1,2-dibromoethane

Structural formula
General
Surname	1,2-dibromoethane
other names	Ethylene dibromide; EDB;
Molecular formula	C 2 H 4 Br 2
Brief description	colorless liquid with a sweet odor
External identifiers / databases
EC number	203-444-5
ECHA InfoCard	100.003.132
PubChem	7839
Wikidata	Q161471
properties
Molar mass	187.86 g mol −1
Physical state	liquid
density	2.18 g cm −3
Melting point	10 ° C
boiling point	131 ° C
Vapor pressure	1.13 k Pa (20 ° C); 15.98 kPa (75 ° C); 38.03 kPa (100 ° C);
solubility	heavy in water (4.04 g l −1 at 20 ° C); soluble in diethyl ether and ethanol ;
Refractive index	1.539 (20 ° C)
safety instructions
H and P phrases	H: 301 + 311 + 331-315-319-335-350-411
	P: 201-273-280-302 + 352-304 + 340-305 + 351 + 338-308 + 310
MAK	Switzerland: 0.1 ml m −3 or 0.8 mg m −3
Toxicological data	108 mg kg −1 ( LD 50 , rat , oral ) ; 300 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
Thermodynamic properties
ΔH f 0	−79.2 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-Dibromoethane ( IUPAC ) is a colorless, poisonous liquid that smells similar to chloroform and is mainly used as a solvent , for container fumigation and as an intermediate synthesis product.

Extraction and presentation

1,2-Dibromoethane can be produced by the direct bromination of ethene (i.e. by a classic halogen addition reaction ) or by the reaction of hydrobromic acid with ethyne .

{\ displaystyle \ mathrm {CH_ {2} {=} CH_ {2} + Br_ {2} \ longrightarrow BrCH_ {2} CH_ {2} Br}}

properties

Dibromoethane is a non-flammable, colorless to yellowish liquid with a sweetish, chloroform-like odor. The compound boils at 131 ° C. under normal pressure. The enthalpy of vaporization here is 41.78 kJ mol ⁻¹ . According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in bar, T in K) with A = 7.36914, B = 4101.146 and C = 153.034 im Temperature range from 246 K to 405 K. Vapors from dibromoethane are 6.5 times as heavy as air. Two polymorphic crystal forms can exist in the solid phase . The transition point from low-temperature form II to high-temperature form I is −23 ° C. The enthalpy of transformation of this solid-phase transition is 1.94 kJ mol ⁻¹ . Both forms are enantiotropic to one another. The crystal form I shows a melting point at 10 ° C with a melting enthalpy of 10.94 kJ · mol ⁻¹ . The triple point is 10 ° C. and 9.2 mbar Dibromoethane decomposes slowly in sunlight, otherwise the connection is stable.

use

The use of 1,2-dibromoethane as an additive in leaded fuel as a radical scavenger to avoid lead residues in the engine, which was still common in the 1980s, was discontinued in industrialized countries due to its toxicity. Its use as an insect fumigant was also banned in the 1980s. In organic chemistry, it is used as a starting material for the production of drugs (e.g. tetramisole and theodrenaline ), herbicides (e.g. diquatdibromide ) and dyes where an ethylene bridge is to be introduced into a molecule.

safety instructions

1,2-Dibromoethane causes severe skin and mucous membrane irritation and is absorbed through the skin. It causes headaches, vomiting, urinary poisoning, liver and kidney damage. In addition, it is a carcinogen in animal experiments that poses a risk to be considered for humans and has been assigned to MAK group III A 2.

