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2012 Fiscal Year Final Research Report

Multiphase Reaction Medium Including Dense Phase Carbon Dioxide and Water for Rate Acceleration and Selectivity Control of Synthetic Organic Reactions

Research Project

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Project/Area Number 22360327
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Reaction engineering/Process system
Research InstitutionHokkaido University

Principal Investigator

ARAI Masahiko  北海道大学, 大学院・工学研究院, 教授 (60125490)

Co-Investigator(Kenkyū-buntansha) FUJITA Shinichiro  北海道大学, 大学院・工学研究院, 講師 (80156869)
SENBOKU Hisanori  北海道大学, 大学院・工学研究院, 准教授 (50241360)
Project Period (FY) 2010 – 2012
Keywords二酸化炭素 / 膨張液相 / 水 / 多相系反応場
Research Abstract

Multiphase reaction media including dense phase carbon dioxide and/or water have been applied for hydrogenation reactions, photocatalytic reactions, and so on. The practical usefulness of those reactions was examined and the physical and chemical functions of carbon dioxide and water were investigated. The reactions studied include selective hydrogenation of nitriles to primary amines, hydrogenation of phenol, photocatalytic water splitting, and others. In situ high pressure Fourier transform infrared spectroscopy was used to examine the interactions between carbon dioxide and organic substrates and those between supported catalytic metal particles and reacting species (carbon monoxide formed from carbon dioxide and hydrogen, organic substrates, water). There were observed acceleration of reaction rate, modification of product selectivity, and/or suppression of catalyst deactivation for those reactions in the multiphase media. The chemical functions of carbon dioxide and water d pended on the chemical reactions examined.

  • Research Products

    (32 results)

All 2013 2012 2011 2010 Other

All Journal Article (13 results) (of which Peer Reviewed: 13 results) Presentation (16 results) Book (3 results)

  • [Journal Article] A multiphase reaction medium including pressurized carbon dioxide and water for selective hydrogenation of benzonitrile with a Pd/Al2O3 catalyst2013

    • Author(s)
      H. Yoshida, Y. Wang, S. Narisawa, S. Fujita, R. Liu, M. Arai
    • Journal Title

      Appl. Catal. A Gen.

      Volume: 456 Pages: 215-222

    • Peer Reviewed
  • [Journal Article] Selective photoreduction of CO_2 to CO in CO_2-dissolved expanded liquid phase with heterogeneous CO_2-philic Pd complex catalysts2013

    • Author(s)
      R. Liu, H. Yoshida, S. Fujita, N. Lu, W.-H.Tu, M. Arai
    • Journal Title

      Appl. Catal. A Gen

      Volume: 455 Pages: 32-38

    • DOI

      DOI:10.1016/j.apcata.2013.01.018

    • Peer Reviewed
  • [Journal Article] The dispersion of TiO_2 modified by the accumulation of CO_2 molecules in water: An effective medium for photocatalytic H_2 production2012

    • Author(s)
      R. Liu, H. Yoshida, S. Narisawa, S. Fujita, M.Arai
    • Journal Title

      RSC Adv

      Volume: 2 Pages: 8002-8006

    • DOI

      DOI:10.1039/C2RA21102E

    • Peer Reviewed
  • [Journal Article] In situ FTIR study on the formation and adsorption of CO on alumina-supported noble metal catalysts from H_2 and CO_2 in the presence of water vapor at high pressures2012

    • Author(s)
      H. Yoshida, S. Narisawa, S. Fujita, R. Liu, M.Arai
    • Journal Title

      Phys. Chem. Chem. Phys

      Volume: 14 Pages: 4724-4733

    • DOI

      DOI:10.1039/C2CP23590K

    • Peer Reviewed
  • [Journal Article] Some mechanistic studies on electrochemical carboxylation of flavones to yield flavanone-2-carboxylic acids2012

    • Author(s)
      H. Senboku, Y. Yamauchi, N. Kobayashi, A.Fukui, S. Hara
    • Journal Title

