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| verifiedrevid = 414422356 |
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| verifiedrevid = 443637404 |
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| ImageFile = Diethylene triamine.png |
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| Name = Diethylenetriamine |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile = Diethylene triamine.png |
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| ImageSize = |
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| ImageSize = 220 |
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| ImageName = Diethylenetriamine |
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| ImageName = Skeletal formula of diethylenetriamine |
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| ImageFile1 = Diethylenetriamine-3D-balls.png |
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| IUPACName = Bis(2-aminoethyl)amine |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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| OtherNames = ''N''-(2-aminoethyl)-1,2-ethanediamine, 1,4,7-triazaheptane, 3-azapentane-1,5-diamine, dien |
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| ImageName1 = Ball and stick model of diethylenetriamine |
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| Section1 = {{Chembox Identifiers |
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| ImageFile2 = Diethylenetriamine-3D-spacefill.png |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageFile2_Ref = {{chemboximage|correct|??}} |
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| ImageSize2 = 180 |
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| ImageName2 = Spacefill model of diethylenetriamine |
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| PIN = ''N''<sup>1</sup>-(2-Aminoethyl)ethane-1,2-diamine |
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| OtherNames = N-(2-Aminoethyl)-1,2-ethanediamine; bis(2-Aminoethyl)amine; DETA; 2,2'-Diaminodiethylamine |
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|Section1={{Chembox Identifiers |
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| CASNo = 111-40-0 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 8111 |
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| ChemSpiderID = 13835401 |
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| ChemSpiderID = 13835401 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChI = 1/C4H13N3/c5-1-3-7-4-2-6/h7H,1-6H2 |
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| UNII = 03K6SX4V2J |
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| InChIKey = RPNUMPOLZDHAAY-UHFFFAOYAH |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 203-865-4 |
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| UNNumber = 2079 |
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| MeSHName = diethylenetriamine |
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| ChEBI = 30629 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 303429 |
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| ChEMBL = 303429 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| RTECS = IE1225000 |
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| Beilstein = 605314 |
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| Gmelin = 2392 |
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| SMILES = NCCNCCN |
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| StdInChI = 1S/C4H13N3/c5-1-3-7-4-2-6/h7H,1-6H2 |
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| StdInChI = 1S/C4H13N3/c5-1-3-7-4-2-6/h7H,1-6H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = RPNUMPOLZDHAAY-UHFFFAOYSA-N |
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| StdInChIKey = RPNUMPOLZDHAAY-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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| CASNo = 111-40-0 |
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|Section2={{Chembox Properties |
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| UNII = 03K6SX4V2J |
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| ChEBI = 30629 |
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| C=4 | H=13 | N=3 |
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| Appearance = Colourless liquid |
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| SMILES = C(CNCCN)N |
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| Odor = Ammoniacal |
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| Density = 955 mg mL<sup>−1</sup> |
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| MeltingPtK = 234.15 |
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| BoilingPtK = 477.2 |
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| LogP = −1.73 |
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| VaporPressure = 10 Pa (at 20 °C) |
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| RefractIndex = 1.484 |
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| Solubility = miscible<ref name=NIOSH/> |
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}} |
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|Section3={{Chembox Thermochemistry |
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| DeltaHf = −65.7–−64.7 kJ mol<sup>−1</sup> |
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| DeltaHc = −3367.2–−3366.2 kJ mol<sup>−1</sup> |
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| HeatCapacity = 254 J K<sup>−1</sup> mol<sup>−1</sup> (at 40 °C) |
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}} |
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|Section4={{Chembox Hazards |
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| GHSPictograms = {{gHS corrosion}} {{gHS exclamation mark}} |
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| GHSSignalWord = '''DANGER''' |
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| HPhrases = {{h-phrases|302||312|314|317}} |
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| PPhrases = {{p-phrases|280|305+351+338|310}} |
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| FlashPtC = 102 |
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| AutoignitionPtC = 358 |
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| ExploLimits = 2–6.7% |
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| PEL = none<ref name=NIOSH>{{PGCH|0211}}</ref> |
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| IDLH = N.D.<ref name=NIOSH/> |
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| REL = TWA 1 ppm (4 mg/m<sup>3</sup>)<ref name=NIOSH/> |
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}} |
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|Section5={{Chembox Related |
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| OtherFunction_label = amines |
