Ethylbenzene

Structural formula
General
Surname	Ethylbenzene
other names	Ethylbenzene ( IUPAC ); Phenylethane;
Molecular formula	C 8 H 10
Brief description	colorless liquid
External identifiers / databases
EC number	202-849-4
ECHA InfoCard	100.002.591
PubChem	7500
Wikidata	Q409184
properties
Molar mass	106.17 g mol −1
Physical state	liquid
density	0.87 g cm −3
Melting point	−95 ° C
boiling point	136 ° C
Vapor pressure	9.79 hPa (20 ° C); 17.2 hPa (30 ° C); 29 hPa (40 ° C); 47.2 hPa (50 ° C);
solubility	heavy in water (170 mg l −1 at 25 ° C)
Refractive index	1.49594 (20 ° C)
safety instructions
H and P phrases	H: 225-304-332-373
	P: 210-260-301 + 310-331-370 + 378-403 + 235
MAK	DFG : 20 ml m −3 , 88 mg m −3 ; Switzerland: 50 ml m −3 , 220 mg m −3 ; Austria: 100 ml m −3 , 440 mg m −3 ;
Toxicological data	LD 50 oral rat: 3500 mg / kg; LD 50 dermal rabbit: 15400 mg / kg;
	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

Ethylbenzene ( ethylbenzene , phenylethane ) is a colorless liquid that smells like benzene . It is an aromatic hydrocarbon with the molecular formula C ₈ H ₁₀ .

presentation

Ethylbenzene is in the industry for a catalyst by alkylation of benzene produced with ethene, in this case there is the liquid-phase alkylation and vapor phase alkylation. Very little ethylbenzene is isolated from the C ₈ aromatic fraction by fine fractionation . This process is also called superfraction, but it is not competitive with alkylation.

In the laboratory, ethylbenzene can be produced from acetophenone by the Wolff-Kishner reaction .

properties

Ethylbenzene is a colorless, benzene- like smelling liquid with a melting point of −95 ° C and a boiling point of 136 ° C. At this temperature the heat of evaporation is 35.57 kJ / mol.

A.	B.	C.	T
Parameters for the Antoine equation (according to lg P = A − B / (T + C))
4.07488	1419.315	−60.539	329.74-410.27 K
4.40536	1695.026	−23.698	420-600 K

It is insoluble in water, but soluble in organic solvents.

metabolism

In the body, the ethyl residue in ethylbenzene is oxidized. Intermediate products in the metabolism are phenylacetic acid and 1-phenylethanol (methylphenylcarbinol), the end product is mandelic acid , which is sufficiently water-soluble to be excreted in the urine.

Safety-related parameters

Ethylbenzene is considered a flammable liquid. Flammable vapor-air mixtures can form above the flash point. The compound has a flash point at 23 ° C. The explosion range is between 1% by volume (43 g / m ³ ) as the lower explosion limit (LEL) and 7.8% by volume (340 g / m ³ ) as the upper explosion limit (UEL). The ignition temperature is 430 ° C. The substance therefore falls into temperature class T2. It is classified as harmful to health.

use

Ethylbenzene is added to gasoline to increase the octane number (knock resistance). It is a solvent for paints and is found in plastics. It is an important starting material for the synthesis of styrene . In addition to benzene and toluene, ethylbenzene is one of the technically important aromatics, the so-called BTEX aromatics.

literature

Ethylbenzene (published by the Advisory Committee for Environmentally Relevant Existing Substances (BUA) of the German Chemical Society), S. Hirzel Verlag GmbH & Co, 1996, ISBN 3-7776-0722-3 .

Jochen Ackermann: Reaction engineering studies on the synthesis of ethylbenzene from 1,3-butadiene using basic solid catalysts . Shaker Verlag GmbH (2001), ISBN 3-8265-9254-9 .

Albrecht Xahil Tribukait: Investigation of the influence of the angular momentum on the dissociation speed of toluene and ethylbenzene . Cuvillier (1999), ISBN 3-89712-536-6 .

Web links

Commons : Ethylbenzene - Collection of pictures, videos and audio files

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on ethylbenzene in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
↑ Entry on Ethylbenzene 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 100-41-4 or ethylbenzene ), accessed on November 2, 2015.
↑ Limit values for working materials ( Memento from 23 September 2015 in the Internet Archive ) Ordinance of the Federal Minister for Labor, Social Affairs and Consumer Protection ( Limit Values Ordinance GKV 2011), Austria.
^ Association of authors: Organikum , 19th edition, Johann Ambrosius Barth, Leipzig · Berlin · Heidelberg 1993, ISBN 3-335-00343-8 , pp. 456–458.
^ V. Majer, V. Svoboda: Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation , Blackwell Scientific Publications, Oxford, 1985, p. 300.
↑ CB Williamham, WJ Taylor, JM Pignocco, FD Rossini: Vapor Pressures and Boiling Points of Some Paraffin, Alkylcyclopentane, Alkylcyclohexane, and Alkylbenzene Hydrocarbons , in: J. Res. Natl. Bur. Stand. (US) , 1945 , 35 , pp. 219-244.
↑ D. Ambrose, BE Broderick, R. Townsend: The Vapor Pressures Above the Normal Boiling Point and the Critical Pressures of Some Aromatic Hydrocarbons , in: J. Chem. Soc. A , 1967 , pp. 633-641; doi: 10.1039 / J19670000633 .
^ ^A ^b ^c E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on ethylbenzene in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[CRC-2] CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .

[CLP_100.002.591-3] Entry on Ethylbenzene 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 100-41-4 or ethylbenzene ), accessed on November 2, 2015.

[5] Limit values for working materials ( Memento from 23 September 2015 in the Internet Archive ) Ordinance of the Federal Minister for Labor, Social Affairs and Consumer Protection ( Limit Values Ordinance GKV 2011), Austria.

[Organikum-6] Association of authors: Organikum , 19th edition, Johann Ambrosius Barth, Leipzig · Berlin · Heidelberg 1993, ISBN 3-335-00343-8 , pp. 456–458.

[7] V. Majer, V. Svoboda: Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation , Blackwell Scientific Publications, Oxford, 1985, p. 300.

[8] CB Williamham, WJ Taylor, JM Pignocco, FD Rossini: Vapor Pressures and Boiling Points of Some Paraffin, Alkylcyclopentane, Alkylcyclohexane, and Alkylbenzene Hydrocarbons , in: J. Res. Natl. Bur. Stand. (US) , 1945 , 35 , pp. 219-244.

[9] D. Ambrose, BE Broderick, R. Townsend: The Vapor Pressures Above the Normal Boiling Point and the Critical Pressures of Some Aromatic Hydrocarbons , in: J. Chem. Soc. A , 1967 , pp. 633-641; doi: 10.1039 / J19670000633 .

[Sicherheitstechnische_Kenngrößen-10] A ^b ^c E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.