TRIETHYLENETETRAMINE
TRIETHYLENETETRAMINE
Triethylenetetramine (TETA and trien), 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.
Triethylenetetramine is soluble in polar solvents.
The branched isomer tris(2-aminoethyl)amine and piperazine derivatives may also be present in commercial samples of TETA.
Triethylenetetramine (TETA) is a colorless to light-yellow liquid containing linear, branched and cyclic molecules.
TETA is mainly used in the manufacture of fuel oil additives, lubricating oil additives and epoxy curing agents.
Triethylenetetramine (TETA) is also used in the production of asphalt additives.
Triethylenetetramine (TETA) is a moderately viscous, yellowish liquid, less volatile than diethylenetriamine, but resembles it in many other properties.
It is soluble in water.
Triethylenetetramine is primarily used as a hardener in epoxy resins.
Other uses include detergents and softening agents, synthesis of dyestuffs, pharmaceuticals, and rubber accelerators.
Triethylenetetramine is produced by the reaction of aqueous ammonia with 1,2- dichloroethane.
This process yields the entire family of ethyleneamines: ethylenediamine,piperazine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine and aminoethylpiperazine.
These polyamines are produced as their hydrochloride salts, and must be neutralized, typically with aqueous caustic soda, to obtain the free amines.
The by-product salt produced in the neutralisation step is separated and the individual products are isolated by fractional distillation.
TETA can be used as an intermediate in a number of production processes:
· The reaction with polyisobutenylsuccinic anhydride yields the corresponding polybutenylsuccinimides, which are ashless, dispersant- detergent additives for motor oil.
· Polyamide -epichlorohydrin resins are produced by the reaction of epichlorohydrin with a polyamide, such as those formed by polymerisation of adipic acid and TETA.
These are used in the paper industry as wet-strength additives for liner board, toweling, tissue and sanitary applications.
· The ethoxylated products of TETA are curing agents for epoxy resins.
The largest application is surface coatings (35%).
· Imidazolines from the condensation of TETA with two moles of fatty acid are cationic surfactants used as fabric softeners, asphalt emulsifiers, oil field corrosion inhibitors, ore flotation agents and epoxy curing agents.
· Reactive polyamides from the polymerisation of dimer acids with TETA are mostly used as curing agents for epoxy surface coatings.
Triethylenetetramine (TETA) is mainly used as:
· intermediate for curing agents for epoxy resins
· direct curing agent for epoxy resins
· intermediary for auxiliary agents used in the paper industry, the textile industry and in glues
· intermediate for asphalt emulsifiers
· intermediate for transport, fertilizer and plastics industry
· adhesive, binding agent
· hardener for plastic
TETA is completely miscible with water forming an alkaline solution (pH 10 at 10 g/l).
The technical product has a vapour pressure of ca. 1 Pa at 20 °C.
The calculated Log Pow amounts to ca. -1.4 and indicates a low potential for bioaccumulation.
Triethylenetetramine appears as a yellowish liquid.
Triethylenetetramine is less dense than water.
Triethylenetetramine is Combustible, though may be difficult to ignite.
Triethylenetetramine is Corrosive to metals and tissue.
Triethylenetetramine vapors heavier than air.
Toxic oxides of nitrogen produced during combustion.
Used in detergents and in the synthesis of dyes, pharmaceuticals and other chemicals.
Triethylenetatramine (TETA) is a highly selective divalent Cu(II) chelator and orphan drug that revereses copper overload in tissues.
Its salt form, trientine (triethylenetetramine dihydrochloride or 2,2,2-tetramine) was introduced in 1969 as an alternative to D-penicillamine.
It consists of a polyamine-like structure different from D-penicillamine, as it lack sulfhydryl groups.
It was previously approved by FDA in 1985 as second-line pharmacotherapy for Wilson’s disease.
Although penicillamine treatment is believed to be more extensive, TETA therapy has been shown to be an effective initial therapy, even with patients with decompensated liver disease at the outset, and prolonged TETA treatment is not associated with adverse effects as expected in penicillamine treatment.
Its clinical applications on cancer, diabetes mellitus, Alzheimer’s disease and vascular demetia are being studied.
