Triethylenetetramine

Triethylenetetramine

Chembox new
ImageFile=Triethylene tetramine.pngImageSize=200px
ImageName=Chemical structure of triethylenetetramine
IUPACName=N,N'-bis(2-aminoethyl)ethane-1,2-diamine
OtherNames=Trientine
Section1= Chembox Identifiers
CASNo=112-24-3
PubChem=5565
SMILES=C(CNCCNCCN)N
Section2= Chembox Properties
Formula=C6H18N4
MolarMass=146.23392
Appearance=
Density=
MeltingPtC=12
BoilingPt=266-267 °C
Solubility=Miscible
Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

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.Fact|date=February 2008

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.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]

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. 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. [ [http://cancerweb.ncl.ac.uk/cgi-bin/omd?trientine+hydrochloride Trientine hydrochloride] , Centre for Cancer Education, University of Newcastle upon Tyne]

Triethylenetetramine is a tetradentate ligand in coordination chemistry, where it is referred to as "trien." [von Zelewsky, A. "Stereochemistry of Coordination Compounds" John Wiley: Chichester, 1995. ISBN 047195599.] Octahedral complexes of the type M(trien)Cl2 can adopt several diastereomeric structures, most of which are chiral.

References


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