      Electrochimica Acta

      Volume: 82 Pages: 450-456

    • DOI

      DOI:10.1016/j.electacta.2012.03.131

    • Peer Reviewed
  • [Journal Article] An effective medium of H_2O and low-pressure CO_2 for the selectivehydrogenation of aromatic nitro compounds to anilines2011

    • Author(s)
      X. Meng, H. Cheng, S. Fujita, Y. Yu, F. Zhao, M. Arai
    • Journal Title

      Green Chem

      Volume: 13 Pages: 570-752

    • DOI

      DOI:10.1039/c0gc00246a

    • Peer Reviewed
  • [Journal Article] Hydrogenation of nitrostyrene with aPt/TiO_2 catalyst in CO_2 - dissolved expanded polar and non-polar organic liquids: Their macroscopic and microscopic features2011

    • Author(s)
      H. Yoshida, K. Kato, X. Meng, S. Narisawa, S. Fujita, J. Wang, Z. Wu, F. Zhao, M. Arai
    • Journal Title

      J. Phys. Chem. C

      Volume: 115 Pages: 2257-2267

    • DOI

      DOI:10.1021/jp1105339

    • Peer Reviewed
  • [Journal Article] Electrochemical carboxy- lation of flavones: facile synthesis of flavanone-2-carboxylic acids2011

    • Author(s)
      H. Senboku, Y. Yamauchi, N. Kobayashi, A.Fukui, S. Hara
    • Journal Title

      Electro-chemistry

      Volume: 79 Pages: 862-864

    • DOI

      DOI:10.5796/electrochemistry.79.862

    • Peer Reviewed
  • [Journal Article] Facile synthesis of 2,3-dihydrobenzo- furan-3-ylacetic acids by novel electro- chemical sequential aryl radical cyclization- carboxylation of 2-allyloxybromobenzenes using methyl 4-tert-butylbenzoate as an electron-transfer mediator2011

    • Author(s)
      H. Senboku, J. Michinishi, S. Hara
    • Journal Title

      Synlett

      Pages: 1567-1572

    • DOI

      DOI:10.1055/s-0030-1260794

    • Peer Reviewed
  • [Journal Article] Selective hydrogenation of chloro- nitrobenzene to chloroaniline in supercritical carbon dioxide over Ni/TiO2: Significance of molecular interactions2010

    • Author(s)
      X. Meng, H. Cheng, S. Fujita, Y. Hao, Y.Shang, Y. Yu, S. Cai, F. Zhao, M. Arai
    • Journal Title

      J. Catal

      Volume: 269 Pages: 131-139

    • DOI

      DOI:10.1016/j.jcat.2009.10.024

    • Peer Reviewed
  • [Journal Article] Physically and chemically mixed TiO_2-supported Pd and Au catalysts: unexpected synergistic effects on selectivehydrogenation of citral in supercritical CO_22010

    • Author(s)
      R. Liu, Y. Yu, K. Yoshida, G. Li, H. Jiang, M.Zhang, F. Zhao, S. Fujita, M. Arai
    • Journal Title

      J. Catal

      Volume: 269 Pages: 191-200.

    • DOI

      DOI:10.1016/j.jcat.2009.11.007

    • Peer Reviewed
  • [Journal Article] Theoretical study on interaction between CO_2 and carbonyl compounds: Influence of CO_2 on infrared spectroscopy and activity of C=O2010

    • Author(s)
      J. Wang, M. Wang, J. Hao, S. Fujita, M. Arai, Z. Wu, F. Zhao
    • Journal Title

      J. Supercrit. Fluids

      Volume: 54 Pages: 9-15

    • DOI

      DOI:10.1016/j.supflu.2010.03.002

    • Peer Reviewed
  • [Journal Article] Hydrogenation of phenol with supported Rh catalysts in the presence of compressed CO_2: Its effects on reaction rate, product selectivity and catalyst life2010