TRIETHYLENETETRAMINE
N,N’-Bis(2-aminoethyl)-1,2-ethanediamine
3,6-Diazaoctane-1,8-diamine
Trientine
TETA
TETA; N1,N2-Bis(2-aminoethyl)-1,2-ethanediamine; 1,2-Bis(2-aminoethylamino)ethane
TETA is triethylenetetramine.
TETA acts as a curing agent for epoxy resins.
TETA also functions as a corrosion inhibitor, surfactant and mineral processing aid.
TRIETHYLENETETRAMINE is compatible with polyamides.
Triethylenetetramine (TETA) can be used in composites.
Triethylenetetramine (TETA) is used as a polymer and resin modifier.
The shelf life of the product is 24 months
Triethylenetetramine Chemical Properties, Uses, Production
Description
Cross sensitivity is possible with diethylenetriamine and diethylenediamine.
Chemical Properties
Triethylenetetramine is a corrosive liquid.
Uses
Triethylenetetramine is used as an amine hardener in epoxy resin of the bisphenol A type.
It has similar reactivity and uses as ethylenediamine and diethylenetriamine, with applications in epoxy curing.
Uses
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.
Uses
Triethylenetetramine is a selective CuII-chelator; crosslinking agent. Triethylenetetramine is undergoing trials for the treatment of heart failure in patients with diabetes.
Production Methods
TETA is manufactured by reacting ethylene dichloride and ammonia under controlled conditions.
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.
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.
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.
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.
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.]
Triethylenetetramine Preparation Products And Raw materials
Raw materials
Ammonium hydroxide Ethylenediamine Diethylenetriamine 1,2-Dichloroethane Polyethylene-polyamines Dichloroethane 1,4,7,10,13-Pentaazatridecane
Other names: N,N’-Bis(2-aminoethyl)ethane-1,2-diamine; TETA; Trien; Trientine (INN); Syprine (brand name)
CAS Number: 112-24-3
Properties
Chemical formula: C6H18N4
Molar mass: 146.238 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
Solubility in water: Miscible
log P: 1.985
Vapor pressure: <1 Pa (at 20 °C)
Refractive index (nD): 1.496
Uses
The reactivity and uses of TETA are similar to those for the related polyamines ethylenediamine and diethylenetriamine.
It is primarily used as a crosslinker (“hardener”) in epoxy curing.
TETA (Triethylenetetramine) could be used in the following applications:
APPLICATIONS
Bitumen Chemicals
Corrosion Inhibitors
Epoxy Curing Agents
Industrial Surfactants
Lube Oil and Fuel Additives
Mineral Processing Aids
Other applications
BRANCHES
Aerospace, Marine and Automotive
Construction and Housing
Consumer Electronics
Industrial Cleaners and Preservants
Mining
Road Construction
TETA is an organic compound that is a colorless, oily liquid that becomes yellowish due to air-oxidation.
The reactivity and uses of TETA are similar to those for the related polyamines ethylenediamine and diethylenetriamine.
Uses: As a crosslinker in epoxy curing, the hydrochloride salt is used as a chelating agent, and in coordination chemistry. CAS# (112-24-3)
Medical uses
Triethylenetetramine
The hydrochloride salt of TETA, referred to as trientine hydrochloride, is a chelating agent that is used to bind 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.
Trientine hydrochloride (brand name Syprine) was approved for medical use in the United States in November 1985.
Trientine tetrahydrochloride (brand name Cuprior) was approved for medical use in the European Union in September 2017.
It 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.
Trientine dihydrochloride (brand name Cufence) was approved for medical use in the European Union in July 2019.
It 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
TETA 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.
Coordination chemistry
TETA is a tetradentate ligand in coordination chemistry, where it is referred to as trien.
Octahedral complexes of the type M(trien)L2 can adopt several diastereomeric structures.
