Ethylenediamine


Ethylenediamine
Ethylenediamine
Identifiers
Abbreviations EN
CAS number 107-15-3 YesY
PubChem 3301
ChemSpider 13835550 YesY
UNII 60V9STC53F YesY
EC number 203-468-6
UN number 1604
KEGG D01114 YesY
MeSH Ethylenediamine
ChEBI CHEBI:30347 YesY
ChEMBL CHEMBL816 YesY
RTECS number KH8575000
Beilstein Reference 605263
Gmelin Reference 1098
Jmol-3D images Image 1
Image 2
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 Corrosive C
R-phrases R10, R21/22, R34, R42/43
S-phrases (S1/2), S23, S26, S36/37/39, S45
NFPA 704
NFPA 704.svg
3
2
3
Flash point 34-38 °C
Explosive limits 16%
Related compounds
Related polyamines Diethylenetriamine
Triethylenetetramine
Polyethylene amine
Tetramethylethylenediamine
Related compounds Ethanolamine
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

Synthesis

Ethylenediamine is manufactured industrially from 1,2-dichloroethane and ammonia under pressure at 180 °C in an aqueous medium:[3][4]

Ethylendiamin Darstellung.svg

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]

EDA synthesis from MEOA.svg

This process involves passing the gaseous reactants over a bed of nickel heterogeneous catalysts.

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 amines, it readily forms heterocycles such as imidazolidines.

Chelating agent and precursor to other ligands

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]

Precursor to pharmaceuticals and agrochemicals

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]

Role in polymers

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]

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.

Specialized applications

Ethylenamine derivatives

Ethylenediamine is the first member of the so-called polyethylene amines, other members being:

  • Diethylenetriamine, abbreviated dien or DETA, (H2N-CH2CH2-NH-CH2CH2-NH2, an analog of diethylene glycol)
  • Triethylenetetramine, abbreviated trien or TETA, (H2N-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH2)
  • Tetraethylenepentamine, abbreviated TEPA, (H2N-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH2),
  • Pentaethylenehexamine, abbreviated PEHA, (H2N-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH-CH2CH2-NH2), up to polyethylene amine. Similarly piperazine is an analogue of dioxane.

Related derivatives of ethylenediamine include tetramethylethylenediamine (abbreviated TMEDA), (CH3)2N-CH2CH2-N(CH3)2 and tetraethylethylenediamine (abbreviated TEEDA) (C2H5)2N-CH2CH2-N(C2H5)2

Safety

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]

References

  1. ^ Council Regulation (EC) No 129/2007 of 12 February 2007 providing for duty-free treatment for specified pharmaceutical active ingredients bearing an international non-proprietary name (INN) from the World Health Organisation and specified products used for the manufacture of finished pharmaceuticals
  2. ^ Hall, H.K., J. Am. Chem. Soc., 1957, 79, 5441.
  3. ^ a b c d e Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, 2005 Wiley-VCH Verlag, Weinheim. doi:10.1002/14356007.a02_001
  4. ^ Hans-Jürgen Arpe, Industrielle Organische Chemie, 6. Auflage (2007), Seite 245, Wiley VCH
  5. ^ Hans-Jürgen Arpe, Industrielle Organische Chemie, 6. Auflage (2007), Seite 275, Wiley VCH
  6. ^ Kotti, S. R. S. S.; Timmons, C. and Li, G. (2006). "Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry". Chemical Biology & Drug Design 67 (2): 101–114. doi:10.1111/j.1747-0285.2006.00347.x. PMID 16492158. 
  7. ^ Hogan DJ. (January 1990). "Allergic contact dermatitis to ethylenediamine. A continuing problem.". Dermatol Clin. 8 (1): 133–6. PMID 2137392. 
  8. ^ Zuidema J. (1985-08-23). "Ethylenediamine, profile of a sensitizing excipient.". Pharmacy World & Science 7 (4): 134–40. doi:10.1007/BF02097249. PMID 3900925. 

External links


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