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Preparation of acidity-tuned amido compounds with electron-withdrawing halogen atoms and precious metal extraction

Research Project

Project/Area Number 19K12399
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 64030:Environmental materials and recycle technology-related
Research InstitutionSaga University

Principal Investigator

OHTO Keisuke  佐賀大学, 理工学部, 教授 (70243996)

Project Period (FY) 2019-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2021: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2020: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2019: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords金属リサイクル / アニオン抽出 / 抽出試薬開発 / ハロゲン化アミド化合物 / ハロゲン化2級アミド / 金属アニオン / 抽出選択性 / 弱い相互作用 / NMRスペクトル / レアメタルリサイクル / 溶媒抽出 / 抽出剤開発 / 選択性 / 分子設計 / 資源回収 / 貴金属 / 新規抽出試薬開発 / アミド化合物
Outline of Research at the Start

電子吸引性のハロゲンを有する一連の2級アミド化合物を合成し、貴金属類の抽出挙動を検討する。貴金属の選択的な抽出、ならびに新たな分子設計指針を得るという長期展望を目標とするため、貴金属アニオンと弱い相互作用を示す2級アミドプロトンに着眼し、このプロトンの酸性度(δ+性)を2級アミド化合物に導入するハロゲンの種類、数、およびアミド基からの位置を適正にチューニングし目標を達成する。アミド合成に用いるカルボン酸のpKaの値が合成したアミドの抽出性能に大きく関与することを予想しており、両者の相関を取ることで分子設計指針に活用する。

Outline of Final Research Achievements

Secondary amido compounds have been focused as new type of extraction reagents for metal anions. New secondary amido compounds with electron-withdrawing halogen atoms have been prepared to control delta+ nature of amido hydrogen atom and to investigate whether amido hydrogen atom can contribute to extract anionic species without any participation of protonated carbonyl oxygen atoms. As results of extraction of Ga and Pt in chloride media, the contribution of amido hydrogen atom for anion extraction was confirmed by spectroscopic and extraction studies. The anion extraction was affected with tuned amido compounds by changing a kind and number of halogen atoms. It was also found that distance between two amido hydrogen atoms affected the efficiency of anion extraction.

Academic Significance and Societal Importance of the Research Achievements

金属資源に乏しく先端産業の盛んな日本にとって金属資源確保は重要であり、都市鉱山に関心が高まっているが、微量かつ数多くの金属資源があり、選択的に個々の金属を回収することは困難である。乾式や湿式の多くの技術が利用されているが容易ではない。本研究は湿式技術のうち、溶媒抽出試薬、特にガリウムや貴金属のようなアニオン種の新たな分離試薬として、2級アミドの水素原子に着目した。弱い相互作用を分子設計概念に組み込むことで、従来法では困難であった分離が見直される。また、有害元素の除去など、他のアニオン種への適用を可能であり、都市鉱山の有効活用に利用できる試薬開発となり得るため、社会的意義は大きい。

Report

(4 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Research-status Report
  • 2019 Research-status Report
  • Research Products

    (36 results)

All 2022 2021 2020 2019 Other

All Int'l Joint Research (2 results) Journal Article (13 results) (of which Int'l Joint Research: 7 results,  Peer Reviewed: 12 results,  Open Access: 3 results) Presentation (17 results) (of which Int'l Joint Research: 5 results,  Invited: 4 results) Book (1 results) Remarks (3 results)

  • [Int'l Joint Research] ドレスデン工科大学(ドイツ)

    • Related Report
      2021 Annual Research Report
  • [Int'l Joint Research] ガジャマダ大学/マチュン大学(インドネシア)

    • Related Report
      2021 Annual Research Report
  • [Journal Article] Extraction of Platinum Hexachloride Anion Using Two Amido Hydrogen Atoms of Secondary Diamides with Different Spacer Length2022