1,2-Ethanediamine, N1,N2-bis(2-aminoethyl)- [ACD/Index Name]
1,8-diamino-3,6-diazaoctane
112-24-3 [RN]
2,2,2-tetramine
203-950-6 [EINECS]
605448 [Beilstein]
MFCD00008169 [MDL number]
N,N’-Bis(2-aminoethyl)-1,2-ethandiamin [German] [ACD/IUPAC Name]
N,N’-Bis(2-aminoethyl)-1,2-ethanediamine [ACD/IUPAC Name]
N,N’-Bis(2-aminoéthyl)-1,2-éthanediamine [French] [ACD/IUPAC Name]
N,N’-Bis(2-aminoethyl)ethane-1,2-diamine
TETA
trientina [Spanish] [INN]
trientine [French] [INN]
Trientine [BAN] [INN] [JAN] [USAN]
trientinum [Latin] [INN]
triethylene tetramine
TRIETHYLENETETRAAMINE
Triethylenetetramine [Wiki]
(2-aminoethyl)({2-[(2-aminoethyl)amino]ethyl})amine
(2-aminoethyl){2-[(2-aminoethyl)amino]ethyl}amine
1,2-Ethanediamine, N,N’-bis(2-aminoethyl)-
1,2-Ethanediamine, N1,N2-bis(2-aminoethyl)-
1,4,7,10-Tetraazadecane
105093-20-7 [RN]
1067245-32-2 [RN]
110670-33-2 [RN]
14175-14-5 [RN]
253-854-3 [EINECS]
2-aminoethyl-[2-(2-aminoethylamino)ethyl]amine
3,6-Diazaoctane-1,8-diamine
3,6-diazaoctanediethylenediamine
3,6-Diazaoctanethylenediamin
305808-21-3 [RN]
38260-01-4 [RN]
39421-77-7 [RN]
4-04-00-01242 (Beilstein Handbook Reference) [Beilstein]
71124-11-3 [RN]
Araldite hardener HY 951
Araldite HY 951
CHEBI:39501
D014266
DB06824
EINECS 203-950-6
EPH 925
Ethanediamine, N,N’-bis(2-aminoethyl)-
Ethylenediamine, N,N’-bis(2-aminoethyl)-
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:39501
N,N’-Bis(2-aminoethyl)-1,2-diaminoethane
N,N-Bis(2-aminoethyl)-1,2-diaminoethane
N,N’-Bis(2-aminoethyl)ethylenediamine
N’-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine
N’-[2-(2-azanylethylamino)ethyl]ethane-1,2-diamine
N1,N1′-(Ethane-1,2-diyl)bis(ethane-1,2-diamine)
N1,N1′-(Ethane-1,2-diyl)diethane-1,2-diamine
STR03562
Syprine [Trade name]
Tecza
TETA; Trien; Trientine
Triaethylentetramine
trien
Trientene
trientina
trientinum
Trientinum [INN-Latin]
Triethyl enetetramine
Triethylenetetramine-d4 Tetrahydrochoride
UNII:SJ76Y07H5F
UNII-SJ76Y07H5F
WLN: Z2M2M2Z
YE6650000
триентин
ثلاثي إينتين
曲恩汀 [Chinese] [INN]
曲恩汀
3,6-diazaoctanethylenediamin
TRIETHYLENETETRAMINE
3,6-diazaoctanethylenediamin; triethylenetetramine
Triethylenetetramine
triethylenetetramine
Trientine
trientine
1,8-diamino-3,6-diaza-octano (es)
1,8-diamino-3,6-diazaoctaan (nl)
2,2′-(ethylendiimino)di(ethan-1-amin) (cs)
2,2’-(etylénbisimino)di(etán-1-amín) (sk)
3,6-Diasaoktaanetüleendiamiin (et)
3,6-Diatsaoktaanietyleenidiamiini (fi)
3,6-diazaoctan-1,8-diamin (da)
3,6-Diazaoctan-1,8-diamin (de)
3,6-diazaoctane-éthylènediamine;triéthylènetétramine (fr)
3,6-diazaoctanetilenediamina (ro)
3,6-diazaoctano-1,8-diamina (es)
3,6-diazaoctano-1,8-diamina (pt)
3,6-diazaoktan-1,8-diamin (no)
3,6-diazaoktan-1,8-diamin (sl)
3,6-diazaoktan-1,8-diamin (sv)
3,6-diazaoktanetilendiaminas (lt)
3,6-diazaoktano-1,8-diamina (pl)
3,6-diazaoktantilendiamin (hr)
3,6-diazaoktánetilén-diamin (hu)
3,6-diazaottano-1,8-diamina (it)
3,6-diazooktānetilēndiamīns (lv)
3,6-διαζαοκτανο-1,8-διαμίνη τριαιθυλενοτετραμίνη (el)
3,6-диазаоктанетилендиамин (bg)
N,N’-bis(2-aminoetylo)etylenodiamina (pl)
triethyleentetramine (nl)
triethylenteramin (cs)
triethylentetramin (da)
Triethylentetramin (de)
trietilen-tetramina (ro)
trietilenotetramina (pt)
trietilentetramin (hr)
