TRIETHYLENETETRAMINE (Trietilentetramin)

CAS Number: 112-24-3

EC Number: 203-950-6

Synonyms:

Syprine; Trien; Trientine; Trientine Dihydrochloride; Trientine Hydrochloride; Triethylenetetramine; TRIETHYLENETETRAMINE; trientine; 112-24-3; Trien; TETA; Tecza; Triethylene tetramine; Araldite hardener HY 951; 1,2-Ethanediamine, N,N`-bis(2-aminoethyl)-; DEH 24; Araldite HY 951; 1,4,7,10-Tetraazadecane; 8-Diamino-3,6-diazaoctane; N,N`-Bis(2-aminoethyl)-1,2-ethanediamine; 3,6-Diazaoctane-1,8-diamine; N,N`-Bis(2-aminoethyl) Ethylenediamine; Trientinum [INN-Latin]; NSC 443; Trientina [INN-Spanish] UNII-SJ76Y07H5F; HY 951; triethylenetetraamine; 2,2,2-tetramine; CCRIS 6279; Ethylenediamine, N,N`-bis(2-aminoethyl)-; HSDB 1002; N1,N1`-(Ethane-1,2-diyl) bis(ethane-1,2-diamine); N,N`-bis(2-aminoethyl)ethane-1,2-diamine; EINECS 203; -950-6; UN2259; CHEMBL609; BRN 0605448; DEH24; N,N-Bis(2-aminoethyl)-1,2-; Diaminoethane; AI3-24384; Trientine Dihydrochloride; 1,4,7,10-Tetra-Azadecane; CHEBI:39501; 1,2-Ethanediamine, N1,N2-bis(2-Aminoethyl)-; VILCJCGEZXAXTO-; UHFFFAOYSA-N; HY951; MFCD00008169; SBB058767; NCGC00091695-01; NCGC00091695-03; DSSTox_CID_3702; DSSTox_RID_77156; DSSTox_GSID_23702; W-109064; (2-aminoethyl)({2-[(2-aminoethyl)amino]ethyl})amine; Trientinum; Trientina CAS-112-24-3; (2-aminoethyl){2-[(2-aminoethyl)amino]ethyl}amine; Trientene 1,6-diazaoctane; EPH 925; Triaethylentetramine; 3,8-diamine; Tomography, x-ray computed trientine; triethylene tetraamine; AC1L1KMQ; 1,7,10-Tetraazadecane bmse000773; AC1Q54MR; Texlin 300 (Salt/Mix); ACMC-1C99K; 3,6 -;Diazaoctanethylenediamin; SCHEMBL15439; WLN: Z2M2M2Z; 4-04-00-01242 (Beilstein Handbook Reference); BIDD:ER0303; BIDD:GT0014; NSC443; SCHEMBL6423840; SJ76Y07H5F; Triethylenetetramine (Trientine); DTXSID9023702 CTK8A9256; KS-00000WWF; NSC-443; MolPort-003-926-271; Tox21_111162; Tox21_201066; AN-643; ANW-16423; BDBM50323751; DNC011083; FCH931591; LS-549; STL477736; ZINC19364225; N,N`-Di(2-aminoethyl)ethylenediamine; AKOS006223906 Tox21_111162_1; Triethylenetetramine, >=97.0% (T); DB06824; Ethylenediamine,N`-bis(2-aminoethyl)-; MCULE-3203769500; NCGC00091695-04 NCGC00258619-01; AK161731; BC224800; BP-30180; CC-35339; Ethanediamine, N,N`-bis(2-aminoethyl)-; KB-62025; LP067913; OR012581; SBI-0206814.P001; DB-041060 N,N`-Bis(2-aminoethyl)-1,2-diaminoethane; TC-105168; Triethylenetetramine [UN2259] [Corrosive]; Triethylenetetramine, technical grade, 60% ST24048686; ST50824040; Triethylenetetramine [UN2259] [Corrosive]; 12T243C07166; AB00573244_07; N,N“-Bis-(2-amino-ethyl)-ethane-1,2-diamine; 33105-EP2272849A1; 133105-EP2295438A1; C-31298; N1,N1`-(Ethane-1,2-diyl) diethane-1,2-diamine; I05-0456; J-018026; N`-[2-(2-aminoethylamino)ethyl] ethane-1,2-diamine; N,N“-BIS(2-AMINOETHYL)-1,2-ETHANEDIAMINE; 105093-20-7; 110670-33-2; 14175-14-5; 193487-08-0; 39421-77-7; 71124-11-3; 801997-18-2; TRETLENTETRAMN; trietilentetraamine; tirietilen; tiriethylenetetraamin; thriethilentetraamine;trietilentetttramine; trietilentetramin; TET; tiriethilentetamine; TRIETHYLENETETRAMINE; Triethylenetetramine, Trietilentetramin; Trietilentetramine

Triethylenetetramine

Molecular FormulaC6H18N4

Average mass146.234 Da

Monoisotopic mass146.153152 Da

ChemSpider ID21106175

Triethylenetetramine (TETA)

Triethylenetetramine is a mixture of four TETA ethyleneamines with close boiling points including linear,

branched and two cyclic molecules.

These compounds are:

• Triethylenetetramine (CAS #000112-24-3, N,N´-bis (2-aminoethyl)-1,2-ethanediamine)

• Bis AEP (CAS #006531-38-0, N,N´-bis-(2-aminoethyl)piperazine)

• PEEDA (CAS #024028-46-4, N-[(2-aminoethyl)2-aminoethyl]piperazine)

• Branched Triethylenetetramine (CAS #004097-89-6, tris-(2-aminoethyl)amine)

APPLICATIONS OF Triethylenetetramine

• Asphalt additives

• Corrosion inhibitors

• Epoxy curing agents

• Hydrocarbon purification

• Lube oil and fuel additives

• Mineral processing aids

• Polyamide resins

• Surfactants

• Textile additives

SALES SPECIFICATIONS

Property Specifications Test Method*

Amines, mol wt < Triethylenetetramine, wt. % 2.0 max. ST-35.219

Assay, Triethylenetetramine, wt. % 97.0 min. ST-35.219

Color, Pt-Co 50 max. ST-30.12

Water, wt. % 0.50 max. ST-31.53, 6

*Methods of Test are available from Huntsman Corporation upon request.

