Acetic Acid → N,N-Diphenylhydrazine

Participants

Reaction Steps

Into a 500 ml four-neck flask were added 16.9 g (100 mmol) of diphenylamine, 15.1 g (251 mmol) of acetic acid, and 207 g of methanol and the whole was dissolved under stirring. Thereto was added 13.8 g (200 mmol) of sodium nitrite dissolved in 57 g of water, followed by stirring at 15 to 20° C. for 3 hours. After the disappearance of diphenylamine was confirmed by high-performance liquid chromatography, 26.1 g (653 mmol) of sodium hydroxide dissolved in 119 g of water and 259 g (240 mmol) of thiourea dioxide were added, followed by stirring at 38 to 43° C. for 3 hours. After the disappearance of N-nitrosodiphenylamine was confirmed by high-performance liquid chromatography, methanol was removed by distillation under reduced pressure, followed by extraction with 120 g of toluene to obtain a toluene solution of 1,1-diphenylhydrazine. The compositional ratio excluding toluene determined by high-performance liquid chromatography was 88.9% of 1,1-diphenylhydrazine and 10.2% of diphenylamine.

Provenance & Evidence