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Decomposition of cutting-edge fluorinated materials using superheated water in the presence of metal oxides

Research Project

Project/Area Number 18H03402
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 64020:Environmental load reduction and remediation-related
Research InstitutionKanagawa University

Principal Investigator

Hori Hisao  神奈川大学, 理学部, 教授 (50357951)

Co-Investigator(Kenkyū-buntansha) 永長 久寛  九州大学, 総合理工学研究院, 教授 (90356593)
Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥16,250,000 (Direct Cost: ¥12,500,000、Indirect Cost: ¥3,750,000)
Fiscal Year 2020: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2019: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2018: ¥7,540,000 (Direct Cost: ¥5,800,000、Indirect Cost: ¥1,740,000)
Keywordsフッ素 / 分解 / ポリマー / リサイクル / イオン液体 / フッ素樹脂 / 亜臨界水 / 再資源化 / 有機フッ素化合物 / フッ素ポリマー / 廃棄物処理
Outline of Final Research Achievements

Fluorinated materials are used in many industrial applications owing to their high chemical and thermal stability and other specific characters. In the present work, decompositions of melt-processable fluoropolymers [i.e., poly(vinylidene fluoride)(PVDF), VDF-related copolymers, and ethylene-tetrafluoroethylene copolymer (ETFE)], fluorinated ionic liquids, and other high-valued fluorinated compounds, were investigated by means of superheated water reactions. By use of potassium permanganate, these cutting-edge fluorinated materials were efficiently decomposed to form fluoride ions (i.e., mineralization) at relatively low temperatures (250-300 degrees).

Academic Significance and Societal Importance of the Research Achievements

本研究は熱的、化学的に安定で、高い機能性を持ち、多くの産業で用いられる一方で、廃棄物の分解処理方法、さらにはリサイクル方法が確立していないフッ素材料について、過マンガン酸カリウムを添加した亜臨界水で処理すればフッ化物イオンまで効果的に分解できることを明らかにした。フッ化物イオンまで分解できれば、原料であるフッ化カルシウムに変換できるので、本研究はこれらの材料のリサイクル技術の開発に貢献するものである。

Report

(4 results)
  • 2021 Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • Research Products

    (64 results)

All 2021 2020 2019 2018 Other

All Int'l Joint Research (3 results) Journal Article (11 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 10 results,  Open Access: 1 results) Presentation (47 results) (of which Int'l Joint Research: 11 results,  Invited: 6 results) Book (1 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Int'l Joint Research] Institut Charles Gerhardt, CNRS, ENSCM(フランス)

    • Related Report
      2020 Annual Research Report
  • [Int'l Joint Research] Institut Charles Gerhardt, CNRS(フランス)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] ICGM, Univ Montpellier, CNRS(フランス)

    • Related Report
      2018 Annual Research Report
  • [Journal Article] Decomposition of Fluorinated Ionic Liquids to Fluoride Ions Using Superheated Water: An Efficient Approach for Recovering Fluorine from the Waste of Fluorinated Ionic Liquids2021

    • Author(s)
      Hisao Hori
    • Journal Title

      Electrochemistry

      Volume: 89 Issue: 2 Pages: 75-82

    • DOI

      10.5796/electrochemistry.20-65147

    • NAID

      130007995109

    • ISSN
      1344-3542, 2186-2451
    • Year and Date
      2021-03-05
    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Efficient mineralization of a novel fluorotelomer surfactant, 2H,3H,3H,5H,5H,6H,6H-4-thia-perfluoro(2-methyl)-1-dodecanoic acid, in superheated water induced by a combination of potassium permanganate and dioxygen2021

    • Author(s)
      Hisao Hori, Tomoki Ushio, Takuma Asai, Ryo Honma, Nadim Eid, Bruno Ameduri
    • Journal Title

      Chemical Engineering Journal

      Volume: 405 Pages: 127006-127006

    • DOI

      10.1016/j.cej.2020.127006

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Efficient mineralization of ethylene-tetrafluoroethylene copolymer in superheated water with permanganate2021

