TETRAETHYLENEPENTAMINE

Tetraethylenepentamine = TEPA

CAS Number: 112-57-2
EC Number: 203-986-2
Chemical formula: C8H23N5
IUPAC Name: N~1~,N~1'~-[Azanediyldi(ethane-2,1-diyl)]di(ethane-1,2-diamine)

Tetraethylenepentamine (TEPA) is an organic compound and is in the class of chemicals known as ethyleneamines. It is a slightly viscous liquid and is not colorless but, like many amines, has a yellow color. It is soluble in most polar solvents. Diethylenetriamine (DETA), triethylenetetramine (TETA), piperazine, and aminoethylpiperazine are also usually present in commercial available TEPA.

Tetraethylenepentamine appears as a viscous liquid. Slightly less dense than water. Vapors heavier than air. 

Uses
The reactivity and uses of TEPA are similar to those for the related ethylene amines ethylenediamine and diethylenetriamine and triethylenetetramine.
It is primarily used as a curing agent or hardener in epoxy chemistry. This can be on its own or reacted with tall oil fatty acid (TOFA) and its dimer to make an amidoamine.
This amidoamine is then used as the curing agent for epoxy resin systems.
TEPA is a pentadentate ligand in coordination chemistry.

Tetraethylenepentamine (TEPA) is a yellowish liquid containing linear, branched and cyclic molecules. TEPA is commonly used as an additive in fuel and lubricating oil production, as an epoxy curing agent or in the manufacture of asphalt additives.

Tetraethylenepentamine (TEPA) is a viscous hygroscopic liquid.
It is soluble in most organic solvents and water.
TEPA is used in many applications such as asphalt additives, corrosion inhibitors, epoxy curing agents, hydrocarbon purification, lube oil and fuel additives, mineral processing, polyamide resins, surfactants, and textile adhesives.

HANDLING AND STORAGE
In order to maintain the high degree of purity with which tetraethylenepentamine (TEPA) is manufactured and
shipped, the following storage and handling considerations are recommended:

Dry Inert Gas Blanket
This product 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 TEPA is stainless steel or carbon steel.

Storage Temperature
Tetraethylenepentamine (TEPA) has a pour point of -30°C. To avoid freezing, the product should be maintained
above this temperature.

Tetraethylenepentamine was volunteered for the U.S. HPV program and
subsequently the ICCA program by the Ethyleneamines Product Stewardship
Discussion Group in the U.S. Use of data from the analog
triethylenetetramine is proposed to reduce testing needs.
The panel/consortia
(Dow, UCC and Azko-Nobel) searched company files and publicly available
databases to obtain data on TEPA. The “Environmental Risk Assessment of
Complexing Agents” submitted by Germany was also included in this

Molecular Weight: 189.30
XLogP3-AA: -2.9
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count: 10
Topological Polar Surface Area: 88.1 Ų
Heavy Atom Count: 13
Complexity: 78.6
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Boiling Point: 340.30 °C @ Press: 760 Torr
Melting Point: -30 °C
Molar mass: 189.307 g·mol−1
Grade: technical grade
Vapor density: 6.53 (vs air)
Vapor pressure: <0.01 mmHg ( 20 °C)
Autoignition temp.: 610 °F
Refractive index: n20/D 1.505 (lit.)
Mp: 340 °C
Mp: −40 °C (lit.)
Density: 0.998 g/mL at 25 °C (lit.)
SMILES string: NCCNCCNCCNCCN
InChI: 1S/C8H23N5/c9-1-3-11-5-7-13-8-6-12-4-2-10/h11-13H,1-10H2
InChI key: FAGUFWYHJQFNRV-UHFFFAOYSA-N

Environment
TEPA has the following physical chemical properties: melting point, -30 to –46 °C; boiling
point, 320 °C, vapor pressure 1.07 x 10-6
 hPa at 25 °C; partition coefficient –3.16 at pH 7; and it
is completely miscible in water at 20 °C.
The lowest acute EC/LC50 values of TEPA in fish (96-
hr), invertebrates (48-hr) and algae (72-hr) are 310 mg/L, 14.6 mg/L and 2.1 mg/L, respectively.
TEPA is not biodegradable (<10% after 28 days) and it should be noted that complexes of TEPA
are expected to biodegrade even slower.
However, TEPA is not expected to bioconcentrate due
to its estimated low log Kow of –3.16 and high water solubility. It should be noted that TEPA is
protonated at environmental pH and the log Kow is not a good indicator of the chemical’s
sorption behavior.