Web links

Environmental Health Criteria (EHC) for 1,2-dibomoethame

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 1,2-dibromoethane in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f ^g D. Yoffe, R. Frim, SD Ukeles, MJ Dagani, HJ Barda, TJ Benya, DC Sanders: Bromine Compounds. In: Ullmann's Encyclopedia of Technical Chemistry . Wiley-VCH, Weinheim 2013, doi : 10.1002 / 14356007.a04_405.pub2 .
↑ ^a ^b ^c ^d Entry on 1,2-dibromoethane. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
↑ Data sheet 1,2-dibromoethane from Sigma-Aldrich , accessed on March 5, 2011 ( PDF ).
↑ Entry on 1,2-dibromoethane 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): Limits - Current MAK and BAT values (search for 106-93-4 or 1,2-dibromoethane ), 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. 5-22.
↑ V. Svoboda, V. Kubes, P. Basarova: Enthalpies of vaporization and cohesive energies of 1,1,2,2-tetrachloro-1,2-difluoroethane, 1,2-dibromoethane, 1-bromo-2-chloroethane, 1,3-dibromo-propane, and 1,4-dibromo-2,3-dichloro-1,1,2,3,4,4-hexafluorobutane. In: J. Chem. Thermodyn. 24, 1992, pp. 555-558. doi: 10.1016 / S0021-9614 (05) 80125-9
^ DR Stull: Vapor Pressure of Pure Substances Organic Compounds. In: Ind. Eng. Chem. 39, 1947, pp. 517-540, doi: 10.1021 / ie50448a022 .
^ WE Railing: The specific heat of some ethylene halides. In: J. Am. Chem. Soc. 61, 1939, pp. 3349-3353. doi: 10.1021 / ja01267a034
↑ ^a ^b ^c ^d K. S. Pitzer: The heat capacities, heats of transition and fusion, and entropies of ethylene dichloride and ethylene dibromide. In: J. Am. Chem. Soc. 62, 1940, pp. 331-335. doi: 10.1021 / ja01859a028
↑ calculated from the vapor pressure function

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on 1,2-dibromoethane in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[Ullmann-2] ↑ ^a ^b ^c ^d ^e ^f ^g D. Yoffe, R. Frim, SD Ukeles, MJ Dagani, HJ Barda, TJ Benya, DC Sanders: Bromine Compounds. In: Ullmann's Encyclopedia of Technical Chemistry . Wiley-VCH, Weinheim 2013, doi : 10.1002 / 14356007.a04_405.pub2 .

[Römpp-3] Entry on 1,2-dibromoethane. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.

[Sigma-4] Data sheet 1,2-dibromoethane from Sigma-Aldrich , accessed on March 5, 2011 ( PDF ).

[CLP_100.003.132-5] Entry on 1,2-dibromoethane 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 .

[6] Swiss Accident Insurance Fund (Suva): Limits - Current MAK and BAT values (search for 106-93-4 or 1,2-dibromoethane ), accessed on November 2, 2015.

[CRC90_5_22-7] 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.

[8] V. Svoboda, V. Kubes, P. Basarova: Enthalpies of vaporization and cohesive energies of 1,1,2,2-tetrachloro-1,2-difluoroethane, 1,2-dibromoethane, 1-bromo-2-chloroethane, 1,3-dibromo-propane, and 1,4-dibromo-2,3-dichloro-1,1,2,3,4,4-hexafluorobutane. In: J. Chem. Thermodyn. 24, 1992, pp. 555-558. doi: 10.1016 / S0021-9614 (05) 80125-9

[9] DR Stull: Vapor Pressure of Pure Substances Organic Compounds. In: Ind. Eng. Chem. 39, 1947, pp. 517-540, doi: 10.1021 / ie50448a022 .

[Railing-10] WE Railing: The specific heat of some ethylene halides. In: J. Am. Chem. Soc. 61, 1939, pp. 3349-3353. doi: 10.1021 / ja01267a034

[Pitzer-11] K. S. Pitzer: The heat capacities, heats of transition and fusion, and entropies of ethylene dichloride and ethylene dibromide. In: J. Am. Chem. Soc. 62, 1940, pp. 331-335. doi: 10.1021 / ja01859a028

[12] ulated from the vapor pressure function