112-24-3

Basic information

• Product Name: Triethylenetetramine
• Synonyms: N,N'-DI(2-AMINOETHYL)ETHYLENEDIAMINE;N,N'-BIS(2-AMINOETHYL)ETHYLENEDIAMINE;n,n'-bis(2-aminoethyl)-1,2-ethanediamine;Trientine;TRIEN;TRIETHYLENETETRAMINE;1,2-Ethanediamine, N,N'-bis(2-aminoethyl)-;1,2-Ethanediamine,N,N’-bis(2-aminoethyl)-
• CAS NO: 112-24-3
• Molecular Formula: C₆H₁₈N₄
• Molecular Weight: 146.23
• EINECS: 203-950-6
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Polyamines
• Mol File: 112-24-3.mol

Chemical Properties

• Melting Point: 12 °C(lit.)
• Boiling Point: 266-267 °C(lit.)
• Flash Point: 290 °F
• Appearance: colourless to light yellow or amber viscous liquid
• 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.)
• Storage Temp.: Store below +30°C.
• Solubility: alcohol: soluble
• PKA: pK1:3.32(+4);pK2:6.67(+3);pK3:9.20(+2);pK4:9.92(+1) (20°C)
• Explosive Limit: 0.7-7.2%(V)
• Water Solubility: SOLUBLE
• Sensitive: Moisture Sensitive
• Stability: Syable. Incompatible with strong oxidizing agents, strong acids.
• Merck: 14,9663
• BRN: 605448
• CAS DataBase Reference: Triethylenetetramine(CAS DataBase Reference)
• NIST Chemistry Reference: Triethylenetetramine(112-24-3)
• EPA Substance Registry System: Triethylenetetramine(112-24-3)

Safety Data

• Hazard Codes: C
• 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
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 112-24-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Triethylenetetramine is used as a selective CuII-chelator and is undergoing trials for the treatment of heart failure in patients with diabetes. It is also used in the synthesis of pharmaceuticals.
Used in Chemical Industry:
Triethylenetetramine is used as a crosslinking agent, amine hardener in epoxy resin of the bisphenol A type, and in the synthesis of detergents, softeners, and dyestuffs.
Used in Rubber Industry:
Triethylenetetramine is used as a vulcanization accelerator of rubber.
Used in Plastics and Resin Industry:
Triethylenetetramine is used as a thermosetting resin and an epoxy curing agent.
Used in Lubricants Industry:
Triethylenetetramine is used as a lubricating-oil additive.
Used in Analytical Chemistry:
Triethylenetetramine is used as an analytical reagent for Cu and Ni.
Used in Chelating Applications:
Triethylenetetramine is used as a chelating agent and for the treatment of Wilson's disease.

Production Methods

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

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

Nonflammable

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.

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.]

InChI:InChI:1S/C6H18N4/c7-1-3-9-5-6-10-4-2-8/h9-10H,1-8H2

Upstream product

• 64-17-5 ethanol 
• 107-15-3 ethylenediamine 
• 106-93-4 ethylene dibromide 
• 23435-23-6 1-<2-<(2-aminoethyl)amino>ethyl>aziridine 
• 7664-41-7 ammonia 
• 141-43-5 ethanolamine 
• 18907-76-1 2,2’-(ethane-1,2-diylbis(azanediyl))diacetonitrile 
• 120-93-4 imidazolidone 
• 497-25-6 dimethylenecyclourethane 
• 3217-00-3 N,N'-bis-(2-cyanoethyl)ethylenediamine 
• 38260-01-4 N,N'-bis(2-aminoethyl)ethane-1,2-diamine dihydrochloride 
• 24368-15-8 1,1'-(1,2-ethanediyl)di(2-imidazolidinone) 
• 166532-70-3 1,3-di(2-aminoethyl)-imidazolidin-2-one 
• 4961-40-4 triethylenetetramine tetrahydrochloride 

