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TETA (Triethylenetetramine) also known as trientine (INN) when used medically, is an organic compound with the formula [CH2NHCH2CH2NH2]2.
The pure freebase is a colorless oily liquid, but, like many amines, older samples assume a yellowish color due to impurities resulting from air- oxidation.
TETA (Triethylenetetramine) is soluble in polar solvents.
CAS: 112-24-3
MF: C6H18N4
MW: 146.23
EINECS: 203-950-6
Synonyms
N,N'-DI(2-AMINOETHYL)ETHYLENEDIAMINE;N,N'-BIS(2-AMINOETHYL)ETHYLENEDIAMINE;Ethylenediamine, N,N'-bis(2-aminoethyl)-;hy951;n,n’-bis(2-aminoethyl)-2-ethanediamine;N,N’-bis-(2-amino-ethyl)-ethane-1,2-diamine;n,n’-bis(2-aminoethyl)-ethylenediamin;N,N'-Bis(2-aminoethyl)-1,2-diaminoethane
The branched isomer TETA (Triethylenetetramine) and piperazine derivatives may also be present in commercial samples of Triethylenetetramine.
The hydrochloride salts are used medically as a treatment for copper toxicity.
TETA (Triethylenetetramine) is a polyazaalkane that is decane in which the carbon atoms at positions 1, 4, 7 and 10 are replaced by nitrogens.
TETA (Triethylenetetramine) has a role as a copper chelator.
TETA (Triethylenetetramine) is a tetramine and a polyazaalkane.
A yellowish liquid. Less dense than water.
Combustible, though may be difficult to ignite.
Corrosive to metals and tissue.
Vapors heavier than air.
Toxic oxides of nitrogen produced during combustion.
Used in detergents and in the synthesis of dyes, pharmaceuticals and other chemicals.
TETA (Triethylenetetramine), also known as trientine (INN) when used medically, is an organic compound with the formula [CH2NHCH2CH2NH2]2.
The pure free base is a colorless oily liquid, but, like many amines, older samples assume a yellowish color due to impurities resulting from air oxidation.
TETA (Triethylenetetramine) is soluble in polar solvents.
The branched isomer TETA (Triethylenetetramine) and piperazine derivatives may also be present in commercial samples of TETA.
The hydrochloride salts are used medically as a treatment for copper toxicity.
TETA (Triethylenetetramine) is a colorless to light-yellow liquid containing linear, branched and cyclic molecules.
TETA (Triethylenetetramine) is mainly used in the manufacture of fuel oil additives, lubricating oil additives and epoxy curing agents.
TETA (Triethylenetetramine) is also used in the production of asphalt additives.
TETA (Triethylenetetramine), commonly referred to as TETA, is a tetraamine with multiple nitrogen atoms, making it highly reactive and useful in complex formation.
TETA (Triethylenetetramine) is an opaque, light yellow liquid that has an amine-like smell.
TETA (Triethylenetetramine) is water-soluble and is highly reactive to acidic compounds, carbon dioxide and other electrophilic substances.
TETA (Triethylenetetramine) Chemical Properties
Melting point: 12 °C(lit.)
Boiling point: 266-267 °C(lit.)
density: 0.982 g/mL at 25 °C(lit.)
vapor density: ~5 (vs air)
vapor pressure: <0.01 mm Hg ( 20 °C)
refractive index: n20/D 1.496(lit.)
Fp: 290 °F
storage temp.: Store below +30°C.
solubility: alcohol: soluble
form: Slightly viscous yellow liquid; commercially available form is 95–98% pure, and impurities include linear, branched, and cyclic isomers.
pka: pK1:3.32(+4);pK2:6.67(+3);pK3:9.20(+2);pK4:9.92(+1) (20°C)
color: Yellowish liquid or oil
PH: 10-11 (10g/l, H2O, 20℃)
explosive limit: 0.7-7.2%(V)
Water Solubility: SOLUBLE
FreezingPoint: 12℃
Sensitive: Moisture Sensitive
Merck: 14,9663
BRN: 605448
Exposure limits ACGIH: TWA 1 ppm (Skin)
NIOSH: TWA 1 ppm(4 mg/m3)
Stability: Incompatible with strong oxidizing agents, strong acids.
