Refinery of Nitrogen-Containing Biomass over Solid Catalysts

• Project/Area Number: 26709060
• Research Category: Grant-in-Aid for Young Scientists (A)
• Allocation Type: Partial Multi-year Fund
• Research Field: Catalyst/Resource chemical process
• Research Institution: Hokkaido University
• Principal Investigator: KOBAYASHI Hirokazu 北海道大学, 触媒科学研究所, 助教 (30545968)
• Research Collaborator: YOKOYAMA Haruka 北海道大学, 触媒科学研究所
• Project Period (FY): 2014-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥21,970,000 (Direct Cost: ¥16,900,000、Indirect Cost: ¥5,070,000); Fiscal Year 2017: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2016: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2015: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000); Fiscal Year 2014: ¥8,320,000 (Direct Cost: ¥6,400,000、Indirect Cost: ¥1,920,000)
• Keywords: バイオマス変換 / キチン / N-アセチルグルコサミン / 含窒素有機化合物 / 触媒 / バイオマス / 加水分解 / 含窒素有機物 / 含窒素化合物 / N-アセチルグルコサミニトール / グルコサミン / メカノキャタリシス

Outline of Final Research Achievements

Chitin is the most abundant marine biomass, which is contained in crab and shrimp shells. Chitin is a polymer consisting of N-acetylglucosamine (NAG) units, thus characteristically containing nitrogen atoms. This compound is a potential renewable resource for the production of nitrogen-containing chemicals, but the recalcitrance of chitin has strongly limited use of the derivatives such as NAG in industry and daily life.
In this study, co-workers and I found that mechanical force and catalysts synergistically depolymerize chitin to produce NAG in a good yield. In addition, NAG was converted to useful chemicals such as N-acetyl-monoethanolamine and a derivative of standard amino acid, N-acetylglycine.