    • Author(s)
      Hisao Hori, Jin Hamaura
    • Journal Title

      Polymer Degradation and Stability

      Volume: 190 Pages: 109621-109621

    • DOI

      10.1016/j.polymdegradstab.2021.109621

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 高温高圧水を用いた有機フッ素化合物および有機ケイ素化合物の分解・無害化、再資源化反応の開発2021

    • Author(s)
      堀 久男
    • Journal Title

      水環境学会誌

      Volume: 44A Pages: 213-216

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Complete Mineralization of Fluorinated Ionic Liquids in Subcritical Water in the Presence of Potassium Permanganate2020

    • Author(s)
      Hisao Hori, Satomi Oishi, Ryota Kodama
    • Journal Title

      Industrial & Engineering Chemistry Research

      Volume: 59 Issue: 13 Pages: 5566-5575

    • DOI

      10.1021/acs.iecr.9b06198

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Permanganate-induced efficient mineralization of poly(vinylidene fluoride) and vinylidene-fluoride based copolymers in low-temperature subcritical water2019

    • Author(s)
      Ryo Honma, Hisao Hori, Fernando Reis da Cunha, Naoki Horiike, Lucia Steinbach, Bruno Ameduri
    • Journal Title

      Industrial & Engineering Chemistry Research

      Volume: 58 Issue: 29 Pages: 13030-13040

    • DOI

      10.1021/acs.iecr.9b01921

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Decomposition of environmentally persistent cyclic methylsiloxanes in subcritical water2019

    • Author(s)
      Hisao Hori, Takuya Kakizawa, Natsumi Kuriyama, Aozora Kabuki, Miki Otsuki, Yuichi Horii
    • Journal Title

      Sustainable Chemistry and Pharmacy

      Volume: 13 Pages: 100160-100160

    • DOI

      10.1016/j.scp.2019.100160

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 有機フッ素化合物の分解・再資源化反応の開発2019

    • Author(s)
      堀 久男
    • Journal Title

      化学工業

      Volume: 70 Pages: 15-20

    • Related Report
      2019 Annual Research Report
  • [Journal Article] 環境中で検出される有機ケイ素化合物―残留性の解明状況とこれからの課題2019

    • Author(s)
      堀 久男
    • Journal Title

      化学

      Volume: 74(2) Pages: 70-71

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A degradable fluorinated surfactant for emulsion polymerization of vinylidene fluoride2018

    • Author(s)
      Sanjib Banerjee, Judith Schmidt, Yeshayahu Talmon, Hisao Hori, Takuma Asai, Bruno Ameduri
    • Journal Title

      Chemical Communications

      Volume: 54 Issue: 81 Pages: 11399-11402

    • DOI

      10.1039/c8cc05290e

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Oxidative removal of dibenzothiophene and related sulfur compounds from fuel oils under pressurized oxygen at room temperature with hydrogen peroxide and a phosphorus-free catalyst: sodium decatungstate2018

    • Author(s)
      Hisao Hori, Keisuke Ogi, Yuya Fujita, Yuta Yasuda, Eri Nagashima, Yusuke Matsuki, Kenji Nomiya
    • Journal Title

      Fuel Processing Technology

      Volume: 179 Pages: 175-183

    • DOI

      10.1016/j.fuproc.2018.07.003

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Presentation] 過マンガン酸カリウムと酸素ガスを共存させた亜臨界水を用いた フッ素テロマー化合物の高効率分解・無機化2021

    • Author(s)
      堀 久男、海潮 朋希、浅井 琢磨
    • Organizer
      第55回日本水環境学会年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 電解硫酸の光励起を利用した水中アルカノールアミン類の分解・無機化反応2021

    • Author(s)
      川嶋 怜、梅田紗英、岩村健太郎、堀 久男
    • Organizer
      第55回日本水環境学会年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 過マンガン酸カリウムを添加した亜臨界水を用いた有機フッ素化合物の高効率分解・無機化反応2021