    • Author(s)
      Ohto Keisuke、Sato Taisuke、Pang Gehui、Umecky Tatsuya、Morisada Shintaro、Kawakita Hidetaka
    • Journal Title

      Chemistry Letters

      Volume: 51 Issue: 4 Pages: 399-401

    • DOI

      10.1246/cl.210827

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Recent Advances in Guanidinium Salt Based Receptors and Functionalized Materials for the Recognition of Anions2022

    • Author(s)
      Wenzel Marco、Steup Johannes、Ohto Keisuke、Weigand Jan J.
    • Journal Title

      Chemistry Letters

      Volume: 51 Issue: 1 Pages: 20-29

    • DOI

      10.1246/cl.210527

    • NAID

      130008137563

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Allosteric extraction of a second gallium anion assisted by the first, loaded onto a fluorinated secondary amide reagent2021

    • Author(s)
      Pang Gehui、Morisada Shintaro、Kawakita Hidetaka、Hanamoto Takeshi、Umecky Tatsuya、Ohto Keisuke、Song Xi-Ming
    • Journal Title

      Separation and Purification Technology

      Volume: 278 Pages: 119036-119036

    • DOI

      10.1016/j.seppur.2021.119036

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Improved precious metal adsorption by introduction of carboxylic acid groups on methylene crosslinked calix[4]arene resin matrix2021

    • Author(s)
      Priastomo Yoga、Morisada Shintaro、Kawakita Hidetaka、Ohto Keisuke、Jumina Jumina
    • Journal Title

      Journal of Inclusion Phenomena and Macrocyclic Chemistry

      Volume: 101 Issue: 1-2 Pages: 51-61

    • DOI

      10.1007/s10847-021-01079-1

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Effective extraction of Pt(IV) as [PtCl6]2? from hydrochloric acid using a simple urea extractant2021

    • Author(s)
      Ueda Yuki、Morisada Shintaro、Kawakita Hidetaka、Wenzel Marco、Weigand Jan J.、Ohto Keisuke
    • Journal Title

      Separation and Purification Technology

      Volume: 277 Pages: 119456-119456

    • DOI

      10.1016/j.seppur.2021.119456

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Selective Extraction of Platinum(IV) from the Simulated Secondary Resources Using Simple Secondary Amide and Urea Extractants2021

    • Author(s)
      Ueda Yuki、Morisada Shintaro、Kawakita Hidetaka、Ohto Keisuke
    • Journal Title

      Separations

      Volume: 8 Issue: 9 Pages: 139-139

    • DOI

      10.3390/separations8090139

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Comparative Extraction of Aluminum Group Metals Using Acetic Acid Derivatives with Three Different-Sized Frameworks for Coordination2021

    • Author(s)
      Ohto Keisuke、Fuchiwaki Nako、Furugou Hiroaki、Morisada Shintaro、Kawakita Hidetaka、Wenzel Marco、Weigand Jan J.
    • Journal Title

      Separations

      Volume: 8 Issue: 11 Pages: 211-211

    • DOI

      10.3390/separations8110211

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Gold recovery from precious metals in acidic media by using human hair waste as a new pretreatment-free green material2021

    • Author(s)
      Yu Dan、Morisada Shintaro、Kawakita Hidetaka、Sakaguchi Koichi、Osada Satoshi、Ohto Keisuke、Inoue Katsutoshi、Song Xi-Ming、Zhang Guolin、Sathuluri Ramachandra Rao
    • Journal Title

      Journal of Environmental Chemical Engineering

      Volume: 9 Issue: 1 Pages: 104724-104724

    • DOI

      10.1016/j.jece.2020.104724

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Stepwise Recovery of Molybdenum, Vanadium, and Tungsten with Amino-Type “Trident” Molecule by Stripping2021

    • Author(s)
      Ohto Keisuke、Furugou Hiroaki、Morisada Shintaro、Kawakita Hidetaka、Isono Ken-ichi、Inoue Katsutoshi
    • Journal Title