Exposure
TEPA, a synthetic, water soluble amine, is used primarily as a closed system intermediate in the
synthesis of other products which are involved in the manufacturing of lubricating oil additives,
fuel additives, paints and asphalt adhesives.
As of 1998, US production of TETA, TEPA and
higher molecular weight materials was 140 million pounds (63,636 tonnes).
The source of
release to the environment is primarily manufacturing sites. In the US, releases to the
environment are anticipated to be small and limited to activities such as product transfer and
maintenance operations.
These activities could lead to TEPA being potentially released to
surface water, air and soil. Based on well-controlled use and release from manufacturing sites,
there is a low potential for exposure.
In the US, there is no evidence to indicate that TEPA
maybe present in consumer products.
However, some other OECD member countries (Sweden,
France and Denmark) records indicate that there is the possibility of TEPA being present in their
consumer products.
As a result, it is recommended that each OECD member country evaluate
their own exposure scenarios to determine the chemical’s priority for further work.
cTEPA is a highly reactive molecule and will react with acids, oxides and other materials to make
products sold into consumer and industrial applications.
In the production of these materials,
TEPA is the initial reactant and may undergo one, two or three subsequent reactions prior to the
manufacture of the final product.
Thus the concentration of TEPA in the final product is quite low.
Exposure to high concentrations or pure TEPA is only expected to occur in manufacturing sites or
during epoxy curing applications in industrial settings.
Personal protective equipment is
recommended whenever possibility of exposure may occur.
The source of release to the
environment is primarily manufacturing sites, which may occur during upset conditions.
TEPA could potentially be released to surface water, air or soil.

Some OECD member countries (Sweden, France, Switzerland, Finland and Denmark) provided
varied information from their respective product registries.
In general, the product registries were unable to provide additional information regarding other components (chemicals) that were present
in the consumer products in which TEPA was reported to be present.
These other components are
believed to be acids, oxides and other materials, which react with TEPA. Reporting indicated that
that less than 10% of products that contain TEPA are available for consumer use.
Switzerland
provided data indicating that TEPA was present in concentrations >10% in three hardner
applications.
Overall reporting indicated a total of six products containing TEPA in quantities
between 1-10% (2 paints, varnishes and coatings; 2 hardners and 2 glue fillers.) One registry
indicated that TEPA was present in paints, varnishes and coatings at <1%. 

Tetraethylenepentamine (TEPA), consisting mainly of primary and secondary amines, exhibits a high CO2 sorption capacity; however, its poor thermal stability hampers practical utilization in the temperature swing adsorption process for CO2 capture.
Here, a facile functionalization of TEPA with 1,2-epoxybutane (EB) substantially enhanced its thermal stability as well as the CO2 adsorption kinetics.
Our careful analysis on the liquid-state 13C NMR disclosed the amine state distribution of EB-functionalized TEPA (EB-TEPA).
Although the increase in tertiary amine portion induced by EB-functionalization reduced CO2 sorption capacity, the 0.64EB-TEPA (i.e., TEPA functionalized with EB with a TEPA/EB molar ratio of 1:3)/SiO2 showed an excellent long-term stability over the 10 consecutive cycles of adsorption/desorption processes with a CO2 swing capacity of 2.0 mmol CO2 g–1 under dry CO2/N2 (15/85 mol/mol) feed conditions.
Also, the first-principles calculation identified the configuration of modified TEPA molecules with XRD measurements, supporting an easy access of CO2 into amine moieties of our modified TEPA molecules.

Tetraethylenepentamine (TEPA)-modified mesocellular silica foams (MSFs) were fabricated via physical impregnation (MSF-T-x) and chemical grafting (MSF-CT-y) methods.
The CO2 adsorption on these TEPA-modified MSFs was measured by using microbalances at 348 K and their adsorption capacities were observed to be 26.4–193.6 mg CO2/g-sorbent under ambient pressure using dry 15 % CO2.
It was found that the CO2 adsorption capacities of MSF-CT-y were smaller than those of MSF-T-x sorbents which may be attributed to their higher density of amine groups.
On the contrary, MSF-CT-y exhibited enhanced stability during repeated adsorption-desorption cycles compared to MSF-T-x sorbents.
This notable enhancement in the durability of CO2 adsorption-desorption process was probably attributed to the decreased leaching of TEPA which is chemically bonded to the surface of MSF.

Tetraethylenepentamine (TEPA) is a low-molecular-weight linear polyamine exerting metal-chelating properties. TEPA is widely used in industrial applications.
The principal hazards that arise in working with TEPA are those associated with similar organic amines; namely, a corrosive action on skin and eyes.
TEPA biological activity was attributed to its effect on cellular Cu levels as (a) treatment with TEPA resulted in reduction of cellular Cu, and (b) excess of Cu reversed TEPA's activity and accelerated differentiation.
TEPA was shown to attenuate the differentiation of ex vivo cultured hematopoietic cells resulting in preferential expansion of early progenitors.
A phase I/II trial was performed to test the feasibility and safety of transplantation of CD133+ cord blood (CB) hematopoietic progenitors cultured in media containing stem cell factor, FLT-3 ligand, interleukin-6, thrombopoietin and TEPA.
Transplanting a population of CD133+ CB cells which were expanded ex vivo for 21 days using SCF, FLT3, IL-6, TPO and the copper chelator TEPA (StemEx) was feasible.
The expanded cells were well tolerated, with no infusion-related adverse events observed.

