Methylhydroquinone → Durohydroquinone

HRID 380773

Reaction equation

HRID 380773 reaction equation
[CH3:1]C1C=C(O)C=CC=1O.C[O-].[Na+].CC1C(C)=C(C=CC=1O)O.[CH3:23][C:24]1[C:25]([OH:33])=[C:26]([CH3:32])[C:27]([CH3:31])=[C:28]([CH:30]=1)[OH:29]>CO>[CH3:23][C:24]1[C:25]([OH:33])=[C:26]([CH3:32])[C:27]([CH3:31])=[C:28]([OH:29])[C:30]=1[CH3:1]

Participants

6

Reactant 4

HCID 7253Methylhydroquinone2×HCID 12785TrimethylhydroquinoneHCID 691002,3-DimethylhydroquinoneHCID 10942334Sodium Methoxide

Product 1

HCID 136346Durohydroquinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into an autoclave (inner volume: 9 ml, made of Stainless Steel (SUS 316), equipped with amanometer) were charged 0.112 g of methylhydroquinone (manufactured by Wako Pure Chemical Ind., Ltd.), 3.372 g of methanol (extra fine reagent grade, manufactured by Wako Pure Chemical Ind., Ltd.) and 0.2 mg of sodium methylate (manufactured by Wako Pure Chemical Ind., Ltd.). The reaction was started by elevating the temperature up to 350° C. with sand bath. The pressure during the reaction was 16 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 59% by mole, the selectivity of dimethylhydroquinone was 69% by mole, the selectivity of trimethylhydroquinone was 10% by mole and no tetramethylhydroquinone was produced.

Workup

  1. customup to 350° C.
  2. temperaturethe autoclave was quickly cooled

Sources & evidence

ORD record
ord-f4eafcf00494464d85a86476adefc404
Source dataset
uspto-grants-2001_10
Patent number
US06303801B1

Linked notes

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