Diethanolamine

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
Chemical formula	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)
Solubility in water	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
Std enthalpy of formation (ΔfHo298)	−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):
LD50 (Median dose)	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

• Preparation of morpholine
• Corrosion inhibitor
• Surfactant
• Remove hydrogen sulfide
• Synthesis of Ditazole

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

• Diethanolamine from 2-Chloroethanol