Diethylhydroxylamine

Diethylhydroxylamine (DEHA) is an organic compound with the formula (C2H5)2NOH. It is a colorless liquid, although it is usually encountered as a solution. It is mainly used as an oxygen scavenger in water treatment.

Diethylhydroxylamine
Skeletal formula of diethylhydroxylamine
Ball-and-stick model of the diethylhydroxylamine molecule
Names
IUPAC name
N,N-Diethylhydroxylamine[1]
Other names
N-Ethyl-N-hydroxyethanamine
Identifiers
3D model (JSmol)
1731349
ChemSpider
ECHA InfoCard 100.020.960
EC Number
  • 223-055-4
MeSH N,N-diethylhydroxylamine
RTECS number
  • NC3500000
UNII
UN number 1993
Properties
C4H11NO
Molar mass 89.138 g·mol−1
Appearance Colorless liquid
Odor Ammoniacal
Density 867 mg mL−1
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
Miscible
Vapor pressure 500 Pa (at 0 °C)
Acidity (pKa) 5.67 (est) [2]
Thermochemistry
370.8 J K−1 mol−1
Std enthalpy of
formation (ΔfH⦵298)
 −175.47–−174.03 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −2.97201–−2.97069 MJ mol−1
Hazards
GHS pictograms
GHS Signal word Warning
GHS hazard statements
 H226, H312, H315, H319, H332
P280, P305+351+338
Explosive limits 1.9–10%
Lethal dose or concentration (LD, LC):
  • 1.3 g kg−1 (dermal, rabbit)
  • 2.19 g kg−1 (oral, rat)
Related compounds
Related alkanols
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

It is a volatile oxygen scavenger[3][4] 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.

It has these other uses:

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

References
  1. "N,N-diethylhydroxylamine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification. Retrieved 17 March 2012.
  2. 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/
  3. 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.
  4. 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.
  5. 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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