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Development of dealkylation process for smart conversion of heavy oils

Research Project

Project/Area Number 16H04568
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Catalyst/Resource chemical process
Research InstitutionTottori University

Principal Investigator

KATADA Naonobu  鳥取大学, 工学研究科, 教授 (00243379)

Co-Investigator(Kenkyū-buntansha) 辻 悦司  鳥取大学, 工学研究科, 准教授 (80610443)
菅沼 学史  鳥取大学, 工学研究科, 准教授 (90731753)
Project Period (FY) 2016-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥17,680,000 (Direct Cost: ¥13,600,000、Indirect Cost: ¥4,080,000)
Fiscal Year 2020: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Fiscal Year 2019: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Fiscal Year 2018: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Fiscal Year 2017: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2016: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Keywords重質油 / 固体触媒 / シリカモノレイヤー / ゼオライト / 芳香族 / 触媒反応 / 固体酸触媒 / モリブデン / 水素化触媒 / 石油有効利用
Outline of Final Research Achievements

Alumina-supported silica monolayer catalyst with pore diameter > 6 nm (Si surface density of 8 nm-2) dealkylated to remove all the alkyl chains with >C3 length from approximately 100% of alkyl aromatics with two or more rings in practical vacuum gas oil under the optimized conditions. Liquid phase separation of aromatics and aliphatics was enabled, and parameters in the kinetics of separation, which controlled the performance, were clarified. For partial hydrogenation of naphthalene into tetralin, 100% of naphthalene was converted into tetralin with a 99% selectivity on a dispersed molybdenum oxide monolayer catalyst, derived from phosphomolybdic acid). For the decomposition of tetralin, molybdenum-added * BEA zeolite showed a tetralin conversion of 95% and selectivity into LPG / alkylbenzene of 85%.

Academic Significance and Societal Importance of the Research Achievements

[1]重質油中のアルキル多環芳香族を脱アルキル化し,[2]脂肪族と芳香族を分離し,[3]ナフタレンをテトラリンに転換し,[4]有用なベンゼン誘導体に転換することを試みた.[1]では有用成分を損なわないこと,分離の障害となる成分を残さないことが必要で,新規なシリカモノレイヤー触媒によって実現した.[2]では課題が速度にあることと対策を示した.[3],[4]にも新規触媒を見出し,高い効率を実証した.

Report

(6 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • Research Products

    (57 results)

All 2021 2020 2019 2018 2017 2016

All Journal Article (10 results) (of which Peer Reviewed: 8 results,  Open Access: 1 results) Presentation (47 results) (of which Int'l Joint Research: 13 results,  Invited: 13 results)

  • [Journal Article] Selective dealkylation of alkyl polycyclic aromatic hydrocarbons towards innovative upgrading process of practical heavy oil2021

    • Author(s)
      Nakano Fumiya、Goma Tomohide、Suganuma Satoshi、Tsuji Etsushi、Katada Naonobu
    • Journal Title

      Catalysis Science & Technology

      Volume: 11 Issue: 1 Pages: 239-249

    • DOI

      10.1039/d0cy01590c

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Innovation of catalytic technology for upgrading of crude oil in petroleum refinery2020

    • Author(s)
      Suganuma Satoshi、Katada Naonobu
    • Journal Title

      Fuel Processing Technology

      Volume: 208 Pages: 106518-106518

    • DOI

      10.1016/j.fuproc.2020.106518

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Mechanism of tetralin conversion on zeolites for the production of benzene derivatives2020

    • Author(s)
      Nakajima Kazuki、Suganuma Satoshi、Tsuji Etsushi、Katada Naonobu
    • Journal Title

      Reaction Chemistry & Engineering

      Volume: 5 Issue: 7 Pages: 1272-1280

    • DOI

      10.1039/d0re00128g

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Adsorption kinetics in removal of basic nitrogen-containing compounds from practical heavy oils by amorphous silica-alumina2020

    • Author(s)
      Suganuma Satoshi、Arita Kohsuke、Nakano Fumiya、Tsuji Etsushi、Katada Naonobu
    • Journal Title

      Fuel

      Volume: 266 Pages: 117055-117055

    • DOI

      10.1016/j.fuel.2020.117055

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] ゼオライトの酸性質制御を目指して2019

    • Author(s)
      片田直伸
    • Journal Title

      化学工業

      Volume: 70 Pages: 22-26

    • Related Report
      2019 Annual Research Report
  • [Journal Article] Removal of Basic Compounds and Dealkylation of Alkyl Polycyclic Aromatic Hydrocarbons in Vacuum Gas Oil2018

