Benzoic Acid → HCID 19805595, compound

HRID 1679576Notes

Reaction equation

HRID 1679576 reaction equation
BrBr.C(O)(=O)[C:4]1[C:5](=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:6]([OH:8])=[O:7].O=O.C(O)(=[O:24])C1C=CC=CC=1>O>[C:6]([OH:8])(=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:4]=1.[OH2:24]

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 977OxygenHCID 1017Phthalic AcidHCID 24408Bromine

Product 1

HCID 19805595HCID 19805595, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a continuous process for iso- or terephthalic acid product production in and recovery from a benzoic acid-water solvent system wherein m- or p-xylene is oxidized with air in the presence of catalysis provided by manganese, cobalt or cobalt and manganese and a source of bromine and a liquid phase of said solvent system at a temperature within the range of from 175° to 235° C. and a constant gauge pressure within the range of 7 to 21 kg/cm2 in a stirred reaction zone to produce a suspension of crystalline phthalic acid product in said solvent system as fluid oxidation zone effluent and a gas-vapor mixture containing nitrogen, oxygen, oxides of carbon and vapors of benzoic acid and water as exhaust effluent; wherein heat of reaction is removed at least in part by cooling said exhaust to provide a benzoic acid-water liquid reflux to the oxidation zone; and wherein said phthalic acid product is separated as a crystalline mass from the fluid oxidation effluent, washed to remove mother liquor and dried; the improvements comprising, conducting the m- or p-xylene oxidation in the presence of from 2 to 6 weight parts of solvent system consisting essentially of 90-97 weight percent benzoic acid and 10-3 weight percent water for each weight part of xylene and at a substantially constant oxidation zone temperature within said temperature range controlled by varying the rate of water condensate returned to the oxidation zone inversely with respect to change required in oxidation zone temperature; evaporating water from fluid effluent from the oxidation zone under conditions maintaining benzoic acid in the liquid phase; separating the suspended crystalline product mass from the water-free oxidation zone fluid effluent; and washing the separated crystalline product mass at a temperature of from 122° up to 135° C first with liquid benzoic acid and then with xylene corresponding to the product.

Workup

  1. customto produce
  2. temperaturewherein heat of reaction
  3. customis removed at least in part
  4. temperatureby cooling

Sources & evidence

ORD record
ord-549275c57a90489dbf51e03a5eeb7c80
Source dataset
uspto-grants-1978_03
Patent number
US04081464

Reaction notes

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