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CAS Number 107-15-3
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Linear Formula NH2CH2CH2NH2
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Molecular Weight 60.10
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Beilstein Registry Number 605263
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EC Number 203-468-6
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MDL number MFCD00008204
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PubChem Substance ID 329747731
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eCl@ss 39030201
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 strongly basic amine.
Detailed Description:
It is a widely used building block in
chemical synthesis, with approximately 500,000 tonnes produced in 1998.[6] 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).
Applications
Ethylenediamine is used in large quantities for
production of many industrial chemicals. It forms derivatives with carboxylic acids(including fatty acids), nitriles, alcohols (at elevated temperatures),
alkylating agents, carbon disulfide,
and aldehydes and ketones. Because of its bifunctional nature,
having two amines, it readily forms heterocycles such as imidazolidines.
Precursor
to chelation agents, drugs, and agrochemicals
A most prominent derivative of ethylenediamine is
the chelating agent EDTA,
which is derived from ethylenediamine via a Strecker synthesis involving cyanide and formaldehyde. Hydroxyethylethylenediamine is
another commercially significant chelating agent.[6]Numerous bio-active compounds and
drugs contain the N-CH2-CH2-N linkage, including
some antihistamines.[9] Salts of
ethylenebisdithiocarbamate are commercially significant fungicides under the
brand names Maneb, Mancozeb, Zineb,
and Metiram. Some imidazoline-containing
fungicides are derived from ethylenediamine.[6]
Pharmaceutical
ingredient
Ethylenediamine is an ingredient in the common bronchodilator drug aminophylline, where it serves to solubilize
the active ingredient theophylline.
Ethylenediamine has also been used in dermatologic preparations, but has been
removed from some because of causing contact dermatitis.[10] When used as a pharmaceutical
excipient, after oral administration its bioavailability is about 0.34, due to a
substantial first-pass effect.
Less than 20% is eliminated by urinal excretion.[11]
Role in
polymers
Ethylenediamine, because it contains two amine groups,
is a widely used precursor to various polymers. Condensates derived from
formaldehyde are plasticizers. It is widely used in the production of
polyurethane fibers. The PAMAM class of dendrimers are derived from
ethylenediamine.[6]
Tetraacetylethylenediamine
The bleaching activator tetraacetylethylenediamine is
generated from ethylenediamine. The derivative N,N-ethylenebis(stearamide)(EBS) is a
commercially significant mold-release agent and a surfactant in gasoline and motor oil.
Other
applications
·
as
a solvent, it is miscible with polar solvents and is used
to solubilize proteins such
as albumins and casein. It is also used in certain electroplating baths.
·
as
a corrosion inhibitor in
paints and coolants.
·
ethylenediamine
dihydroiodide (EDDI) is added to animal feeds as a source of
iodide.
·
chemicals
for color photography developing, binders, adhesives, fabric softeners, curing agents
for epoxys, and dyes.
PRICES
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