ADDITIONAL INFORMATION

Regulatory Information

DOT/TDG Classification Triethylenetetramine

HMIS Code 3-1-0

WHMIS Classification D1B, D2A, D2B, E

Chemical Control Laws

Canada, DSL Listed

United States, TSCA Listed

Typical Physical Properties

Amine value, mg KOH/g 1443

Boiling point, °C (°F) 260 (500)

Coefficient of expansion, 1/°C, 20°C 0.00075

Density, g/ml, 20°C 0.981

Dielectric constant, 25°C and 1 kHz 11.4

Electrical conductivity, µmhos/cm, 24°C 0.038

Flash point, PMCC, °C (°F) 118 (245)

Freezing point, °C (°F) – 35 (-31)

Heat of formation, kcal/mol – 17.6

Heat of vaporization, BTU/lb 160.2

Heat of combustion, BTU/lb 14297

Ionization constants, Kb 1 6.7E-5

Ionization constants, Kb 2, 25°C 7.0E-6

Kinematic viscosity, cSt, 25°C 21.4

Kinematic viscosity, cSt, 40°C 10.3

Molecular weight, Linear component 146.24

Molecular weight , Typical product 151

Nitrogen content, % 37.0

pH (1 wt. % solution) 10

Refractive index, n 1.496 20D

Specific gravity, 25/25°C 0.983

Specific heat, cal/g °C, 20°C 0.482

Surface tension, dynes/cm, 20°C 22.2

Thermal conductivity,

cal/cm-sec-°C, 20°C 0.000450

Vapor pressure, mm Hg, 20°C (68°F) <0.1

Viscosity, cP, 20°C 13.9

Water solubility (%) >10

TOXICITY AND SAFETY

Because of the fragility of eye tissue, almost any eye contact with any ethyleneamine may cause irreparable damage,

even blindness. A single, short exposure to ethyleneamines, may cause severe skin burns, while a single, prolonged

exposure may result in the material being absorbed through the skin in harmful amounts. Exposures have caused

allergic skin reactions in some individuals. Single dose oral toxicity of ethyleneamines is low. The oral LD50 for rats is in

the range of 1000 to 4500 mg/kg for the ethyleneamines.

The principal hazards that arise in working with triethylenetetramine (Triethylenetetramine) are those associated with similar organic

amines; namely, a corrosive action on skin and eyes. Precautions should be taken to prevent contact with these parts of

the body such as by use of protective clothing and chemical goggles. If contact occurs, immediately flush the exposed

area with plenty of water for at least 15 minutes. Eye exposures should be examined by a physician. Contaminated

clothing should be laundered before reuse. If ingestion occurs, do not induce vomiting. Have the individual drink a large

amount of water (or milk, if Triethylenetetramine is readily available) and transport them to a medical facility immediately.

For additional information on the toxicity and safe handling of this product, consult the Material Safety Data Sheet

(Safety Data Sheet in Europe) prior to use of this product.

HANDLING AND STORAGE of Triethylenetetramine

In order to maintain the high degree of purity with which triethylenetetramine (TETA) is manufactured and shipped, the

following storage and handling considerations are recommended:

Dry Inert Gas Blanket

Triethylenetetramine should be stored under a dry inert gas blanket, such as nitrogen, to minimize contamination resulting from

contact with air and water.

Materials of Construction

If slight coloration of the ethyleneamine is acceptable, storage tanks may be made of carbon steel or black iron,

provided they are free of rust and mill scale. However, if the amine is stored in such tanks, color may develop due to

iron contamination. If iron contamination cannot be tolerated, tanks constructed of types 304 or 316 stainless steel

should be used. (Note: Because they are quickly corroded by amines, do not use copper, copper alloys, brass, or

bronze in tanks or lines.) Recommended storage construction for Triethylenetetramine is stainless steel.

Storage Temperature

Triethylenetetramine (TETA) has a pour point of -35.1°C. To avoid freezing, the product should be maintained above

this temperature.

Spills or Leaks

Small spills should be covered with inorganic absorbents and disposed of properly. Organic absorbents have been

known to ignite when contaminated with amines in closed containers. Certain cellulosic materials used for spill cleanup

such as wood chips or sawdust have shown reactivity with ethyleneamines and should be avoided. Large spills should

be contained and recovered. Water may be used for clean-up purposes, but avoid disposing of the material into sewers

or natural water bodies. Disposal should be in accordance with all federal, state and local laws, regulations, and

ordinances. Ethyleneamine leaks will frequently be identified by the odor (ammoniacal) or by the formation of a white,

solid, waxy substance (amine carbamates). Inorganic absorbents or water may be used to clean up the amine waste.

AVAILABILITY

Triethylenetetramine (TETA) is available in bulk and in 55-gallon drums of 200 Kg net weight. Samples are available by

contacting our sample department at 1-800-662-0924.

Triethylenetetramine appears as 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.

CAMEO Chemicals

Triethylenetetramine (TETA) is a highly selective divalent Cu(II) chelator and orphan drug that revereses copper overload in tissues. Triethylenetetramine s salt form, trientine (triethylenetetramine dihydrochloride or 2,2,2-tetramine) was introduced in 1969 as an alternative to D-penicillamine. Triethylenetetramine consists of a polyamine-like structure different from D-penicillamine, as Triethylenetetramine lack sulfhydryl groups. Triethylenetetramine was previously approved by FDA in 1985 as second-line pharmacotherapy for Wilson’s disease. Although penicillamine treatment is believed to be more extensive, Triethylenetetraminetherapy has been shown to be an effective initial therapy, even with patients with decompensated liver disease at the outset, and prolonged Triethylenetetraminetreatment is not associated with adverse effects as expected in penicillamine treatment. Triethylenetetramine ‘s clinical applications on cancer, diabetes mellitus, Alzheimer’s disease and vascular demetia are being studied.

