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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.
Ethylenediamine is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998.
Ethylenediamine is the first member of the so-called polyethylene amines.
CAS Number: 107-15-3
Chemical formula: C2H8N2
Ethylenediamine is a colorless, ammonia-like, highly basic liquid compound ((C_{2}H_{8}N_{2})) primarily used as a versatile building block in chemical synthesis and industrial applications.
Ethylenediamine serves as a precursor for chelating agents (like EDTA), polyamide resins, fuel additives, lubricants, and fungicides.
Ethylenediamine is a well-known bidentate chelating ligand for coordination compounds, with the two nitrogen atoms donating their lone pairs of electrons when ethylenediamine acts as a ligand.
Ethylenediamine is often abbreviated "en" in inorganic chemistry.
The complex [Co(en)3]3+ is a well studied example.
Schiff base ligands easily form from ethylenediamine.
For example, the diamine condenses with 4-Trifluoromethylbenzaldehyde to give to the diimine.
The salen ligands, some of which are used in catalysis, are derived from the condensation of salicylaldehydes and ethylenediamine.
Ethylenediamine is an organic compound that is used as a building block for the production of many other chemical products.
Ethylenediamine is also used as an excipient in many pharmacological preparations such as creams.
Notably, ethylenediamine is a contact sensitizer capable of producing local and generalized reactions
1. Sensitivity to Ethylenediamine may be identified with a clinical patch test.
Ethylenediamine (EDA) is a colorless to yellow liquid with an ammonia-like odor.
Ethylenediamine is a single component pure product that is mainly used as a raw material for crop protection products, in the synthesis of chelating agents and for low-temperature-active bleaching agents.
Ethylenediamine is also found in such applications as lubricants, fuel additives, textiles and polyamide resins.
Applications
Ethylenediamine is used in large quantities for production of many industrial chemicals.
Ethylenediamine 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 amino groups, Ethylenediamine 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. Ethylenediaminee is another commercially significant chelating agent.
Numerous bio-active compounds and drugs contain the N–CH2–CH2–N linkage, including some antihistamines.
Salts of ethylenebisdithiocarbamate are commercially significant fungicides under the brand names Maneb, Mancozeb, Zineb, and Metiram.
Some imidazoline-containing fungicides are derived from ethylenediamine.
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.
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 renal excretion.
Ethylenediamine-derived antihistamines are the oldest of the five classes of first-generation antihistamines, beginning with piperoxan aka benodain, discovered in 1933 at the Pasteur Institute in France, and also including mepyramine, tripelennamine, and antazoline.
The other classes are derivatives of ethanolamine, alkylamine, piperazine, and others (primarily tricyclic and tetracyclic compounds related to phenothiazines, tricyclic antidepressants, as well as the cyproheptadine-phenindamine family)
Role in polymers
Ethylenediamine, because it contains two amine groups, is a widely used precursor to various polymers.
Condensates derived from formaldehyde are plasticizers.
Ethylenediamine is widely used in the production of polyurethane fibers.
The PAMAM class of dendrimers are derived from ethylenediamine.
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
Ethylenediamine as a solvent, it is miscible with polar solvents and is used to solubilize proteins such as albumins and casein.
Ethylenediamine is also used in certain electroplating baths.
as a corrosion inhibitor in paints and coolants.
Ethylenediamine is added to animal feeds as a source of iodide.
chemicals for color photography developing, binders, adhesives, fabric softeners, curing agents for epoxies, and dyes.
Ethylenediamine as a compound to sensitize nitromethane into an explosive.
This mixture was used at Picatinny Arsenal during World War II, giving the nitromethane and ethylenediamine mixture the nickname PLX, or Picatinny Liquid Explosive.
