Diethylenetriamine

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

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	111-40-0 Y
3D model (JSmol)	Interactive image
Beilstein Reference	605314
ChEBI	CHEBI:30629 Y
ChEMBL	ChEMBL303429 Y
ChemSpider	13835401 Y
ECHA InfoCard	100.003.515
EC Number	203-865-4
Gmelin Reference	2392
MeSH	diethylenetriamine
PubChem CID	8111
RTECS number	IE1225000
UNII	03K6SX4V2J Y
UN number	2079
CompTox Dashboard (EPA)	DTXSID2025050
InChI InChI=1S/C4H13N3/c5-1-3-7-4-2-6/h7H,1-6H2 Y Key: RPNUMPOLZDHAAY-UHFFFAOYSA-N Y
SMILES NCCNCCN
Properties
Chemical formula	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
Solubility in water	miscible[1]
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
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[1]
REL (Recommended)	TWA 1 ppm (4 mg/m3)[1]
IDLH (Immediate danger)	N.D.[1]
Related compounds
Related amines	Dimethylamine Trimethylamine N-Nitrosodimethylamine Diethylamine Triethylamine Diisopropylamine Dimethylaminopropylamine N,N-Diisopropylethylamine Triisopropylamine Tris(2-aminoethyl)amine Mechlorethamine HN1 (nitrogen mustard) HN3 (nitrogen mustard)
Related compounds	Unsymmetrical dimethylhydrazine Biguanide Dithiobiuret Agmatine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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

• Triethylenetetramine

References

1. 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.

External links

• Media related to Diethylenetriamine at Wikimedia Commons