Difference between revisions of "Ethylenediamine"
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'''Ethylenediamine''' is an [[organic compound]] with the formula C<sub>2</sub>H<sub>4</sub>(NH<sub>2</sub>)<sub>2</sub>, and is often abbreviated en when used as a [[ligand]]. It is a common ligand in [[Coordination complex|coordination chemistry]] and a ubiquitous chemical building block in [[organic synthesis]]. It is volatile, but tends to form a mist in air, which is quite toxic. | '''Ethylenediamine''' is an [[organic compound]] with the formula C<sub>2</sub>H<sub>4</sub>(NH<sub>2</sub>)<sub>2</sub>, and is often abbreviated en when used as a [[ligand]]. It is a common ligand in [[Coordination complex|coordination chemistry]] and a ubiquitous chemical building block in [[organic synthesis]]. It is volatile, but tends to form a mist in air, which is quite toxic. | ||
| − | |||
| + | ==Properties== | ||
===Physical properties=== | ===Physical properties=== | ||
Ethylenediamine is a clear, colorless liquid at room temperature. It freezes at 8 °C and boils at 116 °C, both of which are close to the melting and boiling points of water. It has an ammoniacal smell, and its vapors are extremely irritating. It is miscible with water at all concentrations. | Ethylenediamine is a clear, colorless liquid at room temperature. It freezes at 8 °C and boils at 116 °C, both of which are close to the melting and boiling points of water. It has an ammoniacal smell, and its vapors are extremely irritating. It is miscible with water at all concentrations. | ||
| + | |||
===Chemical properties=== | ===Chemical properties=== | ||
Ethylenediamine is a powerful [[chelating agent]] and will readily [[Coordination complex|complex]] to many metal ions, notably, [[cobalt]], [[nickel]], [[copper]], and [[chromium]] (with some difficulty). The stability of these complexes is due to an increase in [[entropy]] by freeing 2 monodentate [[Ligand|ligands]] per complexed ethylenediamine molecule. | Ethylenediamine is a powerful [[chelating agent]] and will readily [[Coordination complex|complex]] to many metal ions, notably, [[cobalt]], [[nickel]], [[copper]], and [[chromium]] (with some difficulty). The stability of these complexes is due to an increase in [[entropy]] by freeing 2 monodentate [[Ligand|ligands]] per complexed ethylenediamine molecule. | ||
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Energetic materials can be made with ethylenediamine and metal [[perchlorate]]s, most notably [[tris(ethylenediamine)nickel perchlorate]] and [[bis(ethylenediamine)copper(II) perchlorate]]. | Energetic materials can be made with ethylenediamine and metal [[perchlorate]]s, most notably [[tris(ethylenediamine)nickel perchlorate]] and [[bis(ethylenediamine)copper(II) perchlorate]]. | ||
| − | == | + | ==Availability== |
| + | Ethylenediamine is sold by chemical suppliers. | ||
| + | ==Preparation== | ||
| + | Ethylenediamine is manufactured industrially by reacting [[1,2-dichloroethane]] with [[ammonia]] under pressure, at 180 °C in an aqueous medium. This process is complex for the amateur chemist. | ||
| + | ==Projects== | ||
| + | *EDTA synthesis | ||
| + | *Make various complexes | ||
| + | *Make [[tris(ethylenediamine)nickel perchlorate]] | ||
| + | *Make ethylenediamine dinitrate | ||
| − | ==Safety== | + | ==Handling== |
| + | ===Safety=== | ||
Ethylenediamine is toxic and has serious adverse health effects when inhaled. As a pure liquid, it will vaporize and form a mist in the air. If pure ethylenediamine must be used, it should be handled in a fume hood. Otherwise, it is preferable to use a 20% solution, which does not emit fumes and still allows for complexation. | Ethylenediamine is toxic and has serious adverse health effects when inhaled. As a pure liquid, it will vaporize and form a mist in the air. If pure ethylenediamine must be used, it should be handled in a fume hood. Otherwise, it is preferable to use a 20% solution, which does not emit fumes and still allows for complexation. | ||
| + | |||
| + | ===Storage=== | ||
| + | Should be stored in closed bottles, and sealed to prevent the smell from leaking. | ||
| + | |||
| + | ===Disposal=== | ||
| + | Ethylenediamine can be burned. | ||
| + | |||
| + | ==References== | ||
| + | <references/> | ||
| + | ===Relevant Sciencemadness threads=== | ||
| + | |||
| + | [[Category:Chemical compounds]] | ||
| + | [[Category:Organic compounds]] | ||
[[Category:Amines]] | [[Category:Amines]] | ||
[[Category:Primary amines]] | [[Category:Primary amines]] | ||
| − | |||
| − | |||
| − | |||
[[Category:Ligands]] | [[Category:Ligands]] | ||
| + | [[Category:Chelating agents]] | ||
[[Category:Solvents]] | [[Category:Solvents]] | ||
[[Category:Nonpolar solvents]] | [[Category:Nonpolar solvents]] | ||
[[Category:Nonpolar compounds]] | [[Category:Nonpolar compounds]] | ||
Revision as of 13:40, 30 August 2015
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Ethylenediamine is an organic compound with the formula C2H4(NH2)2, and is often abbreviated en when used as a ligand. It is a common ligand in coordination chemistry and a ubiquitous chemical building block in organic synthesis. It is volatile, but tends to form a mist in air, which is quite toxic.
Contents
Properties
Physical properties
Ethylenediamine is a clear, colorless liquid at room temperature. It freezes at 8 °C and boils at 116 °C, both of which are close to the melting and boiling points of water. It has an ammoniacal smell, and its vapors are extremely irritating. It is miscible with water at all concentrations.
Chemical properties
Ethylenediamine is a powerful chelating agent and will readily complex to many metal ions, notably, cobalt, nickel, copper, and chromium (with some difficulty). The stability of these complexes is due to an increase in entropy by freeing 2 monodentate ligands per complexed ethylenediamine molecule.
Energetic materials can be made with ethylenediamine and metal perchlorates, most notably tris(ethylenediamine)nickel perchlorate and bis(ethylenediamine)copper(II) perchlorate.
Availability
Ethylenediamine is sold by chemical suppliers.
Preparation
Ethylenediamine is manufactured industrially by reacting 1,2-dichloroethane with ammonia under pressure, at 180 °C in an aqueous medium. This process is complex for the amateur chemist.
Projects
- EDTA synthesis
- Make various complexes
- Make tris(ethylenediamine)nickel perchlorate
- Make ethylenediamine dinitrate
Handling
Safety
Ethylenediamine is toxic and has serious adverse health effects when inhaled. As a pure liquid, it will vaporize and form a mist in the air. If pure ethylenediamine must be used, it should be handled in a fume hood. Otherwise, it is preferable to use a 20% solution, which does not emit fumes and still allows for complexation.
Storage
Should be stored in closed bottles, and sealed to prevent the smell from leaking.
Disposal
Ethylenediamine can be burned.