trietilentetramin (sl)
trietilentetramina (es)
trietilentetramina (it)
trietilentetraminas (lt)
trietiléntetramin (hu)
trietilēntetraamīns (lv)
Trietyleenitetramiini (fi)
trietylenotetramina (pl)
trietylentetramin (no)
trietylentetramin (sv)
trietyléntetramín (sk)
trietüleentetraamiin (et)
triéthylènetétramine (fr)
триетилентетрамин (bg)
CAS names
1,2-Ethanediamine, N1,N2-bis(2-aminoethyl)-
IUPAC names
(2-aminoethyl)({2-[(2-aminoethyl)amino]ethyl})amine
1,2 Ethanediamine, N,N’-Bis(2-aminoethyl)-
1,2-Ethanediamine, N,N’-bis(2-aminoethyl)-
3,6-diazaoctanethylenediamin
3,6-diazaoctanethylenediamin triethylenetetramine
3,6-diazaoctanethylenediamin; triethylenenetetramine
3,6-diazaoctanethylenediamine
3,6-diazooctanethylenediamin
N N’-bis (2-aminoethyl) ethane.1,2 diamine
N’-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine
N,N'-bis(2-aminoethyl)ethane-1,2-diamine
N,N’-bis(2-aminoethyl)
N,N’-bis(2-aminoethyl)-1,2-ethane diamine
N,N’-bis(2-aminoethyl)ethane-1,2-diamine
N,N’-bis(2-aminoethyl)ethylene diamine
N,N-bis(2-aminoethyl)ethane-1,2-diamine
N,N′-Bis(2-aminoethyl) ethylendiamin
N-N’-bis(2-aminoethyl)ethane-1,2-diamine
trien
Trientine
trientine
trientine-
Triethlentetramine
TRIETHYLENETETRAMINE
Triethylenetetramine
triethylenetetramine
Segment by Application, the Triethylenetetramine (TETA) market is segmented into:
● Bitumen Chemicals
● Corrosion Inhibitors
● Epoxy Curing Agents
● Dye
● Resin
● Others
Triethylenetetramine is a mixture of four TETA ethyleneamines with close boiling points including linear, branched and two cyclic molecules.
Triethylenetetramine is a chemical substance that occurs in the form of an oily, dense yellowish liquid.
It has the molecular formula C6H18N4 and is widely used to manufacture corrosion inhibitor fluids.
The use of triethylenetetramine as a corrosion inhibitor is one of the many methods available to protect metals against corrosion.
Triethylenetetramine also serves as a corrosion inhibitor for zinc metal in a 0.5N HCl acid solution.
Triethylenetetramine is also referred to as TETA.
Corrosionpedia explains Triethylenetetramine (TETA)
Triethylenetetramine (TETA) is used as a corrosion inhibitor for metallic surfaces that are used in aqueous media applications.
It was empirically discovered that TETA is effective for corrosion prevention by introducing steel into chloride-contaminated concrete specimens through a technique called bidirectional electromigration rehabilitation (BIEM).
BIEM involves the following actions to successfully execute:
Introduction of an electric field between the steel cathodes and external anodes
Injection of TETA from the external electrolytes
Extraction of the chloride ions
Drilling to search for concentration profiles of the corrosion inhibitor, chlorides and hydroxyl ions after completion
1.2 Synonyms and Tradenames
1,2-Bis-(2-aminoethylamino)-ethan
1,2-Di-(aminoethylamino) -ethan
1,4,7,10-Tetraazadecan
1,8-Diamino-3,6-diaza-octan
2,2′-(1.2-Ethylenbis-amino-)bis-ethanamin
3,6-Diazaoctan-1,8-diamin
N,N’-Bis-(2-aminoethyl)-1,2-ethanediamine
N,N’-Bis-(2-aminoethyl)-ethylendiamin
N,N’-Di-(2-aminoethyl) -1.2-ethandiamin
N,N’-Di-(2-aminoethyl) -1.2-ethylendiamin
TETA
Tetramin
Trien
Triethylentetramin