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{{Chembox |
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| verifiedrevid = 398780081 |
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| verifiedrevid = 409535272 |
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| Name = |
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| ImageFileL1 = Ethylenediamine-2D-skeletal.png |
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| ImageFile = Ethylene diamine fuming.jpg |
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| ImageFileL1_Ref = {{Chemboximage|correct|??}} |
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| ImageFile1 = Ethane-1,2-diamine 200.svg |
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| ImageSizeL1 = 121 |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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| ImageNameL1 = Structural formula of ethylenediamine |
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| ImageName1 = Skeletal formula of ethylenediamine |
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| ImageFileR1 = Ethylenediamine-3D-balls.png |
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| ImageFileL1 = Ethylenediamine-3D-balls-2.png |
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| ImageFileR1_Ref = {{Chemboximage|correct|??}} |
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| ImageFileL1_Ref = {{Chemboximage|correct|??}} |
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| ImageSizeR1 = 121 |
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| ImageNameR1 = Ball and stick model of ethylenediamine |
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| ImageNameL1 = Ball and stick model of ethylenediamine |
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| ImageFileR1 = Ethylenediamine-3D-spacefill.png |
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| IUPACName = 1,2-Diaminoethane |
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| ImageFileR1_Ref = {{Chemboximage|correct|??}} |
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| SystematicName = Ethane-1,2-diamine |
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| ImageNameR1 = Space-filling model of ethylenediamine |
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| OtherNames = Edamine<ref></ref> |
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| ImageFile2_Ref = {{Chemboximage|correct|??}} |
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| ImageName2 = Sample of ethylenediamine in a jar |
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| PIN = Ethane-1,2-diamine<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |page=676 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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| OtherNames = Edamine,<ref>{{Cite web|title=32007R0129|url=http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=CELEX:32007R0129:EN:NOT|publisher=European Union|access-date=3 May 2012|date=12 February 2007|at=Annex II}}</ref> 1,2-Diaminoethane, 'en' when a ligand |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| Abbreviations = EN |
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| Abbreviations = en |
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| CASNo = 107-15-3 |
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| CASNo = 107-15-3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 3301 |
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| PubChem = 3301 |
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| ChemSpiderID = 13835550 |
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| PubChem_Ref = {{Pubchemcite|correct|PubChem}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13835550 |
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| UNII = 60V9STC53F |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 60V9STC53F |
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| EINECS = 203-468-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 203-468-6 |
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| UNNumber = 1604 |
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| UNNumber = 1604 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = D01114 |
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| KEGG = D01114 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| MeSHName = Ethylenediamine |
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| MeSHName = ethylenediamine |
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| ChEBI = 30347 |
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| ChEMBL = 816 |
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| ChEBI = 30347 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| RTECS = KH8575000 |
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| ChEMBL = 816 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| Beilstein = 605263 |
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| Gmelin = 1098 |
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| RTECS = KH8575000 |
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| SMILES = NCCN |
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| Beilstein = 605263 |
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| SMILES1 = C(CN)N |
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| Gmelin = 1098 |
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| StdInChI = 1S/C2H8N2/c3-1-2-4/h1-4H2 |
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| SMILES = NCCN |