DrugBank

Triethylenetetramine is an oral copper chelating agent used to treat Wilson disease. Trientine has not been associated with worsening of serum enzyme elevations during therapy or with cases of clinically apparent liver injury with jaundice.

Triethylenetetramine

Skeletal formula of triethylenetetramine

Ball and stick model of triethylenetetramine

Spacefill model of triethylenetetramine

Names

Other names of Triethylenetetramine

N,N’-Bis(2-aminoethyl)ethane-1,2-diamine; TETA; Trien; Trientine (INN); Syprine (brand name)

Identifiers of Triethylenetetramine

CAS Number of Triethylenetetramine

112-24-3 ☑

3D model (JSmol)

Interactive image

Beilstein Reference

605448

ChEBI

CHEBI of Triethylenetetramine :39501 ☑

ChEMBL

ChEMBL609 ☑

ChemSpider of Triethylenetetramine

21106175 ☑

ECHA InfoCard of Triethylenetetramine 100.003.591

EC Number of Triethylenetetramine

203-950-6

Gmelin Reference of Triethylenetetramine

27008

KEGG

C07166 ☑

MeSH Trientine

PubChem CID

5565

RTECS number

YE6650000

UNII

SJ76Y07H5F ☑

UN number 2259

CompTox Dashboard (EPA)

DTXSID9023702 Edit this at Wikidata

InChI[show]

SMILES[show]

Properties of Triethylenetetramine

Chemical formula of Triethylenetetramine

C6H18N4

Molar mass of Triethylenetetramine 146.238 g·mol-1

Appearance of Triethylenetetramine Colorless liquid

Odor of Triethylenetetramine Fishy, ammoniacal

Density of Triethylenetetramine 982 mg mL-1

Melting point of Triethylenetetramine -34.6 °C; -30.4 °F; 238.5 K

Boiling point of Triethylenetetramine 266.6 °C; 511.8 °F; 539.7 K

Solubility of Triethylenetetramine in water

Miscible

log P 1.985

Vapor pressure of Triethylenetetramine <1 Pa (at 20 °C)

Refractive index of Triethylenetetramine (nD)

1.496

Thermochemistry of Triethylenetetramine

Heat capacity of Triethylenetetramine (C)

376 J K-1 mol-1 (at 60 °C)

Pharmacology

ATC code

A16AX12 (WHO)

Hazards

GHS pictograms GHS05: Corrosive GHS07: Harmful

GHS Signal word Danger

GHS hazard statements

H312, H314, H317, H412

GHS precautionary statements

P273, P280, P305+351+338, P310

Flash point of Triethylenetetramine 129 °C (264 °F; 402 K)

Lethal dose or concentration (LD, LC):

LD50 (median dose)

550 mg kg-1 (dermal, rabbit)

2.5 g kg-1 (oral, rat)

Related compounds

Related amines

Ethylenediamine

Diethylenetriamine

Cyclam

Related compounds

Ethylenediaminetetraacetic acid

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

☑ verify (what is ☑☒ ?)

Infobox references

Triethylenetetramine (Triethylenetetramine 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. of 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.[1]

Uses of Triethylenetetramine

The reactivity and uses of Triethylenetetramine are similar to those for the related polyamines ethylenediamine and diethylenetriamine. It is primarily used as a crosslinker (“hardener”) in epoxy curing.[2]

The hydrochloride salt of Triethylenetetramine, 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.[3]

Cost

In the United States, Valeant Pharmaceuticals International raised the price of its Syprine brand of Triethylenetetraminefrom $625 to $21,267 for 100 pills over five years. The New York Times said that this “egregious” price increase caused public outrage. Teva Pharmaceuticals developed a generic, which patients and doctors expected to be cheaper, but when it was introduced in February, 2018, Teva’s price was $18,375 for 100 pills. Aaron Kesselheim, who studies drug pricing at Harvard Medical School, said that drug companies price the product at what they think the market will bear.[4]

Production

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.[2][5]

Coordination chemistry

Triethylenetetramine is a tetradentate ligand in coordination chemistry, where it is referred to as trien.[6] Octahedral complexes of the type M(trien)Cl3 can adopt several diastereomeric structures, most of which are chiral.

Triethylenetetramine (TETA)/Ethanol Solutions

Zheng et al. have reported that triethylenetetramine (TETA) dissolved in ethanol can produce a solid precipitate after CO2 absorption (Figure 12(a) and (b)), which can then be easily separated and regenerated.19 In comparison, a Triethylenetetramine /water solution does not form any precipitates after CO2 absorption. The TTriethylenetetramine/ethanol solution offers several advantages for CO2 capture in regard to absorption rate, absorption capacity, and absorbent regenerability. Both the rate and capacity of CO2 absorption with the Triethylenetetramine/ethanol solution are significantly higher than those of a Triethylenetetramine/water solution. This is because ethanol cannot only promote the solubility of CO2 in the liquid phase but can also facilitate the chemical reaction between Triethylenetetramineand CO2. This approach is found able to capture 81.8% of the absorbed CO2 in the solid phase as Triethylenetetramine-carbamate (Figure 12(c)). The absorption-desorption tests using a temperature-swing process reveals that the absorption performance of the Triethylenetetramine /ethanol solution is relatively stable (Figure 12(d)). One limitation of using the Triethylenetetramine/ethanol solution for CO2 removal is that ethanol is a solvent with a high vapor pressure and measures must be taken to mitigate solvent evaporation.

Name

Triethylenetetramine

Accession Number

DB06824

Type

Small Molecule

Groups

Approved, Investigational

Description

Triethylenetetramine (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. Triethylenetetramineconsists of a polyamine-like structure different from D-penicillamine, as Triethylenetetramine lack sulfhydryl groups. Triethylenetetramine was previously approved by FDA in 1985 as second-line pharmacotherapy for Wilson’s disease. Although penicillamine treatment is believed to be more extensive, Triethylenetetraminetherapy has been shown to be an effective initial therapy, even with patients with decompensated liver disease at the outset, and prolonged Triethylenetetraminetreatment is not associated with adverse effects as expected in penicillamine treatment. Triethylenetetramine’s clinical applications on cancer, diabetes mellitus, Alzheimer’s disease and vascular demetia are being studied.

