Triethylenetetramine

"TETA" redirects here. For the album by Propagandhi, see Today's Empires, Tomorrow's Ashes.

Triethylenetetramine

Skeletal formula of triethylenetetramine
Ball and stick model of triethylenetetramine
Spacefill model of triethylenetetramine
Names
Other names N,N'-Bis(2-aminoethyl)ethane-1,2-diamine
Identifiers
CAS Number	112-24-3 Y
Beilstein Reference	605448
ChEBI	CHEBI:39501 Y
ChEMBL	ChEMBL609 Y
ChemSpider	21106175 Y
EC Number	203-950-6
Gmelin Reference	27008
Jmol 3D model	Interactive image
KEGG	C07166 Y
MeSH	Trientine
PubChem	5565
RTECS number	YE6650000
UNII	SJ76Y07H5F Y
UN number	2259
InChI InChI=1S/C6H18N4/c7-1-3-9-5-6-10-4-2-8/h9-10H,1-8H2 Y Key: VILCJCGEZXAXTO-UHFFFAOYSA-N Y
SMILES NCCNCCNCCN
Properties
Chemical formula	C6H18N4
Molar mass	146.24 g·mol−1
Appearance	Colourless liquid
Odor	Ichtyal, ammoniacal
Density	982 mg mL−1
Melting point	−34.6 °C; −30.4 °F; 238.5 K
Boiling point	266.6 °C; 511.8 °F; 539.7 K
Solubility in water	Miscible
log P	1.985
Vapor pressure	<1 Pa (at 20 °C)
Refractive index (nD)	1.496
Thermochemistry
Specific heat capacity (C)	376 J K−1 mol−1 (at 60 °C)
Vapor pressure	{{{value}}}
Related compounds
Related amines	ethylenediamine diethylenetriamine cyclam
Related compounds	ethylenediaminetetraacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
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 piperazine derivatives also comprise commercial samples of TETA.

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.

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 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.

Coordination chemistry

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