View source for Triethylenetetramine

{{Redirect|TETA|the album by Propagandhi|Today's Empires, Tomorrow's Ashes}}
{{chembox
| verifiedrevid = 285099547
|ImageFile=Triethylene tetramine.png
|ImageSize=200px
|ImageName=Chemical structure of triethylenetetramine
|IUPACName=N,N'-bis(2-aminoethyl)ethane-1,2-diamine
|OtherNames=Trientine 
|Section1= {{Chembox Identifiers
|  CASNo_Ref = {{cascite}}
| CASNo=112-24-3 
|  PubChem=5565
|  SMILES=C(CNCCNCCN)N
  }}
|Section2= {{Chembox Properties
|  Formula=C<sub>6</sub>H<sub>18</sub>N<sub>4</sub>
|  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 [CH<sub>2</sub>NHCH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>]<sub>2</sub>. This oily liquid is colourless but, like many [[amine]]s, 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(CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>)<sub>3</sub> and the cyclic triamine [[TACN|(CH<sub>2</sub>CH<sub>2</sub>NH)<sub>3</sub>]] 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.<ref name=Ullmann>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</ref>

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

Triethylenetetramine is a tetradentate [[ligand]] in [[coordination chemistry]], where it is referred to as "trien."<ref>von Zelewsky, A. "Stereochemistry of Coordination Compounds" John Wiley: Chichester, 1995. ISBN 047195599.</ref>  Octahedral complexes of the type M(trien)Cl<sub>2</sub> can adopt several diastereomeric structures, most of which are [[Chirality (chemistry)|chiral]].

==References==
{{reflist}}

[[Category:Polyamines]]
[[Category:Chelating agents]]

[[de:Triethylentetramin]]
[[nl:Triethyleentetramine]]
[[Category:2Fix]]