      Solvent Extraction and Ion Exchange

      Volume: 39 Issue: 5-6 Pages: 1-21

    • DOI

      10.1080/07366299.2021.1876370

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Review of adsorbents incorporating calixarene derivatives used for metals recovery and hazardous ions removal: the concept of adsorbent design and classification of adsorbents2021

    • Author(s)
      Ohto Keisuke
    • Journal Title

      Journal of Inclusion Phenomena and Macrocyclic Chemistry

      Volume: 99 Issue: 3-4 Pages: 1-20

    • DOI

      10.1007/s10847-021-01053-x

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Extraction behavior of trivalent rare earth metal ions with diphosphonic acid type extraction reagent2021

    • Author(s)
      Ohto Keisuke、Nakashima Shimpei、Tanaka Yudai、Morisada Shintaro、Kawakita Hidetaka、Oshima Tatsuya
    • Journal Title

      Key Engeering Materials

      Volume: 884 Pages: 133-139

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of macrocyclic polyphenol resin by methylene crosslinked calix[4]arene (MC-[4]H) for the adsorption of palladium and platinum ions2019

    • Author(s)
      Yoga Priastomo, S. Morisada, H. Kawakita, K. Ohto, Jumina
    • Journal Title

      New J. Chem.

      Volume: 43 Issue: 21 Pages: 8015-8023

    • DOI

      10.1039/c9nj00435a

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] カリックスアレーン誘導体による金属イオンの抽出分離挙動に及ぼすさまざまな構造効果に関する研究2019

    • Author(s)
      大渡啓介
    • Journal Title

      日本イオン交換学会誌

      Volume: 30 Pages: 17-28

    • NAID

      130007652503

    • Related Report
      2019 Research-status Report
    • Open Access
  • [Presentation] Preparation of extraction reagents with specific coordination structures for metal separation and advanced research2022

    • Author(s)
      Keisuke Ohto
    • Organizer
      9th Japan-U.S. Bilateral Meeting on Rare Metals
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 2種の2級アミド化合物を用いたガリウムの選択的抽出と抽出機構の解明2021

    • Author(s)
      大渡啓介、Pang, Gehui、森貞真太郎、川喜田 英孝
    • Organizer
      日本分析化学会 第81回分析化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] フッ素非含有・含有の2級アミド抽出試薬を用いたガリウムの抽出挙動2021

    • Author(s)
      大渡啓介、Pang Gehui、森貞真太郎、川喜田英孝
    • Organizer
      化学工学会第 52回秋季大会
    • Related Report
      2021 Annual Research Report
  • [Presentation] アミン型ホウキ分子によるMo,V,及びWの抽出分離挙動2021

    • Author(s)
      古郷宏明、森貞真太郎、川喜田英孝、大渡啓介
    • Organizer
      連合年会2021(第40回溶媒抽出討論会・第35回日本イオン交換研究発表会)
    • Related Report
      2021 Annual Research Report
  • [Presentation] 白金の抽出に及ぼす2級ジアミド化合物のスペーサー長の影響2021

    • Author(s)
      大渡 啓介,佐藤太亮,Pang, Gehui,森貞真太郎,川喜田英孝
    • Organizer
      連合年会2021(第40回溶媒抽出討論会・第35回日本イオン交換研究発表会)
    • Related Report
      2021 Annual Research Report
  • [Presentation] ジホスホン酸型抽出試薬による希土類金属イオンの抽出分離2021

    • Author(s)
      田中雄大、古郷宏明、森貞真太郎、川喜田英孝、大渡啓介
    • Organizer
      連合年会2021(第40回溶媒抽出討論会・第35回日本イオン交換研究発表会)
    • Related Report
      2021 Annual Research Report
  • [Presentation] フッ素を含むおよび含まない2級アミド化合物による塩酸媒体からのガリウムの抽出2021