    • Author(s)
      S. Fujita, T. Yamada, Y. Akiyama, H. Cheng, F. Zhao, M. Arai
    • Journal Title

      J.Supercrit. Fluids

      Volume: 54 Pages: 190-201

    • DOI

      DOI:10.1016/j.supflu.2010.05.008

    • Peer Reviewed
  • [Presentation] 電解カルボキシル化反応を用いるα-アミノ酸誘導体の合成2013

    • Author(s)
      仙北久典,峯村嘉一,米田賢司,原正治
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこくさつキャンパス(草津市)
    • Year and Date
      2013-03-22
  • [Presentation] アルカリ添加合成スメクタイト触媒によるCO_2の化学的固定化-CO_2と2-アミノベンゾニトリルからの2,4(1H,3H)-キナゾリンジオン合成2013

    • Author(s)
      田中雅大,藤田進一郎,荒井正彦
    • Organizer
      第22回化学工学・粉体工学研究発表会
    • Place of Presentation
      函館市産官学交流プラザ(函館市)
    • Year and Date
      2013-02-01
  • [Presentation] Electrochemical Fixation of Carbon Dioxide to Benzyl Carbonates: Synthesis of Phenylacetic Acids and2-Phenylpropanoic Acids2012

    • Author(s)
      H. Senboku
    • Organizer
      17th MalaysianChemical Congress
    • Place of Presentation
      Putra World Trade Centre (KualaLumpur, Malaysia)
    • Year and Date
      2012-10-16
  • [Presentation] Effects of water in liquid-phase hydrogenation of benzonitrile in dense phaseCO_2 over Pd/Al_2O_3 catalyst2012

    • Author(s)
      H. Yoshida, Y. Wang, S. Fujita, M. Arai
    • Organizer
      15thInternational Congress on Catalysis
    • Place of Presentation
      International Congress Centre(Munich, German)
    • Year and Date
      2012-07-04
  • [Presentation] An effective medium of CO_2 and surfactant for H_2 production by photocatalytic splitting of H_2O over TiO_22012

    • Author(s)
      R. Liu, S. Fujita, M. Arai
    • Organizer
      15th International Congress on Catalysis
    • Place of Presentation
      InternationalCongress Centre (Munich, German)
    • Year and Date
      2012-07-03
  • [Presentation] In situ FTIR study on the formation and adsorption of CO on alumina-supported noble metal catalysts from H2 and CO2 in the presence of water vapor at high pressures2012

    • Author(s)
      H. Yoshida, S. Narisawa, R. Liu, S. Fujita, M.Arai
    • Organizer
      5th GCOE international Symposium
    • Place of Presentation
      Hokkaido University (Sapporo, Japan)
    • Year and Date
      2012-02-21
  • [Presentation] Electrochemical reduction of benzyl carbonates in the presence and absence of carbon dioxide: Synthesis of phenylacetic acids and 2-phenylpropanoic acids2011

    • Author(s)
      H. Senboku, M. Ohkoshi, J. Michinishi, K.Yoneda, S. Hara
    • Organizer
      10th International Symposium on Organic Reaction 2011 (ISOR 10)
    • Place of Presentation
      Keio University(横浜)
    • Year and Date
      2011-11-22
  • [Presentation] Selective hydrogenation of benzonitrile in dense phase CO_2 and water system2011

    • Author(s)
      Y. Wang, H. Yoshida, S. Narisawa , S. Fujita, M. Arai
    • Organizer
      6th Asia Pacific Chemical Engineering Symposium
    • Place of Presentation
      Jiuhua Resort & Convention Centre (Beijing, China)
    • Year and Date
      2011-09-21
  • [Presentation] Hydrogenation of nitrostyrene with a Pt/TiO_2 catalyst in CO_2 - dissolved expanded polar and non-polar organic liquids: Their macroscopic and microscopic features2011

