Diethylenetriamine (abbreviated Dien or DETA) and also known as 2,2’-Iminodi(ethylamine)) is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula HN(CH₂CH₂NH₂)₂. This colourless

hygroscopic Hygroscopy is the phenomenon of attracting and holding water molecules via either absorption (chemistry), absorption or adsorption from the surrounding Natural environment, environment, which is usually at normal or room temperature. If water mol ...

liquid is soluble in water and polar organic solvents, but not simple

hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...

s. Diethylenetriamine is structural analogue of

diethylene glycol Diethylene glycol (DEG) is an organic compound with the formula (HOCH2CH2)2O. It is a colorless, practically odorless, and hygroscopic liquid with a sweetish taste. It is a four carbon Dimer (chemistry), dimer of ethylene glycol. It is miscible in ...

. Its chemical properties resemble those for

ethylene diamine 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 5 ...

, and it has similar uses. It is a

weak base A weak base is a base that, upon dissolution in water, does not dissociate completely, so that the resulting aqueous solution contains only a small proportion of hydroxide ions and the concerned basic radical, and a large proportion of undissocia ...

and its aqueous solution is alkaline. DETA is a byproduct of the production of

ethylenediamine 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 ...

from

ethylene dichloride The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl ...

Reactions and uses

Diethylenetriamine is a common curing agent for

epoxy resin Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also co ...

s in epoxy adhesives and other thermosets. It is N-alkylated upon reaction with epoxide groups forming crosslinks. VernetzteEpoxidharze

coordination chemistry A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...

, it serves as a tridentate

ligand In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...

forming complexes such as Co(dien)(NO₂)₃. Like some related amines, it is used in oil industry for the extraction of

acid gas Acid gas is a particular typology of natural gas or any other gas mixture containing significant quantities of hydrogen sulfide (H2S), carbon dioxide (CO2), or similar acidic gases. A gas is determined to be acidic or not after it is mixed with wat ...

. Like

ethylenediamine 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 ...

, DETA can also be used to sensitize

nitromethane Nitromethane, sometimes shortened to simply "nitro", is an organic compound with the chemical formula . It is the simplest organic nitro compound. It is a polar liquid commonly used as a solvent in a variety of industrial applications such as in ...

, making a liquid explosive compound similar to PLX. This compound is cap sensitive with an explosive velocity of around 6200 m/s and is discussed in patent #3,713,915. Mixed with

unsymmetrical dimethylhydrazine Unsymmetrical dimethylhydrazine (abbreviated as UDMH; also known as 1,1-dimethylhydrazine, heptyl or Geptil) is a chemical compound with the formula H2NN(CH3)2 that is primarily used as a rocket propellant. At room temperature, UDMH is a colorle ...

it was used as Hydyne, a propellent for

liquid-fuel rocket A liquid-propellant rocket or liquid rocket uses a rocket engine burning liquid propellants. (Alternate approaches use gaseous or solid propellants.) Liquids are desirable propellants because they have reasonably high density and their combustio ...

s. DETA has been evaluated for use in the Countermine System under development by the U.S.

Office of Naval Research The Office of Naval Research (ONR) is an organization within the United States Department of the Navy responsible for the science and technology programs of the U.S. Navy and Marine Corps. Established by Congress in 1946, its mission is to plan ...

, where it would be used to ignite and consume the explosive fill of land mines in beach and

surf zone The surf zone or breaker zone is the nearshore part of a body of open water between the line at which the waves break and the shore. As ocean surface waves approach a shore, they interact with the bottom, wave shoaling, get taller and steeper, an ...

References

External links

* {{Ionotropic glutamate receptor modulators Aminoethyl compounds Amine solvents Chelating agents Rocket fuels NMDA receptor antagonists Secondary amines

Reactions and uses

See also

References

Further reading

External links