Diethanolamine

Diethanolamine

Names
IUPAC name 2,2'-Iminodiethanol
Other names Bis(hydroxyethyl)amine N,N-Bis(2-hydroxyethyl)amine 2,2'-Dihydroxydiethylamine β,β'-Dihydroxydiethylamine Diolamine 2-[(2-Hydroxyethyl)amino]ethanol 2,2'-Iminobisethanol Iminodiethanol Di(2-hydroxyethyl)amine bis(2-Hydroxyethyl)amine 2,2'-Iminodiethanol
Identifiers
CAS Number	111-42-2 Y
3D model (Jmol)	Interactive image
3DMet	B01050
Beilstein Reference	605315
ChEBI	CHEBI:28123 Y
ChEMBL	ChEMBL119604 Y
ChemSpider	13835604 Y
ECHA InfoCard	100.003.517
EC Number	203-868-0
KEGG	D02337 Y
MeSH	diethanolamine
PubChem	8113
RTECS number	KL2975000
UNII	AZE05TDV2V Y
InChI InChI=1S/C4H11NO2/c6-3-1-5-2-4-7/h5-7H,1-4H2 Y Key: ZBCBWPMODOFKDW-UHFFFAOYSA-N Y
SMILES OCCNCCO
Properties
Chemical formula	C4H11NO2
Molar mass	105.14 g·mol−1
Appearance	Colourless crystals
Odor	Ammonia odor.
Density	1.097 g mL−1
Melting point	28.00 °C; 82.40 °F; 301.15 K
Boiling point	271.1 °C; 519.9 °F; 544.2 K
Solubility in water	Miscible
log P	1.761
Vapor pressure	<1 Pa (at 20 °C)
UV-vis (λmax)	260 nm
Refractive index (nD)	1.477
Thermochemistry
Specific heat capacity (C)	137 J K−1 mol−1
Std enthalpy of formation (ΔfHo298)	−496.4–−491.2 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−26.548–−26.498 MJ kmol−1
Hazards
Safety data sheet	sciencelab.com
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H302, H315, H318, H373
GHS precautionary statements	P280, P305+351+338
EU classification (DSD)	Xn
R-phrases	R22, R38, R41, R48/22
S-phrases	(S2), S26, S36/37/39
Flash point	138 °C (280 °F; 411 K)
Autoignition temperature	365 °C (689 °F; 638 K)
Explosive limits	1.6–9.8%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	120 mg kg−1(intraperitoneal, rat) 710 mg kg−1(oral, rat) 778 mg kg−1(intravaneous, rat) 12.2 g kg−1(dermal, rabbit)
US health exposure limits (NIOSH):
PEL (Permissible)	none
REL (Recommended)	TWA 3 ppm (15 mg/m3)
IDLH (Immediate danger)	N.D.
Related compounds
Related alkanols	N-Methylethanolamine Dimethylethanolamine Diethylethanolamine 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).
Y  (what is YN ?)
Infobox references

Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH₂CH₂OH)₂. Pure diethanolamine is a white solid at room temperature, but its tendency to absorb water and to supercool mean it is often encountered as a colorless, viscous liquid. Diethanolamine is polyfunctional, being a secondary amine and a diol. Like other organic amines, diethanolamine acts as a weak base. Reflecting the hydrophilic character of the secondary amine and hydroxyl groups, DEA is soluble in water. Amides prepared from DEA are often also hydrophilic. Recently, the chemical has been classified by the International Agency for Research on Cancer as "possibly carcinogenic to humans (Group 2B)".

The reaction of ethylene oxide with aqueous ammonia first produces ethanolamine:

which reacts with a second and third equivalent of ethylene oxide to give DEA and triethanolamine:

About 300M kg are produced annually in this way. The ratio of the products can be controlled by changing the stoichiometry of the reactants.

DEA is used as a surfactant and a corrosion inhibitor. It is used to remove hydrogen sulfide and carbon dioxide from natural gas.

In oil refineries, a DEA in water solution is commonly used to remove hydrogen sulfide from sour gas. It has an advantage over a similar amine ethanolamine in that a higher concentration may be used for the same corrosion potential. This allows refiners to scrub hydrogen sulfide at a lower circulating amine rate with less overall energy usage.