    • Author(s)
      H. Yoshida, K. Kato, X. Meng, S. Narisawa,S. Fujita, J. Wang, Z. Wu, F. Zhao, M. Arai
    • Organizer
      6th Asia Pacific Chemical Engineering Symposium
    • Place of Presentation
      Jiuhua Resort & Convention Centre (Beijing, China)
    • Year and Date
      2011-09-20
  • [Presentation] SelectiveHydrogenation of Citral with Ru/TPPTS Complexes in scCO_2/H_2O2011

    • Author(s)
      R. Liu, S. Fujita, F. Zhao, M. Arai
    • Organizer
      6th Asia Pacific Chemical Engineering Symposium
    • Place of Presentation
      Jiuhua Resort & Convention Centre (Beijing, China)
    • Year and Date
      2011-09-20
  • [Presentation] Electrochemical Carboxylation of Flavones2011

    • Author(s)
      H. Senboku, Y. Yamauchi, N. Kobayashi, S.Hara
    • Organizer
      62nd Annual Meeting of the International Society of Electrochemistry
    • Place of Presentation
      Toki Messe (新潟市)
    • Year and Date
      2011-09-12
  • [Presentation] Synthesis of Fluorinated Analogues of Non-steroidal Anti- inflammatory Agents by Electrochemical Fixation of Carbon Dioxide2011

    • Author(s)
      H. Senboku
    • Organizer
      14th Asia Chemical Congress
    • Place of Presentation
      Queen Srikit National Convention Center (Bangkok, Thailand)
    • Year and Date
      2011-09-06
  • [Presentation] Effects of CO_2 pressurization on liquid phase selective hydrogenation of nitrostyrene with a Pt/TiO_2 catalyst2011

    • Author(s)
      H. Yoshida, K. Kato, X. Meng, S. Narisawa,S. Fujita, J. Wang, Z. Wu, F. Zhao, M. Arai
    • Organizer
      The 11th International Conference on CO_2 Utilization
    • Place of Presentation
      Universite de Bourgogne(Dijon, France)
    • Year and Date
      2011-06-30
  • [Presentation] Pt/TiO_2触媒を用いたニトロスチレンの液相水素化反応に対するCO_2加圧の影響2011

    • Author(s)
      加藤克昌,成澤里美,芳田嘉志,藤田進一郎,荒井正彦
    • Organizer
      第20回化学工学・粉体工学研究発表会
    • Place of Presentation
      JSTイノベーションプラザ(札幌市)
    • Year and Date
      2011-02-04
  • [Presentation] ニトロベンゼンの液相水素化反応における高圧二酸化炭素の化学的機能と水添加効2010

    • Author(s)
      藤田進一郎,芳田嘉志,孟祥春,荒井正彦
    • Organizer
      第106回触媒討論会
    • Place of Presentation
      ベルクラシック甲府(甲府市)
    • Year and Date
      2010-09-16
  • [Presentation] Influence of dense phase carbon dioxide on the selective hydrogenation of nitrostyrene toaminostyrene over Pt/TiO2 catalysts2010

    • Author(s)
      S. Fujita, K. Asai, X. Meng, M. Arai
    • Organizer
      9th Conference on Supercritical Fluids and Their Applications
    • Place of Presentation
      Hilton Sorrento Palace (Sorrento, Italy)
    • Year and Date
      2010-09-06
  • [Book] 新しい溶媒を用いた有機合成2013

    • Author(s)
      藤田進一郎,芳田嘉志,荒井正彦
    • Total Pages
      56-66
    • Publisher
      S&T
  • [Book] 新しい溶媒を用いた有機合成2013

    • Author(s)
      仙北久典(分担執筆)
    • Total Pages
      130-142
    • Publisher
      S&T
  • [Book] Chemical functions of dense phase CO_2 as accelerator/ modifier in organic synthetic reactions" in S. L. Suib (Ed.)

    • Author(s)
      R. Liu, H. Yoshida, S. Fujita, M. Arai
    • Publisher
      Elsevier, (印刷中)

URL: 

Published: 2014-08-29  

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