Methylhydroquinone → Durohydroquinone

HRID 380779

Reaction equation

HRID 380779 reaction equation
[CH3:1]C1C=C(O)C=CC=1O.CC1C(C)=C(C=CC=1O)O.[CH3:20][C:21]1[C:22]([OH:30])=[C:23]([CH3:29])[C:24]([CH3:28])=[C:25]([CH:27]=1)[OH:26]>[Zn].CO>[CH3:20][C:21]1[C:22]([OH:30])=[C:23]([CH3:29])[C:24]([CH3:28])=[C:25]([OH:26])[C:27]=1[CH3:1]

Participants

6

Reactant 3

HCID 7253Methylhydroquinone2×HCID 12785TrimethylhydroquinoneHCID 691002,3-Dimethylhydroquinone

Product 1

HCID 136346Durohydroquinone

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Into an autoclave (inner volume: 9 ml, made of SUS 316, equipped with a manometer) were charged 0.092 g of methylhydroquinone, 3.895 g of methanol and 7.2 mg of zinc powders (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 17 MPa. After 2 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 methylhydroquinone was 23% by mole, the selectivity of dimethylhydroquinone was 92% by mole, the selectivity of trimethylhydroquinone was 8% by mole and 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-2e8d7521a058424daad922cc8427032b
Source dataset
uspto-grants-2001_10
Patent number
US06303801B1

Linked notes

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