Acetic Acid → N,N-Diphenylhydrazine

HRID 1363642

Reaction equation

HRID 1363642 reaction equation
C1(NC2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C.N([O-])=O.[Na+].[OH-].[Na+].[NH2+]([O-])(=O)C(N)=S.[N:30]([N:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=O>O.CO>[C:33]1([N:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[NH2:30])[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 6838N-NitrosodiphenylamineHCID 11487Diphenylamine2×HCID 14798Sodium HydroxideHCID 23668193Sodium Nitrite

Product 1

HCID 10739N,N-Diphenylhydrazine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

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.

Workup

  1. dissolutionthe whole was dissolved
  2. stirringby stirring at 15 to 20° C. for 3 hours
  3. stirringby stirring at 38 to 43° C. for 3 hours
  4. customwas removed by distillation under reduced pressure
  5. extractionfollowed by extraction with 120 g of toluene

Sources & evidence

ORD record
ord-7f63dda49f474447b69ca3b0b2fb0d6a
Source dataset
uspto-grants-2011_02
Patent number
US07884245B2

Linked notes

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