1,1-dichloroethene

Structural formula
General
Surname	1,1-dichloroethene
other names	Vinylidene dichloride; Vinylidene chloride; 1,1-dichloroethylene;
Molecular formula	C 2 H 2 Cl 2
Brief description	colorless to yellowish flammable liquid with a sweetish odor
External identifiers / databases
EC number	200-864-0
ECHA InfoCard	100,000,786
PubChem	6366
Wikidata	Q161284
properties
Molar mass	96.95 g mol −1
Physical state	liquid
density	1.25 g cm −3
Melting point	−122 ° C
boiling point	32 ° C
Vapor pressure	660 h Pa (20 ° C); 954 hPa (30 ° C);
solubility	poor in water (3.4 g l −1 at 25 ° C)
Refractive index	1.4249 (20 ° C)
safety instructions
H and P phrases	H: 224-301-332-315-319-351
	P: 210-281-301 + 310-305 + 351 + 338
MAK	DFG / Switzerland: 2 ml m −3 or 8 mg m −3
Thermodynamic properties
ΔH f 0	−23.9 kJ / mol
	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.

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 .

[GESTIS-1] ↑ ^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) .

[CRC90_3_154-2] 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.

[CLP_100.000.786-3] 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 .

[4] 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.

[CRC90_5_21-5] 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.

[6] 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 .

[Brandes-7] 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.

[8] 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 .