Tetraethylenepentamine

Last updated
Tetraethylenepentamine
Tetraethylenepentamine.svg
Names
Preferred IUPAC name
N1-(2-Aminoethyl)-N2-{2-[(2-aminoethyl)amino]ethyl}ethane-1,2-diamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ECHA InfoCard 100.003.624 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-986-2
PubChem CID
RTECS number
  • KH8585000
UNII
UN number 2320
  • InChI=1S/C8H23N5/c9-1-3-11-5-7-13-8-6-12-4-2-10/h11-13H,1-10H2
    Key: FAGUFWYHJQFNRV-UHFFFAOYSA-N
  • C(CNCCNCCNCCN)N
Properties
C8H23N5
Molar mass 189.307 g·mol−1
Hazards
GHS pictograms GHS-pictogram-acid.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
GHS Signal word Danger
H302, H312, H314, H317, H411
P260, P261, P264, P270, P272, P273, P280, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P322, P330, P333+313, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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. [1]

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. [2] This amidoamine is then used as the curing agent for epoxy resin systems. TEPA is a pentadentate ligand in coordination chemistry.

Related Research Articles

Epoxy

Epoxy refers to any of the basic components or cured end products of epoxy resins, as well as a colloquial name for the epoxide functional group. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups.

Thermosetting polymer

A thermosetting polymer, or plastic, often called a thermoset, is a polymer that is irreversibly hardened by curing from a soft solid or viscous liquid prepolymer or resin. Curing is induced by heat or suitable radiation and may be promoted by high pressure, or mixing with a catalyst. Heat is not necessarily to be applied externally. It is often generated by the reaction of the resin with a curing agent. Curing results in chemical reactions that create extensive cross-linking between polymer chains to produce an infusible and insoluble polymer network.

Epoxide

An epoxide is a cyclic ether with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.

Cocamidopropyl betaine (CAPB) is a mixture of closely related organic compounds derived from coconut oil and dimethylaminopropylamine. CAPB is available as a viscous pale yellow solution and it is used as a surfactant in personal care products. The name reflects that the major part of the molecule, the lauric acid group, is derived from coconut oil. Cocamidopropyl betaine to a significant degree has replaced cocamide DEA.

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine readily reacts with moisture in humid air to produce a corrosive, toxic and irritating mist, to which even short exposures can cause serious damage to health (see safety). Ethylenediamine is the first member of the so-called polyethylene amines.

Diethylenetriamine Chemical compound

Diethylenetriamine (abbreviated Dien or DETA) and also known as 2,2’-Iminodi(ethylamine)) is an organic compound with the formula HN(CH2CH2NH2)2. This colourless hygroscopic liquid is soluble in water and polar organic solvents, but not simple hydrocarbons. Diethylenetriamine is structural analogue of diethylene glycol. Its chemical properties resemble those for ethylene diamine, and it has similar uses. It is a weak base and its aqueous solution is alkaline. DETA is a byproduct of the production of ethylenediamine from ethylene dichloride.

Triethylenetetramine Chemical compound

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. It is soluble in polar solvents. The branched isomer tris(2-aminoethyl)amine and piperazine derivatives may also be present in commercial samples of TETA.

Tall oil, also called "liquid rosin" or tallol, is a viscous yellow-black odorous liquid obtained as a by-product of the kraft process of wood pulp manufacture when pulping mainly coniferous trees. The name originated as an anglicization of the Swedish "tallolja". Tall oil is the third largest chemical by-product in a Kraft mill after lignin and hemicellulose; the yield of crude tall oil from the process is in the range of 30–50 kg / ton pulp. It may contribute to 1.0–1.5% of the mill's revenue if not used internally.

