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Metal Cation-Exchanged Clay-Catalyzed Organic Unit Reactions

Research Project

Project/Area Number 07555279
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section試験
Research Field 有機工業化学
Research InstitutionKYOTO UNIVERSITY

Principal Investigator

UEMURA Sakae  Graduate School of Engineering, Kyoto University Professor, 工学研究科, 教授 (70027069)

Co-Investigator(Kenkyū-buntansha) YAMAUCHI Takayoshi  Nissei Chemical Inc., Director, 取締役
HASHIMOTO Keiji  Osaka Municipal Technical Research Institute, Senior Researcher, 副主幹
OHE Kouichi  Graduate School of Engineering, Kyoto University Associate Professor, 工学研究科, 助教授 (90213636)
伊藤 修  京都大学, 工学研究科, 助手 (10026023)
Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥2,500,000 (Direct Cost: ¥2,500,000)
Fiscal Year 1996: ¥2,500,000 (Direct Cost: ¥2,500,000)
Keywordsmontmorillonite / clay-catalyst / catalytic organic reaction / environmentally benign / Friedel-Crafts reaction / aromatic alkylation / acetalization / alkane oxidation / フリーデル-クラフツ反応 / 核アルオル化 / 雲母 / フリーデル・クラフツ型反応 / プリンス反応 / アセタール化 / 転位反応
Research Abstract

We have carried out the catalytic use of metal cation-exchanged montmorillonite (M^<n+>mont), a modified natural clay with a layr structure, and metal cationexchanged fluorotetrasilicic mica (M^<n+>-TSM), a synthetic clay with a layr structure, for the following organic unit reactions : (1) Friedel-Crafts alkylation of phenol with 4-hydroxybutan-2-one to produce 4- (4-hydroxyphenyl) butan-2-one (raspbery ketone), (2) rearrangement of alkyl phenyl ethers to the corresponding alkylphenols, (3) aromatic alkylation of phenol with aldehydes and ketones to produce the corresponding gem-bis (hydroxyphenyl) alkanes (bisphenols) and alkylphenols, respectively, (4) a facile and an almost quantitative substrateselective acetalization, (5) alkane oxidation with aqueous tert-butyl hydroperoxide, (6) Prins reaction of stirenes with aldehydes using a clay as a Bronsted acid, and (7) inter-and intramolecular carbonyl-ene reaction using a clay as a Lewis acidunder similar condition to that of Prins reaction. In almost all cases, the clay catalyst can be regenerated and reused for several times after filtration, washing, and drying.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • Research Products

    (19 results)

All Other

All Publications (19 results)

  • [Publications] S. Uemura 他4名: "Cation-Exchanged Montmorillonite-Catalyzed Facile-Friedel- Crafts Alkylation of Hydroxy and Methoxy Aromatics with 4-Hydroxybutan-2-One to Produce Raspberry Ketone and Some Pharmaceutically Active Compounds" Journa of Organic Chemistry. 59. 5901-5904 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S. Uemura 他2名: "Ce^<3+>-Exchanged Montmorillonite (Ce^<+->Mont) as a Useful Substrate-Selective Acetalization Catalyst" Journa of Organic Chemistry. 60. 4039-4043 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S. Uemura 他2名: "Catim-Exchanged Fluorotehasihcic Mica-Catalysed Oxidation of Alkanes with t-BuOOH" Journal of Chemical Society Povhim Trans. 2. 8. 2013-2017 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S. Uemura 他3名: "Al^<3+>-Mont so as Effective Solid Catalyst for selective Synthesis of alkylphemls and Bisphenols" Chem. Lett.1. 59-60 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S. Uemura 他3名: "Cation-Exchanged Mont-Catalyzed Prns Reaction" Bull. Chem. Soc. Jpn.69. 2361-2368 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Uemura et al.: "Cation-Exchanged Mont-Catalyzed facile Friedel-Crafts Alkylation of Hydroxy and Methoxy Aromatics" J.Org.Chem.59. 5901-5904 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Uemura et al.: "Ce^<3+>-Exchanged Mont as a Useful Substrate-Selective Acetalization Catalyst" J.Org.Chem.60. 4039-4043 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Uemura et al.: "Cation-Exchanged Fluorotetrasilicic Mica-Catalyzed Oxidation of Alkanes with t-BuOOH" J.Chem.Soc., Perkin Trans. 2, No.8. 2013-2017 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Uemura et al.: "Al^<3+>-Mont as an Effective Solid Catalyst for Selective Synthesis of Alkylphenols and Bisphenols" Chem.Lett.No.1. 59-60 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Uemura et al.: "Cation-Exchanged Mont-Catalyzed Prins Reaction" Bull.Chem.Soc., Jpn.69. 2361-2368 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Uemura 他 4名: "Cation-Exchaugcol Mont-Catalyzed Facile Friedel-Crufts Alkylation of Hydroxy and Methexy Aromahes" Journal of Organic Chemistry. 59. 5901-5904 (1994)

    • Related Report
      1996 Annual Research Report
  • [Publications] S.Uemura 他 2名: "Ce^<3+>-Exchanged Mont as a Useful Substrate-Selective Acetalization Catalyst" Journal of Organic Chemistry. 60. 4039-4043 (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] S.Uemura 他 2名: "Cation-Exchanged Fluorotehasilicic Mica-Catalysed Oxidation of Alkanes with t-BuDOH" Journal of Chemical Society Perhin Trans.2. 8. 2013-2017 (1995)

    • Related Report
      1996 Annual Research Report
  • [Publications] S.Uemura 他 3名: "Al^<3+>-Mont as an Effective Solid Catalyst for Selective Synthesis of Alkylphenols and Bisphenols" Chem.Lett.1. 59-60 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] S.Uemura 他 3名: "Cation-Exchanged Mont-Catalyzed Prins Reaction" Bull.Chem.Soc.Jpn.69. 2361-2368 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Uemura, S.: "Rearrauglmint of Alkgl Phengl Ethen to Alkulplinolds to the Presonce of Cation-Aschanged Montmorillonite" J. Chem. Soc., Perkin Trans. 1. 3367-3371 (1994)

    • Related Report
      1995 Annual Research Report
  • [Publications] Uemura, S.: "Ce^<3+>Exchanged Montmorillonite as a Useful Substrate-Selectire Acetalization Catalyst" J. Org. Chem.60. 4039-4043 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Uemura, S.: "Cation-Exchanged Fluiro tetoasilic Mica-Catalyzed Caidation of Alkunes with t-BuOOH" J. Chem. Soc., Perkin 2. 2013-2017 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Uemura, S.: "AC^<3+>-Exchenged Mint-Cntalyzed Aromatoc Allighatopm of Pheut with bidehydes and kitemes to prednce Bispnenolsed Alkolphends" Chem. Lett.59-60 (1996)

    • Related Report
      1995 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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