Conversion of sugars into important chemical imtermediates over solid Lewis acid catalysts wokable in water

• Project/Area Number: 24760636
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Catalyst/Resource chemical process
• Research Institution: Tokyo Institute of Technology
• Principal Investigator: KIYOTAKA Nakajima 東京工業大学, 応用セラミックス研究所, 助教 (90451997)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Project Status: Completed (Fiscal Year 2014)
• Budget Amount: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000); Fiscal Year 2014: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000); Fiscal Year 2013: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000); Fiscal Year 2012: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
• Keywords: 固体酸塩基 / バイオマス変換 / 固体ルイス酸

Outline of Final Research Achievements

Lewis acid sites on early transition metal oxides and their mixed oxides are found to be active in water. They can convert 1,3-dihydroxyacetone, a triose sugar, into lactic acid through stepwise dehydration and hydride transfer reactions. This finding is one important technology for the development of environmentally benign production of important chemicals from renewable plant-derived carhobydrates after diminising fossil fuel resourses.

Research Products

• [Journal Article] Efficient Mukaiyama aldol reaction in water with TiO4 tetrahedra on a hydrophobic mesoporous silica surface (2014)
  • Author(s): 1.Hiroshi Shintaku, Kiyotaka Nakajima, Masaaki Kitano, Michikazu Hara
  • Journal Title: Chemical Communications Volume: 50 Issue: 88 Pages: 13473-13476
  • DOI: 10.1039/c4cc05711b
  • Peer Reviewed
• [Journal Article] Lewis Acid Catalysis of TiO4 Tetrahedra on Mesoporous Silica in Water (2014)
  • Author(s): H. Shintaku, K. Nakajima, M. Kitano, N. Ichikuni, M. Hara
  • Journal Title: ACS Catal. Volume: 4 Issue: 4 Pages: 1198-1204
  • DOI: 10.1021/cs401149n
  • Peer Reviewed
• [Journal Article] Slow reactant-water exchange and high catalytic performance of water-tolerant Lewis acids (2014)
  • Author(s): Yusuke Koito, Kiyotaka Nakajima, Hisayoshi Kobayashi, Ryota Hasegawa, Michikazu Hara
  • Journal Title: Chemistry-A European Journal Volume: (accepted)(印刷中) Issue: 26 Pages: 8068-8075
  • DOI: 10.1002/chem.201400240
  • Peer Reviewed
• [Journal Article] Lewis acid properties of some metal salts for lactic acid fbrmation in water : ^<31>PNMR spectroscopy with trimethylphosphine oxide as a molecular probe (2014)
  • Author(s): Yusuke Koito, Kiyotaka Nakajima, Ryota Hasegawa, Hisayoshi Kobayashi, Michikazu Hara
  • Journal Title: Catalysis Today Volume: 226 Pages: 198-203
  • DOI: 10.1016/j.cattod.2013.10.071
  • Peer Reviewed
• [Journal Article] MoO3/ZrO2 as a stable, reusable, and highly active solid acid catalyst for polyester polyol synthesis (2013)
  • Author(s): Hironobu Oki, Tsuyoshi Morita, Kiyotaka Nakajima, Michikazu Hara
  • Journal Title: Chemistry Letters Volume: 42 Issue: 10 Pages: 1314-1316
