Diethylenetriamine

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Diethylenetriamine
Skeletal formula of diethylenetriamine
Ball and stick model of diethylenetriamine
Spacefill model of diethylenetriamine
Names
Other names
N-(2-Aminoethyl)-1,2-ethanediamine; bis(2-Aminoethyl)amine; DETA; 2,2'-Diaminodiethylamine
Identifiers
605314
111-40-0 YesY
ChEBI CHEBI:30629 YesY
ChEMBL ChEMBL303429 YesY
ChemSpider 13835401 YesY
EC number 203-865-4
2392
Jmol-3D images Image
MeSH diethylenetriamine
PubChem 8111
RTECS number IE1225000
UNII 03K6SX4V2J YesY
UN number 2079
Properties
C4H13N3
Molar mass 103.17 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 pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H302
P280, P305+351+338, P310
EU Index 612-058-00-X
EU classification Corrosive C
R-phrases R21/22, R34, R43
S-phrases (S1/2), S26, S36/37/39
Flash point 102 °C (216 °F; 375 K)
358 °C (676 °F; 631 K)
Explosive limits 2–6.7%
US health exposure limits (NIOSH):
none[1]
TWA 1 ppm (4 mg/m3)[1]
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).
 N verify (what isYesY/N?)
Infobox references

Diethylenetriamine (abbreviated 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[edit]

Diethylenetriamine is a common curing agent for Epoxy-resins in epoxy adhesives. In coordination chemistry, it serves as a tridentate ligand forming complexes such as Co(dien)(NO2)3.[4]

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.[5]

See also[edit]

References[edit]

  1. ^ a b c d "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. (2005), "Amines, Aliphatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a02_001 
  4. ^ Crayton, P. H.; Zitomer, F.; Lambert, J. (1963). "Inner Complexes of Cobalt(III) with Diethylenetriamine". In Kleinberg, J. Inorganic Syntheses 7. pp. 207–213. doi:10.1002/9780470132388.ch56. 
  5. ^ Hill, Brandon (January 25, 2007). "U.S. Navy Announces "Venom Penetrator" Countermine Projectile". DailyTech. Retrieved July 16, 2013.