2-ethyl-1-butanol

Structural formula
General
Surname	2-ethyl-1-butanol
other names	2-ethylbutan-1-ol ( IUPAC ); 2-ethylbutyl alcohol; 2,2-diethylethanol; 3- (hydroxymethyl) pentane;
Molecular formula	C 6 H 14 O
Brief description	colorless liquid with a pleasant alcohol-like odor
External identifiers / databases
EC number	202-621-4
ECHA InfoCard	100.002.384
PubChem	7358
ChemSpider	7080
Wikidata	Q4596882
properties
Molar mass	102.18 g mol −1
Physical state	liquid
density	0.83 g cm −3 (20 ° C)
Melting point	−52 ° C
boiling point	149 ° C
Vapor pressure	1.20 h Pa (20 ° C); 14.2 hPa (50 ° C);
solubility	slightly soluble in water (10 g l −1 at 20 ° C); Miscible with most organic solvents;
Refractive index	1.4224 (20 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 226-302 + 312
	P: 280
Toxicological data	1850 mg kg −1 ( LD 50 , rat , oral ) ; 1050 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	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

2-Ethyl-1-butanol (2-EB for short) is a fully synthetic, branched primary alcohol with an alcohol-like odor. It is important as a solvent , and some of it is chemically processed.

Extraction and presentation

The industrial production of 2-ethyl-1-butanol takes place by an aldol condensation of butyraldehyde with acetaldehyde , which are first converted to 2-ethylbut-2-en-1-al. After its catalytic hydrogenation , 2-ethyl-1-butanol is obtained. N- hexanol , n- butanol and 2-ethylhexanol are also produced as by-products .

The aldol condensation can take place either with base or acid catalysis . Frequently, however, alkali hydroxides such as sodium or potassium hydroxide are used .

properties

Physical Properties

2-Ethylbutan-1-ol has a relative gas density of 3.52 (density ratio to dry air at the same temperature and pressure ) and a relative density of the steam-air mixture of 1.01 (density ratio to dry air at 20 ° C and normal pressure ). In addition, 2-ethyl-1-butanol has a vapor pressure of 1.20 hPa at 20 ° C and 14.2 hPa at 50 ° C.

Chemical properties

2-Ethylbutan-1-ol is a flammable liquid belonging to the group of alcohols . It is sparingly soluble in water (10 g / l at 20 ° C) and lighter than water. 2-Ethybutanol is difficult or very difficult to volatilize.

use

2-Ethylbutan-1-ol is widely used in the chemical industry . It is mainly used as a solvent for oils , resins , waxes , fats and dyes . It is also used for the synthesis of esters, which in turn are used as plasticizers for plastics [e.g. B. bis (2-ethylbutyl) phthalate] as well as fragrances and aromatic substances (e.g. 2-ethylbutyl acetate ) can be used.

safety instructions

The vapors of 2-ethylbutan-1-ol can form explosive mixtures with air when heated above the flash point. 2-Ethylbutan-1-ol is mainly absorbed through the airways and the skin . Ingestion or ingestion can cause severe irritation to the respiratory tract, skin and eyes . There is also the risk of a disruption of the central nervous system (narcotic effect). After long exposure , those affected showed symptoms such as tears and burning of the eyes, the nasal and pharynx mucous membranes, as well as cough , nausea , headache, dizziness , muscle weakness , shortness of breath and possibly unconsciousness . 2-Ethyl-1-butanol has a lower explosion limit (LEL) of approx. 1.08% by volume (approx. 46 g / cm ³ ) and an upper explosion limit (UEL) of approx. 7.0% by volume (approx. 298 g / cm ³ ). The ignition temperature is 315 ° C. The substance therefore falls into temperature class T2 and explosion group IIA. With a flash point of 58 ° C, 2-ethylbutan-1-ol is considered to be relatively flame-retardant.

Web links

Commons : 2-Ethyl-1-butanol - Collection of pictures, videos, and audio files

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on 2-ethylbutanol in the GESTIS substance database of the IFA , accessed on January 14, 2020(JavaScript required) .
↑ ^a ^b ^c Entry on 2-Ethylbutan-1-ol. In: Römpp Online . Georg Thieme Verlag, accessed on November 20, 2018.
↑ Jürgen Falbe, Helmut Bahrmann, Wolfgang Lipps, Dieter Mayer, Guido D. Frey: Alcohols, Aliphatic. In: Ullmann's Encyclopedia of Industrial Chemistry . Wiley ‐ VCH Verlag GmbH & Co. KGaA., January 15, 2013, p. 2, doi : 10.1002 / 14356007.a01_279.pub2 .
↑ Entry on 2-ethylbutanol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 24, 2018. Manufacturers or distributors can expand the harmonized classification and labeling .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on 2-ethylbutanol in the GESTIS substance database of the IFA , accessed on January 14, 2020(JavaScript required) .

[RÖMPP-2] Entry on 2-Ethylbutan-1-ol. In: Römpp Online . Georg Thieme Verlag, accessed on November 20, 2018.

[ULLMANN-3] Jürgen Falbe, Helmut Bahrmann, Wolfgang Lipps, Dieter Mayer, Guido D. Frey: Alcohols, Aliphatic. In: Ullmann's Encyclopedia of Industrial Chemistry . Wiley ‐ VCH Verlag GmbH & Co. KGaA., January 15, 2013, p. 2, doi : 10.1002 / 14356007.a01_279.pub2 .

[CLP_100.002.384-4] Entry on 2-ethylbutanol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on November 24, 2018. Manufacturers or distributors can expand the harmonized classification and labeling .