2,6-diethylaniline

Structural formula
General
Surname	2,6-diethylaniline
other names	2-amino-1,3-diethylbenzene
Molecular formula	C 10 H 15 N
Brief description	light- and air-sensitive colorless to yellowish liquid
External identifiers / databases
EC number	209-445-7
ECHA InfoCard	100.008.588
PubChem	11369
ChemSpider	21106539
Wikidata	Q209276
properties
Molar mass	149.24 g mol −1
Physical state	liquid
density	0.96 g cm −3
Melting point	3 ° C
boiling point	243 ° C
Vapor pressure	0.03 hPa (20 ° C)
solubility	slightly soluble in water (0.67 g l −1 at 27 ° C); miscible with isooctane, toluene and ethyl alcohol;
Refractive index	1.545 (20 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 302
	P: 301 + 312
Toxicological data	1800 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

2,6-Diethylaniline is a chemical compound from the group of aromatic amino compounds ( amino group on the ring), more precisely the diethylanilines .

Extraction and presentation

2,6-Diethylaniline can be produced by Friedel-Crafts alkylation of aniline with ethene in the presence of aluminum chloride or mercury chloride.

properties

2,6-Diethylaniline is a colorless liquid (as a technical product, dark red liquid), which turns yellow when exposed to light and air. When heated, it decomposes, producing nitrogen oxides , carbon monoxide and carbon dioxide . The hydrochloride of the compound , which is insoluble in water, is formed with hydrogen chloride . The vapor pressure function results according to August according to ln (P) = A− (B / T) (P in Pa, T in K) with A = 27.83 and B = 7869 in the temperature range from 10 to 55 ° C. The enthalpy of vaporization at 25 ° C is 65.89 kJ mol ⁻¹ , the heat capacity c _p 305.942 J K ⁻¹ mol ⁻¹ . The compound forms inflammable vapor-air mixtures at high temperatures. The compound has a flash point of 109 ° C. The ignition temperature is 460 ° C. The substance therefore falls into temperature class T1.

use

2,6-Diethylaniline is used as an intermediate in the manufacture of crop protection products (such as alachlor , butachlor , diafenthiuron ) and other derived chemical compounds. It also reappears as a metabolite of these compounds.

Web links

PMG Bavin, JMW Scott: SOME CHEMISTRY OF 2,6-DIETHYLANILINE . In: Canadian Journal of Chemistry . 36 (9), 1958, pp. 1284-1288, doi : 10.1139 / v58-188 .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on 2,6-diethylaniline in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ ^a ^b ^c data sheet 2,6-diethylaniline from Sigma-Aldrich , accessed on February 9, 2010 ( PDF ).
↑ ^a ^b ( page no longer available , search in web archives: DEA (Albermarle) )@1@ 2Template: dead link / albemarle.in
↑ Entry on 2,6-diethylaniline 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 .
↑ Data sheet 2,6-diethylaniline from AlfaAesar, accessed on February 5, 2010 ( PDF )(JavaScript required) . .
↑ Patent DE951501 : Process for the production of ring-alkylated aromatic amines. Registered on December 25, 1953 , published on October 31, 1956 , applicant: Bayer AG, inventor: Rudolf Stroh, Josef Ebersberger, Hans Haberland. ‌
^ R. Stroh, J. Ebersberger, H. Haberland, W. Hahn: Newer methods of preparative organic chemistry II. 7. Alkylation of aromatic amines. In: Angew. Chem. 69, 1957, pp. 124-131, doi: 10.1002 / anie.19570690403 .
↑ ^a ^b S. P. Verevkin: thermochemical study of the ortho interactions in alkyl substituiertem anilines. In: J. Chem. Thermodyn. 32, 2000, pp. 247-259, doi: 10.1006 / jcht.1999.0587 .
↑ ^a ^b E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on 2,6-diethylaniline in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[sigma-2] ta sheet 2,6-diethylaniline from Sigma-Aldrich , accessed on February 9, 2010 ( PDF ).

[albe-3] ( page no longer available , search in web archives: DEA (Albermarle) )@1@ 2Template: dead link / albemarle.in

[CLP_100.008.588-4] Entry on 2,6-diethylaniline 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 .

[5] Data sheet 2,6-diethylaniline from AlfaAesar, accessed on February 5, 2010 ( PDF )(JavaScript required) . .

[6] Patent DE951501 : Process for the production of ring-alkylated aromatic amines. Registered on December 25, 1953 , published on October 31, 1956 , applicant: Bayer AG, inventor: Rudolf Stroh, Josef Ebersberger, Hans Haberland. ‌

[7] R. Stroh, J. Ebersberger, H. Haberland, W. Hahn: Newer methods of preparative organic chemistry II. 7. Alkylation of aromatic amines. In: Angew. Chem. 69, 1957, pp. 124-131, doi: 10.1002 / anie.19570690403 .

[Verevkin-8] S. P. Verevkin: thermochemical study of the ortho interactions in alkyl substituiertem anilines. In: J. Chem. Thermodyn. 32, 2000, pp. 247-259, doi: 10.1006 / jcht.1999.0587 .

[Brandes-9] E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.