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| StdInChI = 1S/C2H8N2/c3-1-2-4/h1-4H2 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = PIICEJLVQHRZGT-UHFFFAOYSA-N |
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| InChI = 1/C2H8N2/c3-1-2-4/h1-4H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = PIICEJLVQHRZGT-UHFFFAOYSA-N |
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}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey = PIICEJLVQHRZGT-UHFFFAOYAH}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C = 2 |
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| C=2 | H=8 | N=2 |
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| Appearance = Colorless liquid<ref name=GESTIS>{{GESTIS|ZVG=32650}}</ref> |
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| H = 8 |
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| Odor = Ammoniacal<ref name=GESTIS/> |
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| N = 2 |
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| ExactMass = 60.068748266 g mol<sup>-1</sup> |
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| Density = 0.90 g/cm<sup>3</sup><ref name=GESTIS/> |
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| MeltingPtC = 8 |
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| Appearance = Colourless liquid |
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| MeltingPt_ref = <ref name=GESTIS/> |
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| Density = 0.899 g cm<sup>-3</sup> |
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| MeltingPtC = 9 |
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| BoilingPtC = 116 |
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| BoilingPt_ref = <ref name=GESTIS/> |
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| BoilingPtCL = 116 |
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| Solubility = miscible |
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| BoilingPtCH = 118 |
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| LogP = -2.057 |
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| LogP = −2.057 |
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| VaporPressure = 10 mmHg (at 20 °C) |
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| VaporPressure = 1.3 kPa (at 20 °C) |
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| HenryConstant = 5.8 mol Pa<sup>−1</sup> kg<sup>−1</sup> |
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| pKa = 9.98<ref>Hall, H.K., ''J. Am. Chem. Soc.'', '''1957''', ''79'', 5441.</ref>}} |
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| RefractIndex = 1.4565 |
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| Section3 = {{Chembox Structure |
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| MagSus = {{ubl| {{val|-46.26e-6|u=cm<sup>3</sup> mol<sup>−1</sup>}}| {{val|-76.2e-6|u=cm<sup>3</sup> mol<sup>−1</sup>}} (HCl salt)}} |
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| MolShape = Tetrahedral at N and C}} |
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}} |
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| Section3 = {{Chembox Thermochemistry |
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| DeltaHf = −63.55 to −62.47 kJ mol<sup>−1</sup> |
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| DeltaHc = −1.8678 to −1.8668 MJ mol<sup>−1</sup> |
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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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| Section4 = {{Chembox Hazards |
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| Section4 = {{Chembox Hazards |
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| GHSPictograms = {{GHS flame}} {{GHS skull and crossbones}} {{GHS corrosion}} {{GHS health hazard}} |
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| EUIndex = 612-006-00-6 |
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| GHSSignalWord = '''DANGER''' |
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| EUClass = {{Hazchem C}} |
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| HPhrases = {{H-phrases|226|311|302|332|314|334|317|412}} |
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| RPhrases = {{R10}}, {{R21/22}}, {{R34}}, {{R42/43}} |
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| PPhrases = {{P-phrases|405|102|260|280|305+351+338|101|308+313|273|501}} |
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| SPhrases = {{S1/2}}, {{S23}}, {{S26}}, {{S36/37/39}}, {{S45}} |
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| NFPA-H = 2 |
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| NFPA-H = 3 |
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| NFPA-F = 3 |
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| NFPA-F = 2 |
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| NFPA-R = 3 |
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| NFPA-R = 0 |
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| FlashPt = 34-38 °C |
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| FlashPtC =34 |
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| FlashPt_ref = <ref name=GESTIS/> |
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| ExploLimits = 16%}} |
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| AutoignitionPtC = 385 |
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| AutoignitionPt_ref = <ref name=GESTIS/> |
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| ExploLimits = 2.7–16% |