    • Author(s)
      早川 康輝、宇野 秀明、堀 久男
    • Organizer
      第55回日本水環境学会年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] フッ素ポリマーETFEの亜臨界水分解に及ぼすアルカリ試薬の効果2021

    • Author(s)
      濱浦 尋、堀 久男
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] アルカリ試薬を共存させた亜臨界水を用いたフッ素ポリマーPCTFEの高効率分解2021

    • Author(s)
      五十嵐一眞、堀 久男
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 過マンガン酸カリウムと酸素ガスを共存させた亜臨界水を用いた フッ素テロマー界面活性剤の高効率分解・無機化2021

    • Author(s)
      堀 久男
    • Organizer
      日本フッ素化学会第2回産学連携部会
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] アルカリ条件下での亜臨界水反応によるフッ素ポリマーPVDFからのフッ素成分の回収2021

    • Author(s)
      本間 諒、堀 久男
    • Organizer
      第29 回環境化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] フッ素ポリマーPCTFEの亜臨界水分解処理におけるアルカリ試薬の添加効果2021

    • Author(s)
      五十嵐一眞、堀 久男
    • Organizer
      第29 回環境化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 過マンガン酸カリウムを添加した亜臨界水を用いた有機フッ素化合物の高効率酸化分解・無機化反応2021

    • Author(s)
      早川 康輝、堀  久男
    • Organizer
      第29 回環境化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 電解硫酸を用いたCO2吸収用水中アルカノールアミン類の光分解・無機化処理2021

    • Author(s)
      川嶋 怜、梅田 紗英、岩村 健太郎、堀 久男
    • Organizer
      第29 回環境化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 過マンガン酸カリウムと酸素ガスを共存させた亜臨界水を用いたフッ素 テロマー界面活性剤の高効率無機化反応2021

    • Author(s)
      堀 久男,海潮朋希,浅井琢磨
    • Organizer
      第29 回環境化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] アルカリ条件下でのポリフッ化ビニリデンの亜臨界水分解2021

    • Author(s)
      本間 諒、堀 久男
    • Organizer
      第10回 GACI/GSC シンポジウム
    • Related Report
      2020 Annual Research Report
  • [Presentation] ETFEの亜臨界水分解に及ぼす共存ガスおよびアルカリ試薬の効果2021

    • Author(s)
      濱浦 尋、堀 久男
    • Organizer
      第 44 回フッ素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] PVDF複合材料の亜臨界水分解2021

    • Author(s)
      本間 諒、堀 久男、前田大輔、 石井裕規
    • Organizer
      第 44 回フッ素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] パーフルオロポリエーテルの亜臨界水分解2021

    • Author(s)
      五十嵐一眞、堀 久男
    • Organizer
      第 44 回フッ素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 過マンガン酸カリウムと低温の亜臨界水を用いた機能性フッ素ゴムの 完全分解・無機化反応2020

    • Author(s)
      本間 諒、堀 久男
    • Organizer
      第9回JACI/GSCシンポジウム
    • Related Report
      2020 Annual Research Report
  • [Presentation] ポリクロロトリフルオロエチレン(PCTFE)の亜臨界水分解におよぼすアルカリ試薬の効果2020

    • Author(s)
      五十嵐一眞、堀 久男
    • Organizer
      第43回フッ素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] アルカリ条件下でのポリフッ化ビニリデンの亜臨界水分解2020

    • Author(s)
      本間 諒、堀 久男
    • Organizer
      第43回フッ素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 水酸化ナトリウムを添加した亜臨界水を用いたETFEの高効率分解2020

    • Author(s)
      濱浦 尋、堀 久男
    • Organizer
      第43回フッ素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Efficient mineralization of functional fluoropolymers using subcritical water: A step in recover of fluorine element from the fluoropolymer waste2020

    • Author(s)
      Hisao Hori
    • Organizer
      The 1st F-Materials International Symposium (FMS-1)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 過マンガン酸カリウムと亜臨界水を用いたフッ素系イオン液体の完全酸化分解2020

