Triethylenetetramine

Structural formula
General
Surname	Triethylenetetramine
other names	3,6-diazaoctane-1,8-diamine N , N '-bis (2-aminoethyl) ethylenediamine Trentine TETA Trien
Molecular formula	C 6 H 18 N 4
Brief description	oily, yellowish liquid with a faint amine-like odor
External identifiers / databases
CAS number 112-24-3 38260-01-4 (dihydrochloride) 4961-40-4 (tetrahydrochloride) PubChem 5565 DrugBank DB06824 Wikidata Q418386
Drug information
ATC code	A16 AX12
properties
Molar mass	146.24 g mol −1
Physical state	liquid
density	0.98 g cm −3
Melting point	12 ° C
boiling point	278 ° C
Vapor pressure	1.3 Pa (20 ° C)
solubility	miscible with water miscible with polar solvents such as acetone, ethanol, diethyl ether and methanol soluble in n-heptane
Refractive index	1.496-1.5
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 312-314-317-412 P: 280-273-302 + 352-301 + 330 + 331-305 + 351 + 338-309 + 310
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

Triethylenetetramine ( TETA for short ) is an organic chemical compound from the group of aliphatic amines .

Extraction and presentation

Triethylenetetramine is obtained by heating ethylenediamine or by reacting an ammonia solution with 1,2-dichloroethane . This process creates a whole family of ethylene amines such as ethylene diamine, diethylene triamine, triethylene tetramines , tetraethylene pentamines , pentaethylene hexamines and aminoethyl piperazines . These polyamines are formed as hydrochlorides and have to be neutralized (usually with aqueous sodium hydroxide solution ) in order to generate the free amines.

In 1990 the production volume of triethylenetetramine in Germany was 1200 to 1500 t per year (e.g. by Bayer AG ), 6000 t per year in the Netherlands, 1800 t per year in Japan and more than 11,000 t per year in the UNITED STATES. 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

Chemical properties

Triethylenetetramine shows the typical reactivity of amines (similar to ethylenediamine and diethylenetriamine ).

Physical Properties

The melting point of the technical product is lower (down to −35 ° C) than that of the pure substance.

TETA is available in the form of an oily, colorless liquid which, in technical purity , usually has a yellowish color due to contamination caused by oxidation in air. Technical TETA contains up to 40% by-products in the form of the branched isomer 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 diethylenetriamine .

use

Technical use

Triethylenetetramine is used in the production of wetting agents , emulsifiers , textile auxiliaries, acrylate rubber , amine and amide resins and additives for lubricants and fuels (polybutenyl succinimides). It is widely used as a hardener for two-component epoxy resin systems for the impregnation and coating of floors and for the production of mortars and leveling compounds.

It is also used as a chelating agent in complex chemistry (abbreviation after IUPAC trien ), for example it forms a deep blue complex that is readily water-soluble with divalent copper ions. This can be used to complex copper in Wilson's disease .

Therapeutic use

In medicine, triethylenetetramine ( international non- proprietary name Trientin ) is approved as a drug for the treatment of Wilson's disease (copper storage disease) . The copper-complexing property of triethylenetetramine is used. In addition, TETA shows an anti- angiogenic and telomerase -inhibiting effect, making it a promising potential chemotherapeutic agent in cancer is considered.

Trientindi hydrochloride or tetrahydrochloride, crystalline substances that are easily soluble in water, are used in pharmaceuticals . They are given orally. The most commonly observed side effect is nausea. Iron deficiency anemia and colitis can occur during treatment.

safety instructions

Sensitization and subsequent allergic reactions of the skin are possible on contact with triethylenetetramine. The vapors are heavier than air. When spraying or heating above the flash point (135 ° C), the formation of an explosive mixture is possible.

Individual evidence

1. ↑ ^{a b c d e f g h} Entry on 3,6-diazaoctane-1,8-diamine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
2. ↑ ^{a b c} data sheet triethylenetetramine (PDF; 192 kB) at gischem.de, accessed on November 26, 2019.
3. ↑ Entry on triethylenetetramine at ChemBlink , accessed on February 25, 2011.
4. ↑ Entry on Trientine 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. ↑ ^{a b c d e} OECD : Screening Information Dataset (SIDS) Initial Assessment Report (SIAR) for Triethylene tetramine , accessed on October 3, 2014.
6. ↑ Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH Verlag, Weinheim. doi : 10.1002 / 14356007.a02_001 .
7. ↑ J. Lu: Triethylenetetramine pharmacology and its clinical applications. In: Molecular Cancer Therapeutics . Volume 9, Number 9, September 2010, pp. 2458-2467. doi : 10.1158 / 1535-7163.MCT-10-0523 . PMID 20660601 . (Review).
8. ↑ Description Information Synprine , as of December 2016.
9. ↑ ^{a b} CHMP assessment report Cuprior , April 2017.