Ethylenediamine

Ethylenediamine
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IUPAC name	1,2-diaminoethane
Other names	en
Identifiers
CAS number	107-15-3
RTECS number	KH8575000
SMILES	NCCN
Properties
Molecular formula	C2H8N2
Molar mass	60.10 g/mol
Appearance	colourless liquid (impure: yellow)
Density	0.899 g/cm3, liquid
Melting point	9 °C
Boiling point	116 °C
Solubility in water	Miscible in water
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:

• as a solvent for proteins like albumins 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 chelating 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. aminophylline and some antihistamines.
• as a food and cattle feed additive as ethylenediamine dihydroiodide (EDDI).
• as a core for PAMAM dendrimers

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. 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.

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:

• Diethylenetriamine, abbreviated dien or DETA,(H₂N-CH₂CH₂-NH-CH₂CH₂-NH₂, an analog of diethylene glycol)
• Triethylenetetramine, abbreviated trien or TETA, (H₂N-CH₂CH₂-NH-CH₂CH₂-NH-CH₂CH₂-NH₂)
• Tetraethylenepentamine, abbreviated TEPA, (H₂N-CH₂CH₂-NH-CH₂CH₂-NH-CH₂CH₂-NH-CH₂CH₂-NH₂),
• Pentaethylenehexamine, abbreviated PEHA, (H₂N-CH₂CH₂-NH-CH₂CH₂-NH-CH₂CH₂-NH-CH₂CH₂-NH-CH₂CH₂-NH₂), up to polyethylene amine. Similarly piperazine is an analogue of dioxane.
• Tetraethylethylenediamine, abbreviated (TEEDA), (C₂H₅)₂N-CH₂CH₂-N(C₂H₅)₂

See also

• Diethylenetriamine
• Triethylenetetramine
• Polyethylene amine

External links

• IRIS EPA Ethylenediamine
• Chemical datade:Ethylendiamin