    • Author(s)
      堀 久男,大石玲未,加藤弘樹,児玉龍太
    • Organizer
      第54回日本水環境学会年会(書面開催)
    • Related Report
      2019 Annual Research Report
  • [Presentation] Efficient decomposition of new PVDF-related materials in subcritical water in the presence of hydrogen peroxide2020

    • Author(s)
      Kazuma Igarashi, Hisao Hori, Sanjib Banerjee, Bruno Ameduri
    • Organizer
      日本化学会第100春季年会(書面開催)
    • Related Report
      2019 Annual Research Report
  • [Presentation] Permanganate-induced complete decomposition of fluororubbers in low temperature subcritical water2020

    • Author(s)
      Ryo Honma, Hisao Hori, Naoki Horiike, Fernando Reis da Cunha, Bruno Ameduri
    • Organizer
      日本化学会第100春季年会(書面開催)
    • Related Report
      2019 Annual Research Report
  • [Presentation] Efficient mineralization of fluoropolymers using subcritical water2020

    • Author(s)
      Hisao Hori
    • Organizer
      ACS Spring 2020 National Meeting(プレゼン資料ネット公開)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Permanganate-induced efficient mineralization of fluorinated ionic liquids in subcritical water2019

    • Author(s)
      Satomi Oishi, Hiroki Kato, Ryota Kodama, Hisao Hori
    • Organizer
      International Conference on Fluorine Chemistry 2019
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Permanganate-induced efficient mineralization of poly(vinylide fluoride) in low temperature subcritical water2019

    • Author(s)
      Ryo Honma, Hisao Hori
    • Organizer
      International Conference on Fluorine Chemistry 2019
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 過マンガン酸カリウムと亜臨界水を用いたフッ素系イオン液体の高効率分解・無機化反応2019

    • Author(s)
      大石怜未,加藤弘樹,児玉龍太,堀 久男
    • Organizer
      第28回環境化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 過マンガン酸カリウムと亜臨界水を用いたフッ素ゴムの高効率低温分解・無機化反応2019

    • Author(s)
      本間 諒,堀池直輝,堀 久男
    • Organizer
      第28回環境化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Efficient and selective photochemical recovery of rhenium from aqueous solutions: A greener approach for rhenium metallurgical processing2019

    • Author(s)
      Hisao Hori, Takafumi Otsu
    • Organizer
      23rd Annual Green Chemistry & Engineering Conference and 9th International Conference on Green and Sustainable Chemistry
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Efficient photochemical recovery of rhenium from aqueous mixed metal solutions2019

    • Author(s)
      Hisao Hori, Takafumi Otsu
    • Organizer
      Copper 2019
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Efficient mineralization of PVDF-related fluoropolymers using subcritical water in the presence of potassium permanganate2019

    • Author(s)
      Hisao Hori, Ryo Honma, Naoki Horiike, Lucia Steinbach, Bruno Ameduri
    • Organizer
      19th European Symposium on Fluorine Chemistry
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Efficient mineralization of Poly(VDF-co-MAF) in low-temperature subcritical water in the presence of potassium permanganate2019

    • Author(s)
      Ryo Honma, Hisao Hori, Sanjib Banerjee, Fernando Reis da Cunha, Bruno Ameduri
    • Organizer
      19th European Symposium on Fluorine Chemistry
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 光化学的手法による水中からのレニウム成分の回収:白金との選択分離2019

    • Author(s)
      米里勇紀,堀 久男
    • Organizer
      第9回CSJ化学フェスタ
    • Related Report
      2019 Annual Research Report
  • [Presentation] グラファイト状窒化炭素を光触媒として用いた油中ジベンゾチオフェン類の酸化除去2019

    • Author(s)
      大野裕也,佐野泰三,西村ゆきの,堀 久男
    • Organizer
      第9回CSJ化学フェスタ
    • Related Report
      2019 Annual Research Report
  • [Presentation] Efficient mineralization of fluoropolymers using subcritical water: An essential step in recover of fluorine element from the fluoropolymer waste2019

