Ethylenediamine

Ethylenediamine

Names
Preferred IUPAC name Ethane-1,2-diamine
Systematic IUPAC name Ethane-1,2-diamine
Other names Edamine 1,2-Diaminoethane,
Identifiers
CAS Number	107-15-3 Y
3D model (Jmol)	Interactive image
Abbreviations	en
Beilstein Reference	605263
ChEBI	CHEBI:30347 Y
ChEMBL	ChEMBL816 Y
ChemSpider	13835550 Y
ECHA InfoCard	100.003.154
EC Number	203-468-6
Gmelin Reference	1098
KEGG	D01114 Y
MeSH	ethylenediamine
PubChem	3301
RTECS number	KH8575000
UNII	60V9STC53F Y
UN number	1604
InChI InChI=1S/C2H8N2/c3-1-2-4/h1-4H2 Y Key: PIICEJLVQHRZGT-UHFFFAOYSA-N Y
SMILES NCCN
Properties
Chemical formula	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)
Solubility in water	miscible
log P	−2.057
Vapor pressure	1.3 kPa (at 20 °C)
Henry's law constant (kH)	5.8 mol Pa−1 kg−1
Magnetic susceptibility (χ)	-46.26·10−6 cm3/mol -76.2·10−6 cm3/mol (HCl salt)
Refractive index (nD)	1.4565
Thermochemistry
Specific heat capacity (C)	172.59 J K−1 mol−1
Std molar entropy (So298)	202.42 J K−1 mol−1
Std enthalpy of formation (ΔfHo298)	−63.55–−62.47 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−1.8678–−1.8668 MJ mol−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H226, H302, H312, H314, H317, H334
GHS precautionary statements	P261, P280, P305+351+338, P310
EU classification (DSD)	C
R-phrases	R10, R21/22, R34, R42/43
S-phrases	(S1/2), S26, S36/37/39, S45
NFPA 704	3 3 0
Flash point	34 °C (93 °F; 307 K)
Autoignition temperature	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).
Y  (what is YN ?)
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.