Abstract

Telomerase inhibition can be achieved by stabilization of G-quadruplex structure. Triethylene tetraamine, a small linear molecule, has been identified as a potent telomerase inhibitor. It stabilizes both intra- and inter-molecular G-quadruplexes and shows a good differential between potent telomerase inhibition and acute cytotoxicity.

A small linear molecule, triethylene tetraamine, has been identified as potent telomerase inhibitor. Triethylenetetramine stabilizes both intra- and inter-molecular G-quadruplexes and shows a good differential between potent telomerase inhibition and acute cytotoxicity.

Description of Triethylenetetramine

Application of Triethylenetetramine

Triethylenetetramine has been used as an additive to enhance the peak resolution ability of capillary zone electrophoresis (CZE) running buffer system to separate and quantitate the monoclonal antibodies by the CZE method.[1] Triethylenetetramine may be used for the amination of polyacrylonitrile fibers to form novel fiber catalysts for Knoevenagel condensation in aqueous media.[2] Triethylenetetraminealso acts as a copper (II)-selective chelator.[3]Triethylenetetramine may also be used as a growth-orientator in the formation of 1D zinc sulfide nanoarchitectures.[4]

Triethylenetetramine is a mixture of four TETA ethyleneamines with close boiling points including linear, branched and two cyclic molecules.

These compounds are:

• Triethylenetetramine (CAS #000112-24-3, N,N´-bis (2-aminoethyl)-1,2-ethanediamine)

• Bis AEP (CAS #006531-38-0, N,N´-bis-(2-aminoethyl)piperazine)

• PEEDA (CAS #024028-46-4, N-[(2-aminoethyl)2-aminoethyl]piperazine)

• Branched TETA (CAS #004097-89-6, tris-(2-aminoethyl)amine)

Triethylenetetramine is 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. Triethylenetetramine S Used in detergents and in the synthesis of dyes, pharmaceuticals and other chemicals.

Triethylenetetramine is COLOURLESS-TO-YELLOW HYGROSCOPIC VISCOUS LIQUID WITH CHARACTERISTIC ODOUR.

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 Triethylenetetramine. These are used in the paper industry as wet-strength additives for liner board, toweling, tissue and sanitary applications.

• The ethoxylated products of Triethylenetetramine are curing agents for epoxy resins. The largest application is surface coatings (35%).

• Imidazolines from the condensation of Triethylenetetramine 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 Triethylenetetramine are mostly used as curing agents for epoxy surface coatings.

General Description

Triethylenetetramine S A yellowish liquid. Less dense than water. Combustible, though may be difficult to ignite. Triethylenetetramine S Corrosive to metals and tissue, Vapors heavier than air. Toxic oxides of nitrogen produced during combustion. Triethylenetetramine S Used in detergents and in the synthesis of dyes, pharmaceuticals and other chemicals.

Air & Water Reactions

Soluble in water.

Reactivity Profile

Triethylenetetramine is a strong base; reacts violently with strong oxidants; attacks aluminum, zinc, copper and its alloys.

APPLICATIONS of Triethylenetetramine

Triethylenetetramine has similar activity and uses to ethylenediamine and diethylenetriamine.

Triethylenetetramine finds use as a crosslinker (hardener) in epoxy curing, as an intermediate in the synthesis of cellulose chemicals and paper auxillaries, and in lube oil and fuel additives.

• Asphalt additives

• Corrosion inhibitors

• Epoxy curing agents

• Hydrocarbon purification

• Lube oil and fuel additives

• Mineral processing aids

• Polyamide resins

• Surfactants

• Textile additives

Trietilentetramin

trietilentetramin

Trietilentetraminin iskelet formülü

Trietilenetetraminin top ve çubuk modeli

Trietilenetetraminin boluk doldurma modeli

simler

Dier isimler

N , N ‘ -Bis (2-aminoetil) etan-1,2-diamin; TETA; trien; Trientin ( INN ); Syprine (marka ad)

Trietilentetramin Tanmlayclar

Trietilentetramin CAS numaras

112-24-3 ☑

3D model ( JSmol )

Etkileimli görüntü

Beilstein Referans

605448

Chebi

Trietilentetramin Chebi: 39501 ☑

ChEMBL

ChEMBL609 ☑

ChemSpider

21106175 ☑

Trietilentetramin ECHA Bilgi Kart 100.003.591

Trietilentetramin EC Numaras

203-950-6

Gmelin Referans

27008

Trietilentetramin KEGG

C07166 ☑

Trietilentetramin MeSH trientin

Trietilentetramin PubChem CID

5565

Trietilentetramin RTECS numaras

YE6650000

Trietilentetramin UNII

SJ76Y07H5F ☑

BM numaras 2259

CompTox Kontrol Paneli ( EPA )

DTXSID9023702 Bunu Wikidata’da düzenle

InChl[göstermek]

Smiles[göstermek]

Trietilentetramin Özellikleri

Trietilentetramin Kimyasal formül

C 6 , H 18 , N 4

Trietilentetramin Molar kütle 146.238 g · mol -1

Trietilentetramin Görünüm Renksiz sv

Trietilentetramin Koku Balk, amonyak

TrietilentetraminYounluk 982 mg mL -1

TrietilentetraminErime noktas -34.6 ° C; -30.4 ° F; 238,5 K

Trietilentetramin Kaynama noktas 266.6 ° C; 511.8 ° F; 539,7 K

sudaki çözünürlük

kartrlabilir

log P 1,985

Trietilentetramin Buhar basnc <1 Pa (20 ° C’de)

Trietilentetramin Krlma indisi ( n D )

