Diethylethanolamine

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.

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
CAS Number	100-37-8 Y
3D model (JSmol)	Interactive image
Beilstein Reference	741863
ChEBI	CHEBI:52153 Y
ChEMBL	ChEMBL1183 Y
ChemSpider	13842001 Y
ECHA InfoCard	100.002.587
EC Number	202-845-2
MeSH	2-diethylaminoethanol
PubChem CID	7497
RTECS number	KK5075000
UNII	S6DL4M053U Y
UN number	2686
CompTox Dashboard (EPA)	DTXSID5021837
InChI InChI=1S/C6H15NO/c1-3-7(4-2)5-6-8/h8H,3-6H2,1-2H3 Y Key: BFSVOASYOCHEOV-UHFFFAOYSA-N Y
SMILES CCN(CC)CCO
Properties
Chemical formula	C6H15NO
Molar mass	117.192 g·mol−1
Appearance	Colourless liquid
Odor	Ammoniacal and irritating
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 labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H302, H312, H314, H317, H332
Precautionary statements	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)	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

Applications

Diethylethanolamine 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

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 nucleophilic substitution of diethylamine and 2-chloroethanol.^[5]

Safety

Diethylethanolamine is an irritant to the eyes, skin, and lungs. 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]