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| LD50 = 500 mg/kg (oral, rat)<br/>470 mg/kg (oral, guinea pig)<br/>1160 mg/kg (oral, rat)<ref>{{IDLH|107153|Ethylenediamine}}</ref> |
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| PEL = TWA 10 ppm (25 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0269}}</ref> |
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| IDLH = 1000 ppm<ref name=PGCH/> |
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| REL = TWA 10 ppm (25 mg/m<sup>3</sup>)<ref name=PGCH/> |
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}} |
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| Section5 = {{Chembox Related |
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| Section5 = {{Chembox Related |
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| OtherFunction_label = alkanamines |
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| Function = ]s |
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| OtherFunction =], ] |
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| OtherFunctn = ]<br>]<br>]<br>] |
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| OtherCompounds = ], ] |
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| OtherCpds = ]}} |
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}} |
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| Section6 = |
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'''Ethylenediamine''' (abbreviated as '''en''' when a ]) is the ] with the ] C<sub>2</sub>H<sub>4</sub>(NH<sub>2</sub>)<sub>2</sub>. This colorless liquid with an ]-like odor is a strongly ] ]. It is a widely used building block in chemical synthesis, with approximately 500,000,000 kg being produced in 1998.<ref name=Ullmann>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}}</ref> |
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'''Ethylenediamine''' (abbreviated as '''en''' when a ]) is the ] with the ] C<sub>2</sub>H<sub>4</sub>(NH<sub>2</sub>)<sub>2</sub>. This colorless liquid with an ]-like odor is a ] ]. It is a widely used building block in chemical synthesis, with approximately 500,000 ] produced in 1998.<ref name=Ullmann>{{cite encyclopedia|first1=Karsten |last1=Eller |first2=Erhard |last2=Henkes |first3=Roland |last3=Rossbacher |first4=Hartmut |last4=Höke |title=Amines, Aliphatic |entry=Amines, Aliphatic |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry |date=2005 |publisher=Wiley-VCH Verlag |location=Weinheim |doi=10.1002/14356007.a02_001|isbn=3-527-30673-0 }}</ref> Ethylenediamine is the first member of the so-called ]. |
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==Synthesis== |
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==Synthesis== |
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{{seealso|ethyleneamines}} |
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Ethylenediamine is manufactured by reacting ] and ]. The reaction yields the mixture of ethylenediamine and the linear polyamines. A simplified equation would be: |
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Ethylenediamine is produced industrially by treating ] with ] under pressure at 180 °C in an aqueous medium:<ref name=Ullmann/><ref name="arpe1">{{cite book|first=Hans-Jürgen |last=Arpe |title=Industrielle Organische Chemie |edition=6th |date=2007 |page=245 |location=Wiley VCH}}</ref> |
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::ClCH<sub>2</sub>CH<sub>2</sub>Cl + 4 NH<sub>3</sub> → H<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub> + 2 NH<sub>4</sub>Cl |
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:] |
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In this reaction ] is generated, which forms a salt with the amine. The amine is liberated by addition of ] and can then be recovered by ]. ] (DETA) and ] (TETA) are formed as by-products. |
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Another industrial route to ethylenediamine involves the reaction of ] and ammonia:<ref name="arpe2">Hans-Jürgen Arpe, Industrielle Organische Chemie, 6. Auflage (2007), Seite 275, Wiley VCH</ref> |
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:] |
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This process involves passing the gaseous reactants over a bed of nickel ]s. |
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It can be produced in the lab by the reaction of ] and ].{{Citation needed|date=December 2021}} |
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Ethylenediamine can be purified by treatment with sodium hydroxide to remove water followed by distillation.<ref name=JCB>{{cite book|doi=10.1002/9780470132333.ch60|chapter=Tris(ethylenediamine)chromium(III) Salts|pages=196–200|volume=2|year=1946|last1=Rollinson|first1=Carl L.|title=Inorganic Syntheses|last2=Bailar|first2=John C. Jr.|isbn=978-0-470-13233-3}}</ref> |
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==Applications== |
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==Applications== |
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Ethylenediamine is used in large quantities for production of many industrial chemicals. It forms derivatives with ]s (including ]s), ]s, ]s (at elevated temperatures), alkylating agents, ], and ]s and ]s. Because of its bifunctional nature, having two amines, it readily forms heterocycles such as ]s. Ethylenediamine is a well-known ] ] for ]s, such as </nowiki><sup>3+</sup>]]. |
