Nitrobenzene → 2-Nitrobiphenyl

HRID 1658646Notes

Reaction equation

HRID 1658646 reaction equation
[C:1]1(C)[C:2](S(O)(=O)=O)=[CH:3][C:4](S(O)(=O)=O)=[CH:5][CH:6]=1.[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([O-:18])=[O:17]>>[N+:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([O-:18])=[O:17]

Participants

3

Reactant 2

HCID 7416NitrobenzeneHCID 671294-Methyl-1,3-benzenedisulfonic acid

Product 1

HCID 68292-NitrobiphenylYield 87%

Procedure

5 parts of toluene-2,4-disulfonic acid was adsorbed to 6 parts of diatomaceous earth the same as in Example 1 to prepare solid catalyst. The solid catalyst was added to 300 parts of nitrobenzene and heated at a temperature not exceeding 120°C under reduced pressure to remove water as an azeotropic mixture with nitrobenzene. Thus 100 parts of nitrobenzene was distilled off with water. Thereafter, 15 parts of biphenyl was added to the dried mixture and one part of fuming nitric acid was added dropwise with stirring to the mixture cooled to 3° to 5°C in 30 minutes. The nitration reaction and post-treatment were conducted in the same manner as in Example 1, whereby mononitrobiphenyl was obtained with p/o ratio of 1.3. Yield was 87%.

Workup

  1. customto prepare solid catalyst
  2. temperatureheated at a temperature not
  3. customexceeding 120°C under reduced pressure
  4. customto remove water as an azeotropic mixture with nitrobenzene
  5. distillationThus 100 parts of nitrobenzene was distilled off with water
  6. additionThereafter, 15 parts of biphenyl was added to the dried mixture and one part of fuming nitric acid
  7. additionwas added dropwise
  8. temperaturecooled to 3° to 5°C in 30 minutes
  9. customThe nitration reaction

Sources & evidence

ORD record
ord-c690d07aa6c04aa8a0ed3e916d8e615d
Source dataset
uspto-grants-1976_06
Patent number
US03965200

Reaction notes

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