1,496

Termokimya

Trietilentetramin Is kapasitesi ( C )

376 JK -1 mol -1 (60 ° C’de)

Farmakoloji

ATC kodu

A16AX12 ( WHO )

Tehlikeler

GHS piktogramlar GHS05: Andrc GHS07: Zararl

GHS Sinyal kelimesi Tehlike

GHS tehlike bildirimleri

H312 , H314 , H317 , H412

GHS ihtiyati beyanlar

P273 , P280 , P305 + 351 + 338 , P310

Trietilentetramin Alevlenme noktas 129 ° C (264 ° F; 402 K)

Ölümcül doz veya konsantrasyon (LD, LC):

LD 50 ( ortalama doz )

550 mg kg -1 (dermal, tavan)

2,5 g kg -1 (oral, sçan)

Bantl bileikler

lgili aminler

Etilendiamin

dietilentriamin

cyclam

Bantl bileikler

Etilendiamintetraasetik asit

Aksi belirtilmedikçe, standart halindeki malzemeler için veriler verilir (25 ° C [77 ° F], 100 kPa’da).

☑ dorula ( nedir ?) ☑☒

Bilgi kutusu referanslar

Trietilentetramin ( TETA ve trien olarak da adlandrlr), trientin ( INN ), bir bir organik bileik ile formül [CH 2 NHCH 2 , CH 2 , NH 2 ] 2 . Bu yal sv renksizdir, ancak birçok amin gibi hava oksidasyonundan kaynaklanan safszlklar nedeniyle sarms bir renk alr. Polar çözücülerde çözünür. Dallanm izomer tris (2-aminoetil) amin ve piperazin türevleri, ticari Trietilentetramin numunelerinde de bulunabilir. [1]

Trietilentetramin Kullanmlar

Trietilentetramin’nn reaktivitesi ve kullanmlar, ilgili poliaminler etilendiamin ve dietilentriamininkilere benzer . Esas olarak epoksi kürlemesinde bir çapraz balayc (“sertletirici”) olarak kullanlr . [2]

Trietilentetramin hidroklorür tuzu, trientin hidroklorür Olarak adlandrlr , a, kenetleme maddesi balama ve çkarmak için kullanlan bakr tedavi etmek için vücuttaki Wilson hastal , özellikle tolere edemeyen olanlarda, penisilamin . Bazlar birinci basamak tedavi olarak trientini önerir, ancak penisillamin ile ilgili deneyim daha kapsamldr. [3]

Trietilentetramin Maliyet

Amerika Birleik Devletleri’nde Valeant Pharmaceuticals International , be yl boyunca 100 hap için Syprine marka Trietilentetramin’nn fiyatn 625 dolardan 21.267 dolara çkard. New York Times, bu “Aleni” fiyat art halk arasnda tepkiye neden olduunu belirtti. Teva Pharmaceuticals , hastalar ve doktorlarn daha ucuz olmas beklenen bir jenerik gelitirdi, ancak ubat 2018’de piyasaya sürüldüünde, Teva’nn fiyat 100 hap için 18.375 dolard. Harvard Tp Okulu’nda ilaç fiyatlandrmas okuyan Aaron Kesselheim, ilaç irketlerinin ürünü pazarn tayacan düündükleri fiyata fiyatlandrdn söyledi. [4]

Trietilentetramin Üretim

Trietilentetramin, etilendiamin veya etanolamin / amonyak karmlarnn bir oksit katalizörü üzerinde stlmasyla hazrlanr . Bu ilem çeitli aminleri, özellikle damtma ve süblimasyon ile ayrlan etilen aminleri verir. [2] [5]

Trietilentetramin Koordinasyon kimyas

Trietilentetramin, bir tetradentat bir ligand olarak koordinasyon kimyas bu trien olarak ifade edilir. [6] tipi M (trien) oktahedral kompleksi C 3 En olan birkaç diastereomerik yaplar, benimseyebilir kiral .

Trientine (INN) olarak da adlandrlan trietilentetramin (Trietilentetramin ve trien), [CH2NHCH2CH2NH2] 2 formülüne sahip organik bir bileiktir. Bu yal sv renksizdir, ancak birçok amin gibi hava oksidasyonundan kaynaklanan safszlklar nedeniyle sarms bir renk alr. Trietilentetramin, polar çözücüler içinde çözünür. Dall izomer tris (2-aminoetil) amin ve piperazin türevleri, ticari Trietilentetramin numunelerinde de bulunabilir. [1]

Trietilentetramin Kullanmlar

Trietilentetraminin reaktivitesi ve kullanmlar, ilgili poliaminler etilendiamin ve dietilentriamininkilere benzerdir. Esas olarak epoksi kürlemesinde bir çapraz balayc (“sertletirici”) olarak kullanlr. [2]

Trietilen hidroklorür olarak adlandrlan Trietilentetraminin hidroklorür tuzu, Wilson hastaln, özellikle penisillamine kar toleranssz olanlarda tedavi etmek için vücuttaki bakrn balanmas ve çkarlmas için kullanlan bir kenetleme maddesidir. Bazlar birinci basamak tedavi olarak trientini önerir, ancak penisillamin ile ilgili deneyim daha kapsamldr. [3]

Maliyet

Amerika Birleik Devletleri’nde Valeant Pharmaceuticals International, be yl boyunca 100 hap için Syprine Triethylenetetramine markasnn fiyatn 625 dolardan 21.267 dolara çkard. New York Times, bu “berbat” fiyat artnn kamu öfkesine neden olduunu söyledi. Teva Pharmaceuticals, hastalar ve doktorlarn daha ucuz olmas beklenen bir jenerik gelitirdi, ancak ubat 2018’de piyasaya sürüldüünde, Teva’nn fiyat 100 hap için 18.375 dolard. Harvard Tp Okulu’nda ilaç fiyatlandrmas inceleyen Aaron Kesselheim, ilaç irketlerinin ürünü pazarn tayacan düündükleri fiyata fiyatlandrdn söyledi. [4]

Üretim

Trietilentetramin, etilendiamin veya etanolamin / amonyak karmlarnn bir oksit katalizörü üzerinde stlmasyla hazrlanr. Bu ilem, çeitli aminleri, özellikle damtma ve süblimleme ile ayrlan etilen aminleri verir. [2] [5]

Kimya koordinasyonu

Trietilentetramin, trien olarak adlandrlan koordinasyon kimyasnda bir tetradentat liganddr. [6] M (trien) Cl3 tipinin oktahedral kompleksleri, çou kiral olan birkaç diastereomerik yap benimseyebilir.

