Hydrogen Bromide → 4-Nitrobenzoic Acid

HRID 1165088Notes

Reaction equation

HRID 1165088 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1C)([O-:3])=[O:2].[N+](C1C=CC(C)=CC=1)([O-])=O.Br.[N+](C1C=CC=CC=1[C:27]([OH:29])=[O:28])([O-])=O>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C([O-])(=O)C.[Mn+2].C([O-])(=O)C.[Ti].C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:27]([OH:29])=[O:28])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

9

Reactant 4

HCID 260Hydrogen BromideHCID 69442-Nitrotoluene2×HCID 74734-Nitrotoluene3×HCID 110872-Nitrobenzoic acid

Product 1

HCID 61084-Nitrobenzoic Acid

Reagents, catalysts & solvents 4

HCID 6277Cobalt diacetateCatalystHCID 12525Manganous AcetateCatalystHCID 23963TitaniumCatalystHCID 176Acetic AcidSolvent

Procedure

Ortho-nitrotoluene (35 g), para-nitrotoluene (35 g), acetic acid (400 g), cobalt (II) acetate (1.0 g), manganese (II) acetate (1.0 g), and 48% hydrobromic acid (1.4 g) were charged into a one liter titanium autoclave. Ortho-nitrotoluene and para-nitrotoluene were present in equal mole ratio, the para-nitrotoluene being added to the reaction as a batch amount. The oxidation was initiated by introducing air into the reactor at an initial temperature of 293° F. and an initial pressure of 250 psig. The oxidation was completed after 70 minutes and it had reached a temperature of 360° F. at a pressure of 350 psig. Ortho-nitrobenzoic acid was found in 49.7 mol % yield and para-nitrobenzoic acid in 73.1 mol % yield (based on LC analysis of the slurry) from the oxidation. Also present in the slurry was ortho-nitrotoluene (43.9 mol %), paranitrotoluene (18.1 mol %), para-nitrobenzaldehyde (4.5 mol %), and p-nitrobenzyl acetate (3.0 mol %).

Workup

  1. additionby introducing air into the reactor at an initial temperature of 293° F.
  2. customa temperature of 360° F.
  3. customyield

Sources & evidence

ORD record
ord-5223416496ac49a3827953024c8a91f3
Source dataset
uspto-grants-1990_03
Patent number
US04906771

Reaction notes

Loading…