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SYNTHESIS OF RAW MATERIALS FOR FINE CHEMICALS BY LIQUID PHASE OXYGENATION OF AROMATIC COMPOUNDS

Research Project

Project/Area Number 63470069
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionTHE UNIVERSITY OF TOKYO

Principal Investigator

KAMIYA Yoshio  THE UNIVERSITY OF TOKYO, FACULTY OF ENGINEERING, PROFESSOR, 工学部, 教授 (40010764)

Co-Investigator(Kenkyū-buntansha) FUTAMURA Shigeru  THE UNIVERSITY OF TOKYO, FACULTY OF ENGINEERING, RESEARCH ASSISTANT, 工学部, 助手 (60165446)
Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥5,800,000 (Direct Cost: ¥5,800,000)
Fiscal Year 1989: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1988: ¥4,700,000 (Direct Cost: ¥4,700,000)
KeywordsBase-catalyst / Oxygenation / Aromatic compounds / Oxidation rate / Products / Solvent effect / Additive effect / メチル芳香族炭化水素 / アントラキノン / p-ヒドロキシベンズアルデヒド / 芳香族炭化水素 / 酸化生成物
Research Abstract

The oxygenation of 9-methylanthracene with t-BuOK (0.2 M) in HMPA-t-BuOH afforded anthraquinone selectively. On the other hand, no anthraquinone was obtained from 2-methylanthracene or from anthracene. Reaction mechanism is of interest.
The oxygenation of p-cresol in the presence of NAOH and CoCl_2 in a polar solvent affords p-hydroxybenzaldehyde, which is an important synthetic intermediate. In the oxygenation of p-cresol in the presence of NAOH (4.5 M) and CoCl_2 (0.1 M) in MeOH-t-BuOH at 60゚C for 50 h, the p-cresol conversion was 90 % and p-hydroxybenzaldehyde was obtained in 66% selectivity. In aprotic polar solvents such as HMPA, the p-hydroxybenzaldehyde selectivity was as low as 10%, and the yield of p-hydroxybenzaldehyde was not greater than 38% in a single solvent such as methanol, ethanol, and t-butanol. Among the transition metal chlorides, CoCl_2 was the most effective additive, compared with the chlorides of Ni, Fe, and Mn. As for the Co catalysts, satisfactory results were obtained except for Co_3O_4.
In this research, the effects of base catalysts, solvent, and transition metal salt additives on the oxidation rate and the product distribution were investigated in the base-catalyzed oxygenation of aromatic compounds in order to effectively convert methylaromatics to aldehydes and carboxylic acids, and important results were obtained.

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (10 results)

All Other

All Publications (10 results)

  • [Publications] 神谷佳男: "芳香族側鎖メチル基の遷移金属触媒による自動酸化" 石油学会誌. 32. 171-182 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 神谷佳男,田口敏樹,二タ村森: "芳香族側鎖メチル基のCo-Mn-Br系触媒による酸素酸化における水の添加効果" 石油学会誌. 32. 273-276 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 神谷佳男,岡林直也,神山統光,二タ村森: "塩基触媒による芳香族炭化水素の酸素酸化" 石油学会誌(予定).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] YOSHIO KAMIYA: "THE METAL-CATALYZED AUTOXIDATION OF METHYL GROUP ON THE AROMATIC RING" SEKIYU GAKKAISHI, 32-4, 171-182, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] YOSHIO KAMIYA, TOSHIKI TAGUCHI, SHIGERU FUTAMURA: "ADDITIVE EFFECT OF WATER ON THE Co-Mn-Br-CATALYZED AUTOXIDATION OF METHYL GROUP ON THE AROMATIC RING" SEKIYU GAKKAISHI, 32-5 273-276, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 神谷佳男: "芳香族側鎖メチル基の遷移金属触媒による自動酸化" 石油学会誌. 32. 171-182 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 神谷佳男,田口敏樹,二タ村森: "芳香族側鎖メチル基のCo-Mn-Br系触媒による酸素酸化における水の添加効果" 石油学会誌. 32. 273-276 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 神谷佳男,岡林直也,神山統光,二タ村森: "塩基触媒による芳香族炭化水素の酸素酸化" 石油学会誌.

    • Related Report
      1989 Annual Research Report
  • [Publications] Yoshio,Kamiya: 石油学会誌.

    • Related Report
      1988 Annual Research Report
  • [Publications] Yoshio,Kamiya: 日本化学会誌.

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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