triethylamine

Triethylamine is an organic compound with the formula N(C2H5)3, commonly abbreviated TEA. It is a colorless, volatile liquid with a strong, characteristic fishy odor. As a tertiary amine, it acts as a base: the conjugate acid has a pKa around 10.75, corresponding to a pKb near 3.2. It is miscible with water and many organic solvents, and it boils at about 89.5 °C.

Industrial production typically involves the exhaustive alkylation of ammonia with ethyl halides (usually ethyl chloride) to yield a mixture of amines, which is then separated to isolate triethylamine by distillation. TEA is widely used as a non-nucleophilic base in organic synthesis, where it neutralizes acids to form triethylammonium salts and facilitates reactions such as acylations and esterifications. It also serves as a solvent and as a reagent in the preparation of quaternary ammonium salts, dyes, pharmaceuticals, and polymerization inhibitors. In some processes, TEA is used as a scavenger for hydrogen chloride in polymerizations and to promote condensation reactions.

Safety and handling: Triethylamine is flammable and can be irritating to skin, eyes, and the respiratory tract. Vapors are denser than air and may accumulate in poorly ventilated spaces. It can slowly oxidize in air to form peroxides, so storage in tightly closed containers, under appropriate conditions, is advised. It should be kept away from oxidizers and acids, and handled in a fume hood with appropriate personal protective equipment. Waste disposal follows standard hazardous-organic-waste protocols.

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