Triethylenetetramine

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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
112-24-3 YesY
605448
ChEBI CHEBI:39501 YesY
ChEMBL ChEMBL609 YesY
ChemSpider 21106175 YesY
EC Number 203-950-6
27008
Jmol 3D model Interactive image
KEGG C07166 YesY
MeSH Trientine
PubChem 5565
RTECS number YE6650000
UNII SJ76Y07H5F YesY
UN number 2259
Properties
C6H18N4
Molar mass 146.24 g·mol−1
Appearance Colorless liquid
Odor Fishy, 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
Miscible
log P 1.985
Vapor pressure <1 Pa (at 20 °C)
1.496
Thermochemistry
376 J K−1 mol−1 (at 60 °C)
Hazards
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H312, H314, H317, H412
P273, P280, P305+351+338, P310
Corrosive C
R-phrases R21, R34, R43, R52/53
S-phrases (S1/2), S26, S36/37/39, S45
Flash point 129 °C (264 °F; 402 K)
Lethal dose or concentration (LD, LC):
  • 550 mg kg−1 (dermal, rabbit)
  • 2.5 g kg−1 (oral, rat)
Related compounds
Related amines
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Triethylenetetramine, abbreviated TETA and trien and also called trientine (INN), is an organic compound with the formula [CH2NHCH2CH2NH2]2. This oily liquid is colorless but, like many amines, assumes a yellowish color due to impurities resulting from air-oxidation. It is soluble in polar solvents. The branched isomer N(CH2CH2NH2)3 and piperazine derivatives may also be present in commercial samples of TETA.[1]

Production[edit]

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.[2]

Uses[edit]

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.[2]

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.[3]

Coordination chemistry[edit]

Triethylenetetramine is a tetradentate ligand in coordination chemistry, where it is referred to as trien.[4] Octahedral complexes of the type M(trien)Cl3 can adopt several diastereomeric structures, most of which are chiral.[5]

References[edit]

  1. ^ "Ethyleneamines" (PDF). Huntsman. 2007. 
  2. ^ a b Eller, K.; Henkes, E.; Rossbacher, R.; Höke, H. (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. 
  3. ^ Roberts, E. A.; Schilsky, M. L. (2003). "A practice guideline on Wilson disease" (pdf). Hepatology. 37 (6): 1475–1492. doi:10.1053/jhep.2003.50252. PMID 12774027. 
  4. ^ von Zelewsky, A. (1995). Stereochemistry of Coordination Compounds. Chichester: John Wiley. ISBN 047195599X. 
  5. ^ Utsuno, S.; Sakai, Y.; Yoshikawa, Y.; Yamatera, H. (1985). "Three Isomers of the Trans-Diammine-[N,N′-bis(2-Aminoethyl)-1,2-Ethanediamine]-Cobalt(III) Complex Cation". Inorganic Syntheses. 23: 79–82. doi:10.1002/9780470132548.ch16.