I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
Phase transfer catalyst Tetra-n-butylammonium bromide is used as a phase transfer catalyst for the preparation of lactones by cyclization of potassium salt of µ-bromocarboxylic acids and beta-lactones from beta-bromoacid by cyclization. It is also involved in the Curtius rearrangement, N-alkylation of aromatic carboxamides. It plays an important role as an ionic liquid in the regioselective O-alkylation reactions. It is also used in the preparation of polymer solar cells and single component green-light emitting electrochemical cells.
Phase-transfer catalyst of wide application. Some illustrative examples are given below. See also Appendix 2.
K salts of ω-bromocarboxylic acids can be cyclized to lactones under effectively "high-dilution" conditions by extracting into toluene in the presence of a small amount of catalyst. The 16-membered ring lactone was formed in 92% yield: J. Org. Chem., 48, 1533 (1983).
Primary alkyl chlorides can be converted to alcohols in excellent yield by phase-transfer reaction with sodium formate and hydrolysis of the resulting formate esters: Synthesis, 763 (1986).
ß-Lactones are formed by the cyclization of ß-bromoacids under phase-transfer conditions: Chem. Pharm. Bull., 29, 1063 (1981).
An improved procedure for the Curtius rearrangement involves reaction of acid chlorides with azide ion under phase-transfer conditions: Synthesis, 38 (1983).
Aromatic carboxamides undergo N-alkylation with alkyl halides using KOH under solvent-free conditions: Synth. Commun., 22, 1661 (1992).
Has been used as an "ionic liquid" in the regioselective O-alkylation of ambident nucleophiles: Tetrahedron Lett., 33, 4435 (1992). A method is described whereby the "solvent" can be recovered quantitatively. A semi-molten mixture with KF or CsF has been found to be an effective system for fluorodehalogenation of, e.g., benzyl bromide: J. Fluorine Chem., 73, 185 (1995).
Effective catalyst for amination reactions of alkyl or activated aryl halides, by increasing the solubility of ammonia in organic media: J. Chem. Soc., Chem. Commun., 267 (1987).
Tzirakis, F.; Stringari, P.; Von Solms, N.; Coquelet, C.; Kontogeorgis, G. Hydrate equilibrium data for the CO2+ N2 system with the use of Tetra-n-butylammonium bromide (TBAB), cyclopentane (CP) and their mixture. Fluid Phase Equilib. 2015, 408, 240-247.
Akiba, H.; Ueno, H.; Ohmura, R. Crystal Growth of Ionic Semiclathrate Hydrate Formed at the Interface between CO2 Gas and Tetra-n-butylammonium Bromide Aqueous Solution. Cryst. Growth Des. 2015, 15 (8), 3963-3968.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant