Diethylenetriamine (abbreviated Dien or DETA) and also known as 2,2’-Iminodi(ethylamine)[2]) 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.[3]
Diethylenetriamine is a common curing agent for epoxy resins in epoxy adhesives and other thermosets.[4] It is N-alkylated upon reaction with epoxide groups forming crosslinks.
Structure of a triamine-cured epoxy glue. The resin's epoxide groups have all reacted with the hardener. The resulting highly crosslinked material contains many OH groups, which confer adhesive properties.
^"Health Council of the Netherlands: Committee on Updating of Occupational Exposure Limits. 2,2'-Iminodi(ethylamine); Health-based Reassessment of Administrative Occupational Exposure Limits" (PDF). 2005.
^Brydson, J. A. (1999). "Epoxide Resins". In J. A. Brydson (ed.). Plastics Materials (Seventh ed.). Oxford: Butterworth-Heinemann. pp. 744–777. doi:10.1016/B978-075064132-6/50067-X. ISBN9780750641326.
^Crayton, P. H.; Zitomer, F.; Lambert, J. (1963). "Inner Complexes of Cobalt(III) with Diethylenetriamine". In Kleinberg, J. (ed.). Inorganic Syntheses. Vol. 7. pp. 207–213. doi:10.1002/9780470132388.ch56. ISBN9780470132388.
^Hill, Brandon (January 25, 2007). . DailyTech. Archived from the original on October 4, 2014. Retrieved July 16, 2013.
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Media related to Diethylenetriamine at Wikimedia Commons
December 18, 2023
diethylenetriamine, abbreviated, dien, deta, also, known, iminodi, ethylamine, organic, compound, with, formula, ch2ch2nh2, this, colourless, hygroscopic, liquid, soluble, water, polar, organic, solvents, simple, hydrocarbons, structural, analogue, diethylene,. Diethylenetriamine abbreviated Dien or DETA and also known as 2 2 Iminodi ethylamine 2 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 3 Diethylenetriamine NamesPreferred IUPAC name N1 2 Aminoethyl ethane 1 2 diamineOther names N 2 Aminoethyl 1 2 ethanediamine bis 2 Aminoethyl amine DETA 2 2 DiaminodiethylamineIdentifiersCAS Number 111 40 0 Y3D model JSmol Interactive imageBeilstein Reference 605314ChEBI CHEBI 30629 YChEMBL ChEMBL303429 YChemSpider 13835401 YECHA InfoCard 100 003 515EC Number 203 865 4Gmelin Reference 2392MeSH diethylenetriaminePubChem CID 8111RTECS number IE1225000UNII 03K6SX4V2J YUN number 2079CompTox Dashboard EPA DTXSID2025050InChI InChI 1S C4H13N3 c5 1 3 7 4 2 6 h7H 1 6H2 YKey RPNUMPOLZDHAAY UHFFFAOYSA N YSMILES NCCNCCNPropertiesChemical formula C 4H 13N 3Molar mass 103 169 g mol 1Appearance Colourless liquidOdor AmmoniacalDensity 955 mg mL 1Melting point 39 00 C 38 20 F 234 15 KBoiling point 204 1 C 399 3 F 477 2 KSolubility in water miscible 1 log P 1 73Vapor pressure 10 Pa at 20 C Refractive index nD 1 484ThermochemistryHeat capacity C 254 J K 1 mol 1 at 40 C Std enthalpy offormation DfH 298 65 7 64 7 kJ mol 1Std enthalpy ofcombustion DcH 298 3367 2 3366 2 kJ mol 1HazardsGHS labelling PictogramsSignal word DangerHazard statements H302 H312 H314 H317Precautionary statements P280 P305 P351 P338 P310Flash point 102 C 216 F 375 K Autoignitiontemperature 358 C 676 F 631 K Explosive limits 2 6 7 NIOSH US health exposure limits PEL Permissible none 1 REL Recommended TWA 1 ppm 4 mg m3 1 IDLH Immediate danger N D 1 Related compoundsRelated amines DimethylamineTrimethylamineN NitrosodimethylamineDiethylamineTriethylamineDiisopropylamineDimethylaminopropylamineN N DiisopropylethylamineTriisopropylamineTris 2 aminoethyl amineMechlorethamineHN1 nitrogen mustard HN3 nitrogen mustard Related compounds Unsymmetrical dimethylhydrazineBiguanideDithiobiuretAgmatineExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Reactions and uses 2 See also 3 References 4 External linksReactions and uses editDiethylenetriamine is a common curing agent for epoxy resins in epoxy adhesives and other thermosets 4 It is N alkylated upon reaction with epoxide groups forming crosslinks nbsp Structure of a triamine cured epoxy glue The resin s epoxide groups have all reacted with the hardener The resulting highly crosslinked 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 5 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 6 See also editTriethylenetetramineReferences edit a b c d NIOSH Pocket Guide to Chemical Hazards 0211 National Institute for Occupational Safety and Health NIOSH Health Council of the Netherlands Committee on Updating of Occupational Exposure Limits 2 2 Iminodi ethylamine Health based Reassessment of Administrative Occupational Exposure Limits PDF 2005 Eller K Henkes E Rossbacher R Hoke H Amines Aliphatic Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a02 001 Brydson J A 1999 Epoxide Resins In J A Brydson ed Plastics Materials Seventh ed Oxford Butterworth Heinemann pp 744 777 doi 10 1016 B978 075064132 6 50067 X ISBN 9780750641326 Crayton P H Zitomer F Lambert J 1963 Inner Complexes of Cobalt III with Diethylenetriamine In Kleinberg J ed Inorganic Syntheses Vol 7 pp 207 213 doi 10 1002 9780470132388 ch56 ISBN 9780470132388 Hill Brandon January 25 2007 U S Navy Announces Venom Penetrator Countermine Projectile DailyTech Archived from the original on October 4 2014 Retrieved July 16 2013 External links edit nbsp Media related to Diethylenetriamine at Wikimedia Commons Retrieved from https en wikipedia org w index php title Diethylenetriamine amp oldid 1093987918, wikipedia, wiki, book, books, library,
