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Development of Reaction Field for Converting Directly Polyalcohols to Allyl Compounds

Research Project

Project/Area Number 24656477
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

MASUDA Takao  北海道大学, 工学(系)研究科(研究院), 教授 (20165715)

Co-Investigator(Kenkyū-buntansha) TAGO Teruoki  北海道大学, 大学院工学研究院, 准教授 (20304743)
NAKASAKA Yuta  北海道大学, 大学院工学研究院, 助教 (30629548)
Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords反応工学 / 触媒・化学プロセス / バイオマス / 触媒設計 / 多価アルコール / グリセリン / エチレングリコール / エリスリトール / ギ酸 / 酸化鉄系触媒 / ブタジエン / アリルアルコール / 酸化分解 / 水 / アルカリ
Research Abstract

Main object of this research is to develop a catalytic reaction process to achieve direct allyl compounds synthesis from liner polyalcohols. Potassium supported iron oxide catalysis containing zirconia or alumina showed higher allyl alcohol yield from glycerol compared to the glycerol conversion over the iron oxide catalyst without potassium. In addition, it was clarified that polyalcohol conversion with formic acid, which is hydrogen donor, over the potassium supported iron oxide catalysis increase allyl compounds yield. Moreover, developed catalyst was effective for allyl alcohol formation from crude glycerol generated as a by-product in biodiesel production process.

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • Research Products

    (32 results)

All 2014 2013 2012 Other

All Journal Article (9 results) (of which Peer Reviewed: 8 results) Presentation (17 results) (of which Invited: 2 results) Patent(Industrial Property Rights) (6 results) (of which Overseas: 1 results)

  • [Journal Article] Conversion of Glycerol into Allyl Alcohol over Potassium-Supported Zirconia-Iron Oxide Catalyst2014

    • Author(s)
      A. Konaka, T. Tago, T. Yoshikawa, A. Nakamura, T. Masuda
    • Journal Title

      Appl. Catal. B. Environ.

      Volume: 16 Pages: 267-273

    • NAID

      120005372320

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Production of phenols from lignin-derived Slurry Liquid using Iron Oxide Catalyst2014

    • Author(s)
      T. Yoshikawa, S. Shinohara, T. Yagi, N. Ryumon, Y. Nakasaka, T. Tago, T. Masuda
    • Journal Title

      Appl. Catal. B. Environ.

      Volume: 146 Pages: 289-297

    • DOI

      10.1016/j.apcatb.2013.03.010

    • NAID

      120005372322

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Conversion of Glycerol into Allyl Alcohol over Potassium-Supported Zirconia-Iron Oxide Catalyst2014

    • Author(s)
      Aya Konaka, Teruoki Tago, Takuya Yoshikawa, Ayaka Nakamura, and Takao Masuda
    • Journal Title

      Applied Catalysis B: Environmental

      Volume: 146 Pages: 267-273

    • DOI

      10.1016/j.apcatb.2013.03.007

    • NAID

      120005372320

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Conversion of Biodiesel-Derived Crude Glycerol into Useful Chemicals over a Zirconia-Iron Oxide Catalyst2013

    • Author(s)
      A. Konaka, T. Tago, T. Yoshikawa, H. Shitara, Y. Nakasaka, T. Masuda
    • Journal Title

      Ind. Eng. Chem. Res.

      Volume: 52 Issue: 44 Pages: 15225-15684

    • DOI

      10.1021/ie4006645

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Production of ketones from pyroligneous acid of woody biomass pyrolysis over an iron-oxide catalyst2013

    • Author(s)
      Dieni Mansur, Takuya Yoshikawa, Koyo Norinaga, Jun-ichiro Hayashi, Teruoki Tago, Takao Masuda
    • Journal Title

      Fuel

      Volume: vol.103 Pages: 130-134

    • DOI

      10.1016/j.fuel.2011.04.003

    • NAID

      120005108186

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Production of phenols from lignin via depolymerization and catalytic cracking2013

    • Author(s)
      Takuya Yoshikawa
    • Journal Title

      Fuel Processing Technology

      Volume: Vol. 108 Pages: 69-75

    • DOI

      10.1016/j.fuproc.2012.05.003

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Conversion of ethanol stillage into aliphatc ketones by two-step process of hydrothermal treatment and catalytic reaction2013

    • Author(s)
      Dieni Mansur, Mana Shimokawa, Kiyoshi Oba, Yuta Nakasaka, Teruoki Tago, Takao Masuda
    • Journal Title

      Fuel Processing Technology

      Volume: 108 Pages: 139-145

    • DOI

      10.1016/j.fuproc.2012.05.026

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 酸化鉄系触媒による含水非可食バイオマスの石油関連有用化学物質への転換反応2013

    • Author(s)
      多湖輝興,吉川琢也,中坂佑太,増田隆夫
    • Journal Title

      触媒

      Volume: 55 Pages: 270-275

    • NAID

      10031200227

    • Related Report
      2013 Annual Research Report
  • [Journal Article] “Conversion of Glycerol into Allyl Alcohol over Potassium-Supported Zirconia-Iron Oxide Catalyst”2012

