Diethylethanolamine (DEAE) is the organic compound with the molecular formula (C2H5)2NCH2CH2OH. A colorless liquid, is used as a precursor in the production of a variety of chemical commodities such as the local anesthetic procaine.
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| Names | |
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| 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)
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| 741863 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.002.587 |
| EC Number |
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| MeSH | 2-diethylaminoethanol |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 2686 |
CompTox Dashboard (EPA)
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| 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) |
Refractive index (nD)
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1.441–1.442 |
| Hazards | |
| GHS labelling: | |
  
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| 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): | |
LD50 (median dose)
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LC50 (median concentration)
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924 ppm (rat, 4 hr) 1027 ppm (mouse)[2] |
| NIOSH (US health exposure limits): | |
PEL (Permissible)
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TWA 10 ppm (50 mg/m3) [skin][1] |
REL (Recommended)
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TWA 10 ppm (50 mg/m3) [skin][1] |
IDLH (Immediate danger)
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100 ppm[1] |
| Related compounds | |
Related alkanols
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Related compounds
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Diethylhydroxylamine |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Applications
editDiethylethanolamine is used as a corrosion inhibitor in steam and condensate lines by neutralizing carbonic acid and scavenging oxygen.
Diethylethanolamine reacts with 4-aminobenzoic acid to make procaine.
DEAE is a precursor for DEAE-cellulose resin, which is commonly used in ion exchange chromatography.
it can decrease the surface tension of water when the temperature is increased.[3]
Solutions of DEAE absorb carbon dioxide (CO2).
Preparation
editDiethylethanolamine 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
editDiethylethanolamine 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
edit- ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0210". National Institute for Occupational Safety and Health (NIOSH).
- ^ "2-Diethylaminoethanol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ 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.
- ^ 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.
- ^ W. W. Hartman (1934). "β-Diethylaminoethyl Alcohol". Organic Syntheses. 14: 28. doi:10.15227/orgsyn.014.0028.
- ^ "NIOSH Pocket Guide to Chemical Hazards". CDC. 2011-04-04. Retrieved 2013-11-08.