Triethylenetetramine

Triethylenetetramine
IUPAC name

N,N'-bis(2-aminoethyl)ethane-1,2-diamine
Other names

Trientine
Identifiers
CAS number 112-24-3 Y
PubChem 5565
ChemSpider 21106175 Y
UNII SJ76Y07H5F Y
KEGG C07166 Y
ChEBI CHEBI:39501 N
ChEMBL CHEMBL609 Y
Jmol-3D images Image 1
Properties
Molecular formula C6H18N4
Molar mass 146.23392
Melting point

12 °C, 285 K, 54 °F
Boiling point

266-267 °C, 539-540 K, 511-513 °F
Solubility in water Miscible
 N (verify) (what is: Y/N?)
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 typical for amines. The branched isomer N(CH2CH2NH2)3 and the cyclic triamine (CH2CH2NH)3 also comprise commercial samples of TETA.

Contents

Production

Triethylenetetramine is prepared by heating ethylenediamine or ethanolamine/ammonia mixtures 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 of triethylenetetramine, referred to as trientine hydrochloride, is a chelating agent, and is used to bind up and remove copper in the body to treat Wilson's disease, particularly in those who are intolerant to penicillamine. Some recommend trientine as first-line treatment, but experience with penicillamine is more extensive.[2]

Coordination chemistry

Triethylenetetramine is a tetradentate ligand in coordination chemistry, where it is referred to as trien.[3] Octahedral complexes of the type M(trien)Cl3 can adopt several diastereomeric structures, most of which are chiral.[4]

References

  1. ^ a b Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a02_001
  2. ^ Roberts EA, Schilsky ML (2003). "A practice guideline on Wilson disease" (PDF). Hepatology 37 (6): 1475–92. doi:10.1053/jhep.2003.50252. PMID 12774027. http://www3.interscience.wiley.com/cgi-bin/fulltext/106595824/PDFSTART. 
  3. ^ von Zelewsky, A. "Stereochemistry of Coordination Compounds" John Wiley: Chichester, 1995. ISBN 047195599.
  4. ^ S. Utsuno, Y. Sakai, Y. Yoshikawa, H. Yamatera "Three Isomers of the Trans-Diammine-[N,N′-bis(2-Aminoethyl)-1,2-Ethanediamine]-Cobalt(III) Complex Cation" Inorganic Syntheses, 1985, Volume 23, Pages: 79–82. doi:10.1002/9780470132548.ch16