||||||
Molar mass | 96.95 g mol −1 | |||||||||||||||
Physical state |
liquid |
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density |
1.25 g cm −3 |
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Melting point |
−122 ° C |
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boiling point |
32 ° C |
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Vapor pressure |
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solubility |
poor in water (3.4 g l −1 at 25 ° C) |
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Refractive index |
1.4249 (20 ° C) |
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safety instructions | ||||||||||||||||
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MAK |
DFG / Switzerland: 2 ml m −3 or 8 mg m −3 |
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Thermodynamic properties | ||||||||||||||||
ΔH f 0 |
−23.9 kJ / mol |
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C |
1,1-dichloroethene (also vinylidene chloride ) is an unsaturated halogenated hydrocarbon that does not occur in nature and is used as the starting material for the production of the plastic polyvinylidene chloride ( PVdC ).
presentation
The technical preparation is possible from the intermediate 1,1,1-trichloroethane (CCl 3 –CH 3 ) by splitting off hydrogen chloride with sodium hydroxide solution (NaOH) .
properties
Physical Properties
1,1-dichloroethene is a pungent, colorless liquid that is insoluble in water, readily soluble in ethanol , diethyl ether , acetone , benzene and chloroform . According to Antoine, the vapor pressure function results from log 10 (P) = A− (B / (T + C)) (P in kPa, T in K) with A = 4.10780, B = 1104.726 and C = −35.403 in the temperature range from 244.79 K to 305.6 K.
Safety-related parameters
1,1-dichloroethene forms highly flammable vapor-air mixtures. The compound has a flash point of −25 ° C. The explosion range is between 6.57% by volume (260 g / m 3 ) as the lower explosion limit (LEL) and 15% by volume (6005 g / m 3 ) as the upper explosion limit (UEL). The limit gap width was determined to be 3.91 mm. This results in an assignment to explosion group IIA. The ignition temperature is 530 ° C. The substance therefore falls into temperature class T1.
use
The main use is the polymerization to polyvinylidene chloride (PVdC), mostly as a copolymer with other monomers such as vinyl chloride or acrylonitrile . Brand names of the products are Diophan , Vertan , Diorit , Saran and Saranex . These thermoplastics are processed into foils, coatings or fibers for special fabrics, acid-resistant ropes and bristles. It is also used in semiconductor production for the production of high-purity silicon dioxide films.
Safety instructions / toxicity
1,1-dichloroethene has an effect on the central nervous system and causes symptoms such as tiredness, intoxication, convulsions and, in high concentrations, unconsciousness. The MAK value for vinylidene chloride is 8 mg m −3 .
The IARC classified 1,1-dichloroethene as a possible carcinogen in 2017.
literature
- Beyer, Walter: Textbook of the org. Chemistry . Hirzel Verlag Stuttgart, 23rd edition, p. 87.
See also
Individual evidence
- ↑ a b c d e f g h i j k l m n o Entry on 1,1-dichloroethene in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
- ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-154.
- ↑ Entry on 1,1-dichloroethylene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
- ↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 75-35-4 or 1,1-dichloroethene ), accessed on November 2, 2015.
- ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-21.
- ↑ Hildenbrand, DL; McDonald, RA; Kramer, WR; Stull, DR, Thermodynamic and spectroscopic study of vinylidene chloride. I. Thermodynamic properties of the solid, liquid, and ideal gas in J. Chem. Phys. 30 (1959) 930-934; doi: 10.1063 / 1.1730128 .
- ^ A b c d E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.
- ↑ Yann Grosse, Dana Loomis, Kathryn Z Guyton, Fatiha El Ghissassi, Véronique Bouvard, Lamia Benbrahim-Tallaa, Heidi Mattock, Kurt Straif: Some chemicals that cause tumors of the urinary tract in rodents. In: The Lancet Oncology . 18, 2017, pp. 1003-1004, doi : 10.1016 / S1470-2045 (17) 30505-3 .