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{{chembox | {{chembox | ||
| Verifiedfields = changed | |||
| Watchedfields = changed | | Watchedfields = changed | ||
| verifiedrevid = |
| verifiedrevid = 443637404 | ||
| ImageFile = Diethylene triamine.png | |||
| Name = Diethylenetriamine | |||
| ImageFile_Ref = {{chemboximage|correct|??}} | |||
| ImageFile = Diethylene triamine.png | |||
| |
| ImageSize = 220 | ||
| |
| ImageName = Skeletal formula of diethylenetriamine | ||
| ImageFile1 = Diethylenetriamine-3D-balls.png | |||
| IUPACName = Bis(2-aminoethyl)amine | |||
| ImageFile1_Ref = {{chemboximage|correct|??}} | |||
| OtherNames = ''N''-(2-aminoethyl)-1,2-ethanediamine, 1,4,7-triazaheptane, 3-azapentane-1,5-diamine, dien | |||
| ImageName1 = Ball and stick model of diethylenetriamine | |||
| Section1 = {{Chembox Identifiers | |||
| ImageFile2 = Diethylenetriamine-3D-spacefill.png | |||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| ImageFile2_Ref = {{chemboximage|correct|??}} | |||
| ImageSize2 = 180 | |||
| ImageName2 = Spacefill model of diethylenetriamine | |||
| PIN = ''N''<sup>1</sup>-(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 = 13835401 | ||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| InChI = 1/C4H13N3/c5-1-3-7-4-2-6/h7H,1-6H2 | |||
| UNII = 03K6SX4V2J | |||
| InChIKey = RPNUMPOLZDHAAY-UHFFFAOYAH | |||
| |
| UNII_Ref = {{fdacite|correct|FDA}} | ||
| EINECS = 203-865-4 | |||
| UNNumber = 2079 | |||
| MeSHName = diethylenetriamine | |||
| ChEBI = 30629 | |||
| ChEBI_Ref = {{ebicite|correct|EBI}} | |||
| ChEMBL = 303429 | | 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 = 1S/C4H13N3/c5-1-3-7-4-2-6/h7H,1-6H2 | ||
| |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | ||
| StdInChIKey = RPNUMPOLZDHAAY-UHFFFAOYSA-N | | StdInChIKey = RPNUMPOLZDHAAY-UHFFFAOYSA-N | ||
| |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | ||
}} | |||
| CASNo = 111-40-0 | |||
|Section2={{Chembox Properties | |||
| UNII = 03K6SX4V2J | |||
| |
| C=4 | H=13 | N=3 | ||
| Appearance = Colourless liquid | |||
| SMILES = C(CNCCN)N | |||
| Odor = Ammoniacal | |||
| Density = 955 mg mL<sup>−1</sup> | |||
| MeltingPtK = 234.15 | |||
| BoilingPtK = 477.2 | |||
| LogP = −1.73 | |||
| VaporPressure = 10 Pa (at 20 °C) | |||
| RefractIndex = 1.484 | |||
| Solubility = miscible<ref name=NIOSH/> | |||
}} | |||
|Section3={{Chembox Thermochemistry | |||
| DeltaHf = −65.7–−64.7 kJ mol<sup>−1</sup> | |||
| DeltaHc = −3367.2–−3366.2 kJ mol<sup>−1</sup> | |||
| HeatCapacity = 254 J K<sup>−1</sup> mol<sup>−1</sup> (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<ref name=NIOSH>{{PGCH|0211}}</ref> | |||
| IDLH = N.D.<ref name=NIOSH/> | |||
| REL = TWA 1 ppm (4 mg/m<sup>3</sup>)<ref name=NIOSH/> | |||
}} | |||
|Section5={{Chembox Related | |||
| OtherFunction_label = amines | |||
| OtherFunction = {{unbulleted list|]|]|]|]|]|]|]|]|]|]|]|]|]}} | |||
| OtherCompounds = {{unbulleted list|]|]|]|]}} | |||
}} | }} | ||
| Section2 = {{Chembox Properties | |||
| C = 4 | |||
| H = 13 | |||
| N = 3 | |||
| Density = 0.955 g/cm<sup>3</sup> | |||
| MeltingPtC = -35 | |||
| BoilingPtC = 206 | |||
}} | |||
}} | }} | ||
'''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> |
'''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> | ||
==Reactions and uses== | ==Reactions and uses== | ||
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. | |||
