Ethylene diamine

Encyclopedia : E : ET : ETH : Ethylene diamine

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[Chemical infoboxDisclaimer and references]

Ethylene diamine (EDA or en), or 1,2-diaminoethane, is an organic compound from the amines group. Its formula is ₂-H₂CH₂-NH₂. It is a strongly alkaline, colorless to yellowish liquid, with amine odor, completely miscible with water and soluble in alcohol. Its melting point is 8.5 °C and boiling point 116 °C. Its CAS reference number is 107-15-3. (This is an extremely hazardous substance, as defined by Federal Regulatory Program lists. (scorecard.org))

The ethylenamines

Ethylene diamine is the diamine analogue of the dialcohol ethylene glycol. And as glycol is the first of a series of polyethylene glycols, EDA is the first member of polyethylene amines:

• diethylene triamine, abbreviated dien,(H₂N-CH₂CH₂-NH-CH₂CH₂-NH₂, an analog of diethylene glycol),
• triethylene tetramine abbreviated trien, (H₂N-CH₂CH₂-NH-CH₂CH₂-NH-CH₂CH₂-NH₂),
• tetraethylene pentamine, (H₂N-CH₂CH₂-NH-CH₂CH₂-NH-CH₂CH₂-NH-CH₂CH₂-NH₂),
• pentaethylenehexamine (H₂N-CH₂CH₂-NH-CH₂CH₂-NH-CH₂CH₂-NH-CH₂CH₂-NH-CH₂CH₂-NH₂), up to polyethylene amine. Similarly piperazine is an analogue of dioxane.
• tetraethylethylene diamine (TEEDA) (C₂H₅)₂N-CH₂CH₂-N(C₂H₅)₂

Synthesis

EDA is manufactured by reacting of ammonia and 1,2-dichloroethane. The reaction yields the mixture of EDA and the linear polyamines. A simplified equation leading to EDA is presented (although EDA is more basic than NH₃):

:ClCH₂CH₂Cl + 4 NH₃ → H₂NCH₂CH₂NH₂ + 2 NH₄Cl

Applications

Ethylene diamine is used in the following applied and fundamental ways:

• as a solvent for proteins like albumin or casein, as a part of electroplating baths, lubricant for textiles, stabilizer in latex emulsions, and in polyamide adhesives.
• as a corrosion inhibitor in paints and coolants.
• as a renowned chelateing agent. A representative complex is [Co(H₂NCH₂CH₂NH₂)₃]³⁺
• as part of many medicaments, as a chemical stabilizer
• as a building block to many organic compounds, including pharmaceuticals, e.g. aminophyllin and some antihistamines.
• as a food and cattle feed additive as ethylenediamine dihydriodide.

Ethylene diamine is used in large quantities for production of many industrial chemicals. It is very reactive, readily forms compounds with carboxylic acids (amides), fatty acids (imidazoline), nitriles (amidoamines, polyamides, imidazolines), alcohols and glycols (alkylated or cyclic ethyleneamines), alkylhalides and arylhalides (substituted amines), carbon disulfide (thiocarbamates), and forms water soluble salts with inorganic acids. Some products for which EDA is an important precursor are chelate agents like EDTA, the bleaching activator tetra acetyl ethylene diamine, chemicals for color photography developing, lubricants for the molding and processing of plastics, fuel additives, carbamate fungicides, binders, adhesives, fabric softeners, surfactants, curing agents for epoxys, and dyes.

See also

• diethylene triamine
• triethylene tetramine
• polyethylene amine

External links

• [IRIS EPA Ethylene diamine]
• [Chemical data]

 

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