Ethylenediamine
From Wikipedia, the free encyclopedia
| Ethylenediamine | |
|---|---|
 |
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| IUPAC name | 1,2-diaminoethane |
| Other names | en |
| Identifiers | |
| CAS number | [] |
| 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 |
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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.
Contents |
[edit] 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 leading is presented:
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- ClCH2CH2Cl + 4 NH3 → H2NCH2CH2NH2 + 2 NH4Cl
[edit] 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 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. aminophylline and some antihistamines.
- as a food and cattle feed additive as ethylenediamine dihydriodide (EDDI).
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.
[edit] 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]
[edit] 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
[edit] See also
[edit] References
- ^ Hogan DJ. (Jan 1990). "Allergic contact dermatitis to ethylenediamine. A continuing problem.". Dermatol Clin. 8 (1): 133-6. PMID 2137392.
- ^ 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.