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Ethylenediamine is used in large quantities for production of many industrial chemicals. It forms derivatives with ]s (including ]s), ]s, ]s (at elevated temperatures), alkylating agents, ], and ]s and ]s. Because of its bifunctional nature, having two amino groups, it readily forms heterocycles such as ]s. |
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===Precursor to chelating agents=== |
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===Precursor to chelation agents, drugs, and agrochemicals=== |
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The most prominent derivative of ethylenediamine is ], which is derived from ethylenediamine via a ] involving ] and ]. Hydroxyethylethylenediamine is another commercially significant chelating agent. The ]s, derived from the condensation of ]s and ethylenediamine, are popular chelating agents in the research laboratory although not commercially significant.<ref name=Ullmann/> |
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A most prominent derivative of ethylenediamine is the ] agent ], which is derived from ethylenediamine via a ] involving ] and ]. Hydroxyethylethylenediamine is another commercially significant chelating agent.<ref name=Ullmann/> Numerous bio-active compounds and drugs contain the N–CH<sub>2</sub>–CH<sub>2</sub>–N linkage, including some ]s.<ref>{{cite journal | doi=10.1111/j.1747-0285.2006.00347.x | last1=Kotti | first1=S. R. S. S. | last2=Timmons | first2=C. | last3=Li | first3=G. | title=Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry | pmid=16492158 | journal = Chemical Biology & Drug Design | year = 2006 | volume = 67 | issue = 2| pages=101–114 | s2cid=37177899 }}</ref> Salts of ethylenebisdithiocarbamate are commercially significant fungicides under the brand names ], Mancozeb, ], and Metiram. Some ]-containing fungicides are derived from ethylenediamine.<ref name=Ullmann/> |
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===Pharmaceutical ingredient=== |
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===Precursor to pharmaceuticals and agrichemicals=== |
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Ethylenediamine is an ] in the common ] drug ], where it serves to solubilize the active ingredient ]. Ethylenediamine has also been used in dermatologic preparations, but has been removed from some because of causing contact dermatitis.<ref>{{cite journal| author= Hogan DJ| title= Allergic contact dermatitis to ethylenediamine. A continuing problem. | journal = ] |date=January 1990 | volume = 8 |issue = 1 | pages=133–6 |pmid = 2137392 | doi= 10.1016/S0733-8635(18)30536-9}}</ref> When used as a pharmaceutical excipient, after oral administration its ] is about 0.34, due to a substantial ]. Less than 20% is eliminated by ] excretion.<ref>{{cite journal| last=Zuidema | first=J. | title=Ethylenediamine, profile of a sensitizing excipient | journal = Pharmacy World & Science | date= 1985-08-23 | volume = 7| issue = 4 | pages= 134–140 | doi = 10.1007/BF02097249| pmid = 3900925| s2cid=11016366}}</ref> |
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Numerous bio-active compounds contain the N-CH<sub>2</sub>-CH<sub>2</sub>-N linkage, including ] and some ]s.<ref>{{cite journal | doi=10.1111/j.1747-0285.2006.00347.x | author=Kotti, S. R. S. S.; Timmons, C. and Li, G. | title=Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry | pmid=16492158 | journal = Chemical Biology & Drug Design | year = 2006 | volume = 67 | issue = 2| pages=101–114 }}</ref> Salts of ethylenebisdithiocarbamate are commercially significant fungicides under the brandnames ], Mancozeb, ], and Metiram. Some ]-containing fungicides are derived from ethylenediamine.<ref name=Ullmann/> |
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Ethylenediamine-derived ] are the oldest of the five classes of ], beginning with ] aka benodain, discovered in 1933 at the Pasteur Institute in France, and also including ], ], and ]. The other classes are derivatives of ethanolamine, ], ], and others (primarily tricyclic and tetracyclic compounds related to ], ], as well as the ]-] family) |
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===Role in polymers=== |
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===Role in polymers=== |
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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 ]s are derived from ethylenediamine.<ref name=Ullmann/> |
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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 ]s are derived from ethylenediamine.<ref name=Ullmann/> |
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===Tetraacetylethylenediamine=== |
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===Tetraacetylethylenediamine=== |
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The ]ing activator ] is generated from ethylenediamine. The derivative N,N-ethylenebis(stearamide) (EBS) is a commercially significant mold-] and a ] in gasoline and motor oil. |
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The ]ing activator ] is generated from ethylenediamine. The derivative ] (EBS) is a commercially significant mold-] and a ] in gasoline and motor oil. |
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===Specialized applications=== |
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===Other applications=== |
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*as a ], it is ] with polar solvents and is used to solubilize ]s such as ] and ]. It is also used in certain ] baths |
