Tetrabutylammonium hydrogen sulfate

Chemical properties

It is a stable, hygroscopic, white powder.

The Uses of Tetrabutylammonium hydrogen sulfate

Displays antibacterial properties due to the presence of the quaternary amine and the counter ion.

The Uses of Tetrabutylammonium hydrogen sulfate

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. Tetrabutylammonium hydrogensulfate is used as a cocatalyst in the synthesis of propionic acid and the ketones by hydrocarboxylation of ethylene. It is also 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.

What are the applications of Application

Tetrabutylammonium bisulfate is a compound that displays antibacterial properties

Preparation

Tetrabutylammonium hydrogen sulfate can be prepared from tetrabutylammonium azide by treating it with potassium hydrogen sulfate and 10% aqueous sulfuric acid in aqueous medium or from tetrabutylammonium thiocyanate by treating it with relatively concentrated sulfuric acid (70%) at 75 °C.

General Description

Tetrabutylammonium hydrogensulfate, a quaternary ammonium salt, is a phase-transfer reagent. It It serves as solvent for the dissolution of ruthenium(II) complex fac-[Ru(CO)2(H2O)3(C(O)C2H5)][CF3SO3]. It participates as a cocatalyst in the reaction medium for the preparation of alternating polyketones and propionic acid.

Purification Methods

The sulfate crystallises from acetone. It has been used as a phase transfer catalyst.

References

[1] H. N. KARADE M. P K M Sathe. An efficient synthesis of 1, 8-dioxo-octahydroxanthenes using tetrabutylammonium hydrogen sulfate[J]. Arkivoc, 2007, 2007 1. DOI:10.3998/ARK.5550190.0008.D28.
[2] A. J. PARDEY. New media in homogeneous catalysis: wet sodium or tetrabutylammonium hydrogensulfate salts for reppe syntheses catalyzed by a ru(ii) carbonyl complex[J]. Journal of Coordination Chemistry, 2004, 57 1: 871-882. DOI:10.1080/00928970410001721998.
[3] A. J. PARDEY. Hydrocarboxylation and stepwise alternating oligomerization of carbon monoxide and ethylene catalyzed by cis-[Rh(CO)2(amine)2](PF6) complexes in a wet liquid tetrabutylammonium hydrogensulfate[J]. Polyhedron, 2004, 23 1: 1677-1683. DOI:10.1016/J.POLY.2004.03.023.
[4] NEETU TEWARI Rama P T Namrata Dwivedi. Tetrabutylammonium hydrogen sulfate catalyzed eco-friendly and efficient synthesis of glycosyl 1,4-dihydropyridines[J]. Tetrahedron Letters, 2004, 45 49: Pages 9011-9014. DOI:10.1016/j.tetlet.2004.10.057.