What is it?
Ethylenediamine is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a strongly basic amine.
Synthesis
Ethylenediamine is manufactured industrially from 1,2-dichloroethane and ammonia under pressure at 180 °C in an aqueous medium.
Another industrial route to ethylenediamine involves the reaction of ethanolamine and ammonia.
Coordination Chemistry
Ethylenediamine is a well-known chelating ligand for coordination compounds. It is often abbreviated "en" in inorganic chemistry. The complex [Co(ethylenediamine)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.
Applications
Ethylenediamine is used in large quantities for production of many industrial chemicals. It forms derivatives with carboxylic acids and because of its bifunctional nature, having two amines, it readily forms heterocycles such as imidazolidines.
Dangers
Ethylenediamine, like ammonia and other low-molecular weight amines, is a skin and respiratory irritant.
Ethylenediamine is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a strongly basic amine.
Synthesis
Ethylenediamine is manufactured industrially from 1,2-dichloroethane and ammonia under pressure at 180 °C in an aqueous medium.
Another industrial route to ethylenediamine involves the reaction of ethanolamine and ammonia.
Preferred IUPAC name: Ethane-1,2-diamine
Abbreviations: en
Chemical formula: C2H8N2
Molar mass: 60.10 g·mol−1
Appearance: Colorless liquid
Odor: Ammoniacal
Density: 0.90 g/cm
Melting point: 8 °C
Boiling point 116 °C (389 K)
Solubility in water: miscible
Vapor pressure: 1.3 kPa (at 20 °C)
Specific heat capacity (C): 172.59 J K−1 mol−1
Coordination Chemistry
Ethylenediamine is a well-known chelating ligand for coordination compounds. It is often abbreviated "en" in inorganic chemistry. The complex [Co(ethylenediamine)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.
Applications
Ethylenediamine is used in large quantities for production of many industrial chemicals. It forms derivatives with carboxylic acids and because of its bifunctional nature, having two amines, it readily forms heterocycles such as imidazolidines.
- A most prominent derivative of ethylenediamine is the chelating agent EDTA
- Numerous bio-active compounds and drugs contain the N-CH2-CH2-N linkage, including some antihistamines.
- Some imidazoline-containing fungicides are derived from ethylenediamine.
- 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.
- Ethylenediamine, because it contains two amine groups, is used precursor to various polymers. It is widely used in the production of polyurethane fibers.
- The bleaching activator tetraacetylethylenediamine is generated from ethylenediamine.
- As a solvent, it is miscible with polar solvents and is used to solubilize proteins, such as albumins and casein.
- Used 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.
Dangers
Ethylenediamine, like ammonia and other low-molecular weight amines, is a skin and respiratory irritant.
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, such as irritation in skin, eyes, lungs and mucus membranes.
Exposure to a relatively small amount of vapor or mist by inhalation can seriously damage health and may even result in death.
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