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Ethyleneamines are a class of
amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...
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.


Production

There are two main routes for the production of ethyleneamines, the reaction between
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 ...
and
ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous was ...
, and the reductive amination of monethanolamine. World capacity of ethyleneamines for the year 2001 was estimated to be 385,000 tonnes/year, with the majority comprising the ethylene dichloride route. In the ethylene dichloride route, the initial product of this reaction is
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 ...
. In the presence of excess ethylene dichloride, the initial ethyleneamine is extended by one ethylene unit. The terminal alkyl chloride reacts with ammonia to give the amine, and the polyamine chain can be extended further in this fashion. Addition of a polyamine to the initial reaction mixture can increase the concentration of higher-order polyamines. In all these examples, stoichiometric base is needed to convert the amine hydrochloride to free amines. In the monoethanolamine route,
monoethanolamine Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is an organic chemical compound with the formula or . The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid wit ...
reacts with ammonia, catalyzed by transition metal catalysts. This process is reported to generate more cyclic compounds than the ethylene dichloride route. As a practical matter, a mixture of products is obtained in both routes. This mixture is influenced by the composition of the feedstock, and various products are obtained by continuous distillation. By returning lower-order polyamines or polyamine derivatives into the process, more higher-order polyamines can be obtained.


Side products

In addition to the ethyleneamine homologs (also spelled as homologue), side products exist.
Aziridine Aziridine is an organic compound consisting of the three-membered heterocycle . It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivati ...
occurs by the cyclization of chloroethylamine;
piperazine Piperazine () is an organic compound that consists of a six-membered ring containing two nitrogen atoms at opposite positions in the ring. Piperazine exists as small alkaline deliquescent crystals with a saline taste. The piperazines are a broad ...
s are formed by cyclization of a two-ethylene unit compound to give the six-membered ring.


Examples


References


Further reading

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External links

*{{Commonscat-inline, Ethyleneamines Polyamines