    • Author(s)
      Hisao Hori
    • Organizer
      Fluoropolymers: Research, Production Problems, New Applications
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 過マンガン酸カリウムと亜臨界水を用いたETFEの完全分解反応2019

    • Author(s)
      濱浦 尋,高橋利明,堀 久男
    • Organizer
      第42回フッ素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 過マンガン酸カリウムと低温の亜臨界水を用いたPoly(VDF-co-MAF)の高効率無機化2019

    • Author(s)
      本間 諒,堀 久男,Sanjib Banerjee, Fernando Reis da Cunha, Bruno Ameduri
    • Organizer
      第42回フッ素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 過マンガン酸カリウムと亜臨界水を用いたフッ素系イオン液体の高効率分解・無機化反応2019

    • Author(s)
      大石怜未,加藤弘樹,児玉龍太,堀 久男
    • Organizer
      第42回フッ素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 亜臨界水を用いた環状揮発性メチルシロキサン類の無機化処理の検討2019

    • Author(s)
      大槻美喜、蕪木青空、堀井勇一、堀 久男
    • Organizer
      第53回日本水環境学会年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Efficient mineralization of poly(vinylidene fluoride) and related copolymers in low-temperature subcritical water in the presence of manganese compound2019

    • Author(s)
      Ryo Honma, Hisao Hori
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 低温の亜臨界水を用いたフッ素ポリマーPVDFおよび関連物質の高効率分解2018

    • Author(s)
      本間 諒、堀 久男
    • Organizer
      第27回環境化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Efficient Mineralization of Poly(vinylidene fluoride) in Low-temperature Subcritical Water in the Presence of Potassium Permanganate2018

    • Author(s)
      Ryo Honma, Hisao Hori
    • Organizer
      Fluoropolymer 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Efficient Mineralization of PVDF-Related Fluoropolymers Using Subcritical Water in the Presence of Hydrogen Peroxide2018

    • Author(s)
      Hisao Hori, Hirotaka Tanaka, Takahiro Tsuge, Ryo Honma, Sanjib Banerjee, Abdellatif Manseri, Bruno Ameduri
    • Organizer
      Fluoropolymer 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] デカタングステートと加圧酸素を用いた実燃料油の室温超深度脱硫システム2018

    • Author(s)
      藤田裕也、野宮健司、堀 久男
    • Organizer
      錯体化学会第68回討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 機能性有機フッ素化合物の分解・再資源化反応の開発2018

    • Author(s)
      堀 久男
    • Organizer
      住友化学講演会「含フッ素化合物の合成・材料・リサイクルに係る最近の動向」
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] マンガン化合物と亜臨界水を用いたVDF関連ポリマーの分解・無機化反応2018

    • Author(s)
      本間 諒,堀 久男
    • Organizer
      第41回フッ素化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 亜臨界水を用いたペルフルオロアルキルスルホニルフルオリドのスルホン酸への一段階変換2018

    • Author(s)
      堀 久男、小野間優奈
    • Organizer
      第41回フッ素化学討論会
    • Related Report
      2018 Annual Research Report
  • [Book] Opportunities for Fluoropolymers: Synthesis, Characterization, Processing, Simulation and Recycling (B. Ameduri, S. Fomin Editors)2020

    • Author(s)
      Hisao Hori, Ryo Honma
    • Total Pages
      359
    • Publisher
      Elsevier
    • ISBN
      9780128219669
    • Related Report
      2020 Annual Research Report
  • [Remarks] 有機フッ素化合物「フッ素テロマー界面活性剤」の高効率な分解・無機化に成功しました

    • URL

      https://www.kanagawa-u.ac.jp/att/21275_00.pdf

    • Related Report
      2020 Annual Research Report
  • [Patent(Industrial Property Rights)] フッ素原子含有ポリマーの分解方法、及びフッ素原子含有ポリマーの分解装置2021

    • Inventor(s)
      堀 久男
    • Industrial Property Rights Holder
      神奈川大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2021-177521
    • Filing Date
      2021
    • Related Report
      2020 Annual Research Report

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Published: 2018-04-23   Modified: 2023-12-25  

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