Chemical Properties
colourless to light yellow or amber viscous liquid
Uses
Triethylenetetramine is a selective CuII-chelator; crosslinking agent. Triethylenetetramine is undergoing trials for the treatment of heart failure in patients with diabetes.
General Description
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.
Reactivity Profile
TRIETHYLENETETRAMINE(112-24-3) is a strong base; reacts violently with strong oxidants; attacks aluminum, zinc, copper and its alloys. Handling Chemicals Safely 198. p. 934).
Air & Water Reactions
Soluble in water.
Health Hazard
Vapors from hot liquid can irritate eyes and upper respiratory system. Liquid burns eyes and skin. May cause sensitization of skin.
Fire Hazard
Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
Description
Cross sensitivity is
possible with diethylenetriamine and diethylenediamine.
Definition
ChEBI: 2,2,2-tetramine is a polyazaalkane that is decane in which the carbon atoms at positions 1, 4, 7 and 10 are replaced by nitrogens. It has a role as a copper chelator. It is a tetramine and a polyazaalkane.
Production Methods
TETA is manufactured by reacting ethylene dichloride and
ammonia under controlled conditions.
Brand name
Syprine (Merck).
Flammability and Explosibility
Nonflammable
Toxicology
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. Triethylenetetramine proved to be a mutagen in vitro but not in vivo.
Carcinogenicity
TETA was mutagenic in bacterial assays
and was positive in sister chromatid exchanges
and unscheduled DNA synthesis tests in vitro.8
It was not clastogenic in the mouse micronucleus
test in vivo after oral or intraperitoneal
administration.
Purification Methods
Dry the amine with sodium, then distil it under a vacuum. Further purification has been via the nitrate or the chloride salts. For example, Jonassen and Strickland [J Am Chem Soc 80 312 1958] separated TRIEN from admixture with TREN (38%) by solution in EtOH, cooling to approximately 5o in an ice-bath and adding conc HCl dropwise from a burette, keeping the temperature below 10o, until all of the white crystalline precipitate of TREN.HCl (see p 191) had formed and was removed. Further addition of HCl then precipitated thick, creamy white TRIEN.HCl (see below) which was crystallised several times from hot water by adding an excess of cold EtOH. The crystals were finally washed with Me2CO, then Et2O and dried in a vacuum desiccator. [Beilstein 4 H 255, 4 II 695, 4 III 542, 4 IV 1242.]
