2-methylbenzene-1,4-diol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into an autoclave (inner volume: 4.5 ml, made of SUS 316, without manometer) were charged 0.016 g of hydroquinone, 1.355 g of methanol and 2.5 mg of calcium oxide (manufactured by Wako Pure Chemical Ind., Ltd.). The reaction was started by elevating the temperature up to425° C. with sand bath. After 8 minutes, 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 87% by mole, the selectivity of monomethylhydroquinone was 30% by mole, the selectivity of dimethylhydroquinone was 42% by mole and the selectivity of trimethylhydroquinone was 18% by mole. As byproducts, tetramethylhydroquinone was produced with a selectivity of 3% by mole. the autoclave was quickly cooled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into an autoclave (inner volume: 4.5 ml, made of SUS 316, without manometer) were charged 0.031 g of hydroquinone, 1.370 g of methanol and 0.063 mg of lithium hydroxide monohydrate (manufactured by Wako Pure Chemical Ind., Ltd.). The reaction was started by elevating the temperature up to 420° C. with sand bath. After 7 minutes, 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 72% by mole, the selectivity of monomethylhydroquinone was 34% by mole, the selectivity of dimethylhydroquinone was 42% by mole and the selectivity of trimethylhydroquinone was 18% by mole. As byproducts, tetramethylhydroquinone and p-methoxyphenol were produced with selectivities of 2% by mole and 1% by mole, respectively. up to 420° C. the autoclave was quickly cooled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into an autoclave (inner volume: 9 ml, made of SUS 316, equipped with a manometer) were charged 0.098 g of methylhydroquinone, 3.491 g of methanol and 7 mg of lanthanum oxide (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 18 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 32% by mole, the selectivity of dimethylhydroquinone was 80% by mole, the selectivity of trimethylhydroquinone was 10% by mole and no tetramethylhydroquinone was produced. equipped with a manometer) up to 350° C. the autoclave was quickly cooled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. equipped with a manometer) up to 350° C. the autoclave was quickly cooled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into an autoclave (inner volume: 9 ml, made of SUS 316, equipped with a manometer) were charged 0.115 g of methylhydroquinone, 3.268 g of methanol and 4.6 mg of chromium oxide (manufactured by High Purity Chemicals). The reaction was started by elevating the temperature up to 350° C. with sand bath. The pressure during the reaction was 18 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 17% by mole, the selectivity of dimethylhydroquinone was 74% by mole and the selectivity of trimethylhydroquinone was 2% by mole. No tetramethylhydroquinone was produced. equipped with a manometer) up to 350° C. the autoclave was quickly cooled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into an autoclave (inner volume: 9 ml, made of SUS 316, equipped with a manometer) were charged 0.104 g of methylhydroquinone, 3.4078 g of methanol and 8.3 mg of iron powders (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 20 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 16% by mole, the selectivity of dimethylhydroquinone was 82% by mole and the selectivity of trimethylhydroquinone was 3% by mole. No tetramethylhydroquinone was produced. equipped with a manometer) up to 350° C. the autoclave was quickly cooled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. equipped with a manometer) up to 350° C. the autoclave was quickly cooled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into an autoclave (inner volume: 9 ml, made of SUS 316, equipped with a manometer) were charged 0.111 g of methylhydroquinone, 3.463 g of methanol and 4.6 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 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 45% by mole, the selectivity of dimethylhydroquinone was 64% by mole, the selectivity of trimethylhydroquinone was 17% by mole and no tetramethylhydroquinone was produced. As byproducts, methyl ethers of dimethylquinone and trimethylquinone, represented by the formulae shown above, were formed with a selectivity of 6% and 2%, respectively. equipped with a manometer) up to 350° C. the autoclave was quickly cooled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into an autoclave (inner volume: 9 ml, made of SUS 316, equipped with a manometer) were charged 0.108 g of methylhydroquinone, 3.573 g of methanol and 0.2 mg of sodium methylate. The reaction was started by elevating the temperature up to 350° C. with sand bath. The pressure during the reaction was 16 MPa. After 4 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 86% by mole, the selectivity of dimethylhydroquinone was 38% by mole, the selectivity of trimethylhydroquinone was 37% by mole and no tetramethylhydroquinone was produced. As byproducts, methyl ethers of monomethylhydroquinone, dimethylhydroquinone and trimethylhydroquinone, represented by the formulae shown above, were formed with a selectivity of 6%, 4% and 3%, respectively. equipped with a manometer) up to 350° C. the autoclave was quickly cooled