Naphthalene → Phthalic Anhydride

HRID 461398Notes

Reaction equation

HRID 461398 reaction equation
C1C2C(=CC=CC=2)C=CC=1.C1C=CC2C(=O)C=CC(=O)C=2C=1.[C:23]([OH:34])(=[O:33])[C:24]1[C:25](=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:26]([OH:28])=O.C(O)(=O)/C=C\C(O)=O.C(O)(=O)CCC(O)=O>[O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5]>[C:26]1(=[O:28])[O:34][C:23](=[O:33])[C:24]2=[CH:32][CH:31]=[CH:30][CH:29]=[C:25]12

Participants

7

Reactant 5

HCID 931NaphthaleneHCID 1017Phthalic AcidHCID 1110Succinic AcidHCID 85301,4-Naphthoquinone2×HCID 444266Maleic Acid

Product 1

HCID 6811Phthalic AnhydrideYield 99%

Reagents, catalysts & solvents 1

HCID 178419084HCID 178419084, compoundCatalyst

Procedure

The optimum yield of phthalic anyhdride is produced in the temperature range of 360° ± 10° C, with temperatures over or under this range resulting in over or under oxidation, respectively, of the napthalene yielding undesirable products such as 1-4 napthoquinone, phthalic acid, maleic acid, succinic acid, etc. With a vanadium pentoxide catalyst structure made according to the present invention, a yield of 99% phthalic anhydride was obtained with only a slight trace of 1-4 napthoquinone. Throughout this reaction, the temperature of the catalyst structure was easily maintainable within the optimum operating temperature range of 360° C ± 10° C.

Workup

  1. customThe optimum yield of phthalic anyhdride is produced in the temperature range of 360° ± 10° C, with temperatures over or under this range
  2. customresulting in over or under oxidation

Sources & evidence

ORD record
ord-9c7841d5250b4b158d7b59a13727c286
Source dataset
uspto-grants-1977_12
Patent number
US04062872

Reaction notes

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