Triethanolamine

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Triethanolamine
Names
IUPAC name
2-[Bis(2-hydroxyethyl)amino]ethanol
Preferred IUPAC name
2,2',2"-Nitrilotri(ethan-1-ol)
Other names
2,2',2"-Nitrilotriethanol
2,2′,2″-Trihydroxytriethylamine
TEA
TELA
TEOA
Triethylolamine
Tris(2-hydroxyethyl)amine
Trolamine
Properties
C6H15NO3
(OHCH2CH2)3N
Molar mass 149.190 g/mol
Appearance Viscous colorless liquid
Odor Odorless
Density 1.1242 g/cm3 (20 °C)
Melting point 21.6 °C (70.9 °F; 294.8 K)
Boiling point 335.4 °C (635.7 °F; 608.5 K)
Miscible
Solubility Reacts with acids
Miscible with acetone, chloroform, ethanol, isopropanol, methanol
Immiscible with benzene, CCl4, diethyl ether, heptane, petroleum ether
Vapor pressure 3.59·10-6 mmHg at 25 °C
Acidity (pKa) 7.74
Thermochemistry
−665.7 – −662.7 kJ/mol
Hazards
Safety data sheet Sigma-Aldrich
Flash point 179 °C (354 °F; 452 K)
Lethal dose or concentration (LD, LC):
5,530 mg/kg (rat, oral)
5,846 mg/kg (mouse, oral)
Related compounds
Related compounds
Ethanolamine
Diethanolamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Triethanolamine or trolamine (abbreviated as TEOA or TELA, but rarer TEA, which is more often used for triethylamine) is a viscous organic compound that is both a tertiary amine and an alcohol (a triol to be exact). It has the formula (OHCH2CH2)3N.

Properties

Chemical

Triethanolamine is a strong base and readily reacts with acids. In the presence of water, it will readily absorb carbon dioxide from air to form its corresponding carbonate and bicarbonate salts.

Physical

Triethanolamine is a colorless odorless viscous liquid, miscible with many organic solvents. Degraded samples appear yellowish.

Availability

Triethanolamine is sold by chemical suppliers.

Triethanolamine is found in many OTC products, like sunscreen lotions, liquid laundry detergents, dishwashing liquids, general cleaners, hand sanitizers, polishes, etc. However, there is too little TEA in these products to be a viable source.

TEOA is listed under Schedule 3, part B of the Chemical Weapons Convention as it can be used in the manufacture of HN3 nitrogen mustard. Suspicious transactions may be monitored.

Preparation

Triethanolamine is produced by reacting ethylene oxide with aqueous ammonia. The reaction also produces ethanolamine and diethanolamine. The ratio of the products can be controlled by changing the stoichiometry of the reactants.

Projects

  • Carbon dioxide scrubber
  • Synthesis of trolnitrate
  • Complexing agent in amateur photography and electroless plating

Handling

Safety

Triethanolamine is irritant and may cause allergies.

Storage

Triethanolamine should be kept in closed plastic or glass bottles.

Disposal

Should be mixed with a more flammable solvent and incinerated.

References

Relevant Sciencemadness threads