| Ethylenediamine | |
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1,2-Diaminoethane |
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Ethane-1,2-diamine |
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Other names
Edamine[1] |
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| Identifiers | |
| Abbreviations | EN |
| CAS number | 107-15-3 |
| PubChem | 3301 |
| ChemSpider | 13835550 |
| UNII | 60V9STC53F |
| EC number | 203-468-6 |
| UN number | 1604 |
| KEGG | D01114 |
| MeSH | Ethylenediamine |
| ChEBI | CHEBI:30347 |
| ChEMBL | CHEMBL816 |
| RTECS number | KH8575000 |
| Beilstein Reference | 605263 |
| Gmelin Reference | 1098 |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C2H8N2 |
| Molar mass | 60.1 g mol−1 |
| Exact mass | 60.068748266 g mol-1 |
| Appearance | Colourless liquid |
| Density | 0.899 g cm-3 |
| Melting point |
9 °C, 282 K, 48 °F |
| Boiling point |
116-118 °C, 389-391 K, 241-244 °F |
| log P | -2.057 |
| Vapor pressure | 10 mmHg (at 20 °C) |
| Acidity (pKa) | 9.98[2] |
| Structure | |
| Molecular shape | Tetrahedral at N and C |
| Hazards | |
| EU Index | 612-006-00-6 |
| EU classification | C |
| R-phrases | R10, R21/22, R34, R42/43 |
| S-phrases | (S1/2), S23, S26, S36/37/39, S45 |
| NFPA 704 |
3
2
3
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| Flash point | 34-38 °C |
| Explosive limits | 16% |
| Related compounds | |
| Related polyamines | Diethylenetriamine Triethylenetetramine Polyethylene amine Tetramethylethylenediamine |
| Related compounds | Ethanolamine |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a strongly basic amine. The liquid fumes upon contact with humid air. It is a widely used building block in chemical synthesis, with approximately 500,000,000 kg being produced in 1998.[3]
Contents |
Ethylenediamine is manufactured industrially from 1,2-dichloroethane and ammonia under pressure at 180 °C in an aqueous medium:[3][4]
In this reaction hydrogen chloride is generated, which forms a salt with the amine. The amine is liberated by addition of sodium hydroxide and can then be recovered by rectifcation. Diethylenetriamine (DETA) and triethylenetetramine (TETA) are formed as by-products.
Another industrial route to ethylenediamine involves the reaction of ethanolamine and ammonia:[5]
This process involves passing the gaseous reactants over a bed of nickel heterogeneous catalysts.
Ethylenediamine is used in large quantities for production of many industrial chemicals. It forms derivatives with carboxylic acids (including fatty acids), nitriles, alcohols (at elevated temperatures), alkylating agents, carbon disulfide, and aldehydes and ketones. Because of its bifunctional nature, having two amines, it readily forms heterocycles such as imidazolidines.
Ethylenediamine is a well-known chelating ligand for coordination compounds, such as [Co(ethylenediamine)3]3+. The most prominent derivative of ethylenediamine is EDTA, which is derived from ethylenediamine via a Strecker synthesis involving cyanide and formaldehyde. Hydroxyethylethylenediamine is another commercially significant chelating agent. The salen ligands, derived from the condensation of salicylaldehydes and ethylenediamine, are popular chelating agents in the research laboratory although not commercially significant.[3]
Numerous bio-active compounds contain the N-CH2-CH2-N linkage, including aminophylline and some antihistamines.[6] Salts of ethylenebisdithiocarbamate are commercially significant fungicides under the brand names Maneb, Mancozeb, Zineb, and Metiram. Some imidazoline-containing fungicides are derived from ethylenediamine.[3]
Ethylenediamine, because it contains two amine groups, is widely used precursor to various polymers. Condensates derived from formaldehyde are plasticizers. It is widely used in the production of polyurethane fibers. The PAMAM class of dendrimers are derived from ethylenediamine.[3]
The bleaching activator tetraacetylethylenediamine is generated from ethylenediamine. The derivative N,N-ethylenebis(stearamide) (EBS) is a commercially significant mold-release agent and a surfactant in gasoline and motor oil.
Ethylenediamine is the first member of the so-called polyethylene amines, other members being:
Related derivatives of ethylenediamine include tetramethylethylenediamine (abbreviated TMEDA), (CH3)2N-CH2CH2-N(CH3)2 and tetraethylethylenediamine (abbreviated TEEDA) (C2H5)2N-CH2CH2-N(C2H5)2
Ethylenediamine, like most amines, is a skin irritant. It was used in commercially available skin products including Mycolog cream.[7] 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 urinal excretion.[8]
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