Triethylenetetramine
- 3,6- diazaoctane -1 ,8 -diamine
- N, N'- bis (2- aminoethyl ) ethylenediamine
- Trientine
- TETA
Oily, yellowish liquid with a faint amine-like odor
Liquid
0.98 g · cm -3
12 ° C
266 ° C
1.3 Pa (20 ° C)
- Miscible with water
- Miscible with polar solvents such as acetone, ethanol, diethyl ether and methanol
- Soluble in n- heptane
1.496 to 1.5
Risk
> 2000 mg · kg -1 ( LD50, rat, oral)
Template: Infobox chemical / molecular formula search available
Triethylenetetramine ( TETA short ) is an organic chemical compound consisting of the group of aliphatic amines.
Production and representation
Triethylenetetramine is obtained by heating from ethylene diamine or by the reaction of an ammonia solution with 1,2- dichloroethane. In this process produces a family of ethyleneamines, such as ethylenediamine, diethylenetriamine, Triethylentetraminen, tetraethylene pentamines, and Pentaethylenhexaminen Aminoethylpiperazinen. These polyamines are formed as the hydrochlorides, and must be neutralized (usually with aqueous sodium hydroxide solution), in order to generate free amines.
The production of triethylenetetramine was in the year 1990 1200 bis 1500 t per year in Germany (eg by Bayer AG ), 6000 t per year in the Netherlands, 1800 t per year in Japan and more than 11,000 tonnes per year in the United States.
Properties
Chemical Properties
Triethylenetetramine shows (similar to ethylenediamine and diethylenetriamine ) the typical reactivity of amines.
Physical Properties
When technical product of melting point lower ( down to -35 ° C) than for the pure substance.
TETA is in the form of an oily, colorless liquid which by impurities formed by oxidation in air, usually has a yellowish color in industrial purity. Technical TETA contains up to 40% by-products in the form of branched isomers of tris ( 2-aminoethyl) -amine, or other organic compounds such as N, N'-bis (2-aminoethyl ) piperazine, N-(1 - (2- piperazine -1-yl -ethyl) ) -ethane - 1 ,2-diamine or diethylene triamine.
Use
Triethylenetetramine is used for the production of wetting agents, emulsifiers, textile auxiliaries, acrylate, amine and amide resins and additives for lubricants and fuels ( Polybutenylsuccinimide ). It is widely used as a curing agent for two-component epoxy resin systems for impregnation and coating of soils and for the production of mortars and filler compositions.
Furthermore, it is used as chelating agents in complex chemistry used (abbreviated according to IUPAC trien ), so it makes for example with divalent copper ions form a highly water-soluble, deep blue complex. Which can be used for complexing copper in Wilson's disease.
In medicine, the dihydrochloride trientine is approved as a drug for the treatment of Wilson's disease (copper storage disease). The kupferkomplexierende property of triethylenetetramine is used. In addition, TETA is a anti-angiogenic and telomerase - inhibiting activity, and therefore it is seen as a promising potential chemotherapeutic agent for cancers.
Safety
A sensitization and subsequent allergic skin reactions are possible when in contact with triethylenetetramine. The vapor is heavier than air. When sprayed or heated above the flash point (135 ° C) the formation of an explosive mixture is possible.