Ethylenediamine

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Ethylenediamine
Image:Ethylene diamine.png
General
Systematic name	1,2-diaminoethane
Other names	ethylenediamine, en
Molecular formula	C₂H₈N₂
SMILES	NCCN
Molar mass	60.10 g/mol
Appearance	colourless liquid (impure: yellow)
CAS number	[107-15-3]
Properties
Density and phase	0.899 g/cm³, liquid
Solubility in water	infinite
Other solvents	polar organic solvents
Melting point	9 °C
Boiling point	116 °C
Basicity (pK_b)	3.92
Viscosity	? cP at ? °C
Structure
Coordination geometry	tetrahedral at C and N
Dipole moment	? D
Hazards
MSDS	External MSDS
Main hazards	flammable, corrosive
NFPA 704
Flash point	? °C
R/S statement	R: 10-21/22-34-42/43 S: 23-26-36/37/39-45
RTECS number	KH8575000
Supplementary data page
Structure and properties	n = 1.4565
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related compounds	Me₂NCH₂CH₂NMe₂, ethanolamine
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Ethylene diamine is the organic compound with the formula H₂N-CH₂CH₂-NH₂. It is a strongly alkaline, colorless to yellowish liquid, with ammonia-like odor, completely miscible with water and soluble in alcohol. It is widely used as a building block for polymers and as a ligand for coordination compounds.

1 The ethylenamines
2 Synthesis
3 Applications
4 See also
5 External links

[edit] 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 or DETA,(H₂N-CH₂CH₂-NH-CH₂CH₂-NH₂, an analog of diethylene glycol),
triethylene tetramine abbreviated trien or TETA, (H₂N-CH₂CH₂-NH-CH₂CH₂-NH-CH₂CH₂-NH₂),
tetraethylene pentamine 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.
tetraethylethylene diamine (TEEDA) (C₂H₅)₂N-CH₂CH₂-N(C₂H₅)₂

[edit] 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

[edit] 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.