  • DOI: 10.1246/cl.130635
  • NAID: 10031201350
  • Peer Reviewed
• [Journal Article] Effect of Preparation Conditions on the Structural and Acid Catalytic Properties of Protonated Titanate Nanotubes (2013)
  • Author(s): E. Wada, M. Kitano, K. Nakajima, M. Hara
  • Journal Title: J. Mater. Chem. A Volume: 1 Issue: 41 Pages: 12768-12774
  • DOI: 10.1039/c3ta13015k
  • Peer Reviewed
• [Journal Article] Titania as an Early Transition Metal Oxide with a High Density of Lewis Acid Sites workable in Water (2013)
  • Author(s): K. Nakajima, R. Noma, M. Kitano, M. Hara
  • Journal Title: J. Phys. Chem. C Volume: 117 Issue: 31 Pages: 16028-16033
  • DOI: 10.1021/jp404523r
  • Peer Reviewed
• [Journal Article] Synthesis and Acid Catalysis of Zeolite-Templated Microporous Carbons with SO3H Groups (2013)
  • Author(s): Kiichi Fukuhara, Kiyotaka Nakajima, Masaaki Kitano, Shigenobu Hayashi, Michikazu Hara
  • Journal Title: Physical Chemistry Chemical Physics Volume: 15 Issue: 23 Pages: 9343-9350
  • DOI: 10.1039/c3cp43853h
  • Peer Reviewed
• [Journal Article] Protonated Titanate Nanotubes with Lewis and Brønsted Acidity : Relationship between Nanotube Structure and Catalytic Activity (2013)
  • Author(s): M. Kitano, E. Wada, K. Nakajima, S. Hayashi, S. Miyazaki, H. Kobayashi, M. Hara
  • Journal Title: Chem. Mater Volume: 25 Issue: 3 Pages: 385-393
  • DOI: 10.1021/cm303324b
  • Peer Reviewed
• [Journal Article] Amorphous Carbon with SO3H Groups as a Strong Brønsted Acid Catalyst (2012)
  • Author(s): Kiyotaka Nakajima, Michikazu Hara
  • Journal Title: ACS Catalysis Volume: 2 Issue: 7 Pages: 1296-1304
  • DOI: 10.1021/cs300103k
  • Peer Reviewed
• [Journal Article] sp3-linked Amorphous Carbon with SO3H Groups as a Heterogeneous Acid Catalyst (2012)
  • Author(s): Satoshi Suganuma, Kiyotaka Nakajima, Masaaki Kitano, Shigenobu Hayashi, Michikazu Hara
  • Journal Title: ChemSusChem Volume: 5 Issue: 9 Pages: 1841-1846
  • DOI: 10.1002/cssc.201200010
  • Peer Reviewed
• [Presentation] 酸化チタンの水中ルイス酸特性とグリセロール水溶液からの乳酸合成への応用 (2015)
  • Author(s): 中島清隆
  • Organizer: 日本化学会第９５回春季年会
  • Place of Presentation: 日本大学船橋キャンパス
  • Year and Date: 2015-03-26 – 2015-03-29
  • Invited
• [Presentation] 酸化チタン触媒による水中でのグルコースからのHMF生成メカニズム (2014)
  • Author(s): 中島清隆，野間遼平，北野政明，原亨和
  • Organizer: 第４４回石油・石油化学討論会
  • Place of Presentation: 北海道，旭川
  • Year and Date: 2014-11-16 – 2014-11-17
• [Presentation] Lactic acid production from a triose sugar over solid Lewis acid catalysts in water (2014)
  • Author(s): Kiyotaka Nakajima
  • Organizer: 第４４回石油・石油化学討論会
  • Place of Presentation: 北海道，旭川
  • Year and Date: 2014-11-16 – 2014-11-17
  • Invited
• [Presentation] 固体ルイス酸による糖類からフラン類・有機酸の環境低負荷合成 (2014)
  • Author(s): 中島清隆
  • Organizer: 触媒学会規則性多孔体研究会，第１７回規則性多孔体セミナー
  • Place of Presentation: 鳥取大学
  • Year and Date: 2014-11-13
  • Invited
• [Presentation] 5-hydroxymethyl furfural production from glucose aqueous solution over Nb2O5 with water-tolerant Lewis acid site (2014)
