Ethylene diamine
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| Names | |||
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Preferred IUPAC name
Ethane-1,2-diamine
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Systematic IUPAC name
Ethane-1,2-diamine
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| Other names
Edamine 1,2-Diaminoethane,
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| Identifiers | |||
107-15-3 
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| 3D model (Jmol) | Interactive image | ||
| Abbreviations | en | ||
| 605263 | |||
| ChEBI |
CHEBI:30347
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| ChEMBL |
ChEMBL816
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| ChemSpider |
13835550
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| ECHA InfoCard | 100.003.154 | ||
| EC Number | 203-468-6 | ||
| 1098 | |||
| KEGG |
D01114
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| MeSH | ethylenediamine | ||
| PubChem | 3301 | ||
| RTECS number | KH8575000 | ||
| UNII |
60V9STC53F
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| UN number | 1604 | ||
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| Properties | |||
| C2H8N2 | |||
| Molar mass | 60.10 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Odor | Ammoniacal | ||
| Density | 0.90 g/cm3 | ||
| Melting point | 8 °C (46 °F; 281 K) | ||
| Boiling point | 116 °C (241 °F; 389 K) | ||
| miscible | |||
| log P | −2.057 | ||
| Vapor pressure | 1.3 kPa (at 20 °C) | ||
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Henry's law
constant (kH) |
5.8 mol Pa−1 kg−1 | ||
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Refractive index (nD)
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1.4565 | ||
| Thermochemistry | |||
| 172.59 J K−1 mol−1 | |||
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Std molar
entropy (S |
202.42 J K−1 mol−1 | ||
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Std enthalpy of
formation (ΔfH |
−63.55–−62.47 kJ mol−1 | ||
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Std enthalpy of
combustion (ΔcH |
−1.8678–−1.8668 MJ mol−1 | ||
| Hazards | |||
| GHS pictograms |
   
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| GHS signal word | DANGER | ||
| H226, H302, H312, H314, H317, H334 | |||
| P261, P280, P305+351+338, P310 | |||
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EU classification (DSD)
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 C |
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| R-phrases | R10, R21/22, R34, R42/43 | ||
| S-phrases | (S1/2), S26, S36/37/39, S45 | ||
| NFPA 704 | |||
| Flash point | 34 °C (93 °F; 307 K) | ||
| 385 °C (725 °F; 658 K) | |||
| Explosive limits | 2.7–16% | ||
| Lethal dose or concentration (LD, LC): | |||
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LD50 (median dose)
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500 mg/kg (oral, rat) 470 mg/kg (oral, guinea pig) 1160 mg/kg (oral, rat) |
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| US health exposure limits (NIOSH): | |||
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PEL (Permissible)
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TWA 10 ppm (25 mg/m3) | ||
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REL (Recommended)
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TWA 10 ppm (25 mg/m3) | ||
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IDLH (Immediate danger)
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1000 ppm | ||
| Related compounds | |||
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Related alkanamines
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1,2-Diaminopropane, 1,3-Diaminopropane | ||
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Related compounds
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ethylamine | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is  ?) |
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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. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine readily reacts with moisture in humid air to produce a corrosive, toxic and irritating mist, to which even short exposures can cause serious damage to health (see safety).
Ethylenediamine is manufactured industrially from 1,2-dichloroethane and ammonia under pressure at 180 °C in an aqueous medium:
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 rectification. Diethylenetriamine (DETA) and triethylenetetramine (TETA) are formed as by-products.
Another industrial route to ethylenediamine involves the reaction of ethanolamine and ammonia:
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.
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