InChI: 1S/C6H18N4/c7-1-3-9-5-6-10-4-2-8/h9-10H,1-8H2
InChIKey: VILCJCGEZXAXTO-UHFFFAOYSA-N
LogP: -2.65 at 20℃
CAS DataBase Reference: 112-24-3(CAS DataBase Reference)
NIST Chemistry Reference: TETA (Triethylenetetramine)(112-24-3)
EPA Substance Registry System: TETA (Triethylenetetramine) (112-24-3)
TETA (Triethylenetetramine) is hygroscopic, corrosive, and has a strong ammoniacal odor.
With water a crystalline hydrate is formed.
Like DETA, TETA (Triethylenetetramine) is completely miscible with water and many polar organic solvents, but less so with lipids; with CCl4 a violent reaction occurs.
Its four pKa values are 3.32, 6.67, 9.20, and 9.92.
Technical-grade TETA (Triethylenetetramine) is sometimes available as a distillation cut that also contains branched isomers and cyclic compounds.
Uses
TETA (Triethylenetetramine) is used as an amine hardener in epoxy resin of the bisphenol A type.
TETA (Triethylenetetramine) is used in synthesis of detergents, softeners, and dyestuffs; manufacture of pharmaceuticals; vulcanization accelerator of rubber; thermo setting resin; epoxy curing agent; lubricating-oil additive; analytical reagent for Cu, Ni; chelating agent; treatment of Wilson's disease.
Epoxy uses
The reactivity and uses of TETA (Triethylenetetramine) are similar to those for the related polyamines ethylenediamine and diethylenetriamine.
TETA (Triethylenetetramine) is primarily used as a crosslinker ("hardener") in epoxy curing.
TETA (Triethylenetetramine), like other aliphatic amines, react quicker and at lower temperatures than aromatic amines due to less negative steric effects since the linear nature of the molecule provides it the ability to rotate and twist.
TETA (Triethylenetetramine) was approved for medical use in the United States in November 1985.
TETA (Triethylenetetramine) was approved for medical use in the European Union in September 2017.
TETA (Triethylenetetramine) is indicated for the treatment of Wilson's disease in adults, adolescents and children five years of age or older who are intolerant to D-penicillamine therapy.
TETA (Triethylenetetramine) was approved for medical use in the European Union in July 2019.
TETA (Triethylenetetramine) is indicated for the treatment of Wilson's disease in adults, adolescents and children five years of age or older who are intolerant to D-penicillamine therapy.
The most common side effects include nausea, especially when starting treatment, skin rash, duodenitis (inflammation of the duodenum, the part of the gut leading out of the stomach), and severe colitis (inflammation in the large bowel causing pain and diarrhea).
Production Methods
TETA (Triethylenetetramine) is manufactured by reacting ethylene dichloride and ammonia under controlled conditions.
Production
TETA (Triethylenetetramine) is prepared by heating ethylenediamine or ethanolamine/ammonia mixtures over an oxide catalyst.
This process gives a variety of amines, especially ethylene amines which are separated by distillation and sublimation.
An idealized equation follows:
Health Hazard
Vapors from hot liquid can irritate eyes and upper respiratory system.
Liquid burns eyes and skin.
May cause sensitization of skin.
Toxicology
TETA (Triethylenetetramine) may induce lung edema on inhalation of its vapors.
The compound is also an effective skin sensitizer.
Following repeated dosing (ca. 50 mg each, 17 – 55 times) onto the skin of pregnant and nonpregnant guinea pigs, significant amounts were absorbed by the strongly irritated skin, leading to toxic effects in the kidneys, liver, brain, and placenta and causing abortion.
TETA (Triethylenetetramine) proved to be a mutagen in vitro but not in vivo.
