Hydroquinone → Durohydroquinone

HRID 380776Notes

Reaction equation

HRID 380776 reaction equation
[C:1]1(C=CC(O)=CC=1)O.CC1C=C(O)C=CC=1O.CC1C(C)=C(C=CC=1O)O.[CH3:28][C:29]1[C:30]([OH:38])=[C:31]([CH3:37])[C:32]([CH3:36])=[C:33]([CH:35]=1)[OH:34]>[O-2].[O-2].[Mn+4].CO>[CH3:28][C:29]1[C:30]([OH:38])=[C:31]([CH3:37])[C:32]([CH3:36])=[C:33]([OH:34])[C:35]=1[CH3:1]

Participants

7

Reactant 4

HCID 785Hydroquinone2×HCID 7253MethylhydroquinoneHCID 12785TrimethylhydroquinoneHCID 691002,3-Dimethylhydroquinone

Product 1

HCID 136346Durohydroquinone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Procedure

Into an autoclave (inner volume: 9 ml, made of SUS 316, equipped with a manometer) were charged 0.105 g of hydroquinone (manufactured by Wako Pure Chemical Ind., Ltd.), 3.602 g of methanol and 1.3 mg of manganese dioxide (manufactured by High Purity Chemicals Co.). The reaction was started by elevating the temperature up to 350° C. with sand bath. The pressure during the reaction was 15 MPa. After 8 hours, the autoclave was quickly cooled and the reaction solution was taken out from the autoclave when the temperature was cooled back to the room temperature. The measurement according to the process described above revealed that the conversion of hydroquinone was 41% by mole, the selectivity of monomethylhydroquinone was 43% by mole, the selectivity of dimethylhydroquinone was 13% by mole and the selectivity of trimethylhydroquinone was 1% by mole. No tetramethylhydroquinone was produced.

Workup

  1. customequipped with a manometer)
  2. customup to 350° C.
  3. temperaturethe autoclave was quickly cooled

Sources & evidence

ORD record
ord-5abd543ba6784fc094a7622f13858cfe
Source dataset
uspto-grants-2001_10
Patent number
US06303801B1

Reaction notes

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