    • Author(s)
      Aya Konaka, Teruoki Tago, Takuya Yoshikawa, Ayaka Nakamura, and Takao Masuda
    • Journal Title

      Applied Catalysis B: Environmental

      Volume: -

    • NAID

      120005372320

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] リグニンから単環芳香族類を合成する触媒反応プロセスの開発2014

    • Author(s)
      篠原悟志・小西亮太・小山啓人・中坂佑太・多湖輝興・増田隆夫
    • Organizer
      化学系学協会北海道支部2014年冬季研究発表会
    • Place of Presentation
      北海道大学(札幌)
    • Related Report
      2013 Annual Research Report
  • [Presentation] アルミナ担持酸化鉄触媒によるグリセリンからのアリルアルコールの選択合成2014

    • Author(s)
      設楽裕史・寺井和宏・中坂佑太・多湖輝興・増田隆夫
    • Organizer
      化学工学会第79年会
    • Place of Presentation
      岐阜大学(岐阜)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Recovery of Petroleum- related Useful Chemicals from Inedible Biomass Wastes Using Iron Oxide Catalyst without any Hydrogen2013

    • Author(s)
      T. Masuda
    • Organizer
      Joint Symposium of PCOSS, Xiamen Univ. and CRC, Hokkaido Univ.
    • Place of Presentation
      Sapporo, Japan
    • Year and Date
      2013-05-09
    • Related Report
      2013 Final Research Report
  • [Presentation] Conversion of Biodiesel-Derived Crude Glycerol into Useful Chemicals over Zirconia-Iron Oxide Catalyst2013

    • Author(s)
      A. Konaka, T. Tago, T. Yoshikawa, A. Nakamura, Y. Nakasaka, T. Masuda
    • Organizer
      3^<rd> North American Symposium on Chemical Reaction Engineering (NASCRE-3)
    • Place of Presentation
      Westin Galleria Hotel, USA
    • Related Report
      2013 Final Research Report
  • [Presentation] 固体酸触媒/水/ブタノール溶媒を反応場とするリグニンの低分子機構2013

    • Author(s)
      篠原悟志,吉川琢也,八木太一,梶谷智史,中坂佑太,多湖輝興,増田隆夫
    • Organizer
      石油学会第62回研究発表会
    • Place of Presentation
      タワーホ-ル船堀(東京)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 酸化鉄触媒を用いた過熱水蒸気雰囲気下でのリグニン可溶化液からの芳香族化合物製造”2013

    • Author(s)
      篠原悟志,吉川琢也,八木太一,梶谷智史,中坂佑太,多湖輝興,増田隆夫
    • Organizer
      第53回オーロラセミナー
    • Place of Presentation
      ホテル神楽坂(旭川)
    • Related Report
      2013 Annual Research Report
  • [Presentation] アルカリ金属担持酸化鉄系触媒を用いたグリセリンからのアリルアルコール選択合成2013

    • Author(s)
      設楽裕史・古仲彩・中坂佑太・多湖輝興・増田隆夫
    • Organizer
      第112回触媒討論会
    • Place of Presentation
      秋田大学(秋田)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 含水バイオマス廃棄物からの化学品生成触媒プロセスに関する研究2013

    • Author(s)
      増田隆夫
    • Organizer
      第112回触媒討論会
    • Place of Presentation
      秋田大学(秋田)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 2段反応プロセスによるリグニンからのフェノール類製造-リグニン低分子化機構の検討-2013

    • Author(s)
      篠原悟志,吉川琢也,八木太一,小山啓人,中坂佑太,多湖輝興,増田隆夫
    • Organizer
      第43回石油・石油化学討論会
    • Place of Presentation
      北九州国際会議場(北九州)
    • Related Report
      2013 Annual Research Report
  • [Presentation] Liginin Conversion to Aromatic Chemicals2013

    • Author(s)
      Takuya Yoshikawa, Taichi Yagi, Satoshi Shinohara, Teruoki Tago and Takao Masuda
    • Organizer
      the 6th Japan-China Workshop on Environmental Catalysis and Eco-Materials
    • Place of Presentation
      愛媛大学(松山)
    • Related Report
      2013 Annual Research Report
  • [Presentation] 酸化鉄系触媒によるグリセリンからのアリルアルコールの選択合成2013

    • Author(s)
      古仲彩,中村文香,吉川琢也,中坂佑太,多湖輝興,増田隆夫
    • Organizer
      化学系学協会北海道支部2013年冬季研究発表会
    • Place of Presentation
      北海道大学(札幌市)
    • Related Report
      2012 Research-status Report
  • [Presentation] “Conversion of Biodiesel-Derived Crude Glycerol into Useful Chemicals over Zirconia-Iron Oxide Catalyst”2013

