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One-pot synthesis of lactic acid from biomass-derived carbohydrates over water-tolerant solid catalyst

Research Project

Project/Area Number 15H05556
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Catalyst/Resource chemical process
Research InstitutionHokkaido University

Principal Investigator

Kiyotaka Nakajima  北海道大学, 触媒科学研究所, 准教授 (90451997)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥24,180,000 (Direct Cost: ¥18,600,000、Indirect Cost: ¥5,580,000)
Fiscal Year 2017: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥13,780,000 (Direct Cost: ¥10,600,000、Indirect Cost: ¥3,180,000)
Keywords固体触媒 / バイオマス変換 / ルイス酸塩基 / 酸塩基触媒 / グリーンケミストリー / 固体酸塩基触媒 / 乳酸 / 環境調和型プロセス / グリーン科学 / 酸塩基反応 / バイオマス / 固体酸塩基 / グリーン化学
Outline of Final Research Achievements

Chemocatalytic conversion of biomass-derived carbohydrates including glycerol and glucose to lactic acid was studied using a stable and highly active solid catalysts. We found that metallic Pt sites and Lewis acid sites on TiO2-supported Pt nanoparticles are active for aerobic oxidation of glycerol to triose sugars and subsequent transformation of these C3 sugars to lactic acid, respectively. A combination Lewis acid and base sites on niobium-containing mixed oxides is effective for step-wise conversion of glucose to lactic acid that contains isomerization (glucose to fructose), retro-aldol condensation (fructose to triose sugars), and dehydration/isomerization (triose sugars to lactic acid) in water.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • Research Products

    (40 results)

All 2018 2017 2016 2015

All Journal Article (14 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 14 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (26 results) (of which Int'l Joint Research: 13 results,  Invited: 11 results)

  • [Journal Article] Metal-Free and Selective Oxidation of Furfural to Furoic Acid with an N-Heterocyclic Carbene Catalyst2018

    • Author(s)
      Gupta Navneet Kumar、Fukuoka Atsushi、Nakajima Kiyotaka
    • Journal Title

      ACS Sustainable Chemistry & Engineering

      Volume: 6 Issue: 3 Pages: 3434-3442

    • DOI

      10.1021/acssuschemeng.7b03681

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Facile Formation of Lactic Acid from a Triose Sugar in Water over Niobium Oxide with a Deformed Orthorhombic Phase2018

    • Author(s)
      Kiyotaka Nakajima, Jun Hirata, Minjune Kim, Navneet Kumar Gupta, Toru Murayama, Akihiro Yoshida, Norihito Hiyoshi, Atsushi Fukuoka, Wataru Ueda
    • Journal Title

      ACS Catalysis

      Volume: 8 Issue: 1 Pages: 283-290

    • DOI

      10.1021/acscatal.7b03003

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Rare Earth Niobate and Tantalate Powders via a Peroxo Complex Route2017

    • Author(s)
      H. Kato, K. Shimizu, K. Nakajima, M. Kobayashi, M. Kakihana
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 10 Pages: 1515-1517

    • DOI

      10.1246/cl.170652

    • NAID

      130006140011

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Facile Formation of Gold Nanoparticles on Periodic Mesoporous Bipyridine-silica2017

    • Author(s)
      4.Nobuhiro Ishito, Kiyotaka Nakajima, Yoshifumi Maegawa, Shinji Inagaki, Atsushi Fukuoka
    • Journal Title

      Catalysis Today

      Volume: 印刷中 Pages: 258-262

    • DOI

      10.1016/j.cattod.2017.03.012

    • NAID

      120006769930

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hydrothermal synthesis of a layered-type W-Ti-O mixed metal oxide and its solid acid activity2017

    • Author(s)
      Toru Murayama, Kiyotaka Nakajima, Jun Hirata, Kaori Omata, Emiel J. M. Hensen and Wataru Ueda
    • Journal Title

      Catalysis Science & Technology

      Volume: 7 Issue: 1 Pages: 243-250

    • DOI

      10.1039/c6cy02198k

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Amorphous Nb2O5 as a Selective and Reusable Catalyst for Furfural Production from Xylose in Biphasic Water and Toluene2017

