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2007 Fiscal Year Final Research Report Summary

Syntheses of diphenylmethane derivatives on solid acid catalysts with controlled hydrophobicity, acidity, and reaction space

Research Project

Project/Area Number 17560683
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Catalyst/Resource chemical process
Research InstitutionTeikyo University of Science & Technology

Principal Investigator

KURIBAYASHI Kiyoshi  Teikyo University of Science & Technology, Department of Environmental Science, Professor (70234573)

Co-Investigator(Kenkyū-buntansha) KUGITA Tsuyoshi  Teikyo University of Science & Technology, Department of Environmental Science, Associate Professor (80225127)
Project Period (FY) 2005 – 2007
KeywordsSolid acid catalyst / Bisphenol F / Metlylenedianiline / Tetramethylbisphenol F / Zeolite / Mesoporous molecular sieve / Formalin / Diphenylmethane derivative
Research Abstract

Catalyst heterogenization in syntheses of chemicals by homogeneous catalyses is important from the viewpoint of green chemistry. The purpose of this study is to find suitable solid acid catalysts for the following three reactions in which homogeneous catalysts are used in practical processes:(1) Synthesis of bisphenol F from formaldehyde and phenol, (2) Synthesis of bis(4-hydroxy-3, 5-dimethylphenyl)methane from formaldehyde and 2, 6-dimethylphenol, (3) Synthesis of bis(4-aminophenyl)methane from formaldehyde and aniline. The catalysts examined were various types of zeolite and mesoporous aluminosilicate molecular sieves(Al-MCM-41). All the reactions were carried out in liquid phase at atmospheric pressure. Commercial phenol, 2, 6-dimethylphenol, aniline, and formalin were used as reactants without purification. It is clarified in this study that weak acid sites are responsible for three reactions because of a high reactivity of formaldehyde and the following catalysts and reaction conditions for each reaction are suitable. That is, for reaction (1) the suitable catalysts are high silica H-beta zeolite and Al-MCM-41 and a high phenol/formaldehyde ratio is required to attain a high selectivity, for reaction (2) the suitable catalyst is Al-MCM-41 and the selectivity is almost 100% at any reactant ratios, and for reaction (3) the active catalysts are Al-MCM-41 and H-beta and USY zeolites, the selectivity is affected by reaction spaces, and USY exhibits the highest selectivity.

  • Research Products

    (32 results)

All 2008 2007 2006 2005

All Journal Article (6 results) (of which Peer Reviewed: 3 results) Presentation (26 results)

  • [Journal Article] Catalytic Activity of Zeolites for Synthesis Reaction of Methylenediamine from Aniline and Formaldehyde2006

    • Author(s)
      T.Kugita
    • Journal Title

      Catalysis Today 111

      Pages: 275-279

    • Description
      「研究成果報告書概要(和文)」より
    • Peer Reviewed
  • [Journal Article] Introduction of Si-H bond onto the surface of mesoporous molecular sieves and functionalization by hydrosilylation reaction2006

    • Author(s)
      T.Kugita
    • Journal Title

      Chemistry Letter 2006

      Pages: 906-907

    • Description
      「研究成果報告書概要(和文)」より
    • Peer Reviewed
  • [Journal Article] Catalytic Activity of Zeolites for Synthesis Reaction of Methylenediamine from Aniline and Formaldehyde2006

    • Author(s)
      T. Kugita S. Hirose, S. Namba
    • Journal Title

      Catalysis Today 111

      Pages: 275-279

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Introduction of Si-H bond onto the surface of meso-porous molecular sieves and functionalization by hydrosilylation reaction2006

    • Author(s)
      T. Kugita, H. Higuchi
    • Journal Title

      Chemistry Letter 2006

      Pages: 906-907

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Selective Synthesis of Bisphenol F Catalyzed by Microporous H-beta Zeolite2005

    • Author(s)
      S.K.Jana
    • Journal Title

      Appllied Catalysis A:General 288

      Pages: 80-85

    • Description
      「研究成果報告書概要(和文)」より
    • Peer Reviewed
  • [Journal Article] Selective Synthesis of Bisphenol F Catalyzed by Microporous H-beta Zeolite2005

    • Author(s)
      S.K. Jana, T. Okamoto, T. Kugita, S. Namba
    • Journal Title

      Applied Catalysis A : General 288

      Pages: 80-85

    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] アルキル基導入によるMCM-41細孔内の疎水性制御2008

    • Author(s)
      釘田 強志
    • Organizer
      第8回GSCNシンポジウム
    • Place of Presentation
      東京
    • Year and Date
      2008-03-06
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Control of hydrophobicity of MCM-41 pores by introducing alkyl groups2008

    • Author(s)
      K. Maruyama, et. al.
    • Organizer
      The 8th GSCN Symp.
    • Place of Presentation
      Tokyo, Japan
    • Year and Date
      2008-03-06
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] ヒドロシリル化によるMCM-41細孔内の疎水化2007

    • Author(s)
      釘田 強志
    • Organizer
      第37回石油・石油化学討論会
    • Place of Presentation
      札幌
    • Year and Date
      2007-10-25
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Hydrophobicitiiation of MCM-41 pores by hydrosilylation2007

    • Author(s)
      T. Kugita, et. al.
    • Organizer
      The 37th Petroleurnpetrochemical Symp.
    • Place of Presentation
      Sapporo, Japan
    • Year and Date
      2007-10-25
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] Functionalization of Mesoporous Molecular Sieves by Hydrosilylation Reaction2007

    • Author(s)
      T.Kugita
    • Organizer
      EUROPACAT VIII
    • Place of Presentation
      Turku,Finland
    • Year and Date
      2007-08-28
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Functionalization of mesoporous molecular sieves by hydrosilylation reaction2007

