Diethanolamine

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Diethanolamine
Names
IUPAC name
2,2'-Aminodiethanol
Other names
2,2'-Dihydroxydiethylamine
2,2'-Iminobisethanol
2,2'-Iminodiethanol
2-[(2-Hydroxyethyl)amino]ethanol
Bis(hydroxyethyl)amine
Iminodiethanol
N,N-Bis(2-hydroxyethyl)amine
Properties
C4H11NO2
HN(CH2CH2OH)2
Molar mass 105.137 g/mol
Appearance Colorless solid
Odor Mild, ammonia, fish-like
Density 1.097 g/cm3 (20 °C)
Melting point 28 °C (82 °F; 301 K)
Boiling point 271.1 °C (520.0 °F; 544.2 K)
Miscible
Solubility Miscible with alcohols, chloroform, glycerol, ketones
Slightly soluble in benzene, diethyl ether
Vapor pressure 2.8·10-4 mmHg at 25 °C
Thermochemistry
−496.4 – −491.2 kJ/mol
Hazards
Safety data sheet Sigma-Aldrich
Flash point 138 °C (280 °F; 411 K)
Lethal dose or concentration (LD, LC):
710 mg/kg (rat, oral)
Related compounds
Related compounds
Ethanolamine
Triethanolamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH2CH2OH)2 or C4H11NO2.

Properties

Chemical

Dehydration of diethanolamine with conc. sulfuric acid yields morpholine.

Diethanolamine is a base, and will react with acids to form salts.

Physical

Diethanolamine is a colorless solid that melts slightly above the room temperature. It has an ammonia-like odor and is miscible with water and many organic solvents.

Availability

Diethanolamine is sold by chemical suppliers.

Preparation

Diethanolamine can be produced from the reaction of ethylene oxide with aqueous ammonia. The reaction produces ethanolamine, diethanolamine and triethanolamine, depending on the ratio of reagents used:

C2H4O + NH3 → H2NCH2CH2OH
C2H4O + H2NCH2CH2OH → HN(CH2CH2OH)2
C2H4O + HN(CH2CH2OH)2 → N(CH2CH2OH)3

Projects

Handling

Safety

Diethanolamine is a potential skin irritant in workers sensitized by exposure to water-based metalworking fluids.

Storage

In closed bottles.

Disposal

Diethanolamine is not particularly harmful. Since it's sometimes found in cosmetics, which do not require special disposal, diethanolamine can be strongly diluted with water and poured down the drain.

Alternatively, it may be mixed with a more flammable solvent and burned.

References

Relevant Sciencemadness threads