  • Author(s): Kiyotaka Nakajima, Masaaki Kitano, Michikazu Hara
  • Organizer: 8th International Symposium on Group Five Elements
  • Place of Presentation: Malaga, Spain
  • Year and Date: 2014-06-24 – 2014-06-27
• [Presentation] チタン含有メソポーラスシリカによる水中での向山アルドール反応 (2014)
  • Author(s): 中島清隆，新宅泰，北野政明，原亨和
  • Organizer: 石油学会第６３回研究発表会
  • Place of Presentation: 東京，船堀
  • Year and Date: 2014-05-27 – 2014-05-28
• [Presentation] 固体ルイス酸を用いた水中でのバイオマス変換：植物から化学品原料の環境低負荷合成 (2014)
  • Author(s): 中島清隆
  • Organizer: 触媒学会規則性多孔体研究会主催，第16回「規則性多孔体研究会」セミナー
  • Place of Presentation: 東京大学生産技術研究所
  • Invited
• [Presentation] 固体ルイス酸を用いた糖水溶液内からのフラン類・有機酸合成 (2013)
  • Author(s): 中島清隆
  • Organizer: 第112回触媒討論会
  • Place of Presentation: 秋田大学
  • Invited
• [Presentation] 固体NMRによるカーボン固体強酸の構造解析と機能解明 (2013)
  • Author(s): 中島清隆
  • Organizer: ナノテクノロジープラットホーム技術セミナー「固体NMR」
  • Place of Presentation: 産業技術総合研究所つくばセンター
  • Invited
• [Presentation] メソポーラスチタノシリケートの水中ルイス酸特性 (2013)
  • Author(s): 中島清隆・新宅泰・北野政明・一國伸之・原亨和
  • Organizer: 公益社団法人石油学会 第62回研究発表会
  • Place of Presentation: タワーホール船堀
• [Presentation] カーボン固体酸の高機能化および含水ニオブ酸の水中ルイス酸触媒特性 (2013)
  • Author(s): 中島清隆
  • Organizer: 公益社団法人石油学会 第62回研究発表会
  • Place of Presentation: タワーホール船堀
  • Invited
• [Presentation] タングステン担持ジルコニア触媒の水中ルイス酸特性 (2013)
  • Author(s): 中島清隆・竹田大樹・北野政明・原亨和
  • Organizer: 公益社団法人石油学会 第43回石油・石油化学討論会
  • Place of Presentation: 北九州国際会議場
• [Presentation] Selective Production of Lactic Acid from Triose over Phosphate/TiO2 with Water-Tolerant Lewis Acid sites (2013)
  • Author(s): Kiyotaka Nakajima, Masaaki Kitano, Michikazu Hara
  • Organizer: 11th European Congress on Catalysis
  • Place of Presentation: Lyon, France
• [Presentation] Selective Production of Lactic Acid from Triose over Phosphate/TiO2 with Water-Tolerant Lewis Acid sites (2013)
  • Author(s): Kiyotaka Nakajima, Masaaki Kitano, Michikazu Hara
  • Organizer: 7th International symposium on acid-base catalysis
  • Place of Presentation: Tokyo, Japan
• [Presentation] Selective Production of Lactic Acid from Triose over Phosphate/TiO2 with Water-Tolerant Lewis Acid sites (2012)
  • Author(s): Kiyotaka Nakajima, Masaaki Kitano, Michikazu Hara
  • Organizer: International Congress on Catalysis 2012
  • Place of Presentation: Munich, Germany
• [Presentation] 固体ルイス酸を用いたトリオース水溶液からの乳酸合成 (2012)
  • Author(s): 中島清隆・北野政明・原亨和
  • Organizer: 第１１０回触媒討論会
  • Place of Presentation: 福岡県、九州大学
• [Presentation] スルホン化したミクロポーラスカーボンの酸触媒特性 (2012)
  • Author(s): 中島清隆・福原紀一・北野政明・林繁信・原亨和
  • Organizer: ゼオライト研究発表会
  • Place of Presentation: 東京都、タワーホール船堀
• [Presentation] 酸化チタンの水中ルイス酸特性 (2012)
  • Author(s): 中島清隆・野間遼平・北野政明・原亨和
  • Organizer: 第42回石油・石油化学討論会
  • Place of Presentation: 秋田県、秋田大学
• [Presentation] 固体ルイス酸触媒によるトリオース水溶液からの乳酸合成 (2012)
  • Author(s): 中島清隆・北野政明・原亨和
  • Organizer: 石油学会第60回研究発表会
  • Place of Presentation: 東京都、タワーホール船堀
• [Presentation] 固体ルイス酸による水溶液内での糖類の脱水・異性化反応 (2012)
  • Author(s): 中島清隆
  • Organizer: 2012年 触媒学会北海道支部 札幌講演会
  • Place of Presentation: 北海道、北海道大学
  • Invited