diethylenetriamine
{{chembox
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| Watchedfields = changed
| verifiedrevid = 443637404
| ImageFile = Diethylene triamine.png
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageSize = 220
| ImageName = Skeletal formula of diethylenetriamine
| ImageFile1 = Diethylenetriamine-3D-balls.png
| ImageFile1_Ref = {{chemboximage|correct|??}}
| ImageName1 = Ball and stick model of diethylenetriamine
| ImageFile2 = Diethylenetriamine-3D-spacefill.png
| ImageFile2_Ref = {{chemboximage|correct|??}}
| ImageSize2 = 180
| ImageName2 = Spacefill model of diethylenetriamine
| PIN = N1-(2-Aminoethyl)ethane-1,2-diamine
| OtherNames = N-(2-Aminoethyl)-1,2-ethanediamine; bis(2-Aminoethyl)amine; DETA; 2,2'-Diaminodiethylamine
|Section1={{Chembox Identifiers
| CASNo = 111-40-0
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 8111
| ChemSpiderID = 13835401
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = 03K6SX4V2J
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 203-865-4
| UNNumber = 2079
| MeSHName = diethylenetriamine
| ChEBI = 30629
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 303429
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = IE1225000
| Beilstein = 605314
| Gmelin = 2392
| SMILES = NCCNCCN
| StdInChI = 1S/C4H13N3/c5-1-3-7-4-2-6/h7H,1-6H2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RPNUMPOLZDHAAY-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| C=4 | H=13 | N=3
| Appearance = Colourless liquid
| Odor = Ammoniacal
| Density = 955 mg mL−1
| MeltingPtK = 234.15
| BoilingPtK = 477.2
| LogP = −1.73
| VaporPressure = 10 Pa (at 20 °C)
| RefractIndex = 1.484
}}
|Section3={{Chembox Thermochemistry
| DeltaHf = −65.7–−64.7 kJ mol−1
| DeltaHc = −3367.2–−3366.2 kJ mol−1
| HeatCapacity = 254 J K−1 mol−1 (at 40 °C)
}}
|Section4={{Chembox Hazards
| GHSPictograms = {{gHS corrosion}} {{gHS exclamation mark}}
| GHSSignalWord = DANGER
| HPhrases = {{h-phrases|302||312|314|317}}
| PPhrases = {{p-phrases|280|305+351+338|310}}
| FlashPtC = 102
| AutoignitionPtC = 358
| ExploLimits = 2–6.7%
| PEL = none{{PGCH|0211}}
}}
|Section5={{Chembox Related
| OtherFunction_label = amines
| OtherFunction = {{unbulleted list|Dimethylamine|Trimethylamine|N-Nitrosodimethylamine|Diethylamine|Triethylamine|Diisopropylamine|Dimethylaminopropylamine|N,N-Diisopropylethylamine|Triisopropylamine|Tris(2-aminoethyl)amine|Mechlorethamine|HN1 (nitrogen mustard)|HN3 (nitrogen mustard)}}
| OtherCompounds = {{unbulleted list|Unsymmetrical dimethylhydrazine|Biguanide|Dithiobiuret|Agmatine}}
}}
}}
Diethylenetriamine (abbreviated Dien or DETA) and also known as 2,2’-Iminodi(ethylamine){{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}}) is an organic compound with the formula HN(CH2CH2NH2)2. This colourless hygroscopic liquid is soluble in water and polar organic solvents, but not simple hydrocarbons. Diethylenetriamine is structural analogue of diethylene glycol. Its chemical properties resemble those for ethylene diamine, and it has similar uses. It is a weak base and its aqueous solution is alkaline. DETA is a byproduct of the production of ethylenediamine from ethylene dichloride.{{Ullmann | author = Eller, K. | author2 = Henkes, E. | author3 = Rossbacher, R. | author4 = Höke, H. | title = Amines, Aliphatic | doi = 10.1002/14356007.a02_001 }}
Reactions and uses
Diethylenetriamine is a common curing agent for epoxy resins in epoxy adhesives and other thermosets.{{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}} It is N-alkylated upon reaction with epoxide groups forming crosslinks.
File:VernetzteEpoxidharze.svged material contains many OH groups, which confer adhesive properties.]]
In coordination chemistry, it serves as a tridentate ligand forming complexes such as Co(dien)(NO2)3.{{ 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 }}
Like some related amines, it is used in oil industry for the extraction of acid gas.
Like ethylenediamine, DETA can also be used to sensitize nitromethane, making a liquid explosive compound similar to PLX. This compound is cap sensitive with an explosive velocity of around 6200 m/s and is discussed in patent #3,713,915. Mixed with unsymmetrical dimethylhydrazine it was used as Hydyne, a propellent for liquid-fuel rockets.
DETA has been evaluated for use in the Countermine System under development by the U.S. Office of Naval Research, where it would be used to ignite and consume the explosive fill of land mines in beach and surf zones.{{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=DailyTech | 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 }}
See also
References
{{Reflist}}
Further reading
- {{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}}
External links
- {{Commons category-inline}}
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