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> | |||
]ed material contains many OH groups, which confer adhesive properties.]] | |||
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> | |||
Like some related amines, it is used in oil industry for the extraction of ]. | |||
Like some related amines, it is used in oil industry for the extraction of ]. | |||
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. | |||
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. | |||
== See also == | |||
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> | |||
==See also== | |||
* ] | * ] | ||
== |
==References== | ||
{{Reflist}} | |||
<references/> | |||
== 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}} | |||
{{Ionotropic glutamate receptor modulators}} | |||
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Latest revision as of 15:52, 31 December 2024
Names | |
---|---|
Preferred IUPAC name N-(2-Aminoethyl)ethane-1,2-diamine | |
Other names N-(2-Aminoethyl)-1,2-ethanediamine; bis(2-Aminoethyl)amine; DETA; 2,2'-Diaminodiethylamine | |
Identifiers | |
CAS Number | |
3D model (JSmol) | |
Beilstein Reference | 605314 |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.515 |
EC Number |
|
Gmelin Reference | 2392 |
MeSH | diethylenetriamine |
PubChem CID | |
RTECS number |
|
UNII | |
UN number | 2079 |
CompTox Dashboard (EPA) | |
InChI
| |
SMILES
| |
Properties | |
Chemical formula | C4H13N3 |
Molar mass | 103.169 g·mol |
Appearance | Colourless liquid |
Odor | Ammoniacal |
Density | 955 mg mL |
Melting point | −39.00 °C; −38.20 °F; 234.15 K |
Boiling point | 204.1 °C; 399.3 °F; 477.2 K |
Solubility in water | miscible |
log P | −1.73 |
Vapor pressure | 10 Pa (at 20 °C) |
Refractive index (nD) | 1.484 |
Thermochemistry | |
Heat capacity (C) | 254 J K mol (at 40 °C) |
Std enthalpy of formation (ΔfH298) |
−65.7–−64.7 kJ mol |
Std enthalpy of combustion (ΔcH298) |
−3367.2–−3366.2 kJ mol |
Hazards | |
GHS labelling: | |
Pictograms | |
Signal word | Danger |
Hazard statements | H302, H312, H314, H317 |
Precautionary statements | P280, P305+P351+P338, P310 |
Flash point | 102 °C (216 °F; 375 K) |
Autoignition temperature |
358 °C (676 °F; 631 K) |
Explosive limits | 2–6.7% |
NIOSH (US health exposure limits): | |
PEL (Permissible) | none |
REL (Recommended) | TWA 1 ppm (4 mg/m) |
IDLH (Immediate danger) | N.D. |
Related compounds | |
Related amines | |
Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references |
Diethylenetriamine (abbreviated Dien or DETA) and also known as 2,2’-Iminodi(ethylamine)) 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.
Reactions and uses
Diethylenetriamine is a common curing agent for epoxy resins in epoxy adhesives and other thermosets. It is N-alkylated upon reaction with epoxide groups forming crosslinks.
In coordination chemistry, it serves as a tridentate ligand forming complexes such as Co(dien)(NO2)3.
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.
See also
References
- ^ 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.; Höke, H. "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 978-3-527-30673-2.
- 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.
Further reading
- Schmidt, Eckart W. (2022). "Diethylenetriamine". Aliphatic Amines. Encyclopedia of Liquid Fuels. De Gruyter. pp. 127–134. doi:10.1515/9783110750287-002. ISBN 978-3-11-075028-7.
External links
- [REDACTED] Media related to Diethylenetriamine at Wikimedia Commons