Ethylenediamine

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Template:Chembox E numberTemplate:Chembox SolubilityInWater
Ethylenediamine
IUPAC name 1,2-diaminoethane
Other names en
Identifiers
3D model (JSmol)
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RTECS number KH8575000
Properties
C2H8N2
Molar mass 60.10 g/mol
Appearance colourless liquid (impure: yellow)
Density 0.899 g/cm3, liquid
Melting point
Boiling point
Solubility Most polar solvents
Basicity (pKb) 3.92
Structure
Molecular shape Tetrahedral at N and C
Hazards
Main hazards Flammable, corrosive
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Ethylenediamine is the organic compound with the formula C2H8N2. It is a colorless to yellowish liquid, with an ammonia-like odor. It is relatively basic, and is completely miscible in polar solvents such as water and ethanol. It is widely used as a building block for polymers and as a ligand for coordination compounds.

Synthesis

Ethylenediamine is manufactured by reacting ammonia and 1,2-dichloroethane. The reaction yields the mixture of ethylenediamine and the linear polyamines. A simplified equation would be:

ClCH2CH2Cl + 4 NH3 → H2NCH2CH2NH2 + 2 NH4Cl

Applications

Ethylenediamine is used in the following applied and fundamental ways:

Ethylenediamine 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.

Safety

Ethylenediamine exposure can cause the skin to become irritated. It was used in commercially available skin products including Mycolog cream.[1] Ethylenediamine has a half-life of about 30 minutes and a small volume of distribution of 0.133 liters/kg. After oral administration its bioavailability is about 0.34, due to a substantial first-pass effect. Less than 20% is eliminated by renal excretion.[2]

Ethylenamines

Ethylenediamine 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:

See also

References

  1. Hogan DJ. (Jan 1990). "Allergic contact dermatitis to ethylenediamine. A continuing problem". Dermatol Clin. 8 (1): 133–6. PMID 2137392.
  2. Zuidema J. (23 Aug 1985 23). "Ethylenediamine, profile of a sensitizing excipient". Pharmacy World & Science. 7 (4): 134–40. doi:10.1007/BF02097249. PMID 3900925. Check date values in: |date= (help)

External links

de:Ethylendiamin


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