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*as a ], it is ] with polar solvents and is used to solubilize ]s such as ] and ]. It is also used in certain ] baths. |
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*as a ] in paints and ]s. |
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*as a ] in paints and ]s. |
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*] (EDDI) is added to animal feeds as a source of iodide. |
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*] (EDDI) is added to animal feeds as a source of iodide. |
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*chemicals for ] developing, ], ]s, ]s, ] agents for ]s, and ]s. |
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*chemicals for ] developing, ], ]s, ]s, ] agents for ], and ]s. |
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*as a compound to sensitize ] into an explosive. This mixture was used at ] during World War II, giving the nitromethane and ethylenediamine mixture the nickname ], or Picatinny Liquid Explosive. |
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* Ethylenediamine (Edamine) is a common organic additive to the plant in vitro culture ]. |
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==Coordination chemistry== |
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==Ethylenamines== |
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Ethylenediamine is a well-known ] ] ] for ]s, with the two nitrogen atoms donating their lone pairs of electrons when ethylenediamine acts as a ligand. It is often abbreviated "en" in inorganic chemistry. The complex <sup>3+</sup>]] is a well studied example. Schiff base ligands easily form from ethylenediamine. For example, the diamine condenses with ] to give to the diimine.<ref>{{cite journal |doi=10.1016/j.jfluchem.2006.02.014 |title=Synthesis, structural and spectroscopic properties of a new Schiff base ligand N,N′-bis(trifluoromethylbenzylidene)ethylenediamine |date=2006 |last1=Habibi |first1=Mohammad Hossein |last2=Montazerozohori |first2=Morteza |last3=Lalegani |first3=Arash |last4=Harrington |first4=Ross W. |last5=Clegg |first5=William |journal=Journal of Fluorine Chemistry |volume=127 |issue=6 |pages=769–773 }}</ref> The ]s, some of which are used in catalysis, are derived from the condensation of ]s and ethylenediamine. |
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Ethylenediamine is the first member of the so-called polyethylene amines, other members being: |
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*], abbreviated dien or DETA, (H<sub>2</sub>N-CH<sub>2</sub>CH<sub>2</sub>-NH-CH<sub>2</sub>CH<sub>2</sub>-NH<sub>2</sub>, an analog of ]) |
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*], abbreviated trien or TETA, (H<sub>2</sub>N-CH<sub>2</sub>CH<sub>2</sub>-NH-CH<sub>2</sub>CH<sub>2</sub>-NH-CH<sub>2</sub>CH<sub>2</sub>-NH<sub>2</sub>) |
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*Tetraethylenepentamine, abbreviated TEPA, (H<sub>2</sub>N-CH<sub>2</sub>CH<sub>2</sub>-NH-CH<sub>2</sub>CH<sub>2</sub>-NH-CH<sub>2</sub>CH<sub>2</sub>-NH-CH<sub>2</sub>CH<sub>2</sub>-NH<sub>2</sub>), |
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*Pentaethylenehexamine, abbreviated PEHA, (H<sub>2</sub>N-CH<sub>2</sub>CH<sub>2</sub>-NH-CH<sub>2</sub>CH<sub>2</sub>-NH-CH<sub>2</sub>CH<sub>2</sub>-NH-CH<sub>2</sub>CH<sub>2</sub>-NH-CH<sub>2</sub>CH<sub>2</sub>-NH<sub>2</sub>), up to ]. Similarly ] is an analogue of ]. |
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==Related diamines== |
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===Related ligands=== |
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Related derivatives of ethylenediamine include ], ] (TMEDA), and ] (TEEDA). Chiral ] of ethylenediamine include ] and ]. |
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In terms of quantities produced, ethylenediamine is the most significant diamine (aside from diaminohexane, which is a precursor to ]). Related derivatives of ethylenediamine include ], abbreviated (TMEDA), (CH<sub>3</sub>)<sub>2</sub>N-CH<sub>2</sub>CH<sub>2</sub>-N(CH<sub>3</sub>)<sub>2</sub> and tetraethylethylenediamine, abbreviated (TEEDA), (C<sub>2</sub>H<sub>5</sub>)<sub>2</sub>N-CH<sub>2</sub>CH<sub>2</sub>-N(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub> |
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==Safety== |
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==Safety== |
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Ethylenediamine, like ] 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 mucous membranes. |
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Ethylenediamine exposure can cause the skin to become irritated. It was used in commercially available skin products including Mycolog cream.<ref>{{cite journal| author= Hogan DJ.| title= Allergic contact dermatitis to ethylenediamine. A continuing problem. | journal = ] |month = January | year = 1990 | volume = 8 |issue = 1 | pages=133–6 |pmid = 2137392 }}</ref> Ethylenediamine has a half-life of about 30 minutes and a small volume of distribution of 0.133 liters/kg. After oral administration its ] is about 0.34, due to a substantial first-pass effect. Less than 20% is eliminated by ] excretion.<ref>{{cite journal| author=Zuidema J. | title=Ethylenediamine, profile of a sensitizing excipient.| journal = Pharmacy World & Science | date= 1985-08-23 | volume = 7| issue = 4 | pages= 134–40 | doi = 10.1007/BF02097249| pmid = 3900925}}</ref> |
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