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Ethylene diamine

Ethylenediamine
Skeletal formula of ethylenediamine
Ball and stick model of ethylenediamine
Space-filling model of ethylenediamine
Sample of ethylenediamine in a jar
Names
Preferred IUPAC name
Ethane-1,2-diamine
Systematic IUPAC name
Ethane-1,2-diamine
Other names
Edamine 1,2-Diaminoethane,
Identifiers
107-15-3 YesY
3D model (Jmol) Interactive image
Abbreviations en
605263
ChEBI CHEBI:30347 YesY
ChEMBL ChEMBL816 YesY
ChemSpider 13835550 YesY
ECHA InfoCard 100.003.154
EC Number 203-468-6
1098
KEGG D01114 YesY
MeSH ethylenediamine
PubChem 3301
RTECS number KH8575000
UNII 60V9STC53F YesY
UN number 1604
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)
5.8 mol Pa−1 kg−1
  • -46.26·10−6 cm3/mol
  • -76.2·10−6 cm3/mol (HCl salt)
1.4565
Thermochemistry
172.59 J K−1 mol−1
202.42 J K−1 mol−1
−63.55–−62.47 kJ mol−1
−1.8678–−1.8668 MJ mol−1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H226, H302, H312, H314, H317, H334
P261, P280, P305+351+338, P310
Corrosive C
R-phrases R10, R21/22, R34, R42/43
S-phrases (S1/2), S26, S36/37/39, S45
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
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):
LD50 (median dose)
500 mg/kg (oral, rat)
470 mg/kg (oral, guinea pig)
1160 mg/kg (oral, rat)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 10 ppm (25 mg/m3)
REL (Recommended)
TWA 10 ppm (25 mg/m3)
IDLH (Immediate danger)
1000 ppm
Related compounds
Related alkanamines
1,2-Diaminopropane, 1,3-Diaminopropane
Related compounds
ethylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
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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