Ethylenediamine
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
Ethane-1,2-diamine[2] | |||
| Other names
Edamine,[1] 1,2-Diaminoethane, 'en' when a ligand
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| Identifiers | |||
3D model (
JSmol ) |
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| Abbreviations | en | ||
| 605263 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
ECHA InfoCard
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100.003.154 | ||
| EC Number |
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| 1098 | |||
| KEGG | |||
| MeSH | ethylenediamine | ||
PubChem CID
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RTECS number
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| UNII | |||
| UN number | 1604 | ||
CompTox Dashboard (EPA)
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| Properties | |||
| C2H8N2 | |||
| Molar mass | 60.100 g·mol−1 | ||
| Appearance | Colorless liquid[3] | ||
| Odor | Ammoniacal[3] | ||
| Density | 0.90 g/cm3[3] | ||
| Melting point | 8 °C (46 °F; 281 K)[3] | ||
| Boiling point | 116 °C (241 °F; 389 K)[3] | ||
| 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 | ||
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Refractive index (nD)
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1.4565 | ||
| Thermochemistry | |||
Heat capacity (C)
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172.59 J K−1 mol−1 | ||
Std molar
entropy (S⦵298) |
202.42 J K−1 mol−1 | ||
Std enthalpy of (ΔfH⦵298)formation |
−63.55 to −62.47 kJ mol−1 | ||
Std enthalpy of (ΔcH⦵298)combustion |
−1.8678 to −1.8668 MJ mol−1 | ||
| Hazards | |||
| GHS labelling: | |||
   
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| Danger | |||
| H226, H302, H311, H314, H317, H332, H334, H412 | |||
| P101, P102, P260, P273, P280, P305+P351+P338, P308+P313, P405, P501 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 34 °C (93 °F; 307 K)[3] | ||
| 385 °C (725 °F; 658 K)[3] | |||
Explosive limits
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2.7–16% | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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500 mg/kg (oral, rat) 470 mg/kg (oral, guinea pig) 1160 mg/kg (oral, rat)[5] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible)
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TWA 10 ppm (25 mg/m3)[4] | ||
REL (Recommended)
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TWA 10 ppm (25 mg/m3)[4] | ||
IDLH (Immediate danger) |
1000 ppm[4] | ||
| Related compounds | |||
Related alkanamines
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1,2-Diaminopropane, 1,3-Diaminopropane | ||
Related compounds
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Ethylamine, Ethylenedinitramine | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ethylenediamine (abbreviated as en when a
Synthesis
Ethylenediamine is produced industrially by treating
In this reaction
Another industrial route to ethylenediamine involves the reaction of ethanolamine and ammonia:[8]
This process involves passing the gaseous reactants over a bed of nickel
It can be produced in the lab by the reaction of ethylene glycol and urea.[citation needed]
Ethylenediamine can be purified by treatment with sodium hydroxide to remove water followed by distillation.[9]
Applications
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 amino groups, it readily forms heterocycles such as imidazolidines.
Precursor to chelation agents, drugs, and agrochemicals
A most prominent derivative of ethylenediamine is the
Pharmaceutical ingredient
Ethylenediamine is an
Ethylenediamine-derived
Role in polymers
Ethylenediamine, because it contains two amine groups, is a 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.[6]
Tetraacetylethylenediamine
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.
Other applications
- as a albumins and casein. It is also used in certain electroplatingbaths.
- as a coolants.
- ethylenediamine dihydroiodide (EDDI) is added to animal feeds as a source of iodide.
- chemicals for color photography developing, binders, adhesives, fabric softeners, curing agents for epoxies, and dyes.
- as a compound to sensitize nitromethane into an explosive. This mixture was used at Picatinny Arsenal during World War II, giving the nitromethane and ethylenediamine mixture the nickname PLX, or Picatinny Liquid Explosive.
Coordination chemistry
Ethylenediamine is a well-known
Related ligands
Related derivatives of ethylenediamine include
Safety
Ethylenediamine, like ammonia and other low-molecular weight amines, is a skin and respiratory irritant. Unless tightly contained, liquid ethylenediamine will release toxic and irritating vapors into its surroundings, especially on heating. The vapors absorb moisture from humid air to form a characteristic white mist, which is extremely irritating to skin, eyes, lungs and mucus membranes.
References
- ^ "32007R0129". European Union. 12 February 2007. Annex II. Retrieved 3 May 2012.
- ISBN 978-0-85404-182-4.
- ^ a b c d e f g Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0269". National Institute for Occupational Safety and Health (NIOSH).
- ^ "Ethylenediamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ ISBN 3-527-30673-0.
- ^ Arpe, Hans-Jürgen (2007). Industrielle Organische Chemie (6th ed.). Wiley VCH. p. 245.
{{cite book}}: CS1 maint: location missing publisher (link) - ^ Hans-Jürgen Arpe, Industrielle Organische Chemie, 6. Auflage (2007), Seite 275, Wiley VCH
- ISBN 978-0-470-13233-3.
- S2CID 37177899.
- PMID 2137392.
- S2CID 11016366.
External links
Media related to Ethylenediamine at Wikimedia Commons