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.)

Flash point:

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.

LogP

-2.65 at 20℃

CAS DataBase Reference

112-24-3(CAS DataBase Reference)

NIST Chemistry Reference

Triethylenetetramine(112-24-3)

EPA Substance Registry System

Triethylenetetramine (112-24-3)

Safety Information

Hazard Codes 

C

Risk Statements 

21-34-43-52/53

Safety Statements 

26-36/37/39-45-61

RIDADR 

UN 2259 8/PG 2

WGK Germany 

2

RTECS 

YE6650000

Autoignition Temperature

335 °C

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29212900

Hazardous Substances Data

112-24-3(Hazardous Substances Data)

Toxicity

LD50 orally in rats: 2.5 g/kg (Spitz)

MSDS

• Language:English Provider:3,6-Diazaoctane-1,8-diamine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Triethylenetetramine Usage And Synthesis

Description

Triethylenetetramine (TETA and trien) 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. It is soluble in polar solvents. The branched isomer tris(2-aminoethyl)amine and piperazine derivatives may also be present in commercial samples of Triethylenetetramine. The hydrochloride salts are used medically as a treatment for copper toxicity.

Chemical Properties

Triethylenetetramine is a corrosive liquid.

Uses

Triethylenetetramine is used as an amine hardener in epoxy resin of the bisphenol A type.It 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.

Production Methods

Triethylenetetramine(TETA) is manufactured by reacting ethylene dichloride and ammonia under controlled conditions.

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.

brand name

Syprine (Merck).

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.

Chemical Properties

Triethylenetetramine (TETA) is hygroscopic, corrosive, and has a strong ammoniacal odor. With water a crystalline hydrate is formed. Like DETA, it 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 is sometimes available as a distillation cut that also contains branched isomers and cyclic compounds.

Reactivity Profile

Triethylenetetramine is a strong base; reacts violently with strong oxidants; attacks aluminum, zinc, copper and its alloys. Handling Chemicals Safely 198. p. 934).

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.

Flammability and Explosibility

Non flammable

Contact allergens

Triethylenetetramine is used as an amine hardener in epoxy resins of the bisphenol A type. Cross-sensitivity is possible with diethylenetriamine and diethylenediamine.

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.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion and skin contact. An experimental teratogen. Experimental reproductive effects. Mutation data reported. A corrosive irritant to skin, eyes, and mucous membranes. Causes skin sensitization. Combustible when exposed to heat or flame. Ignites on contact with cellulose nitrate of high surface area. Can react with oxidizing materials. To fight fire, use CO2, dry chemical, alcohol foam. When heated to decomposition it emits toxic fumes of NOx.

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.]

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