Ethylenediamine

Ethylenediamine is produced industrially by treating 1,2-dichloroethane with ammonia under pressure at 180 °C in an aqueous medium:[6][7] In this reaction hydrogen chloride is generated, which forms a salt with the amine.

It can be prepared in the lab by the reaction of either ethylene glycol or ethanolamine and urea, followed by decarboxylation of the ethyleneurea intermediate.

[11] Salts of ethylenebisdithiocarbamate are commercially significant fungicides under the brand names Maneb, Mancozeb, Zineb, and Metiram.

[12] When used as a pharmaceutical excipient, after oral administration its bioavailability is about 0.34, due to a substantial first-pass effect.

The derivative N,N-ethylenebis(stearamide) (EBS) is a commercially significant mold-release agent and a surfactant in gasoline and motor oil.

Related derivatives of ethylenediamine include ethylenediaminetetraacetic acid (EDTA), tetramethylethylenediamine (TMEDA), and tetraethylethylenediamine (TEEDA).

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 mucous membranes.

Skeletal formula of ethylenediamine
Skeletal formula of ethylenediamine
Ball and stick model of ethylenediamine
Ball and stick model of ethylenediamine
Space-filling model of ethylenediamine
Space-filling model of ethylenediamine
NFPA 704 four-colored diamond Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code