    • Author(s)
      T. Kugita, et. al.
    • Organizer
      EUROPACAT VIII
    • Place of Presentation
      Turku, Finland
    • Year and Date
      2007-08-28
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] ヒドロシリル化反応を用いたMCM-41の有機修飾2007

    • Author(s)
      飯島 樹一
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      大阪
    • Year and Date
      2007-03-25
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Organomodification of MCM-41 by hydrosilylation2007

    • Author(s)
      J. lijima, et. al.
    • Organizer
      The 87th Spring meeting, CSJ
    • Place of Presentation
      Osaka, Japan
    • Year and Date
      2007-03-25
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] 各種無機酸、有機酸を用いたβゼオライトの脱アルミニウム2006

    • Author(s)
      肥後 康将
    • Organizer
      第36回石油・石油化学討論会
    • Place of Presentation
      鹿児島
    • Year and Date
      2006-12-01
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Dealumination of β-zeolite with various inorganic and organic acids2006

    • Author(s)
      Y. Higo, et. al.
    • Organizer
      The 36th Petroleum petrochemical Symp.
    • Place of Presentation
      Kagosima, Japan
    • Year and Date
      2006-12-01
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] ヒドロシリル化反応で有機修飾したMCM-41の水熱安定性と触媒活性2006

    • Author(s)
      観音寺 功三
    • Organizer
      第98回触媒討論会
    • Place of Presentation
      富山
    • Year and Date
      2006-09-28
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Hydrothermal stability and catalytic activity of organomodified MCM-41 by hydrosilylation2006

    • Author(s)
      K. Kannonji, et. al.
    • Organizer
      The 98th CSJ Meeting
    • Place of Presentation
      Toyama, Janan
    • Year and Date
      2006-09-28
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] Functionaliztion of MCM-41 by Hydrosilylation Reaction2006

    • Author(s)
      K.Kannonji
    • Organizer
      The 5th International Mesostructured Material Symposium
    • Place of Presentation
      Shanghai,China
    • Year and Date
      2006-08-05
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Functionaliztion of MCM-41 by hydrosilylation reaction2006

    • Author(s)
      K. Kannonji, et. al.
    • Organizer
      The 5th International Mesostructured Material Symposium
    • Place of Presentation
      Shanghai, China
    • Year and Date
      2006-08-05
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] Methylenedianiline Synthesis over Al Incorporated MCM-41 Catalys2006

    • Author(s)
      T.Kugita
    • Organizer
      International Symposium on Zeolites and Microporous Crystals 2006
    • Place of Presentation
      米子
    • Year and Date
      2006-08-01
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Methylenedianiline synthesis over Al incorporated MCM-41 catalyst2006

    • Author(s)
      T. Kugita, et. al.
    • Organizer
      International Symposium on Zeolites and Microporous Crystals 2006
    • Place of Presentation
      Yonago, Japan
    • Year and Date
      2006-08-01
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] ハイドロシリレーションにより有機修飾したMCM-41への酸点の導入2006

    • Author(s)
      観音寺 功三
    • Organizer
      日本化学会第86春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2006-03-29
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Introduction of acid sites onto MCM-41 organomodified by hydrosilylation2006

    • Author(s)
      K. Kannonji, et. al.
    • Organizer
      The 86th Spring meeting, CSJ
    • Place of Presentation
      Chiba, Japan
    • Year and Date
      2006-03-29
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] Synthesis of Methylene dianiline over zeolite and modified mesoporous aluminosilicate2005

    • Author(s)
      T.Kugita
    • Organizer
      Inter.Chemical Congress of Pacific Basin Society
    • Place of Presentation
      Honolulu,Hawaii,USA
    • Year and Date
      2005-12-19
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] 塩酸処理によるβゼオライトの脱アルミニウムと脱アルミニウムによる吸着特性の変化2005

    • Author(s)
      肥後 康将
    • Organizer
      第35回石油・石油化学討論会
    • Place of Presentation
      盛岡
    • Year and Date
      2005-10-28
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] 有機助剤添加によるMCM-41細孔径の精密制御2005

    • Author(s)
      宇野 裕紀
    • Organizer
      第35回石油・石油化学討論会
    • Place of Presentation
      盛岡
    • Year and Date
      2005-10-28
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Dealumination of β-zeolite with hydrochloric acid and change in adsorption properties by dealumination2005

    • Author(s)
      Y. Higo, et. al.
    • Organizer
      The 35th Petroleum petrochemicalSymp.
    • Place of Presentation
      Morioka, Japan
    • Year and Date
      2005-10-28
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] Fine control of pore size of MCM-41 by using organic auxiliary chemicals2005

    • Author(s)
      Y. Uno, et. al.
    • Organizer
      The 35th Petroleum petrochemical Symp.
    • Place of Presentation
      Morioka, Japan
    • Year and Date
      2005-10-28
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] Synthesis of methylenedianiline over zeolite and modified mesoporous aluminosilicate2005

    • Author(s)
      T. Kugita, et. al.
    • Organizer
      International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2005-10-19
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] Catalytic Activity of Mesoporous and Micropourous Aluminosilicate Molecular Sieves for the Synthesis of Diphenylmethane Derivatives2005

    • Author(s)
      T.Kugita
    • Organizer
      Internal Symposium on Acid-Base Catalysis IV
    • Place of Presentation
      Puerto Vallarta,Mexico
    • Year and Date
      2005-06-29
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Catalytic activity of mesoporous and micropourous aluminosilicate molecular sieves for the synthesis of diphenylmethane derivatives2005

    • Author(s)
      T. Kugita, et. al.
    • Organizer
      Internal Symposium on Acid-Base Catalysis IV
    • Place of Presentation
      Puerto Vallarta, Mexico
    • Year and Date
      2005-06-29
    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2010-02-04  

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