Triethylammonium hydrogen sulfate

A-(4-sulfonic acid) butyl triethylammonium hydrogen sulfate... 

Ion-pair chromatography has also been used for the separation of aspartame from other sweeteners. The ion-pair reagents commonly used are triethylammonium phosphate (32), tetra-ethylammonium hydroxyde (47), tetrapropylammonium hydroxide (40), pentanesulfonate (52), tetrabutylammonium phosphate (34), tetrabutylammonium hydrogen sulfate (66), and tetrabutyl-ammonium p-toluenesulfonate (24). 

PHASE-TRANSFER CATALYSTS Adogen 464. (-)-N-Benzyl-N-methylephedrinium bromide. Benzyltriethylamine. Benzyl triethylammonium chloride. 18-Crown-6. Dibenzo-18-crown-6. Diethyl phenylsulfinylmethylphosphonate. Hexadecyltributyl-phosphonium bromide. Methyltricaprylylammonium chloride. Tetra-n-butylammo-nium hydrogen sulfate. Tetra- -butylammonium iodide. 

Reaction with phosphorus oxychloride 806 Carbon disulfide (18 ml, 0.3 mole) is dropped into a stirred solution of an amine (0.3 mole) and anhydrous triethylamine (126 ml, 0.9 mole) in anhydrous ether (150 ml) at —5° with aromatic amines the mixture is set aside overnight. Then a solution of phosphorus oxychloride (28 ml, 0.3 mole) in anhydrous ether (30 ml) is dropped in, with stirring, at —10° to —5°. Next day the precipitated triethylammonium chloride is filtered off and stirred thoroughly with two portions of ether. The ethereal solutions are extracted with sodium hydrogen carbonate solution and with water, dried over sodium sulfate, concentrated, and fractionated. Yields are about 60%. 

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