Triethylamine is a base used to prepare esters and amides from acyl chlorides as well as in the synthesis of quaternary ammonium compounds. It acts as a catalyst in the formation of urethane foams and epoxy resins, dehydrohalogeantion reactions, acid neutralizer for condensation reactions and Swern oxidations. It finds application in reverse phase high-performance liquid chromatography (HPLC) as a mobile-phase modifier. It is also used as an accelerator activator for rubber, as a propellant, as a corrosion inhibitor, as a curing and hardening agent for polymers and for the desalination of seawater. Furthermore, it is used in automotive casting industry and textile industry.
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Applications
Triethylamine is a base used to prepare esters and amides from acyl chlorides as well as in the synthesis of quaternary ammonium compounds. It acts as a catalyst in the formation of urethane foams and epoxy resins, dehydrohalogeantion reactions, acid neutralizer for condensation reactions and Swern oxidations. It finds application in reverse phase high-performance liquid chromatography (HPLC) as a mobile-phase modifier. It is also used as an accelerator activator for rubber, as a propellant, as a corrosion inhibitor, as a curing and hardening agent for polymers and for the desalination of seawater. Furthermore, it is used in automotive casting industry and textile industry.
Solubility
Miscible with water, ether and ethanol.
Notes
Incompatible with strong oxidizing agents.
RUO – Research Use Only
General References:
- The apparent base strength of triethylamine has been increased by its use in combination with certain metal salts, examined by Rathke. For the acylation of malonic esters with acyl chlorides, MgCl2 was found to be effective, whereas other metal salts had no effect: J. Org. Chem., 50, 2622 (1985); Synth. Commun., 15, 1039 (1985); Tetrahedron, 48, 9233 (1993). For the Horner-Wadsworth-Emmons olefination reaction, LiBr or LiCl gave the best results under most conditions, although Mg salts showed some effect; other metal salts were ineffective: J. Org. Chem., 50, 2624 (1985).
- Addition of triethylamine enables the reaction of Grignard reagents with esters to be interrupted at the ketone stage. Deuterium-labelling shows that this is caused by enolization of the ketone. Good yields are obtained unless the ester itself is readily enolized: Synthesis, 877 (1980).
- Murahashi, S. I.; Zhang, D.; Iida, H.; Miyawaki, T.; Uenaka, M.; Murano, K.; Meguro, K. Flavin-catalyzed aerobic oxidation of sulfides and thiols with formic acid/triethylamine. Chem. Commun. 2014, 50 (71), 10295-10298.
- Soni, R.; Hall, T. H.; Mitchell, B. P.; Owen, M. R.; Wills, M. Asymmetric reduction of electron-rich ketones with tethered ru(II)/TsDPEN catalysts using formic acid/triethylamine or aqueous sodium formate. J. Org. Chem. 2015, 80 (13), 6784-6793.