Research Products

• [Journal Article] Development of Solid Catalyst-Solid Substrate Reactions for Efficient Utilization of Biomass (2018)
  • Author(s): Hirokazu Kobayashi, Atsushi Fukuoka
  • Journal Title: Bull. Chem. Soc. Jpn. Volume: 91 Issue: 1 Pages: 29-43
  • DOI: 10.1246/bcsj.20170263
  • NAID: 130006309044
  • Peer Reviewed / Open Access
• [Journal Article] Hydrolytic hydrogenation of chitin to amino sugar alcohol (2017)
  • Author(s): Hirokazu Kobayashi, Kota Techikawara, Atsushi Fukuoka
  • Journal Title: Green Chem. Volume: 19 Issue: 14 Pages: 3350-3356
  • DOI: 10.1039/c7gc01063j
  • NAID: 120006491446
  • Peer Reviewed
• [Journal Article] Conversion of glycerol to acrolein by mesoporous sulfated zirconia-silica catalyst (2017)
  • Author(s): Hirokazu Kobayashi, Shogo Ito, Kenji Hara, Atsushi Fukuoka
  • Journal Title: Chinese Journal of Catalysis Volume: 38 Issue: 3 Pages: 420-425
  • DOI: 10.1016/s1872-2067(16)62564-0
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] 固体触媒法による木質バイオマスの選択的な分解 (2016)
  • Author(s): 小林広和
  • Journal Title: 触媒 Volume: 58 Pages: 159-162
  • Acknowledgement Compliant
• [Journal Article] Hydrolysis of woody biomass by biomass-derived reusable heterogeneous catalyst (2016)
  • Author(s): Hirokazu Kobayashi, Hiroyuki Kaiki, Abhijit Shrotri, Kota Techikawara, Atsushi Fukuoka
  • Journal Title: Chemical Science Volume: 7 Issue: 1 Pages: 692-696
  • DOI: 10.1039/c5sc03377b
  • NAID: 120005693923
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Catalytic Depolymerization of Chitin with Retention of N-Acetyl Group (2015)
  • Author(s): Mizuho Yabushita, Hirokazu Kobayashi, Kyoichi Kuroki, Shogo Ito, Atsushi Fukuoka
  • Journal Title: ChemSusChem Volume: 8 Issue: 22 Pages: 3760-3763
  • DOI: 10.1002/cssc.201501224
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Dehydration of sorbitol to isosorbide over H-beta zeolites wih high Si/Al ratios (2015)
  • Author(s): Hirokazu Kobayashi, Haruka Yokoyama, Bo Feng, Atsushi Fukuoka
  • Journal Title: Green Chemistry Volume: 未定 Issue: 5 Pages: 2732-2735
  • DOI: 10.1039/c5gc00319a
  • Peer Reviewed / Acknowledgement Compliant
• [Presentation] Development of Solid Catalyst-Solid Substrate Reactions for Efficient Utilization of Biomass (2017)
  • Author(s): Hirokazu Kobayashi
  • Organizer: 日本化学会 第97春季年会
  • Place of Presentation: 慶応大学(神奈川県横浜市)
  • Year and Date: 2017-03-16
  • Invited
• [Presentation] 固体触媒を用いたセルロース・キチンからの有用化学品合成 (2017)
  • Author(s): 小林広和
  • Organizer: 第2回東日本キャタリシスセミナー
  • Invited
• [Presentation] Boron nitride as a new candidate for adsorption and conversion of saccharides (2017)
  • Author(s): Hirokazu Kobayashi, Atsushi Fukuoka
  • Organizer: 13th European Congress on Catalysis
  • Int'l Joint Research
• [Presentation] Hydrolytic hydrogenation of chitin to N-containing polyols (2017)
  • Author(s): Kota Techikawara, Hirokazu Kobayashi, Atsushi Fukuoka
  • Organizer: 13th European Congress on Catalysis
  • Int'l Joint Research
• [Presentation] Three-Step Conversion of Chitin to N-containing Alcohol (2017)
  • Author(s): Kota Techikawara, Hirokazu Kobayashi, Atsushi Fukuoka
  • Organizer: 16th Korea-Japan Symposium on catalysis & 3rd International Symposium of Institute for Catalysis
  • Int'l Joint Research
• [Presentation] キチンからの含窒素糖アルコール合成 (2017)
  • Author(s): 鉄地河原浩太, 小林広和, 福岡淳
  • Organizer: 第120回触媒討論会
• [Presentation] アセチル基を保持したキチンの触媒的解重合 (2016)
  • Author(s): 小林広和, 藪下瑞帆, 黒木杏一, 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
• [Presentation] キチン加水分解水素化による含窒素糖アルコール合成 (2016)
  • Author(s): 鉄地河原浩太, 小林広和, 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
• [Presentation] Depolymerization of chitin by mechanocatalysis (2016)
  • Author(s): Hirokazu Kobayashi, Mizuho Yabushita, Kota Techikawara, Atsushi Fukuoka
  • Organizer: CCESC 2016
  • Place of Presentation: マドリード(スペイン)
  • Year and Date: 2016-09-07
  • Int'l Joint Research
