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Direct Introduction of Functional Groups into Hydrocarbons by Using Low-Temperature Plasma

Research Project

Project/Area Number 01550679
Research Category

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

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionSaitama Institute of Technology

Principal Investigator

TEZUKA Meguru  Saitama Inst. Techn., Prof., 工学部, 教授 (50118668)

Co-Investigator(Kenkyū-buntansha) 萩原 時男  埼玉工業大学, 工学部, 助教授 (80164763)
Project Period (FY) 1989 – 1990
Project Status Completed (Fiscal Year 1990)
Budget Amount *help
¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 1990: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1989: ¥1,300,000 (Direct Cost: ¥1,300,000)
KeywordsOxygen Plasma / Aromatic Oxidation / Alkyl Oxidation / Radiofrequency Discharge / Olefin Oxidation / Oxidation of Cycloalkanes / 高周波放電 / プラズマ酸化 / マイクロ波放電 / グロ-放電電解 / フェノ-ル合成 / シアノ化反応
Research Abstract

Recent advance in synthetic chemistry has enabled the tailormade preparation of a diversity of organic compounds. However, direct introduction of functional groups into the carbon skeletons still remains a problem to be solved. In this study, the application of low-temperature plasma was investigated to introduce oxygen-containing groups such as hydroxyl or carbonyl group into hydrocarbons. The plasma was generated by means of radiofrequency discharge of oxygen gas flowing through a Pyrex reactor tube. Organic substrates were distilled together with oxygen through the reactor into cold traps on liquid nitrogen under reduced pressure.
Some aromatic hydrocarbons were effectively oxidized in a gaseous oxygen plasma. Benzene and naphthalene were partially oxidized to give phenol and naphthol as a single volatile organic product, respectively. When alkylbenzene were reacted, the oxidation of alkyl groups competed with ring hydroxylation. Thus, toluene gave benzaldehyde and benzyl alcohol as well as phenol and three isomeric cresols. With increase in size of alkyl groups, alkyl oxidation became preferential. Based on the result that the oxidation favorably took place on the alpha-carbons, the reaction scheme involving autoxidation of benzyl radicals formed through electron collision onto starting material molecules. From the substrate having olefinic double bond, e. g. styrene, the epoxide or its derivatives, mainly ketones, were obtained in fairly good yields. There, seemingly, atomic oxygen played a significant role.
The oxidation of saturated hydrocarbons was also examined. Cycloalkanes (C_5-C_8) gave the corresponding cycloalkanol and cycloalkanone in almost equimolar amounts, although their yields were unsatisfactory.

Report

(3 results)
  • 1990 Annual Research Report   Final Research Report Summary
  • 1989 Annual Research Report
  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Meguru Tezuka: "Oxidation of Cycloalkanes in a Radiofrequency Plasma" Bull.Chem.Soc.Japan. 64. 1063-1065 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Meguru Tezuka: "Reactions of Aromatic Hydrocarbons with Oxygen in a Gaseous Plasma"

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] 手塚 還: "季刊化学総説 「活性酸素種の化学」 (第4章B プラズマ酸化)" 学会出版センタ-, 264 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Meguru Tezuka: "Oxidation of Cycloalkanes in a Radiofrequency Plasma" Bull. Chem. Soc. Jpn.64. 1063-1065 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Meguru Tezuka: "Reactions of Aromatic Hydrocarbons with Oxygen in a Gaseous Plasma"

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Meguru Tezuka: Chemistry of Active Oxygen Species. Gakkai Shuppan Center, 264 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1990 Final Research Report Summary
  • [Publications] Meguru Tezuka: "Oxidation of Cycloalkanes in a Radiofrequency Plasma" Bull.Chem.Soc.Japan. 64. 1063-1065 (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] Meguru Tezuka: "Reactions of Aromatic Hydrocarbons with Oxygen in a Gaseous Plasma"

    • Related Report
      1990 Annual Research Report
  • [Publications] 手塚 還: "季刊化学総説 「活性酸素種の化学」 (第4章B プラズマ酸化)" 学会出版センタ-, 264 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Meguru Tezuka: "Oxidation of Cycloalkanes in an rf Plasma"

    • Related Report
      1989 Annual Research Report
  • [Publications] Meguru Tezuka: "Aromatic Cyanation by Glow Discharge Electrolysis"

    • Related Report
      1989 Annual Research Report
  • [Publications] 手塚還(共著): "季刊化学総説「活性酸素種の化学」" 学会出版センタ-,

    • Related Report
      1989 Annual Research Report

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Published: 1989-04-01   Modified: 2016-04-21  

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