Triethylenetetramine
From Wikipedia, the free encyclopedia
| Triethylenetetramine | |
|---|---|
 |
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| IUPAC name | N,N'-bis(2-aminoethyl)ethane-1,2-diamine |
| Other names | Trientine |
| Identifiers | |
| CAS number | [112-24-3] |
| PubChem | |
| SMILES | C(CNCCNCCN)N |
| Properties | |
| Molecular formula | C6H18N4 |
| Molar mass | 146.23392 |
| Melting point |
12 °C, 285 K, 54 °F |
| Boiling point |
266-267 °C |
| Solubility in water | Miscible |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Triethylenetetramine, abbreviated TETA and trien, is an organic compound with the formula [CH2NHCH2CH2NH2]2. This oily liquid is colourless but, like many amines, assumes a yellowish color due to impurities resulting from air-oxidation. It is soluble polar solvents and exhibits the reactivity of typical for amines. The branched isomer N(CH2CH2NH2)3 and the cyclic triamine (CH2CH2NH)3 comprise approximately 40% of commercially available TETA.[citation needed]
[edit] Production
Triethylenetetramine is prepared by heating ethylenediamine and related species over an oxide catalyst. This process gives a variety of amines which are separated by distillation and sublimation.[1]
[edit] Uses
The reactivity and uses of TETA are similar to those for the related polyamines ethylenediamine and diethylenetriamine. It was primarily used as a crosslinker ("hardener") in epoxy curing.[1] The hydrochloride salt, referred to as trientine hydrochloride, is a chelating agent and has been discussed for the removal of copper in the treatment of Wilson's disease.[2]
Triethylenetetramine is a tetradentate ligand in coordination chemistry, where it is referred to as "trien."[3] Octahedral complexes of the type M(trien)Cl2 can adopt several diastereomeric structures, most of which are chiral.
[edit] References
- ^ a b Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH Verlag, Weinheim. DOE: 10.1002/14356007.a02 001
- ^ Trientine hydrochloride, Centre for Cancer Education, University of Newcastle upon Tyne
- ^ von Zelewsky, A. "Stereochemistry of Coordination Compounds" John Wiley: Chichester, 1995. ISBN 047195599.