Ethylenediamine is a colourless to yellowish, strongly alkaline liquid, melting at 8.5 C, boiling at 116 C; completely soluble in water and soluble alcohol.
It is a manufactured chemical that does not occur naturally.
It has two primary amine groups.
There are homologous odd number amine (on even number linear carbon chain) series of ethylenediamines; diethylenetriamine (linear C-4 diamine), triethylenetetramine (linear C-6 triamine), tetraethylenepentamine (linear C-8 pentamine), and  pentaethylenehexamine (linear C-10 hexamine).

Diethylenediamine is the simplest cyclic ethyleneamine (C-4), called piperazine.
It has two secondary amine groups in cyclic system.
It is a deliquescent crystalline compound melting at 105 C; soluble in water, alcohol, glycerol, and glycols. It is used as a main ingredient of anthelmintics and psychoactive drugs. Aminoethylpiperazine is also a member of C- 6 cyclic ethyleneamine which has aminoethyl attached to a nitrogen in piperazine.
Accordingly, it has one primary, one secondary, and one tertiary nitrogen atom. It is used in the synthesis of catalysts, epoxy curing agent, and corrosion inhibitors. Aminoethylethanolamine (AEEA) is an analogue of diethylenetriamine.
A hydroxyl group replace for an primary amine group. AEEA has one primary amine, one secondary amine, and one primary hydroxyl group.
AEEA is a useful intermediate in the production of surfactants, chelating agents, and curing agents. Other branched or cyclic ethylenediamines include N,N'-Bis-(2-aminoethyl)piperazine) [CAS #: 6531-38-0], N-[(2-aminoethyl)2-aminoethyl]piperazine) [CAS #: 24028-46-4], tris(2-aminoethyl)amine) [CAS #: 4097-89-6]. 

Ethylenediamines are produced by the reaction of aqueous ammonia with 1,2-dichloroethane.
This process yields the mixture of polyamines in the form of hydrochloride salts.
The next step is neutralisation of the salts with aqueous caustic soda to separate free amines.
The individual free amines are isolated by fractional distillation.
Ethylenediamines are capable of entering into a variety of reactions because of their combination of reactivity, basicity, and surface activity and of the basic functionality of the nitrogen atom. They are therefore important intermediates for a wide variety of chemical syntheses.
Examples of products obtained by reacting amines are as follows:

with carboxylic acid dericatives (acids, esters, anhydrides, or acyl halides): amides and amidoamines
with fatty acid: imidazoline
with cyanides or nitriles: amidoamines, polyamides, imidazolines
with urea: substituted urea and ammonia
with ethyleneimines: hydroxyalkyl amine derivatives
with aliphatic alcohols and glycols: alkylated ethyleneamines or cyclic ethyleneamines
with alkyl or aryl halides: substituted amines
with aliphatic aldehydes: substituted imidazolidines
with carbon disulfide: thiocarbamates
with carbon dioxide: carbamate
with inorganic acids: water soluble salts

Ethylenediamine is used as a very important bidentate ligand forming chelate agents.
The main application is to produce chelating agents such as ethylenediaminetetraacetic acid (EDTA).
It is used in the manufacture of carbamate fungicides,  surfactant and dyes. It is useful also in manufacturing accelerator or curing agent in epoxy industry.
Additional applications include manufacturing photography development chemicals and cutting oils, bleaching activators for washing powders especially at low temperature, lubricant for plastics and polyamide process, and fuel additives.

Diethylenetriamine is a yellow, hygroscopic liquid; boiling point of 206 C; soluble in water and hydrocarbons.
It is used as a solvent for sulfur, acidic gas, resin and as a fuel and oil field component.
It is used as an Intermediate for organic synthesis (modified polyamides, corrosion inhibitors, fuel additives, epoxy curing agents, fabric softeners and adhesion promoters) and saponification agent for acidic materials.

Triethylenetetramine is a clear to yellowish oily liquid; melting point 12 C, boiling point 280 C. It is miscible with water and the solution is alkaline ( (pH 10 at 10% solution).
It reacts with ketones, halogenated hydrocarbons, nitriles, epoxides, and with strong oxidants. Commercial triethylenetetramine is a mixture of linear TETA (typically 60%) and branched or cyclic TETA such as N,N'-Bis(2-aminoethyl)piperazine, N-[1-(2-piperazin-1-yl-ethyl)]ethane -1,2-diamine, tris-(2-aminoethyl)-amine.
TETA and its derivatives are used as an epoxy curing agent.
Their applications are similar to those of ethylenediamine and diethylenetriamine. Tetraethylenepentamine and pentaethylenehexamine are ethylenediamine family products which have similar in structure but containing extra ethylamine.
Due to structural similarity, TEPA and PEHA have almost similar chemical properties and the same applications.

