Difference between revisions of "Ethylenediamine"

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(Created page with "{{stub}} '''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 [...")
 
(→‎Relevant Sciencemadness threads)
 
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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.
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{{Chembox
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==Properties==
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| Name = Ethylenediamine
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| Reference =
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| IUPACName = Ethane-1,2-diamine
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| PIN = Ethane-1,2-diamine
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| SystematicName = Ethane-1,2-diamine
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| OtherNames = 1,2-Diaminoethane<br>Edamine
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| ImageFile = Ethylendiamine.jpg
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| ImageSize = 270
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| ImageCaption = Ethylendiamine fuming in air
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<!-- Sections -->
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| Section1 = {{Chembox Identifiers
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| 3DMet =
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| Abbreviations =
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| SMILES =
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  }}
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| Section2 = {{Chembox Properties
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| AtmosphericOHRateConstant =
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| Appearance = Colorless liquid
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| BoilingPt =
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| BoilingPtC = 116
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| BoilingPt_ref =
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| BoilingPt_notes =
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| Density = 0.9 g/cm<sup>3</sup> (20 °C)<br>0.898 g/cm<sup>3</sup> (25 °C)
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| Formula = C<sub>2</sub>H<sub>8</sub>N<sub>2</sub>
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| HenryConstant = 5.8 mol·Pa<sup>−1</sup>·kg<sup>−1</sup>
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| LogP = −2.057
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| MolarMass = 60.10 g/mol
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| MeltingPt =
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| MeltingPtC = 8
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| MeltingPt_ref =
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| MeltingPt_notes =
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| Odor = Ammonia-like
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| pKa =
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| pKb =
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| Solubility = Miscible
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| SolubleOther = Reacts with mineral acids, [[carboxylic acid]]s<br>Miscible with [[alcohol]]s, [[ether]]s, [[ester]]s
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| Solvent =
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| VaporPressure = 1.3 kPa (at 20 °C)
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  }}
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| Section3 = {{Chembox Structure
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| Coordination =
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| CrystalStruct =
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| Section4 = {{Chembox Thermochemistry
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| DeltaGf =
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| DeltaHc = −1,867.8–−1,866.8 kJ/mol
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| DeltaHf = −63.55–−62.47 kJ/mol
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| Entropy = 202.42 J·K<sup>−1</sup>·mol<sup>−1</sup>
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| HeatCapacity = 172.59 J·K<sup>−1</sup>·mol<sup>−1</sup>
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  }}
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| Section5 = {{Chembox Explosive
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| ShockSens =
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| DetonationV =
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| REFactor =
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| Section6 = {{Chembox Hazards
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| AutoignitionPt = 385 °C (725 °F; 658 K)
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| ExploLimits = 2.7–16%
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| ExternalMSDS = [https://www.docdroid.net/BJEprLq/ethylenediamine-sa.pdf.html Sigma-Aldrich]
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| FlashPt = 34 °C (93 °F; 307 K)
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| LD50 = 500 mg/kg (rat, oral)<br>470 mg/kg (guinea pig, oral)<br>1,160 mg/kg (rat, oral)
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| LC50 =
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| MainHazards = Harmful
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| NFPA-F =
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| Section7 = {{Chembox Related
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| OtherAnions =
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| OtherCations =
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| OtherFunction =
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| OtherFunction_label =
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| OtherCompounds = [[Ethylamine]]
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  }}
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}}
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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.
  
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==Properties==
 
===Physical properties===
 
===Physical properties===
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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.
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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 ammonia-like smell, and its vapors are extremely irritating, which can fume in air. It is miscible with water at all concentrations.
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===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]].
  
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==Sources and production==
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==Availability==
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Ethylenediamine is sold by chemical suppliers.
  
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==Preparation==
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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.
  
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==Projects==
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*EDTA synthesis
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*Make various complexes
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*Make [[tris(ethylenediamine)nickel perchlorate]]
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*Make ethylenediamine dinitrate
  
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==Safety==
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==Handling==
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===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.
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===Storage===
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Should be stored in closed bottles, and sealed to prevent the smell from leaking.
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===Disposal===
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Ethylenediamine should be mixed with a large amount of very flammable solvent then burned, preferably in an incinerator.
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Another option is to neutralize it with an acid, then oxidize the salt with an oxidizing mixture.
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==References==
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<references/>
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===Relevant Sciencemadness threads===
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*[http://www.sciencemadness.org/talk/viewthread.php?tid=61523 Ethylenediamine from ethylenediamine dihydrochloride]
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*[http://www.sciencemadness.org/talk/viewthread.php?tid=20814 Ethylenediamine with a red tint]
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*[http://www.sciencemadness.org/talk/viewthread.php?tid=157788 Ethylenediamine query]
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[[Category:Chemical compounds]]
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[[Category:Organic compounds]]
 
[[Category:Amines]]
 
[[Category:Amines]]
 
[[Category:Primary amines]]
 
[[Category:Primary amines]]
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[[Category:Organic compounds]]
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[[Category:Polyamines]]
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[[Category:Chemical compounds]]
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[[Category:Organic bases]]
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[[Category:Chelating agents]]
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[[Category:Ligands]]
 
[[Category:Ligands]]
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[[Category:Chelating agents]]
 
[[Category:Solvents]]
 
[[Category:Solvents]]
 
[[Category:Nonpolar solvents]]
 
[[Category:Nonpolar solvents]]
 
[[Category:Nonpolar compounds]]
 
[[Category:Nonpolar compounds]]
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[[Category:Liquids]]

Latest revision as of 19:16, 25 November 2021

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Ethylenediamine
Ethylendiamine.jpg
Ethylendiamine fuming in air
Names
IUPAC name
Ethane-1,2-diamine
Preferred IUPAC name
Ethane-1,2-diamine
Systematic IUPAC name
Ethane-1,2-diamine
Other names
1,2-Diaminoethane
Edamine
Properties
C2H8N2
Molar mass 60.10 g/mol
Appearance Colorless liquid
Odor Ammonia-like
Density 0.9 g/cm3 (20 °C)
0.898 g/cm3 (25 °C)
Melting point 8 °C (46 °F; 281 K)
Boiling point 116 °C (241 °F; 389 K)
Miscible
Solubility Reacts with mineral acids, carboxylic acids
Miscible with alcohols, ethers, esters
Vapor pressure 1.3 kPa (at 20 °C)
Thermochemistry
202.42 J·K−1·mol−1
−63.55–−62.47 kJ/mol
Hazards
Safety data sheet Sigma-Aldrich
Flash point 34 °C (93 °F; 307 K)
Lethal dose or concentration (LD, LC):
500 mg/kg (rat, oral)
470 mg/kg (guinea pig, oral)
1,160 mg/kg (rat, oral)
Related compounds
Related compounds
 Ethylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.

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 ammonia-like smell, and its vapors are extremely irritating, which can fume in air. 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

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 should be mixed with a large amount of very flammable solvent then burned, preferably in an incinerator.

Another option is to neutralize it with an acid, then oxidize the salt with an oxidizing mixture.

References

Relevant Sciencemadness threads

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