Trietilentetramin (TETA) / Etanol Çözeltileri

Zheng ve di. etanol içinde çözülmü trietilentetraminin (TETA), CO2 emiliminden sonra kat bir çökelti üretebileceini bildirmitir (ekil 12 (a) ve (b)), bu daha sonra kolayca ayrlabilir ve yeniden üretilebilir.19 Karlatrmada, bir Trietilentetramin/ su çözeltisi CO2 emiliminden sonra herhangi bir çökelti meydana getirir. Trietilentetramin/ etanol çözeltisi, sourma oran, sourma kapasitesi ve emici yenilenebilirlik açsndan CO2 yakalama için çeitli avantajlar sunmaktadr. Trietilentetramin/ etanol çözeltisi ile hem CO2 emilim hz hem de kapasitesi, bir Trietilentetramin/ su çözeltisininkinden önemli ölçüde daha yüksektir. Bunun nedeni, etanolün sadece sv fazda CO2 çözünürlüünü destekleyememesi, ayn zamanda Trietilenetramin ve CO2 arasndaki kimyasal reaksiyonu da kolaylatrmasdr. Bu yaklamn TETA-karbamat olarak kat fazda emilen CO2’nin% 81.8’ini yakalayabildii bulunmutur (ekil 12 (c)). Bir scaklk salnm ilemi kullanlarak emilim – desorpsiyon testleri, Trietilentetramin/ etanol çözeltisinin emilim performansnn nispeten kararl olduunu gösterir (ekil 12 (d)). CO2 giderimi için Trietilentetramin/ etanol çözeltisinin kullanlmasnn bir snrlamas, etanolün yüksek buhar basncna sahip bir çözücü olmas ve çözücü buharlamasn azaltmak için önlemler alnmas gerektiidir.

trietilentetramin

Trietilentetramin Eriim numaras

DB06824

tip

Küçük Molekül

Gruplar

Onayl, Soruturma

Açklama

Trietilentetramin (TETA), dokulardaki bakr ar yüklenmesini göz önünde bulunduran oldukça seçici bir iki deerlikli Cu (II) elat ve yetim ilacdr. Tuz formu, trientin (trietilentetramin dihidroklorür veya 2,2,2-tetramin), D-penisillamine alternatif olarak 1969 ylnda eklendi. Trietilentetramin, Trietilentetramin sülfhidril gruplarna sahip olmadndan, D-penisilaminden farkl bir poliamin benzeri yapdan oluur. Trietilentetramin daha önce 1985 ylnda Wilson hastal için ikinci basamak farmakoterapi olarak FDA tarafndan onaylanmt. Penisillamin tedavisinin daha kapsaml olduuna inanlmakla birlikte, balangçta dekompanse karacier hastal olan hastalarda bile Trietilentetrameterapinin etkili bir balangç tedavisi olduu gösterilmitir ve uzun süreli Trietilentetramin tedavisi, penisilinlamin tedavisinde beklendii gibi yan etkilerle ilikili deildir. Trietilentetraminin kanser, diabetes mellitus, Alzheimer hastal ve vasküler demetia üzerine klinik uygulamalar aratrlmaktadr.

Öz

Telomeraz inhibisyonu, G-quadruplex yapsnn stabilizasyonu ile elde edilebilir. Küçük bir lineer molekül olan trietilen tetraamin, güçlü bir telomeraz inhibitörü olarak tanmlanmtr. Hem moleküler hem de moleküller aras G-dört kutuplarn stabilize eder ve güçlü telomeraz inhibisyonu ile akut sitotoksisite arasnda iyi bir fark gösterir.

Küçük bir dorusal molekül olan trietilen tetraamin, güçlü telomeraz inhibitörü olarak tanmlanmtr. Triethylenetetramin hem moleküler hem de moleküller aras G-dört kutuplarn stabilize eder ve güçlü telomeraz inhibisyonu ile akut sitotoksisite arasnda iyi bir fark gösterir.

Trietilentetramin açklamas

Trietilentetramin Uygulamas

Trietilenetetramin, klcal bölge elektroforezi (CZE) çalan tampon sisteminin zirve çözünürlük yeteneini arttrmak için kullanlmtr ve monoklonal antikorlar CZE yöntemiyle ayrmak ve nicelemek için kullanlmtr. [1] Trietilentetramin, poliakrilonitril liflerinin aminletirilmesi için, sulu ortamda Knoevenagel younlamas için yeni fiber katalizörler oluturmak üzere kullanlabilir. [2] Trietilentetramineal ayrca bakr (II) seçici bir kenetleyici görevi görür.

Trietilentetramin Kullanmlar

Trietilentetramin Maliyet

Trietilentetramin Üretim

Trietilentetramin Koordinasyon kimyas

Trietilentetramin, dorusal, dallanm ve iki siklik molekül içeren yakn kaynama noktalarna sahip dört Trietilentetraminetilenamin karmnn bir karmdr. Bu bileikler unlardr:

• Trietilentetramin(CAS # 000112-24-3, N, N`-bis (2-aminoetil) -1,2-etandiamin)

Bis AEP (CAS # 006531-38-0, N, N`-bis- (2-aminoetil) piperazin)

• PEEDA (CAS # 024028-46-4, N – [(2-aminoetil) 2-aminoetil] piperazin)

• Dallanm Trietilentetramin(CAS # 004097-89-6, tris- (2-aminoetil) amin)

Trietilentetramin sarms bir svdr. Sudan daha az youn. Trietilentetramin Yanabilir, ancak tutumas zor olabilir. Trietilentetramin Metallere ve dokulara kar koroziftir. Trietilentetramin Buhar havadan daha ar. TrietilentetraminYanma esnasnda zehirli oksit üretilir.

