Этилендиамин: свойства, применение и производные

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| ImageFile = Ethylene diamine fuming. jpg
| ImageFile1 = Ethane 1,2 diamine 200. svg
| ImageFile1 Ref =
| ImageName1 = Skeletal formula of ethylenediamine
| ImageFileL1 = Ethylenediamine 3D balls 2. png
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| ImageNameL1 = Ball and stick model of ethylenediamine
| ImageFileR1 = Ethylenediamine 3D spacefill. png
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| ImageNameR1 = Space filling model of ethylenediamine
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| ImageName2 = Sample of ethylenediamine in a jar
| PIN = Ethane 1,2 diamine
| OtherNames = Edamine, 1,2 Diaminoethane, 'en' when a ligand
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| Section2 = Chembox Properties
| C=2 | H=8 | N=2
| Appearance = Colorless liquid
| Odor = Ammoniacal
| PEL = TWA 10 ppm (25 mg/m3)
| IDLH = 1000 ppm Ethylenediamine is the first member of the so called polyethylene amines.

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 amino groups, it readily forms heterocycles such as imidazolidines.

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. Salts of ethylenebisdithiocarbamate are commercially significant fungicides under the brand names Maneb, Mancozeb, Zineb, and Metiram. Some imidazoline containing fungicides are derived from ethylenediamine. 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)

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.

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.

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 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.

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. It is often abbreviated "en" in inorganic chemistry. The complex [Co(en)3]3+ is an archetypical chiral tris chelate complex. The salen ligands, some of which are used in catalysis, are derived from the condensation of salicylaldehydes and ethylenediamine.

Related derivatives of ethylenediamine include ethylenediaminetetraacetic acid (EDTA), tetramethylethylenediamine (TMEDA), and tetraethylethylenediamine (TEEDA). Chiral analogs of ethylenediamine include 1,2 diaminopropane and trans diaminocyclohexane.

Ethylenediamine, like ammonia and other low molecular weight amines, is a skin and respiratory irritant. Unless tightly contained, liquid ethylenediamine will release toxic and irritating vapors into its surroundings, especially on heating. The vapors absorb moisture from humid air to form a characteristic white mist, which is extremely irritating to skin, eyes, lungs and mucus membranes.