Triethylenetetramine

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Triethylenetetramine
Chemical structure of triethylenetetramine
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 112-24-3 YesY
PubChem 5565
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style="background: #F8EABA; text-align: center;" colspan="2" | 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
 YesY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 in 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]

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]

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.

References

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  1. 1.0 1.1 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
  2. Trientine hydrochloride, Centre for Cancer Education, University of Newcastle upon Tyne
  3. von Zelewsky, A. "Stereochemistry of Coordination Compounds" John Wiley: Chichester, 1995. ISBN 047195599.