    • Author(s)
      Pang, Gehui、森貞真太郎、川喜田英孝、大渡啓介
    • Organizer
      連合年会2021(第40回溶媒抽出討論会・第35回日本イオン交換研究発表会)
    • Related Report
      2021 Annual Research Report
  • [Presentation] マイクロリアクターを用いた2級アミド化合物による貴金属抽出2021

    • Author(s)
      野田龍生、本田大貴、佐藤太亮、森貞真太郎、川喜田英孝、大渡啓介、岩崎渉
    • Organizer
      連合年会2021(第40回溶媒抽出討論会・第35回日本イオン交換研究発表会)
    • Related Report
      2021 Annual Research Report
  • [Presentation] Extractive recovery of lithium from seawater with calixarene derivatives by using microreactor system2021

    • Author(s)
      Keisuke Ohto
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2021 (Pacifichem 2021)
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Preparation of Separating Reagents for Metal Recovery and Removal2021

    • Author(s)
      Keisuke Ohto
    • Organizer
      Guest Lecture Series on Sustainable Development Goals at Institut Teknologi Sepuluh Nopember
    • Related Report
      2020 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Rare earth metals extraction with diphosphonic acid reagent2020

    • Author(s)
      Keisuke Ohto
    • Organizer
      6th International Conference on Science and Technology (ICST 2020)
    • Related Report
      2020 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 3種の異なる基体から成る抽出試薬による金属イオンの抽出挙動2020

    • Author(s)
      大渡啓介、渕脇菜子、森貞真太郎、川喜田英孝
    • Organizer
      化学工学会第 52回秋季大会
    • Related Report
      2020 Research-status Report
  • [Presentation] 新規ジホスホン酸系抽出試薬の開発と希土類金属イオンの抽出2020

    • Author(s)
      川喜田英孝、山本真士、森貞真太郎、大渡啓介
    • Organizer
      化学工学会第 52回秋季大会
    • Related Report
      2020 Research-status Report
  • [Presentation] Synthesis of secondary amide compounds and their extraction properties towards Ga(Ⅲ) in hydrochloric acid system2020

    • Author(s)
      PANG Gehui、森貞真太郎、川喜田英孝、大渡啓介
    • Organizer
      化学工学会第 52回秋季大会
    • Related Report
      2020 Research-status Report
  • [Presentation] 3種の骨格の異なるカルボン酸誘導体による金属の抽出挙動2020

    • Author(s)
      大渡啓介、渕脇菜子、森貞真太郎、川喜田英孝
    • Organizer
      第39回溶媒抽出討論会
    • Related Report
      2020 Research-status Report
  • [Presentation] Advanced technique of base metals recovery with amide extractants2020

    • Author(s)
      Gehui Pang, Taisuke Sato, Yuki Ueda, Shintaro Morisada, Hidetaka Kawakita, Keisuke Ohto
    • Organizer
      The 10th Saga University - Liaoning University Joint Seminar, -New Trends in Chemistry and Materials Science-
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] レアメタル資源とこれまでの分離回収技術2020

    • Author(s)
      大渡啓介
    • Organizer
      北九州化学工学懇話会(KACE)第66回講演会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Book] Advances in Microfluidic Technologies for Energy and Environmental Applications2020

    • Author(s)
      Y. S. Kurniawan, R. R. Sathuluri, K. Ohto
    • Total Pages
      168
    • Publisher
      IntechOpen
    • ISBN
      9781789844191
    • Related Report
      2020 Research-status Report
  • [Remarks] 佐賀大学化学工学研究室

    • URL

      http://chemeng.chem.saga-u.ac.jp/index.html

    • Related Report
      2021 Annual Research Report
  • [Remarks]

    • Related Report
      2019 Research-status Report
  • [Remarks]

    • URL

      http://www.mirai-kougaku.jp/eco/pages/150115.php

    • Related Report
      2019 Research-status Report

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Published: 2019-04-18   Modified: 2023-01-30  

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