    • Author(s)
      Navneet Kumar Gupta, Atsushi Fukuoka, Kiyotaka Nakajima
    • Journal Title

      ACS Catalysis

      Volume: 7 Issue: 4 Pages: 2430-2436

    • DOI

      10.1021/acscatal.6b03682

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Concerted Catalysis in Tight Spaces: Palladium-Catalyzed Allylation Reactions Accelerated by Accumulated Active Sites in Mesoporous Silica2017

    • Author(s)
      本倉 健、池田 まりか、南保 雅之、田 旺帝、中島 清隆、田中 真司
    • Journal Title

      ChemCatChem

      Volume: - Issue: 15 Pages: 2924-2929

    • DOI

      10.1002/cctc.201700439

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Selective Synthesis of Carbon Monoxide via Formates in Reverse Water–Gas Shift Reaction over Alumina-Supported Gold Catalyst2016

    • Author(s)
      Nobuhiro Ishito, Kiyotaka Nakajima, Kenji Hara, Atsushi Fukuoka
    • Journal Title

      Journal of Energy Chemistry

      Volume: 25 Issue: 2 Pages: 306-310

    • DOI

      10.1016/j.jechem.2015.12.005

    • NAID

      120006401441

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A combined catalyst of Pt nanoparticles and TiO2 with water-tolerant Lewis acid sites for one-pot conversion of glycerol to lactic acid2016

    • Author(s)
      Tasuku Komanoya, Ayaka Suzuki, Kiyotaka Nakajima, Masaaki Kitano, Keigo Kamata, Michikazu Hara
    • Journal Title

      ChemCatChem

      Volume: 8 Issue: 6 Pages: 1094-1099

    • DOI

      10.1002/cctc.201501197

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Niobium-doped Titanate Nanotubes as Solid Acid Catalysts2016

    • Author(s)
      Emiko Wada, Masaaki Kitano, Kazuto Yamamoto, Kiyotaka Nakajima, Shigenobu Hayashi, Michikazu Hara
    • Journal Title

      Catalysis Science & Techology

      Volume: 未定 Issue: 13 Pages: 4832-4839

    • DOI

      10.1039/c6cy00044d

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synergistic Catalysis by Lewis Acid and Base Sites on ZrO2 for Meerwein-Ponndorf-Verley (MPV) Reduction2015

    • Author(s)
      Tasuku Komanoya, Kiyotaka Nakajima, Masaaki Kitano, Michikazu Hara
    • Journal Title

      Journal of Physical Chemistry C

      Volume: 119 Issue: 47 Pages: 26540-26546

    • DOI

      10.1021/acs.jpcc.5b08355

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formation of 5-(Hydroxymethyl)furfural by Stepwise Dehydration over TiO2 with Water-Tolerant Lewis Acid Sites2015

    • Author(s)
      Ryouhei Noma, Kiyotaka Nakajima, Keigo Kamata, Masaaki Kitano, Shigenobu Hayashi, Michikazu Hara
    • Journal Title

      Journal of Physical Chemistry C

      Volume: 119 Issue: 30 Pages: 17117-17125

    • DOI

      10.1021/acs.jpcc.5b03290

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Transesterification of Triolein over Hydrophobic Microporous Carbon with SO3H Groups2015

    • Author(s)
      Kiichi Fukuhara, Kiyotaka Nakajima, Masaaki Kitano, Shigenobu Hayashi, Michikazu Hara
    • Journal Title

      ChemCatChem

      Volume: 7 Issue: 23 Pages: 3945-3950

    • DOI

      10.1002/cctc.201500525

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Recent Progress in the Development of Solid Catalysts for Biomass Conversion into High Value-added Chemicals2015

    • Author(s)
      Michikazu Hara, Kiyotaka Nakajima, Keigo Kamata
    • Journal Title

      Science and Technology of Advanced Materials

      Volume: 16 Issue: 3 Pages: 034903-034903

    • DOI

      10.1088/1468-6996/16/3/034903

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Presentation] Reaction mechanism on glucose to HMF transformation in water over phosphate/TiO22017

    • Author(s)
      Kiyotaka Nakajima, Atsushi Fukuoka
    • Organizer
      Asia Pasific Congress on catalysis 7
    • Place of Presentation
      Mumbai, India
    • Year and Date
      2017-01-17
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 固体ルイス酸による糖類からの有用フラン類合成2017

