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Diethylhydroxylamine

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Diethylhydroxylamine
Skeletal formula of diethylhydroxylamine
Ball-and-stick model of the diethylhydroxylamine molecule
Names
Preferred IUPAC name N-Ethyl-N-hydroxyethanamine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1731349
ChemSpider
ECHA InfoCard 100.020.960 Edit this at Wikidata
EC Number
  • 223-055-4
MeSH N,N-diethylhydroxylamine
PubChem CID
RTECS number
  • NC3500000
UNII
UN number 1993
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H11NO/c1-3-5(6)4-2/h6H,3-4H2,1-2H3Key: FVCOIAYSJZGECG-UHFFFAOYSA-N
SMILES
  • CCN(O)CC
Properties
Chemical formula C4H11NO
Molar mass 89.138 g·mol
Appearance Colorless liquid
Odor Ammoniacal
Density 867 mg mL
Melting point −26 to −25 °C (−15 to −13 °F; 247 to 248 K)
Boiling point 127.6 °C; 261.6 °F; 400.7 K
Solubility in water Miscible
Vapor pressure 500 Pa (at 0 °C)
Acidity (pKa) 5.67 (est)
Thermochemistry
Heat capacity (C) 370.8 J K mol
Std enthalpy of
formation (ΔfH298) 		−175.47–−174.03 kJ mol
Std enthalpy of
combustion (ΔcH298) 		−2.97201–−2.97069 MJ mol
Hazards
GHS labelling:
Pictograms GHS02: Flammable GHS07: Exclamation mark
Signal word Warning
Hazard statements H226, H312, H315, H319, H332
Precautionary statements P280, P305+P351+P338
Explosive limits 1.9–10%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 1.3 g kg (dermal, rabbit)
  • 2.19 g kg (oral, rat)
Related compounds
Related alkanols
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Diethylhydroxylamine (DEHA) is an organic compound with the formula (C2H5)2NOH. Strictly, this is N,N-diethylhydroxylamine. It has an isomer, N,O-diethylhydroxylamine with the formula EtNHOEt. Pure N,N-diethylhydroxylamine is a colorless liquid, although it is usually encountered as a colourless-to-yellow solution in water with an amine-like odor.

DEHA can be synthesised from a reaction between triethylamine and a peroxide.

Applications

DEHA is largely used as an oxygen scavenger in water treatment.

It is a volatile oxygen scavenger and reacts in a ratio of 2.8/1 DEHA/O2. It is employed in high pressure (>70 bar) boiler systems due to a very low rate of reaction at low temperatures and pressures. Due to its volatility, it acts as an oxygen scavenger throughout the entire boiler system due to steam carryover.

DEHA also reacts with ferrous metals to form a passivized film of magnetite throughout the boiler system. The reduction of toxic heavy metals, such as hexavalent chromium to their more environmentally-friendly counterparts like trivalent chromium, is also performed using aqueous solutions containing DEHA.

Several other applications include its use as:

  1. Polymerisation inhibitor
  2. Color stabilizer (photographics)
  3. Corrosion inhibitor
  4. Discoloration inhibitor (phenolics)
  5. Antiozonant
  6. Radical scavenger

References

  1. Hilal SH et al; pp. 291-353 in Quantitative Treatments of Solute/Solvent Interactions: Theoretical and Computational Chemistry Vol. 1 NY, NY: Elsevier (1994). SPARC (Software Process Automation Reaction Chemistry) Available from, as of Dec 7, 2007: http://ibmlc2.chem.uga.edu/sparc/
  2. Cáceres, T.; Lissi, E. A.; Sanhueza, E. (November 1978). "Autooxidation of diethyl hydroxylamine". International Journal of Chemical Kinetics. 10 (11): 1167–1182. doi:10.1002/kin.550101107.
  3. Shaffer, Dean; Heicklen, Julian (August 1986). "Oxidation of diethylhydroxylamine in water solution at 25-80.degree". The Journal of Physical Chemistry. 90 (18): 4408–4413. doi:10.1021/j100409a039.
  4. Abuin, E.; Encina, M. V.; Diaz, S.; Lissi, E. A. (July 1978). "On the reactivity of diethyl hydroxyl amine toward free radicals". International Journal of Chemical Kinetics. 10 (7): 677–686. doi:10.1002/kin.550100704.
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