    • Author(s)
      Aya Konaka, Teruoki Tago, Takuya Yoshikawa, Ayaka Nakamura, Yuta Nakasaka and Takao Masuda
    • Organizer
      3rd North American Symposium on Chemical Reaction Engineering (NASCRE-3),
    • Place of Presentation
      Westin Galleria Hotel(USA)
    • Related Report
      2012 Research-status Report
  • [Presentation] Conversion of Glycerol into Allyl Alcohol over Potassium-Supported Iron Oxide Catalyst2012

    • Author(s)
      A. Konaka, T. Tago, T. Yoshikawa, A. Nakamura, T. Masuda
    • Organizer
      7^<th> International Conference on Environmental (ICEC 2012)
    • Place of Presentation
      Scientific Campus of La Doua, France
    • Related Report
      2013 Final Research Report
  • [Presentation] アルカリ金属担持酸化鉄触媒を用いたグリセリンからの有用化学物質の製造2012

    • Author(s)
      古仲彩,中村文香,吉川琢也,中坂佑太,多湖輝興,増田隆夫
    • Organizer
      第52回オーロラセミナー
    • Place of Presentation
      グランヴィリオホテル(幕別町)
    • Related Report
      2012 Research-status Report
  • [Presentation] Conversion of Glycerol into Allyl Alcohol over Potassium-Supported Iron Oxide Catalyst2012

    • Author(s)
      Aya Konaka, Teruoki Tago, Takuya Yoshikawa, Ayaka Nakamura, Takao Masuda
    • Organizer
      7th International Conference on Environmental (ICEC 2012)
    • Place of Presentation
      Scientific Campus of La Doua(France)
    • Related Report
      2012 Research-status Report
  • [Presentation] グリセリンからのアリルアルコールの選択合成を可能にする酸化鉄触媒の開発2012

    • Author(s)
      古仲彩,中村文香,吉川琢也,中坂佑太,多湖輝興,増田隆夫
    • Organizer
      第110回触媒討論会
    • Place of Presentation
      九州大学(福岡市)
    • Related Report
      2012 Research-status Report
  • [Presentation] Recovery of Petroleum-related Useful Chemicals from Inedible Biomass Wastes Using Iron Oxide Catalysts without any Hydrogen

    • Author(s)
      増田隆夫
    • Organizer
      Joint Symposium of PCOSS, Xiamen Univ. and CRC, Hokkaido Univ.
    • Place of Presentation
      北海道大学(札幌)
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Patent(Industrial Property Rights)] リグニン分解物の製造方法2014

    • Inventor(s)
      増田隆夫、多湖輝興、小山啓人、龍門尚徳、鳥居孝洋、柴田誠之
    • Industrial Property Rights Holder
      増田隆夫、多湖輝興、小山啓人、龍門尚徳、鳥居孝洋、柴田誠之
    • Industrial Property Rights Type
      特許
    • Patent Publication Number
      2014-015439
    • Filing Date
      2014-01-30
    • Related Report
      2013 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] フェノール類の製造方法2014

    • Inventor(s)
      増田隆夫、多湖輝興、小山啓人、龍門尚徳
    • Industrial Property Rights Holder
      増田隆夫、多湖輝興、小山啓人、龍門尚徳
    • Industrial Property Rights Type
      特許
    • Patent Publication Number
      2014-037354
    • Filing Date
      2014-02-27
    • Related Report
      2013 Annual Research Report
  • [Patent(Industrial Property Rights)] 低品位グリセリンからのアリルアルコールとプロピレンの製造方法,及びそのための触媒2012

    • Inventor(s)
      増田隆夫, 多湖輝興
    • Industrial Property Rights Holder
      増田隆夫, 多湖輝興
    • Industrial Property Rights Type
      特許
    • Filing Date
      2012-08-14
    • Related Report
      2013 Final Research Report
  • [Patent(Industrial Property Rights)] リグニン分解物の製造方法2012

    • Inventor(s)
      出光興産㈱ 北海道大学 増田隆夫 多湖輝興 小山啓人 他3名
    • Industrial Property Rights Holder
      出光興産㈱ 北海道大学 増田隆夫 多湖輝興 小山啓人 他3名
    • Industrial Property Rights Type
      特許
    • Filing Date
      2012-07-11
    • Related Report
      2012 Research-status Report
  • [Patent(Industrial Property Rights)] フェノール類の製造方法2012

    • Inventor(s)
      出光興産㈱ 北海道大学 増田隆夫 多湖輝興 小山啓人 龍門尚徳
    • Industrial Property Rights Holder
      出光興産㈱ 北海道大学 増田隆夫 多湖輝興 小山啓人 龍門尚徳
    • Industrial Property Rights Type
      特許
    • Filing Date
      2012-08-10
    • Related Report
      2012 Research-status Report
  • [Patent(Industrial Property Rights)] 低品位グリセリンからのアリルアルコールとプロピレンの製造方法、及びそのための触媒2012

    • Inventor(s)
      北海道大学 増田隆夫 多湖輝興
    • Industrial Property Rights Holder
      北海道大学 増田隆夫 多湖輝興
    • Industrial Property Rights Type
      特許
    • Filing Date
      2012-08-14
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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