• [Presentation] Catalytic conversion of chitin to monomers with retention of N-acetyl group (2016)
  • Author(s): Hirokazu Kobayashi, Mizuho Yabushita, Kota Techikawara, Atsushi Fukuoka
  • Organizer: 16th International Congress on Catalysis
  • Place of Presentation: 北京市(中国)
  • Year and Date: 2016-07-03
  • Int'l Joint Research
• [Presentation] Hirokazu Kobayashi, Atsushi Fukuoka (2015)
  • Author(s): Catalytic conversion of inedible biomass
  • Organizer: The 45th Petroleum-Petrochemical Symposium of JPI, International Session
  • Place of Presentation: ウインクあいち(愛知県名古屋市)
  • Year and Date: 2015-11-05
  • Int'l Joint Research / Invited
• [Presentation] Catalytic conversion of cellulose to chemicals (2015)
  • Author(s): Hirokazu Kobayashi, Atsushi Fukuoka
  • Organizer: 15th ROC-Japan Joint Symposium on Catalysis
  • Place of Presentation: 高雄市(台灣)
  • Year and Date: 2015-04-20
  • Int'l Joint Research / Invited
• [Presentation] 触媒法による非可食バイオマスの選択的な分解 (2015)
  • Author(s): 小林広和
  • Organizer: 15回北海道エネルギー資源環境研究発表会
  • Place of Presentation: 北海道大学 (北海道札幌市)
  • Year and Date: 2015-01-27
  • Invited
• [Presentation] Biomass conversion into chemicals by heterogeneous catalysts (2014)
  • Author(s): Hirokazu Kobayashi, Atsushi Fukuoka
  • Organizer: EECAT2014
  • Place of Presentation: 天津市 (中国)
  • Year and Date: 2014-10-08 – 2014-10-10
  • Invited
• [Presentation] Adsorption-Controlled Conversion of Sorbitol to 1,4-Sorbitan over Sulfated Zirconia (2014)
  • Author(s): Hirokazu Kobayashi, Mizuho Yabushita, Shogo Ito, Kenji Hara, Atsushi Fukuoka
  • Organizer: 248th ACS National Meeting & Exposition
  • Place of Presentation: San Francisco (USA)
  • Year and Date: 2014-08-10 – 2014-08-14
• [Presentation] Solvolysis of polysaccharide biomass using solid catalysts (2014)
  • Author(s): Hirokazu Kobayashi
  • Organizer: Seminar in National University of Kaohsiung
  • Place of Presentation: 高雄市 (台灣)
  • Year and Date: 2014-07-04
  • Invited
• [Presentation] Depolymerization of polysaccharides over heterogeneous catalysts (2014)
  • Author(s): Hirokazu Kobayashi
  • Organizer: Seminar in Institute of Nuclear Energy Research
  • Place of Presentation: 桃園市 (台灣)
  • Year and Date: 2014-07-03
  • Invited
• [Presentation] Heterogeneous catalysis for conversion of non-food polysaccharide biomass (2014)
  • Author(s): Hirokazu Kobayashi
  • Organizer: Seminar in Taiwan National University
  • Place of Presentation: 台北市 (台灣)
  • Year and Date: 2014-07-01
  • Invited
• [Presentation] Catalytic conversion of sorbitol to sorbitan by means of preferential adsorption (2014)
  • Author(s): Hirokazu Kobayashi, Shogo Ito, Mizuho Yabushita, Atsushi Fukuoka
  • Organizer: TOCAT 7
  • Place of Presentation: 京都テルサ (京都府京都市)
  • Year and Date: 2014-06-01 – 2014-06-06
• [Book] Advances in Catalysis, vol. 60 (2018)
  • Author(s): Abhijit Shrotri, Hirokazu Kobayashi, Atsushi Fukuoka
  • Total Pages: 65
  • Publisher: Elsevier
  • ISBN: 9780128120729
• [Remarks] Researchmap
  • URL: https://researchmap.jp/read0148875
• [Remarks] Researchmap
  • URL: https://researchmap.jp/read0148875/
• [Remarks] Researchmap
  • URL: http://researchmap.jp/read0148875
• [Patent(Industrial Property Rights)] キチンオリゴマー、Ｎ－アセチルグルコサミン及び１－Ｏ－アルキル－Ｎ－アセチルグルコサミンの製造方法 (2016)
  • Inventor(s): 福岡淳, 小林広和
  • Industrial Property Rights Holder: 北海道大学, 昭和電工株式会社
  • Industrial Property Rights Type: 特許
  • Filing Date: 2016-04-28
• [Patent(Industrial Property Rights)] キチンオリゴマー、Ｎ－アセチルグルコサミン及び１－Ｏ－アルキル－Ｎ－アセチルグルコサミンの製造方法 (2016)
  • Inventor(s): 福岡淳, 小林広和, 藤田一郎
  • Industrial Property Rights Holder: 北海道大学, 昭和電工株式会社
  • Industrial Property Rights Type: 特許
  • Filing Date: 2016-04-28
• [Patent(Industrial Property Rights)] 糖アルコールの脱水用固体触媒、およびその触媒を使用する二無水糖アルコールの製造方法 (2014)
  • Inventor(s): 福岡淳、小林広和、馮博、横山春香、陳新
  • Industrial Property Rights Holder: 北海道大学、クラリアント触媒株式会社
  • Industrial Property Rights Type: 特許
  • Filing Date: 2014-07-16