Trietilentetramin Deterjanlarda, boyarmaddelerde, farmasötik maddelerde ve dier kimyasal maddelerde kullanlr.

Trietilentetramin, KARAKTERSTK KOKULU RENKL SUTKARLI HGROSKOPK VSKOZ SIVI ÇNDR.

Trietilentetramin sulu amonyak ile reaksiyona girerek üretilir, 2-dikloroetan yer alr. Bu ilem, etilenaminlerin tüm ailesini üretir:

Etilendiamin, piperazin, dietilentriamin, trietilentetramin, tetraetilentepentamin, pentaetilenheksamin ve aminoetilpiperazin. Bu poliaminler, hidroklorür tuzlar olarak üretilir ve serbest aminleri elde etmek için tipik olarak sulu kostik soda ile nötralize edilmelidir.

Nötrletirme aamasnda üretilen yan ürün tuzu ayrtrlr ve ayr ürünler, fraksiyonel damtma ile izole edilir.

Trietilentetramin, bir dizi üretim sürecinde bir ara madde olarak kullanlabilir:

• Poliizobutenilüksinik anhidrit ile reaksiyon, karlk gelen otor ya için kusursuz, dispersan-deterjan katk maddeleri olan polibütenilsukinimidler.

• Poliamid-etilklorohidrin reçineleri, epiklorohidrin`in, adipik asit ve Trietilentetramin`nn polimerizasyonu ile oluturulanlar gibi bir poliamid ile reaksiyona sokulmasyla üretilir. Bunlar kât endüstrisinde astar tahtas, havlu, doku ve shhi uygulamalar için slak mukavemetli katk maddeleri olarak kullanlrlar.

• Trietilentetramin`nn etoksillenmi ürünleri epoksi reçineleri için kürleme ajanlardr. En büyük uygulama yüzey kaplamalardr (% 35).

• Trietilentetramin`nn iki mol ya asidi ile younlatrlmasndan imidazolinler, kuma yumuatclar, asfalt emülgatörler, ya sahas korozyon inhibitörleri, cevher flotasyon ajanlar ve epoksi kürleme ajanlar olarak kullanlan katyonik yüzey aktif cisimleridir.

• Trietilentetramin ile dimer asitlerin polimerizasyonundan elde edilen reaktif poliamidler çounlukla epoksi yüzey kaplamalar için kürleme maddeleri olarak kullanlr.

Genel açklama

Trietilentetramin S Sarms bir sv. Sudan daha az youn. Yanabilir, ancak tutumas zor olabilir. Trietilentetramin, metallerden ve dokulardan arndrlm, havadan daha ar buharlar. Yanma esnasnda zehirli oksit oksitler üretilir.

Trietilentetramin Deterjanlarda, boyar maddelerin, ilaçlarn ve dier kimyasallarn sentezinde kullanlr.

Hava ve Su Reaksiyonlar

Suda çözünebilir.

Reaktivite Profili

Trietilentetramin güçlü bir bazdr; kuvvetli oksidanlarla iddetle reaksiyona girer; alüminyum, çinko, bakr ve alamlarna saldrr.

UYGULAMALAR

Trietilentetramin benzer etkiye sahiptir ve etilendiamin ve dietilentriamin kullanr. TETA, epoksi kürlenmesinde, selüloz kimyasallarnn ve kat yardmclarnn sentezinde bir ara madde olarak ve yalama ya ve yakt katklarnda bir çapraz balayc (sertletirici) olarak kullanlmaktadr.

• Asfalt katk maddeleri

• Korozyon önleyicileri

• Epoksi kürleme ajanlar

• Hidrokarbon saflatrmas

• Yalama yalar ve yakt katklar

• Mineral ileme yardmclar

• Poliamid reçineler

• Yüzey aktif maddeler

• Tekstil katk maddeleri

Triéthylènetétramine

Image illustrative de l’article Triéthylènetétramine

Identification

DCI Trientine

Nom UICPA N,N’-bis(2-aminoéthyl)éthane-1,2-diamine

Synonymes

trien

TETA

3,6-diazaoctane-1,8-diamine

No CAS 112-24-3

38260-01-4 (dihydrochlorure)

4961-40-4 (tétrahydrochlorure)

305808-21-3 (hydrate, .xH20)

No ECHA 100.003.591

No CE 203-950-6

No RTECS YE6650000

Code ATC A16AX12

PubChem 5565

ChEBI 39501

SMILES

[Afficher]

InChI

[Afficher]

Apparence liquide huileux incolore (pur) à jaune (technique) avec une légère odeur de poisson et d’ammoniac1

Propriétés chimiques

Formule brute C6H18N4 [Isomères]

Masse molaire3 146,2339 ± 0,0069 g/mol

C 49,28 %, H 12,41 %, N 38,31 %,

pKa 9,92 à 20 °C2

Propriétés physiques

T° fusion 12 °C1,2,4

T° ébullition 278 °C1

266-267 °C2,4

Solubilité miscible avec l’eau1 et avec l’acétone, l’éthanol et le méthanol, le diéthyléther5

soluble dans le n-heptane5

Masse volumique 0,982 g cm-3 à 25 °C4

Point d’éclair 129 °C (coupelle fermée)4

Pression de vapeur saturante 1,3 Pa à 20 °C1

4,12 × 10-4 mmHg à 25 °C2

Propriétés optiques

Indice de réfraction {displaystyle {textit {n}}_{D}^{20}}textit{n}_{D}^{20} = 1,4964

Précautions

SGH1,4

SGH05 : Corrosif

H312, H314, H317, H412, P273, P280, P301+P330+P331, P302+P352, P305+P351+P338, P309+P310,

[+]

Transport4

–

2259

[+]

Écotoxicologie

DL50 1600 mg/kg (souris, oral)2

2500 mg/kg (rat, oral)2

5500 mg/kg (lapin, oral)2

350 mg/kg (souris, i.v.)2

468 mg/kg (souris, i.p.)2

LogP (octanol/eau) -2.6502

Unités du SI et CNTP, sauf indication contraire.

modifier Consultez la documentation du modèle

La triéthylènetétramine, plus couramment appelée trien ou Triethylenetetramineen chimie et trientine (DCI) en biologie est un composé organique de formule semi-développée NH2CH2CH2NHCH2CH2NHCH2CH2NH2 et donc de la famille des amines aliphatiques. Comme son nom l’indique, elle est composée de quatre fonctions amines séparées par trois ponts éthylène (-CH2CH2-).

Synthèse

La triéthylènetétramine est obtenue par chauffage d’éthylènediamine ou par réaction d’une solution d’ammoniac avec du 1,2-dichloroéthane6. Dans une telle réaction, de nombreuses d’éthylèneamines sont formées comme l’éthylènediamine, la diéthylènetriamine, les triéthylènetétramines, les tétraéthylènepentamines, les pentaéthylènehexamines et les aminoéthylpipérazines. Ces polyamines sont obtenues sous forme de chlorhydrates et doivent être neutralisées (en général avec une solution aqueuse d’hydroxyde de sodium) afin de produire les amines libres qui sont ensuite séparées les unes des autres par distillation et sublimation.

En 1990, le volume de production de triéthylènetétramine en Allemagne s’est élevé à 1200 à 1 500 t par an (par exemple, par Bayer AG), 6 000 t par an aux Pays-Bas, 1 800 t par an au Japon et plus de 11 000 t par an aux États-Unis7. Ceci en fait l’une des substances chimiques qui sont produites en grande quantité. C’est l’un des composés chimiques produits en grande quantité (High production volume chemicals (en), HPVC) et pour l’Organisation de coopération et de développement économiques (OCDE), une base de données sur les dangers possibles („Screening Information Dataset”, SIDS)7.

Propriétés

La triéthylènetétramine montre la réactivité typique des amines (similaire à l’éthylènediamine et à la diéthylènetriamine). Le point de fusion est plus faible pour le produit technique (jusqu’à -35 °C) que pour la substance pure6.

Triethylenetetraminese présente sous la forme d’un liquide huileux incolore qui, dans la forme technique, a généralement une couleur jaunâtre en raison des impuretés causées par l’oxydation dans l’air. TETA technique contient jusqu’à 40 % des sous-produits sous la forme des isomères ramifiés comme la tris(2-aminoéthyl)amine ou d’autres composés organiques tels que le N, N’-bis(2-aminoéthyl)pipérazine, la N-(1-(2-pipérazine-1-yl-éthyl))-éthane-1,2-diamine ou la diéthylènetriamine6.

Usages

La triéthylènetétramine est utilisé pour la production d’agents mouillants, d’émulsifiants, d’additifs textiles, d’acrylates et des résines d’amines et amides (aminoplaste), et d’additifs pour lubrifiants et carburants (polybuténylsuccinimides). Elle est largement utilisée comme agent de durcissement pour les systèmes de résine époxy à deux composants, pour l’imprégnation et le revêtement des sols, ainsi que pour la production de mortiers et de mastics.

Chimie de coordination

La triéthylènetétramine est un ligand tétradentate utilisé comme un agent chélatant dans la chimie des complexes (Abréviation IUPAC : trien)8. Les complexes octaédriques du type M(trien)Cl3 peuvent adopter plusieurs structures diastéréoisomères, la plupart d’entre elles étant de surcroît chirales9. Trien forme par exemple avec les ions cuivre divalent un complexe bleu-foncé très soluble dans l’eau. Ceci peut être mis à profit pour complexer le cuivre dans la maladie de Wilson.

En médecine, le dichlorhydrate de trientine est approuvée comme médicament pour le traitement de la maladie de Wilson (maladie du surstockage de cuivre). Les bonnes propriétés de complexation du cuivre par la triéthylènetétramine sont utilisées pour lier et éliminer le cuivre en excès dans le corps, en particulier pour les malades de Wilson qui sont intolérants à la pénicillamine. Certains spécialistes recommandent la trientine en traitement de première intention, mais les expériences avec la pénicillamine sont plus courantes10. En outre, la trientine montre des effets anti-angiogénique et inhibiteur de la télomérase, c’est pourquoi elle est considérée avoir un potentiel prometteur dans le traitement du cancer11.

Hydrochlorure de triéthylènetétramine

Il existe au moins deux hydrochlorures de cette tétramine :

Le dihydrochlorate (2 HCl) de numéros CAS 38260-01-4, de numéro EINECS 253-854-3 et d’ InChiKey WYHIICXRPHEJKI-UHFFFAOYSA-N a le numéro RTECS KH8587085 et SGH 07 avec H315, H319, H335 et P261, P305+P351+P33812.

Le tétrahydrochlorure (4 HCl) de numéro CAS 4961-40-4, de numéro EINECS 203-950-6 et d’ InChiKey OKHMDSCYUWAQPT-UHFFFAOYSA-N a le numéro RTECS KH8587087 et SGH 07 et 08 avec H315, H319, H335, H351 et P261, P281, P305+P351+P338. Il fond à 269-270 °C13.

Hydrate de triéthylènetétramine

De formule chimique NH2CH2CH2(NHCH2CH2)2NH2·xH2O, l’hydrate de triéthylènetétramine a pour numéro CAS 305808-21-3, numéro EINECS 253-854-3 et InChiKey XJFQPBHOGJVOHU-UHFFFAOYSA-N. Il a un point de fusion de 45-48 °C et un point d’ébullition de 272 °C. Il n’a aussi un point éclair que 113 °C (coupelle fermée). Ayant les mêmes SGH que trien pur, il a cependant des consignes de transport différentes, en particulier le numéro ONU 326314.

TRIETHYLENETETRAMINE (Trietilentetramin)

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