1,2-dichloroethane

Structural formula
General
Surname	1,2-dichloroethane
other names	Ethylene dichloride; Ethylene chloride; EDC; R150;
Molecular formula	C 2 H 4 Cl 2
Brief description	colorless, oily liquid with a chloroform-like odor
External identifiers / databases
EC number	203-458-1
ECHA InfoCard	100.003.145
PubChem	11
ChemSpider	13837650
DrugBank	DB03733
Wikidata	Q161480
properties
Molar mass	98.97 g mol −1
Physical state	liquid
density	1.25 g cm −3
Melting point	−36 ° C
boiling point	84 ° C
Vapor pressure	86.9 h Pa (20 ° C); 139 hPa (30 ° C); 214 hPa (40 ° C); 319 hPa (50 ° C);
solubility	poor in water (8.7 g l −1 at 20 ° C)
Refractive index	1.4422 (25 ° C)
safety instructions
H and P phrases	H: 225-302-331-315-319-335-350
	P: 201-210-240-302 + 352-304 + 340-305 + 351 + 338-308 + 310
Authorization procedure under REACH	of particular concern : carcinogenic ( CMR ); subject to approval
MAK	DFG : canceled because it is carcinogenic ; Switzerland: 5 ml m −3 or 20 mg m −3 ;
Global warming potential	1 (based on 100 years)
Thermodynamic properties
ΔH f 0	−166.8 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

1,2-dichloroethane ( ethylene dichloride , EDC , formerly also chlorine ether ) is a colorless, flammable and poisonous liquid with a chloroform- like odor. This chemical compound is one of the chlorinated hydrocarbons .

history

1,2-Dichloroethane was first synthesized in 1794 by the four Dutch chemists Adriaan Paets van Troostwijk , Johan Rudolph Deiman , Nicolaas Bondt and Anthonie Lauwerenburgh by reacting ethene with chlorine ( oil from the Dutch chemists ).

Extraction and presentation

1,2-Dichloroethane is produced on an industrial scale by oxychlorination of ethene with hydrogen chloride and oxygen in the gas phase at temperatures of 200-360 ° C. and pressures of 1-9 bar. Copper (II) chloride is used as the catalyst , and iron (III) chloride is also used occasionally .

The catalyst support is arranged as a fixed or fluidized bed and can generally take place in any known type of reactor. Fluidized bed reactors are particularly preferred .

Another industrial process for the production of 1,2-dichloroethane is based on the direct chlorination of ethene . Metal halides such as iron (III) chloride are also used as a catalyst for this purpose.

properties

1,2-dichloroethane is a colorless, flammable liquid. The miscibility with water is very limited. As the temperature rises, the solubility of 1,2-dichloroethane in water increases or the solubility of water in 1,2-dichloroethane increases.

Solubilities between 1,2-dichloroethane and water
temperature	° C	0	9.3	19.7	29.7	39.4	50.3	61.0	70.6	80.7
1,2-dichloroethane in water	in%	0.82	0.77	0.72	0.81	0.98	1.06	1.08	1.13	1.06
Water in 1,2-dichloroethane	in%	0.106	0.133	0.176	0.230	0.276	0.349	0.412		0.492

Safety-related parameters

1,2-dichloroethane forms highly flammable vapor-air mixtures. The compound has a flash point of 13 ° C. The explosion range is between 4.2% by volume (174 g / m ³ ) as the lower explosion limit (LEL) and 16% by volume (660 g / m ³ ) as the upper explosion limit (UEL). Correlating the explosion limits with the vapor pressure function results in a lower explosion point of 8 ° C. The limit gap width was determined to be 1.8 mm. This results in an assignment to explosion group IIA. The ignition temperature is 440 ° C. The substance therefore falls into temperature class T2.

use

Dichloroethane is used to make vinyl chloride . It is converted to vinyl chloride and hydrogen chloride by thermal elimination . 1,1,1-Trichloroethane is also produced from 1,2-dichloroethane . It is a good solvent and extractant. The 1,2-dichloroethane is used in paint strippers , as so-called scavengers in leaded fuels, solvents for resins ( synthetic resin / natural resin ) and asphalt and in bitumen .