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| OtherFunction = {{unbulleted list|]|]|]|]|]|]|]|]|]|]|]|]|]}} |
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| OtherCompounds = {{unbulleted list|]|]|]|]}} |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| C = 4 |
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| H = 13 |
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| N = 3 |
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| Density = 0.955 g/cm<sup>3</sup> |
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| MeltingPtC = -35 |
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| BoilingPtC = 206 |
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}} |
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'''Diethylenetriamine''' (abbreviated DETA) is an ] with the formula HN(CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>)<sub>2</sub>. This colourless ] liquid is soluble in water and polar organic solvents, but not simple ]s. Diethylenetriamine is structural analogue of ]. Its chemical properties resemble those for ], and it has similar uses. It is a ] and its aqueous solution is alkaline. DETA is a byproduct of the production of ethylenediamine from ethylene dichloride.<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. DOE: 10.1002/14356007.a02 001</ref> |
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'''Diethylenetriamine''' (abbreviated '''<span lang="Hi" dir="ltr">Dien or DETA)</span>''' and also known as '''2,2’-Iminodi(ethylamine)'''<ref>{{cite web|title=Health Council of the Netherlands: Committee on Updating of Occupational Exposure Limits. 2,2'-Iminodi(ethylamine); Health-based Reassessment of Administrative Occupational Exposure Limits.|url=http://gr.nl/sites/default/files/0015OSH153.pdf|date=2005}}</ref>) is an ] with the formula HN(CH<sub>2</sub>CH<sub>2</sub>NH<sub>2</sub>)<sub>2</sub>. This colourless ] liquid is soluble in water and polar organic solvents, but not simple ]s. Diethylenetriamine is structural analogue of ]. Its chemical properties resemble those for ], and it has similar uses. It is a ] and its aqueous solution is alkaline. DETA is a byproduct of the production of ] from ].<ref name="Ullmann">{{Ullmann | author = Eller, K. | author2 = Henkes, E. | author3 = Rossbacher, R. | author4 = Höke, H. | title = Amines, Aliphatic | doi = 10.1002/14356007.a02_001 }}</ref> |
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==Reactions and uses== |
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==Reactions and uses== |
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Diethylenetriamine is a common curing agent for ]s in epoxy adhesives and other thermosets.<ref>{{cite book|author=Brydson, J. A.|title=Plastics Materials|edition=Seventh|pages=744–777|chapter=Epoxide Resins|editor=J. A. Brydson|year=1999|publisher=Butterworth-Heinemann |location=Oxford|doi=10.1016/B978-075064132-6/50067-X|isbn=9780750641326}}</ref> It is N-alkylated upon reaction with epoxide groups forming crosslinks. |
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In ], it serves as a tridentate ] forming complexes such as Co(dien)(NO<sub>2</sub>)<sub>3</sub>.<ref>Philip H. Crayton "Inner Complexes of Cobalt(III) with Diethylenetriamine" Inorganic Syntheses, 1963, Volume 7, pages 207–213. {{DOI|10.1002/9780470132388.ch56}}</ref> |
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]ed material contains many OH groups, which confer adhesive properties.]] |
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In ], it serves as a tridentate ] forming complexes such as Co(dien)(NO<sub>2</sub>)<sub>3</sub>.<ref>{{ cite book |author1=Crayton, P. H. |author2=Zitomer, F. |author3=Lambert, J. | editor = Kleinberg, J. | chapter = Inner Complexes of Cobalt(III) with Diethylenetriamine | title = Inorganic Syntheses | year = 1963 | volume = 7 | pages = 207–213 | doi = 10.1002/9780470132388.ch56 |isbn=9780470132388 }}</ref> |
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Like some related amines, it is used in oil industry for the extraction of ]. |
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Like some related amines, it is used in oil industry for the extraction of ]. |
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Like ], DETA can also be used to sensitize ], making a liquid explosive compound similar to ]. This compound is cap sensitive with an explosive velocity of around 6200 m/s and is discussed in patent #3,713,915. Mixed with ] it was used as ], a propellent for ]s. |
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Like ], DETA can also be used to sensitize ], making a liquid explosive compound similar to ]. This compound is cap sensitive with an explosive velocity of around 6200 m/s and is discussed in patent #3,713,915. Mixed with ] it was used as ], a propellent for ]s. |
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== See also == |
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DETA has been evaluated for use in the ] under development by the U.S. ], where it would be used to ignite and consume the explosive fill of land mines in beach and ]s.<ref>{{cite news | url=http://www.dailytech.com/US+Navy+Announces+Venom+Penetrator+Countermine+Projectile/article5838.htm | title=U.S. Navy Announces "Venom Penetrator" Countermine Projectile | work=] | date=January 25, 2007 | access-date=July 16, 2013 | author=Hill, Brandon | archive-url=https://web.archive.org/web/20141004175426/http://www.dailytech.com/US+Navy+Announces+Venom+Penetrator+Countermine+Projectile/article5838.htm | archive-date=October 4, 2014 | url-status=dead }}</ref> |
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==See also== |
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* ] |
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* ] |
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== References == |
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==References== |
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{{Reflist}} |
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<references/> |
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== Further reading == |
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*{{Cite encyclopedia |title=Aliphatic Amines |chapter=Diethylenetriamine|encyclopedia=Encyclopedia of Liquid Fuels |publisher=De Gruyter |last=Schmidt |first=Eckart W. |date=2022 |pages=127–134 |doi=10.1515/9783110750287-002 |isbn=978-3-11-075028-7}} |
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] |
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==External links== |
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*{{Commons category-inline}} |
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