Quick Search
Ethylenediamine 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.
Formula:C2H8N2
CAS Number:107-15-3
Synonyms: 1,2-Diaminoethane, 1,2-Ethanediamine
Ethylenediamine is the first member of the so-called polyethylene amines.
Ethylenediamine is a diamine that is used in the production of polyurethanes.
Ethylenediamine can be produced by reacting ethylene glycol with ammonia.
The reaction mechanism for this synthesis is believed to involve the addition of ethylene glycol to ammonia to form an iminium ion, which then reacts with itself to produce the desired product, ethylenediamine.
The biological properties of ethylenediamine are not well understood, but Ethylenediamine has been shown to have a high affinity for sodium ions and to undergo phase transitions at a temperature near 100°C.
Ethylenediamine can be detected using plasma mass spectrometry and x-ray crystal structures have been obtained from x-ray diffraction data.
Ethylenediamine is a colorless, alkaline liquid with an ammonia-like odor.
Ethylenediamine is a strong base that’s soluble in water, alcohol, ether, and insoluble in benzene.
Ethylenediamine readily absorbs carbon dioxide from the air.
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.
Ethylenediamine 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
As a solvent, Ethylenediamine 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 dihydroiodide (EDDI) 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.
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.
Synthesis
Ethylenediamine is produced industrially by treating 1,2-dichloroethane with ammonia under pressure at 180 °C in an aqueous medium (EDC process):
In this reaction hydrogen chloride is generated, which forms a salt with the amine.
The amine is liberated by addition of sodium hydroxide and can then be recovered by fractional distillation.
Ethylenediamine and triethylenetetramine (TETA) are formed as by-products.
Another industrial route to ethylenediamine involves the reaction of ethanolamine and ammonia:
Ethylenediamine can be prepared in the lab by the reaction of either ethylene glycol or ethanolamine and urea, followed by decarboxylation of the ethyleneurea intermediate.
Ethylenediamine can be purified by treatment with sodium hydroxide to remove water followed by distillation.
