Diethylenetriamine

Diethylenetriamine
Skeletal formula of diethylenetriamine
Skeletal formula of diethylenetriamine
Ball and stick model of diethylenetriamine
Ball and stick model of diethylenetriamine
Spacefill 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
CAS Number
3D model (JSmol)
Beilstein Reference
 605314
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.515
EC Number
  • 203-865-4
Gmelin Reference
 2392
MeSH diethylenetriamine
PubChem CID
RTECS number
  • IE1225000
UNII
UN number 2079
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H13N3/c5-1-3-7-4-2-6/h7H,1-6H2 checkY
    Key: RPNUMPOLZDHAAY-UHFFFAOYSA-N checkY
SMILES
  • NCCNCCN
Properties
Chemical formula
 C4H13N3
Molar mass 103.169 g·mol−1
Appearance Colourless liquid
Odor Ammoniacal
Density 955 mg mL−1; 951 mg mL−1(20°C); 942.3 mg mL−1(30°C); 933.8 mg mL−1(40°C); 917 mg mL−1(60°C); 891.9 mg mL−1(90°C)[1]
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[2]
log P −1.73
Vapor pressure 10 Pa (at 20 °C)
Refractive index (nD)
 1.484
Thermochemistry
Heat capacity (C)
 254 J K−1 mol−1 (at 40 °C)
Std enthalpy of
formation (ΔfH⦵298)
 −65.7–−64.7 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −3367.2–−3366.2 kJ mol−1
Hazards
GHS labelling:
Pictograms
 GHS05: Corrosive GHS07: Exclamation mark
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[2]
REL (Recommended)
 TWA 1 ppm (4 mg/m3)[2]
IDLH (Immediate danger)
 N.D.[2]
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)[3]) 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.[4]

Reactions and uses

Diethylenetriamine is a common curing agent for epoxy resins in epoxy adhesives and other thermosets.[5] It is N-alkylated upon reaction with epoxide groups forming crosslinks.

Idealized structure of a triamine-cured epoxy glue. The resin's epoxide groups have all reacted with the N-H groups of the triamine 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.[6]

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.[7]

See also

References

  1. ^ Hartono, Ardi; Svendsen, Hallvard F. (September 2009). "Density, viscosity, and excess properties of aqueous solution of diethylenetriamine (DETA)". The Journal of Chemical Thermodynamics. 41 (9): 973–979. doi:10.1016/j.jct.2008.11.012.
  2. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0211". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Committee on Updating of Occupational Exposure Limits. 2,2'-Iminodi(ethylamine); Health-based Reassessment of Administrative Occupational Exposure Limits (Report). Health Council of the Netherlands. 2005.
  4. ^ 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.
  5. ^ Brydson, J.A. (1999). "Epoxide Resins". Plastics Materials. pp. 744–777. doi:10.1016/B978-075064132-6/50067-X. ISBN 978-0-7506-4132-6.
  6. ^ Crayton, Philip H.; Zitomer, Fred; Lambert, Jack (1963). "Inner Complexes of Cobalt(III) with Diethylenetriamine". Inorganic Syntheses. Vol. 7. pp. 207–213. doi:10.1002/9780470132388.ch56.
  7. ^ 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). "Aliphatic Amines". Encyclopedia of Liquid Fuels. pp. 55–220. doi:10.1515/9783110750287-002. ISBN 978-3-11-075028-7.
  • Media related to Diethylenetriamine at Wikimedia Commons
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