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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-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. 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. Rinse mouth. 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