    • Author(s)
      中島清隆
    • Organizer
      先端材料・材料技術部会 高選択性反応分科会 講演会,公益社団法人 新化学技術推進協会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 触媒が先導する新しいバイオプラスチックの世界2017

    • Author(s)
      中島清隆
    • Organizer
      エコマテリアル研究会 講演会(主催:高分子学会),東京大学農学部中島董一郎記念ホール
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Lewis acid-base catalysis for sugar conversion2017

    • Author(s)
      Kiyotaka Nakajima
    • Organizer
      TU/e -ICAT Joint International Symposium on Catalysis for Sustainable Society, Eindhoven University of Technology, Eindhoven, the Netherlands
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Selective synthesis of FDCA from HMF by CeO2-supported Au catalyst2017

    • Author(s)
      Minjune Kim,Kiyotaka Nakajima,Atsushi Fukuoka
    • Organizer
      第120回触媒討論会,愛媛大学(愛媛県)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 2相系反応を利用した酸化ニオブによるフルフラール合成2017

    • Author(s)
      中島清隆,Navneet Kumar Gupta,福岡淳
    • Organizer
      第120回触媒討論会,愛媛大学(愛媛県)
    • Related Report
      2017 Annual Research Report
  • [Presentation] Acid-basic property of YNbO4 for lactic acid formation from glucose in water2017

    • Author(s)
      Minjune Kim, Hideki Kato, Atsushi Fukuoka, Kiyotaka Nakajima
    • Organizer
      13th European Congress on Catalysis, Florence, Italy, August 27-31
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Selective conversion of xylose into furfural using Nb2O5 as a heterogeneous catalyst with water-tolerant Lewis acid sites2017

    • Author(s)
      Navneet Kumar Gupta, Atsushi Fukuoka, Kiyotaka Nakajima
    • Organizer
      13th European Congress on Catalysis, Florence, Italy, August 27-31
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Selective Furfural Formation in Water over Amorphous Nb2O5 with Water-Tolerant Lewis Acid Sites2017

    • Author(s)
      Kiyotaka Nakajima, Navneet Kumar Gupta, Atsushi Fukuoka
    • Organizer
      North American Catalysis Society Meeting 2017, Denver, USA
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Lewis Acid Catalysis of Nb2O5 for Selective Furfural Formation from Xylose in Water2017

    • Author(s)
      Kiyotaka Nakajima, Navneet Kumar Gupta, Atsushi Fukuoka
    • Organizer
      8th International Symposium on Acid-Base Catalysis, Rio de Janeiro, Brazil
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Efficient Xylose Dehydration to Furfural over Lewis Acid Catalysts in Biphasic Water and Toluene2017

    • Author(s)
      Navneet Kumar Gupta, Atsushi Fukuoka, Kiyotaka Nakajima
    • Organizer
      16th Korea-Japan Symposium on catalysis & 3rd International Symposium of Institute for Catalysis, Kaderu 2.7, Sapporo, Japan
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Acid-Base Catalysis of YNbO4 for Sugar Conversion in Water2017

    • Author(s)
      Minjune Kim, Hideki Kato, Atsushi Fukuoka, Kiyotaka Nakajima
    • Organizer
      16th Korea-Japan Symposium on catalysis & 3rd International Symposium of Institute for Catalysis, Kaderu 2.7, Sapporo, Japan
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 固体ルイス酸によるバイオマス由来糖類からの有用フラン類・有機酸の合成2017

    • Author(s)
      中島清隆
    • Organizer
      第41回触媒化学融合研究センター講演会
    • Place of Presentation
      産業技術総合研究所つくばセンター,茨城県つくば市
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] ニオブ系酸化物の水中ルイス酸作用と糖変換への応用2017

    • Author(s)
      中島清隆
    • Organizer
      第10回新機能無機物質探索研究センターシンポジウム
    • Place of Presentation
      東北大学,宮城県仙台市
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 結晶性ニオブ酸によるトリオース水溶液からの乳酸合成2016

