Diethylethanolamine

Diethylethanolamine (DEAE) is a chemical compound with the molecular formula C6H15NO. It is used as a precursor in the production of a variety of chemical commodities such as the local anesthetic procaine. It can be reacted with 4-aminobenzoic acid to make procaine. DEAE can be used as a precursor for DEAE-cellulose resin, which is commonly used in ion exchange chromatography. DEAE can also be conveniently obtained from renewable sources. It is chemically stable and able to absorb carbon dioxide (CO2) from its surroundings. In solution, it can decrease the surface tension of water when the temperature is increased.[3]

Diethylethanolamine
Skeletal formula of diethylethanolamine
Names
Preferred IUPAC name
2-(Diethylamino)ethan-1-ol
Other names
2-(Diethylamino)ethanol
Diethylaminoethanol
2-Diethylaminoethanol
N,N-Diethyl-2-aminoethanol
N,N-Diethylethanolamine
Diethyl(2-hydroxyethyl)amine
(2-Hydroxyethyl)diethylamine
2-Diethylaminoethyl alcohol
2-Hydroxytriethylamine
Identifiers
3D model (JSmol)
741863
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.587
EC Number
  • 202-845-2
MeSH 2-diethylaminoethanol
RTECS number
  • KK5075000
UNII
UN number 2686
  • InChI=1S/C6H15NO/c1-3-7(4-2)5-6-8/h8H,3-6H2,1-2H3 checkY
    Key: BFSVOASYOCHEOV-UHFFFAOYSA-N checkY
  • CCN(CC)CCO
Properties
C6H15NO
Molar mass 117.192 g·mol−1
Appearance Colourless liquid
Odor Ammoniacal
Density 884 mg mL−1
Melting point −70 °C; −94 °F; 203 K[1]
Boiling point 161.1 °C; 321.9 °F; 434.2 K
miscible[1]
log P 0.769
Vapor pressure 100 Pa (at 20 °C)
1.441–1.442
Hazards
GHS labelling:
GHS02: Flammable GHS05: Corrosive GHS07: Exclamation mark
Danger
H226, H302, H312, H314, H317, H332
P280, P305+P351+P338, P310
Flash point 50 °C (122 °F; 323 K)
Explosive limits 1.4–11.7%
Lethal dose or concentration (LD, LC):
  • 1.113 g kg−1 (dermal, rabbit)
  • 1.3 g kg−1 (oral, rat)
924 ppm (rat, 4 hr)
1027 ppm (mouse)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 10 ppm (50 mg/m3) [skin][1]
REL (Recommended)
 TWA 10 ppm (50 mg/m3) [skin][1]
IDLH (Immediate danger)
 100 ppm[1]
Related compounds
Related alkanols
Related compounds
 Diethylhydroxylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Applications

Diethylethanolamine is used as a corrosion inhibitor in steam and condensate lines by neutralizing carbonic acid and scavenging oxygen.

Preparation

Diethylethanolamine is prepared commercially by the reaction of diethylamine and ethylene oxide.[4]

(C2H5)2NH + cyclo(CH2CH2)O → (C2H5)2NCH2CH2OH

It is also possible to prepare it by the reaction of diethylamine and ethylene chlorohydrin.[5]

Safety

Diethylethanolamine is an irritant to the eyes, skin, and respiratory system. The Occupational Safety and Health Administration and the National Institute for Occupational Safety and Health have set occupational exposure limits for workers handling the chemical at 10 ppm (50 mg/m3) over an eight-hour workday.[6]

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0210". National Institute for Occupational Safety and Health (NIOSH).
  2. "2-Diethylaminoethanol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. Fu, Dong; Wang, LeMeng; Tian, XiangFeng (2017). "Experiments and model for the surface tension of DEAE-PZ and DEAE-MEA aqueous solutions". The Journal of Chemical Thermodynamics. 105: 71–75. doi:10.1016/j.jct.2016.10.007.
  4. Bollmeier, Jr., Allen F. (1999). "Alkanolamines". In Kroschwitz, Jacqueline I. (ed.). Kirk-Othmer Encyclopedia of Chemical Technology. Vol. 2 (4th ed.). New York: John Wiley & Sons. pp. 1–34. ISBN 978-0471419617.
  5. "Diethylaminoethanol". USDA. 2001-02-15. Retrieved 2012-08-28.
  6. "NIOSH Pocket Guide to Chemical Hazards". CDC. 2011-04-04. Retrieved 2013-11-08.
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