Trimethylolpropane triacrylate Chemical compound

Trimethylolpropane triacrylate (TMPTA) is a trifunctional acrylate ester monomer used in the manufacture of plastics, adhesives, acrylic glue, anaerobic sealants, and ink. It is useful for its low volatility and fast cure response. It has the properties of weather, chemical and water resistance, as well as good abrasion resistance. End products include alkyd coatings, compact discs, hardwood floors, concrete polymers, Dental composites, photolithography, letterpress, screen printing, elastomers, automobile headlamps, acrylics and plastic components for the medical industry.

Aminolysis (/am·i·nol·y·sis/ amino meaning "contains NH2 group", and lysis meaning "to unbind") is any chemical reaction in which a molecule is split into two parts by reacting with ammonia or an amine..

Aminoethylpiperazine Chemical compound

Aminoethylpiperazine is a derivative of piperazine. This ethyleneamine contains three nitrogen atoms; one primary, one secondary and one tertiary. It is a corrosive liquid and can cause second or third degree burns. Aminoethylpiperazine can also cause pulmonary edema as a result of inhalation. Uses include inhibition of corrosion, epoxy curing, surface activation, and as an asphalt additive. When used as an epoxy resin curing agent, it is usually used in conjunction with other amines as an accelerator as it only has 3 amine hydrogens for cross-linking.

Amidoamines are a class of chemical compounds that are formed from fatty acids and diamines. They are used as intermediates in the synthesis of surfactants, such as cocamidopropyl betaine (CAPB), some of which are used in personal care products including soaps, shampoos, and cosmetics. Amidoamines can also serve as curing agents for epoxy resins.

A polyamine is an organic compound having more than two amino groups. Alkyl polyamines occur naturally but are also synthetic. Alkylpolyamines are colorless, hygroscopic, and water soluble. Near neutral pH, they exist as the ammonium derivatives. Most aromatic polyamines are crystalline solids at room temperature.

<i>m</i>-Xylylenediamine Chemical compound

m-Xylylenediamine is an organic compound with the formula C6H4(CH2NH2)2. A colorless oily liquid, it is produced by hydrogenation of isophthalonitrile.

Ethyleneamine

Ethyleneamines are a class of amine compounds containing ethylene (-CH2CH2-) linkages between amine groups. These compounds are generally colorless, low-viscosity liquids with a fishy amine odor. They are primarily used as building block chemicals and in epoxy resin curing agent chemistry.

Isophorone diamine Chemical compound

Isophorone diamine (usually shortened to IPDA) is a diamine with the formula (CH3)3C6H7(NH2)(CH2NH2). It is a colorless liquid. It is a precursor to polymers and coatings.

1,3-BAC Chemical compound

1,3 BAC chemically 1,3-bis(aminomethyl) cyclohexane is an organic molecule belonging to the sub class cycloaliphatic amine. It has the CAS Registry Number of 2579-20-6. Its key use is as an epoxy resin curing agent.

Pentaerythritol tetraacrylate Chemical compound

Pentaerythritol tetraacrylate is an organic compound. It is a tetrafunctional acrylate ester used as a monomer in the manufacture of polymers. As it is a polymerizable acrylate monomer it is nearly always supplied with a polymerisation inhibitor such as MEHQ added.

Waterborne resins are sometimes called water-based resins. They are resins or polymeric resins that use water as the carrying medium as opposed to solvent or solvent-less. Resins are used in the production of coatings, adhesives, sealants, elastomers and composite materials. When the phrase waterborne resin is used it usually describes all resins which have water as the main carrying solvent. The resin could be water soluble, water reducible or water dispersed.

2-Methylpentamethylenediamine Chemical compound

2-Methylpentamethylenediamine is an organic compound part of the amine family with the formula H2NCH2CH2CH2CH(CH3)CCH2NCH2. A colorless liquid, this diamine is obtained by the hydrogenation of 2-methylglutaronitrile.

References

  1. "Ethyleneamines" (PDF). Huntsman. 2007.
  2. "AMIDOAMINES – Epochemie – Epoxy Curing Agents" . Retrieved 2019-04-30.