Downstream Products

• 85224-21-1 1,2-bis-(2-benzyl-4,5-dihydro-imidazol-1-yl)-ethane 
• 117098-87-0 N',N'''-dicyclohexyl-N,N''-(3,6-bis-cyclohexylcarbamoyl-3,6-diaza-octanediyl)-di-urea 
• 869-52-3 triethylenetetramine-N,N,N',N'',N''',N'''-hexaacetic acid 
• 3083-10-1 1,1,4,7,10,10-hexamethyltriethylenetetramine 
• 88658-04-2 N-{2-[2-(2-amino-ethylamino)-ethylamino]-ethyl}-oleamide 
• 103331-37-9 1,2-bis-(2-benzhydryl-4,5-dihydro-imidazol-1-yl)-ethane 
• 103331-67-5 1,2-bis-(2-diphenylaminomethyl-4,5-dihydro-imidazol-1-yl)-ethane 
• 103401-89-4 1,2-bis-[2-(N-benzyl-anilinomethyl)-4,5-dihydro-imidazol-1-yl]-ethane 
• 103858-32-8 1,2-bis-[2-(2-chloro-anilinomethyl)-4,5-dihydro-imidazol-1-yl]-ethane 
• 32582-85-7 N-{2-[2-(2-amino-ethylamino)-ethylamino]-ethyl}-stearamide 
• 112-57-2 N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine 
• 31295-46-2 tris(2-aminoethyl)-N,N,N'-ethyldiamine 
• 128750-47-0 N,N'-Bis-<2-(3-phenylpropylamino)-ethyl>-ethan-1,2-diamin-tetrahydrochlorid 
• 128924-89-0 12-(4-Nitrobenzyl)-1,4,7,10-tetraazacyclotridecane-11,13-dione 

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Multiwalled carbon nanotubes modified with triethylenetetramine (TETA) as an organic nanofiller was used in fabrication of polyvinyl chloride (PVC) nanofiltration membranes. The membranes were prepared by the phase separation method and immersion precipitation technique. For this purpose, variou...detailed

Full Length ArticleCytocompatibility of polyethylene grafted with Triethylenetetramine (cas 112-24-3) functionalized carbon nanoparticles08/27/2019

Various carbon nanostructures are widely researched as scaffolds for tissue engineering. We evaluated the surface properties and cell-substrate interactions of carbon nanoparticles functionalized with triethylenetetramine (CNPs) grafted polymer film. Two forms of polyethylene (HDPE, LDPE) were t...detailed

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Fenton-like reaction has been widely used to decompose organic pollutants via heterogeneous catalysis mechanism. Graphene-based materials have attracted lots of attention in catalysis process, but the catalysis efficiency and stability of these materials are still needed to improve. In this work...detailed

Full Length ArticleGraphene/Si solar cells employing Triethylenetetramine (cas 112-24-3) dopant and polymethylmethacrylate antireflection layer08/25/2019

We report the use of triethylenetetramine (TETA) as a dopant of graphene transparent conducting electrodes (TCEs) for Si heterojunction solar cells. The molar concentration (nD) of TETA is varied from 0.05 to 0.3 mM to optimize the graphene TCEs. The TETA-doped graphene/Si Schottky solar cells s...detailed

Data on Triethylenetetramine (cas 112-24-3) effect on steel-rebar corrosion-rate in concrete immersed in 0.5 M H2SO408/23/2019

In this article, the dataset on the effect of different triethylenetetramine (TETA: C6H18N4) concentrations on the corrosion-rate of steel-rebar embedment in steel-reinforced concrete immersed in 0.5 M H2SO4 (for simulating industrial/microbial environment) is presented. The corrosion test-data ...detailed

Adsorption of Cu2+ and Zn2+ on SBA-15 mesoporous silica functionalized with Triethylenetetramine (cas 112-24-3) chelating agent08/22/2019

Mesoporous silica particles, based on SBA-15 matrix, were functionalized with triethylenetetramine (TETA), and characterized by transmission electron microscopy (TEM), small angle X-ray scattering (SAXS), and N2-adsorption/desorption isotherms (surface area and pore size distribution). The funct...detailed

Mechanisms of Cu2+, Triethylenetetramine (cas 112-24-3) (TETA), and Cu-TETA sorption on rectorite and its use for metal removal via metal-TETA complexation08/20/2019

Uptake of metals, organics, and formation of metal-organic complexes on the surface or in the interlayer of clay minerals had been studied extensively over the last half century. In this study, we investigated the uptake mechanisms of Cu2+, triethylenetetramine (TETA), and Cu-TETA on rectorite a...detailed

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