Diethylenetriamine

Structural formula
General
Surname	Diethylenetriamine
other names	3-azapentane-1,5-diamine; DETA; Ethylene triamine; Bis (2-aminoethyl) amine; 2,2'-diaminodiethylamine; 2,2'-iminodi (ethylamine); Aminoethylethanediamine; N - (2-aminoethyl-1,2-ethanediamine); 1,4,7-triazaheptanes;
Molecular formula	C 4 H 13 N 3
Brief description	hygroscopic, hardly inflammable, yellowish liquid with an ammonia-like odor
External identifiers / databases
EC number	203-865-4
ECHA InfoCard	100.003.515
PubChem	8111
Wikidata	Q416728
properties
Molar mass	103.17 g · mol -1
Physical state	liquid
density	0.96 g cm −3
Melting point	−39 ° C
boiling point	207 ° C
Vapor pressure	27.2 mbar (100 ° C)
solubility	miscible with water
Refractive index	1.481
safety instructions
H and P phrases	H: 330-302-312-314-317-335
	P: 260-280-304 + 340-305 + 351 + 338-310-403 + 233
MAK	Switzerland: 1 ml m −3 or 4 mg m −3
Toxicological data	1140 mg kg −1 ( LD 50 , rat , oral ) ; 1090 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

Diethylenetriamine ( DETA for short ) is a chemical compound from the group of aliphatic amines . This polyamine is in the form of a yellowish (colorless in its pure state) liquid with an ammonia-like odor.

Extraction and presentation

Diethylenetriamine is produced on an industrial scale. In the picture a tank container with DETA on a freight wagon .

Diethylenetriamine can be produced in various ways, for example by adding ammonia to ethene or by reacting dichloroethane with ammonia and then neutralizing it with sodium hydroxide .

Around 25,000 to 30,000 t are produced in Europe every year. This makes it one of the chemical substances that are produced in large quantities (" High Production Volume Chemical ", HPVC) and for which the Organization for Economic Cooperation and Development (OECD) collects data on possible dangers (" Screening Information Dataset ", SIDS).

properties

Chemically, diethylenetriamine is an analogue of diethyleneglycol . The aqueous solution of diethylenetriamine has a strongly alkaline reaction . Diethylenetriamine has a dielectric constant of 12.0 (at 25 ° C and 1 kHz) and an expansion coefficient of 0.00106 1 / ° C (at 20 ° C).

use

In complex chemistry, diethylenetriamine is an important chelating ligand . DTPA (diethylenetriaminepentaacetic acid) is formed by reaction with five moles of bromoacetic acid . It is also used as a hardener (for epoxy resins ) and as an intermediate for the production of other chemical compounds (e.g. Cyclen ). Diethylenetriamine can also be used, similar to ethylenediamine, to sensitize nitromethane to generate liquid explosives. Mixed with UDMH , it can be used as rocket fuel (Hydyne / Hydine = 60% UDMH and 40% diethylenetriamine; MAF-3 = 20% UDMH and 80% diethylenetriamine), which is e.g. B. was used in the American Juno-I missile. Diethylenetriamine also serves as a base monomer for reactive polymers, which u. a. can be used as wet strength agents for paper.

safety instructions

Contact with diethylenetriamine poses a risk of skin sensitization . When diethylenetriamine is burned, toxic gases, including nitrous gases, are formed.

proof

Diethylenetriamine can be detected by HPLC with UV detection.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 3-azapentane-1,5-diamine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
^ ^A ^b Huntsman Corporation: Technical Bulletin .
↑ Entry on 2,2′-iminodi (ethylamine) 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 111-40-0 or diethylenetriamine ), accessed on November 2, 2015.
↑ ^a ^b ^c ^d OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Diethylenetriamine , accessed on October 3, 2014.
↑ Patent DE69226699T2 : Process for the production of resins based on epichlorohydrin with reduced halogen content. Published on June 19, 1991 , inventors: Gorzynski Marek, Pingel Andreas. ‌

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 3-azapentane-1,5-diamine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[huntsman-2] A ^b Huntsman Corporation: Technical Bulletin .

[CLP_100.003.515-3] Entry on 2,2′-iminodi (ethylamine) 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 111-40-0 or diethylenetriamine ), accessed on November 2, 2015.

[SIDS-5] OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Diethylenetriamine , accessed on October 3, 2014.

[6] Patent DE69226699T2 : Process for the production of resins based on epichlorohydrin with reduced halogen content. Published on June 19, 1991 , inventors: Gorzynski Marek, Pingel Andreas. ‌