2-ethylhexanal

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	2-ethylhexanal
other names	2-ethylcaproaldehyde; 2-ethylhexaldehyde; Butylethyl acetaldehyde; Ethyl butyl acetaldehyde; ETHYLHEXANAL ( INCI ) ;
Molecular formula	C 8 H 16 O
Brief description	flammable, yellow liquid with a sharp, strong odor
External identifiers / databases
EC number	204-596-5
ECHA InfoCard	100.004.179
PubChem	31241
Wikidata	Q209379
properties
Molar mass	128.21 g mol −1
Physical state	liquid
density	0.82 g cm −3 (20 ° C)
boiling point	163 ° C
Vapor pressure	2.4 hPa (20 ° C)
solubility	very heavy in water (0.75 g l −1 at 25 ° C); soluble in diethyl ether , ethanol and slightly soluble in carbon tetrachloride ;
Refractive index	1.415 (20 ° C)
safety instructions
H and P phrases	H: 226-317-361
	P: 210-280-201-303 + 361 + 353-308 + 313
Toxicological data	> 2000 mg kg −1 ( LD 50 , rat , oral )
	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-Ethylhexanal is a chemical compound from the group of aldehydes and is an isomer of octanal .

Extraction and presentation

2-Ethylhexanal can be obtained from butanal by a base-catalyzed aldol reaction and subsequent hydrogenation . More than 1000 tons were produced in 1988.

It can also be prepared directly from propylene by hydroformylation and subsequent aldol reaction in a one-pot reaction .

It can also be prepared from 2-ethylhexenal , which in turn is produced by condensation of butanal using aqueous sodium hydroxide solution .

properties

2-Ethylhexanal is a clear, flammable, yellow liquid with a sharp, strong odor. It is weakly acidic in water. The dynamic viscosity of the liquid is 0.9 mPa · s at 20 ° C.

use

In combination with other substances, 2-ethylhexanal is used as a surface disinfectant , solvent and as an intermediate product for the production of 2-ethylhexanol , 2-ethylhexanoic acid and 2-ethylhexylamine , as well as for the production of pharmaceuticals and fragrances. Condensation products of the compound are used as vulcanizing agents and antioxidants in the rubber industry.

The amination of 2-ethylhexanal by reaction with hydroxylamine hydrochloride to form the oxime and subsequent reduction with zinc / hydrochloric acid is a simple one-pot method for the preparation of racemic 2-ethylhexylamine .

safety instructions

The vapors of 2-ethylhexanal can form an explosive mixture with air ( flash point 42 ° C).

Web links

Entry for 2-ethylhexanal . In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD
Entry on 2-ethylhexanal in the Spectral Database for Organic Compounds (SDBS) of the National Institute of Advanced Industrial Science and Technology (AIST)

Individual evidence

↑ entry to ethylhexanal in CosIng database of the European Commission, accessed on 11 March 2020th
↑ ^a ^b ^c ^d ^e ^f ^g Entry on 2-ethylhexanal in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ ^a ^b ^c ^d Toxicological assessment of 2-ethylhexanal (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.
↑ 2-Ethylhexanal data sheet from Sigma-Aldrich , accessed on April 22, 2017 ( PDF ).

↑ Sumeet K Sharma, Raksh V Jasra: Synthesis of 2-Ethylhexanal from Propylene in a Single Pot Using an Ecofriendly Multifunctional Catalyst Synthesized by Intercalation of HRhCO (TPPTS) ₃ Complex in the Interlayer Space of Hydrotalcite , Ind. Eng. Chem. Res. , 2011, 50 (5), pp. 2815-2821; doi: 10.1021 / ie1015365 .

↑ Process for the production of 2-ethylhexenal (patent-de).

↑ ^a ^b data sheet 2-ethylhexanal (PDF; 166 kB) at gischem.

↑ MA Ayedi, Y. Le Bigot, H. Ammar, S. Abid, R. El Gharbi, M. Delmas: Synthesis of Primary Amines by One-Pot Reductive amination of aldehyde . In: Synth. Commun. tape 43 , no. 16 , 2013, p. 2127-2133 , doi : 10.1080 / 00397911.2012.714830 .

[CosIng-1] try to ethylhexanal in CosIng database of the European Commission, accessed on 11 March 2020th

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on 2-ethylhexanal in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[bg-3] Toxicological assessment of 2-ethylhexanal (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.

[Sigma-4] 2-Ethylhexanal data sheet from Sigma-Aldrich , accessed on April 22, 2017 ( PDF ).

[5] Sumeet K Sharma, Raksh V Jasra: Synthesis of 2-Ethylhexanal from Propylene in a Single Pot Using an Ecofriendly Multifunctional Catalyst Synthesized by Intercalation of HRhCO (TPPTS) ₃ Complex in the Interlayer Space of Hydrotalcite , Ind. Eng. Chem. Res. , 2011, 50 (5), pp. 2815-2821; doi: 10.1021 / ie1015365 .

[6] Process for the production of 2-ethylhexenal (patent-de).

[gis-7] ta sheet 2-ethylhexanal (PDF; 166 kB) at gischem.

[8] MA Ayedi, Y. Le Bigot, H. Ammar, S. Abid, R. El Gharbi, M. Delmas: Synthesis of Primary Amines by One-Pot Reductive amination of aldehyde . In: Synth. Commun. tape 43 , no. 16 , 2013, p. 2127-2133 , doi : 10.1080 / 00397911.2012.714830 .