Diethylenetriamine
Skeletal formula of diethylenetriamine
Ball and stick model of diethylenetriamine
Spacefill model of diethylenetriamine
Names
Preferred IUPAC name
N1-(2-Aminoethyl)ethane-1,2-diamine
Other names
N-(2-Aminoethyl)-1,2-ethanediamine; bis(2-Aminoethyl)amine; DETA; 2,2'-Diaminodiethylamine
Identifiers
3D model (JSmol)
605314
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.515
EC Number
  • 203-865-4
2392
MeSH diethylenetriamine
RTECS number
  • IE1225000
UNII
UN number 2079
  • InChI=1S/C4H13N3/c5-1-3-7-4-2-6/h7H,1-6H2 checkY
    Key: RPNUMPOLZDHAAY-UHFFFAOYSA-N checkY
  • NCCNCCN
Properties
C4H13N3
Molar mass 103.169 g·mol−1
Appearance Colourless liquid
Odor Ammoniacal
Density 955 mg mL−1
Melting point −39.00 °C; −38.20 °F; 234.15 K
Boiling point 204.1 °C; 399.3 °F; 477.2 K
miscible[1]
log P −1.73
Vapor pressure 10 Pa (at 20 °C)
1.484
Thermochemistry
254 J K−1 mol−1 (at 40 °C)
−65.7–−64.7 kJ mol−1
−3367.2–−3366.2 kJ mol−1
Hazards
GHS labelling:
GHS05: Corrosive GHS07: Exclamation mark
Danger
H302, H312, H314, H317
P280, P305+P351+P338, P310
Flash point 102 °C (216 °F; 375 K)
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 compounds
Related amines
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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]

Reactions and uses

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.

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

References

  1. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0211". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ "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.
  3. ↑ 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 978-3527306732.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.
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