    • Author(s)
      中島清隆, 村山徹, 上田渉
    • Organizer
      第46回石油・石油化学討論会
    • Place of Presentation
      京都リサーチパーク,京都府京都市
    • Year and Date
      2016-11-17
    • Related Report
      2016 Annual Research Report
  • [Presentation] YNbO4によるグルコースからのHMF合成2016

    • Author(s)
      中島清隆, 松本慶江子, キムミンジュン, 加藤英樹, 福岡淳
    • Organizer
      第118回触媒討論会
    • Place of Presentation
      岩手大学,岩手県盛岡市
    • Year and Date
      2016-09-21
    • Related Report
      2016 Annual Research Report
  • [Presentation] Basic property of YNbO4 in water2016

    • Author(s)
      Kim Minjune, Kiyotaka Nakajima, Hideki Kato, Atsushi Fukuoka
    • Organizer
      第118回触媒討論会
    • Place of Presentation
      岩手大学,岩手県盛岡市
    • Year and Date
      2016-09-21
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthesis of Ru-immobilized periodic mesoporous organosilica and application for selective oxidation of alkanes2016

    • Author(s)
      Nobuhiro Ishito, Hirokazu Kobayashi, Kiyoyaka Nakajima, Yoshifumi Maegawa, Shinji Inagaki, Kenji Hara, Atsushi Fukuoka
    • Organizer
      6th International IUPAC Conference On Green Chemistry ICGC-6
    • Place of Presentation
      Venice, Italy
    • Year and Date
      2016-09-04
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Facile HMF formation from glucose in water over phosphate/TiO2 with water-tolerant Lewis acid catalyst2016

    • Author(s)
      Kiyotaka Nakajima, Ryouhei Noma, Michikazu Hara
    • Organizer
      6th International IUPAC Conference On Green Chemistry ICGC-6
    • Place of Presentation
      Venice, Italy
    • Year and Date
      2016-09-04
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Efficient Production of Furfural from Xylose in Water over Phosphate/TiO22016

    • Author(s)
      Kiyotaka Nakajima, Ryouhei Noma, Michikazu Hara
    • Organizer
      6th International IUPAC Conference On Green Chemistry ICGC-6
    • Place of Presentation
      Venice, Italy
    • Year and Date
      2016-09-04
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Lactic acid formation from 1,3-dihydroxyacetone (DHA) over phosphate/TiO2 with water-tolerant Lewis acid sites2015

    • Author(s)
      Kiyotaka NAKAJIMA, Michikazu HARA
    • Organizer
      The international chemical congress of Pacific basin societies 2015
    • Place of Presentation
      ワイキキ,ハワイ,アメリカ
    • Year and Date
      2015-12-20
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 水中で機能する固体ルイス酸の開発と糖変換反応への応用2015

    • Author(s)
      中島清隆
    • Organizer
      平成27年度触媒学会・触媒工業協会交流サロン
    • Place of Presentation
      化学会館(東京都千代田区)
    • Year and Date
      2015-12-11
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Reaction mechanism on HMF formation from glucose over phosphate/TiO2 catalyst2015

    • Author(s)
      Kiyotaka NAKAJIMA, Michikazu Hara
    • Organizer
      3nd International Congress on Catalysis for Biorefineries
    • Place of Presentation
      リオデジャネイロ,ブラジル
    • Year and Date
      2015-09-30
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 水中で機能する固体ルイス酸の開発と糖変換反応への応用2015

    • Author(s)
      中島清隆
    • Organizer
      第116回触媒討論会
    • Place of Presentation
      三重大学(三重県津市)
    • Year and Date
      2015-09-17
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 配位不飽和チタン種の水中ルイス酸性質と糖変換反応への応用2015

    • Author(s)
      中島清隆
    • Organizer
      触媒学会北海道支部第55回オーロラセミナー
    • Place of Presentation
      ほろしん温泉・ホタル館(北海道沼田町)
    • Year and Date
      2015-07-26
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 固体酸化物の水中ルイス酸性質を利用した糖変換反応2015

    • Author(s)
      中島清隆
    • Organizer
      第361回触媒化学研究センターコロキウム
    • Place of Presentation
      北海道大学(北海道札幌市)
    • Year and Date
      2015-04-08
    • Related Report
      2015 Annual Research Report
    • Invited

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Published: 2015-04-16   Modified: 2019-03-29  

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