Diethylethanolamine

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
CAS Number	100-37-8 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	741863
ChEBI	CHEBI:52153 ;
ChEMBL	ChEMBL1183 ;
ChemSpider	13842001 ;
ECHA InfoCard	100.002.587
EC Number	202-845-2;
MeSH	2-diethylaminoethanol
PubChem CID	7497;
RTECS number	KK5075000;
UNII	S6DL4M053U ;
UN number	2686
CompTox Dashboard (EPA)	DTXSID5021837 ;
	InChI InChI=1S/C6H15NO/c1-3-7(4-2)5-6-8/h8H,3-6H2,1-2H3 Key: BFSVOASYOCHEOV-UHFFFAOYSA-N ;
	SMILES CCN(CC)CCO;
Properties
Chemical formula	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
Solubility in water	miscible[1]
log P	0.769
Vapor pressure	100 Pa (at 20 °C)
Refractive index (nD)	1.441–1.442
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H226, H302, H312, H314, H317, H332
GHS precautionary statements	P280, P305+351+338, P310
Flash point	50 °C (122 °F; 323 K)
Explosive limits	1.4–11.7%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	1.113 g kg−1 (dermal, rabbit); 1.3 g kg−1 (oral, rat);
LC50 (median concentration)	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	N-Methylethanolamine; Dimethylethanolamine; Diethanolamine; N,N-Diisopropylaminoethanol; Methyl diethanolamine; Triethanolamine; Bis-tris methane; Meglumine;
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

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]

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]

gollark: It can generate ~100MHz square waves and you can connect up an antenna, which is *basically* what a radio transmitter would do but stupider and worse.

gollark: Yes, a clock or something.

gollark: A quirk of the raspberry pi means it can transmit FM radio with horrible interference because it can only broadcast square waves or something, because of happening to have a somewhat adjustable ~100MHz clock exposed on external pins or something.

gollark: Technically I *could* transmit FM radio. Also technically, I can't transmit it at any significant power and doing so would be illegal.

gollark: idea: replace osmarks internet radio™ with a constant 440Hz buzzing noise.

References

NIOSH Pocket Guide to Chemical Hazards. "#0210". National Institute for Occupational Safety and Health (NIOSH).
"2-Diethylaminoethanol". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
Fu, Dong; Wang, LeMeng; Tian, XiangFeng. "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 Encylclopedia of Chemical Technology. 2 (4th ed.). New York: John Wiley & Sons, Inc. pp. 1–34. ISBN 978-0471419617.
"Diethylaminoethanol". USDA. 2001-02-15. Retrieved 2012-08-28.
"NIOSH Pocket Guide to Chemical Hazards". CDC. 2011-04-04. Retrieved 2013-11-08.

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[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0210". National Institute for Occupational Safety and Health (NIOSH).

[2] "2-Diethylaminoethanol". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[3] Fu, Dong; Wang, LeMeng; Tian, XiangFeng. "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 Encylclopedia of Chemical Technology. 2 (4th ed.). New York: John Wiley & Sons, Inc. 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.