Phase transfer catalyst Tetra-n-butylammonium hydrogen sulfate shows antibacterial properties due to the presence of the quaternary amine and the counter ion. It serves as a phase-transfer catalyst, surface-active agent, solvent, intermediate, active ingredient for conditioners, antistatic agent, detergent sanitizers, softener for textiles and paper products, emulsifying agents and pigment dispersers. It is used as an efficient catalyst in the N-alkylation reactions of benzanilides, cyclization of beta-amino acids to beta-lactams, conversion of nitriles to amides, dehydrohalogenation of aryl 2-haloethyl ethers to give vinyl ethers and in the oxidation of alcohols.
Widely used phase-transfer catalyst; see Appendix 2. Some illustrative applications are given below:
Benzanilides have been N-alkylated in the presence of NaOH and K2CO3: Synth. Commun., 18, 2011 (1988).
It was the most effective catalyst studied for the cyclization of ß-amino acids to ß-lactams by methanesulfonyl chloride and KHCO3: Chem. Lett., 443 (1981).
In the dehydrohalogenation of aryl 2-haloethyl ethers to give vinyl ethers, this catalyst was found much more effective than the corresponding halides or benzyltriethylammonium salts: Synthesis, 688 (1979).
For use in the permanganate oxidation of benzylic positions, see Potassium permanganate, A12170.
The oxidation of primary alcohols to aldehydes by potassium chromate under phase-transfer conditions is better for higher homologues, where solubility in the aqueous phase is limited: Synthesis, 134 (1979). For phase-transfer catalyzed dichromate oxidation of secondary alcohols to ketones, see: Tetrahedron Lett., 1601 (1978).
For phase-transfer catalyzed conversion of nitriles to amides by alkaline H2O2, see: Synthesis, 243 (1980).
Pandian, T. S.; Choi, Y.; Srinivasadesikan, V.; Lin, M. C.; Kang, J. A dihydrogen phosphate selective anion receptor based on acylhydrazone and pyrazole. New J. Chem. 2015, 39 (1), 650-658.
Taguchi, H.; Yanagisawa, D.; Morikawa, S.; Hirao, K.; Shirai, N.; Tooyama, I. Synthesis and Tautomerism of Curcumin Derivatives and Related Compounds. Aust. J. Chem. 2015, 68 (2), 224-229.
Hazard Statements: H302-H315-H319-H335
Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.