End uses of ethylenediamine family products include:
Dispersant-detergent
Modified Polyamides
Fabric Softeners
Ore Flotation Agents
Emulsifiers
Corrosion Inhibitors
Adhesives
Binding Agents
Chelating Agents
Bleach Activators
Epoxy Curing Agent

Applications
Polymer auxiliaries
Agriculture
Pesticides
Dyestuffs, pigments and optical brighteners
Manufacturing of dyestuffs
Plastic- and Rubberpolymers
Chemical Industry
Construction material
Construction
Manufacturing of fungicides
Manufacturing of additives for feedstuff
Petrochemicals
Petrol components
Bitumen additives
Hardener and crosslinking agents for polymeres
Specialities
Accelerators for polymeres
Petroleum
Catalyst for chemical synthesis
Stabilizers for polymeres
Manufacturing of antioxidans for feedstuffs
Coolants

Other Names for this substance
112-57-2
Tetren
1,4,7,10,13-Pentaazatridecane
Tetraethylene pentamine
3,6,9-Triazaundecamethylenediamine
Tetraethylpentylamine
1,11-Diamino-3,6,9-triazaundecane
3,6,9-Triazaundecane-1,11-diamine
DEH 26
Tetrene
UNII-YZD1C9KQ28
NSC 88603
1,2-Ethanediamine, N-(2-aminoethyl)-N'-[2-[(2-aminoethyl)amino]ethyl]-
YZD1C9KQ28
CHEBI:49798
N-(2-aminoethyl)-N'-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine
NCGC00090964-02
DSSTox_CID_6108
1,2-Ethanediamine, N-(2-aminoethyl)-N'-(2-((2-aminoethyl)amino)ethyl)-
1,2-Ethanediamine, N1-(2-aminoethyl)-N2-[2-[(2-aminoethyl)amino]ethyl]-
DSSTox_RID_78020
DSSTox_GSID_26108
Tetraethylenepentamine, tech.
26913-06-4
TETRAEN
(2-aminoethyl)[2-({2-[(2-aminoethyl)amino]ethyl}amino)ethyl]amine
CAS-112-57-2
PAW
CCRIS 6275
HSDB 5171
EINECS 203-986-2
UN2320
BRN 0506966
Poly[imino(1,2-ethanediyl)]
AI3-10049
1,2-Ethanediamine, N1-(2-aminoethyl)-N2-(2-((2-aminoethyl)amino)ethyl)-
Tetraethylenpentamine
MFCD00008168
Texlin 400
tetraethylene pentaamine
1,6,9-triazaundecane
N-(2-Aminoethyl)-N-(2-((2-aminoethyl)amino)ethyl-1,2-ethanediamine)
Tetraethylenepentamine, CP
Tetraethylenepentamine [UN2320] [Corrosive]
ACMC-209u0l
NCIOpen2_001402
SCHEMBL15797
WLN: Z2M2M2M2Z
4-04-00-01244 (Beilstein Handbook Reference)
MLS000028888
BIDD:ER0305
CHEMBL138297
1,7,10,13-Pentaazatridecane
DTXSID7026108
3,9-Triazaundecane-1,11-diamine
N'-[2-[2-(2-aminoethylamino)ethylamino]ethyl]ethane-1,2-diamine
NSC88603
Tox21_111047
Tox21_200669
ANW-43171
D.E.H. 26
NSC-88603
SBB060752
STL453738
ZINC19363537
AKOS015894482
Tetraethylenepentamine, technical grade
Tox21_111047_1
MCULE-5833194114
UN 2320
Polyethyleneimine, 50% aqueous solution
NCGC00090964-01
NCGC00090964-03
NCGC00090964-04
NCGC00258223-01
SMR000059212
FT-0657261
ST51046872
C14690
Tetraethylenepentamine [UN2320] [Corrosive]
AB00375928_03
SR-01000944425
J-503958
SR-01000944425-1
BRD-K41298358-395-01-8
Q15974770
1, N-(2-aminoethyl)-N'-[2-[(2-aminoethyl)amino]ethyl]-
Phenol-formaldehyde, cross-linked, tetraethylenepentamine activated
n-(2-aminoethyl)-n'-(2-((2-aminoethyl)amino)ethyl)-1,2-ethanediamine
N1-(2-aminoethyl)-N2-(2-(2-aminoethylamino)ethyl)ethane-1,2-diamine
N1-{2-[2-(2-AMINO-ETHYLAMINO)-ETHYLAMINO]-ETHYL}-ETHANE-1,2-DIAMINE