    • Author(s)
      Keisuke Kinugasa, Fumiya Nakano, Satoko Nagano, Satoshi Suganuma, Etsushi Tsuji, Naonobu Katada
    • Journal Title

      Journal of the Japan Petroleum Institute

      Volume: 61 Issue: 5 Pages: 294-301

    • DOI

      10.1627/jpi.61.294

    • NAID

      130007480047

    • ISSN
      1346-8804, 1349-273X
    • Year and Date
      2018-09-01
    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Analysis and Interpretation of Acidic Nature of Aluminosilicates2018

    • Author(s)
      Naonobu Katada
    • Journal Title

      Mol. Catal.

      Volume: in press Pages: 116-126

    • DOI

      10.1016/j.mcat.2017.12.024

    • NAID

      120006894338

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Compensation between activation entropy and enthalpy in reactions of aromatic hydrocarbons catalyzed by solid acids2017

    • Author(s)
      Koshiro Nakamura, Ryo Mizuta, Satoshi Suganuma, Etsushi Tsuji and Naonobu Katada
    • Journal Title

      Catal. Commun.

      Volume: 102 Pages: 103-107

    • DOI

      10.1016/j.catcom.2017.08.033

    • NAID

      120006873125

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 固体酸触媒反応における活性化エンタルピーとエントロピーに関する研究2017

    • Author(s)
      片田直伸, 中村浩史郎, 菅沼学史, 辻悦司
    • Journal Title

      触媒

      Volume: 60 Pages: 21-26

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Dealkylation of Alkyl Polycyclic Aromatic Hydrocarbon over Silica Monolayer Solid Acid Catalyst2017

    • Author(s)
      Katada, Naonobu; Kawaguchi, Yusuke; Takeda, Kazuki; Matsuoka, Taku; Uozumi, Naoki; Kanai, Kazuki; Fujiwara, Shohei; Kinugasa, Keisuke; Nakamura, Koshiro ; Suganuma, Satoshi ; Nanjo, Masato
    • Journal Title

      Appl. Catal., A: Gen.

      Volume: 530 Pages: 93-101

    • DOI

      10.1016/j.apcata.2016.11.018

    • NAID

      120006873123

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Presentation] ゼオライトの触媒作用: 美しい構造と化学的性質の関係2020

    • Author(s)
      片田直伸
    • Organizer
      情報機構セミナー
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] 実減圧軽油中のアルキル多環芳香族の脱アルキル化に対するシリカモノレイヤー触媒の細孔径の影響2020

    • Author(s)
      胡摩智英, 中野史哉, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第126回触媒討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] YNU-5ゼオライトの大細孔からアクセス可能な強ブレンステッド酸点2020

    • Author(s)
      山本花菜, 淺沼開, 稲垣怜史, 窪田好浩, 辻悦司, 菅沼学史, 片田直伸
    • Organizer
      第126回触媒討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 実減圧軽油中のアルキル多環芳香族の脱アルキル化活性に対するアルミナ担持シリカモノレイヤー触媒の担体の影響2020

    • Author(s)
      胡摩智英, 中野史哉, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第50回石油・石油化学討論会 熊本大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Ir/Al2O3を触媒とする高圧水素中でのデカリン開環反応2020

    • Author(s)
      金治弘樹, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第50回石油・石油化学討論会 熊本大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] モリブデン酸化物モノレイヤーを触媒とするナフタレンからテトラリンへの部分水素化反応2020

    • Author(s)
      稲田凌介, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第50回石油・石油化学討論会 熊本大会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 脱アルミニウムYNU-5ゼオライトの酸性質2020

    • Author(s)
      福井萌麗, 山本花菜, 森脇優, 淺沼開, 稲垣怜史, 窪田好浩, 辻悦司, 菅沼学史, 片田直伸
    • Organizer
      第36回ゼオライト研究発表会
    • Related Report
      2020 Annual Research Report
  • [Presentation] YFI型ゼオライト合成へのスケールの影響2020

    • Author(s)
      森脇優, 山本花菜, 福井萌麗, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      石油学会中国・四国支部第38回講演会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Dependence of Chemical Property on Geometry of Broensted Acid Site in Zeolite2019

    • