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Ethylenediamine
Ethylenediamine-2D-skeletal.png
Ethylenediamine-3D-balls.png
IUPAC name
Other names en; ethane-1,2-diamine; Edamine[1]
Identifiers
CAS number 107-15-3 Yes check.svgY
RTECS number KH8575000
SMILES
Properties
Molecular formula C2H8N2
Molar mass 60.103 g/mol
Appearance colourless liquid (impure: yellow)
Density 0.899 g/cm3, liquid
Melting point

9 °C

Boiling point

116 °C

Solubility in water Miscible in water
Solubility Most polar solvents
Basicity (pKb) 3.92
Structure
Molecular shape Tetrahedral at N and C
Hazards
Main hazards Flammable, corrosive
 Yes check.svgY (what is this?)  (verify)
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. It is a widely used building block in chemical synthesis, with approximately 500,000,000 kg being produced in 1998.[2]

Contents

Synthesis

Ethylenediamine is manufactured by reacting ammonia and 1,2-dichloroethane. The reaction yields the mixture of ethylenediamine and the linear polyamines. A simplified equation would be:

ClCH2CH2Cl + 4 NH3 → H2NCH2CH2NH2 + 2 NH4Cl

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. Ethylenediamine is a well-known chelating ligand for coordination compounds, such as [Co(ethylenediamine) 3]3+.

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Precursor to chelating agents

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.[2]

Precursor to pharmaceuticals and agrichemicals

Numerous bio-active compounds contain the N-CH2-CH2-N linkage, including aminophylline and some antihistamines.[3] Salts of ethylenebisdithiocarbamate are commercially significant fungicides under the brandnames Maneb, Mancozeb, Zineb, and Metiram. Some imidazoline-containing fungicides are derived from ethylenediamine.[2]

Role in polymers

Ethylenediamine, by virtue of its bifunctionality (i.e. it contains two reactive amines) is widely used in diverse polyester formulations. 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.[2]

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

Ethylenamines

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

  • Diethylenetriamine, abbreviated dien or DETA, (H2N-CH2CH2-NH-CH2CH 2-NH2, an analog of diethylene glycol)
  • Triethylenetetramine, abbreviated trien or TETA, (H2N-CH2CH2-NH-CH2CH 2-NH-CH2CH2-NH2)
  • Tetraethylenepentamine, abbreviated TEPA, (H2N-CH2CH2-NH-CH2CH 2-NH-CH2CH2-NH-CH2CH2-NH 2),
  • Pentaethylenehexamine, abbreviated PEHA, (H2N-CH2CH2-NH-CH2CH 2-NH-CH2CH2-NH-CH2CH2-NH-CH 2CH2-NH2), up to polyethylene amine. Similarly piperazine is an analogue of dioxane.

Related diamines

In terms of quantities produced, ethylenediamine is the most significant diamine (aside from diaminohexane, which is a precursor to Nylon 6-6). Related derivatives of ethylenediamine include tetramethylethylenediamine, abbreviated (TMEDA), (CH3)2N-CH2CH2-N(CH 3)2 and tetraethylethylenediamine, abbreviated (TEEDA), (C2H5)2N-CH2CH2-N(C 2H5)2

Safety

Ethylenediamine exposure can cause the skin to become irritated. It was used in commercially available skin products including Mycolog cream.[4] 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 renal excretion.[5]

See also

References

  1. ^ http://eur-lex.europa.eu/smartapi/cgi/sga_doc?smartapi!celexplus!prod!DocNumber&lg=fr&type_doc=Regulation&an_doc=2007&nu_doc=129
  2. ^ a b c d 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}}
  3. ^ Kotti, S. R. S. S.; Timmons, C. and Li, G., "Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry", Chemical Biology & Drug Design, 2006, 67, 101-114
  4. ^ Hogan DJ. (January 1990). "Allergic contact dermatitis to ethylenediamine. A continuing problem.". Dermatol Clin. 8 (1): 133–6. PMID 2137392.  
  5. ^ Zuidema J. (1985-08-23). "Ethylenediamine, profile of a sensitizing excipient.". Pharmacy World & Science 7 (4): 134–40. doi:10.1007/BF02097249. PMID 3900925.  

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