It is also used on an industrial scale for the production of ethylene amines, especially ethylene diamine , by ammonolysis :

Decomposition by bacteria

Researchers at Ghent University have succeeded in isolating a bacterial strain that can completely break down the carcinogenic and toxic 1,2-dichloroethane within a few days. The scientists decided to name the strain Desulfitobacterium dichloroeliminans .

safety instructions

1,2-Dichloroethane is irritating, narcotic, mutagenic, carcinogenic and leads to organ damage ( liver , kidneys , blood ). It can also increase premature and dead birth rates. It leads to poisoning if swallowed and is carcinogenic . 1,2-dichloroethane is highly flammable. Dangerous gases can be produced when burned. Reactions with alkali metals can cause explosions. 1,2-dichloroethane is very harmful to the environment and hazardous to water ( water hazard class 3).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s Entry on 1,2-dichloroethane in the GESTIS substance database of the IFA , accessed on January 8, 2020(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 1,2-dichloroethane 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 .
↑ Entry in the SVHC list of the European Chemicals Agency , accessed on July 17, 2014.
↑ Entry in the register of substances subject to authorization of the European Chemicals Agency , accessed on July 17, 2014.
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 107-06-2 or 1,2-dichloroethane ), accessed on September 14, 2019.
↑ G. Myhre, D. Shindell et al .: Climate Change 2013: The Physical Science Basis . Working Group I contribution to the IPCC Fifth Assessment Report. Ed .: Intergovernmental Panel on Climate Change . 2013, Chapter 8: Anthropogenic and Natural Radiative Forcing, pp. 24-39; Table 8.SM.16 ( PDF ).
↑ 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. 5-22.
↑ Entry on dichloroethane. In: Römpp Online . Georg Thieme Verlag, accessed on June 8, 2014.
↑ See also the term oil of the olefiant gas in Justus Liebig . See Albert Faulconer, Thomas Edward Keys: Chloroform. In: Foundations of Anesthesiology. 2 volumes, Charles C Thomas, Springfield (Illinois) 1965, Volume 1, pp. 442-481, here: p. 455.
^ ^A ^b Heiko Urtel, Henrik Junicke, Rupert Wagner, Volker Schuda: Process for the production of 1,2-dichloroethane. In: Google Patents. BASF SE, February 12, 2009, accessed March 14, 2019 .
^ ^A ^b R. M. Stephenson: Mutual Solubilities: Water-Ketones, Water-Ethers, and Water-Gasoline-Alcohols in J. Chem. Eng. Data 37 (1992) 80-95, doi : 10.1021 / je00005a024 .
^ ^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.
↑ Ann Maes, Hilde Van Raemdonck, Katherine Smith, Wendy Ossieur, Luc Lebbe, Willy Verstraete: Transport and Activity of Desulfitobacterium dichloroeliminans Strain DCA1 during Bioaugmentation of 1,2-DCA-Contaminated Groundwater. In: Environmental Science & Technology. 40, 2006, pp. 5544-5552, doi : 10.1021 / es060953i .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s Entry on 1,2-dichloroethane in the GESTIS substance database of the IFA , accessed on January 8, 2020(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_100.003.145-3] Entry on 1,2-dichloroethane 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 .

[SVHC-4] Entry in the SVHC list of the European Chemicals Agency , accessed on July 17, 2014.

[Zulassungspflicht-5] Entry in the register of substances subject to authorization of the European Chemicals Agency , accessed on July 17, 2014.

[6] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 107-06-2 or 1,2-dichloroethane ), accessed on September 14, 2019.

[7] G. Myhre, D. Shindell et al .: Climate Change 2013: The Physical Science Basis . Working Group I contribution to the IPCC Fifth Assessment Report. Ed .: Intergovernmental Panel on Climate Change . 2013, Chapter 8: Anthropogenic and Natural Radiative Forcing, pp. 24-39; Table 8.SM.16 ( PDF ).

[CRC90_5_22-8] 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. 5-22.

[9] Entry on dichloroethane. In: Römpp Online . Georg Thieme Verlag, accessed on June 8, 2014.

[10] See also the term oil of the olefiant gas in Justus Liebig . See Albert Faulconer, Thomas Edward Keys: Chloroform. In: Foundations of Anesthesiology. 2 volumes, Charles C Thomas, Springfield (Illinois) 1965, Volume 1, pp. 442-481, here: p. 455.

[:0-11] A ^b Heiko Urtel, Henrik Junicke, Rupert Wagner, Volker Schuda: Process for the production of 1,2-dichloroethane. In: Google Patents. BASF SE, February 12, 2009, accessed March 14, 2019 .

[Stephenson-12] A ^b R. M. Stephenson: Mutual Solubilities: Water-Ketones, Water-Ethers, and Water-Gasoline-Alcohols in J. Chem. Eng. Data 37 (1992) 80-95, doi : 10.1021 / je00005a024 .

[Brandes-13] 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.

[14] Ann Maes, Hilde Van Raemdonck, Katherine Smith, Wendy Ossieur, Luc Lebbe, Willy Verstraete: Transport and Activity of Desulfitobacterium dichloroeliminans Strain DCA1 during Bioaugmentation of 1,2-DCA-Contaminated Groundwater. In: Environmental Science & Technology. 40, 2006, pp. 5544-5552, doi : 10.1021 / es060953i .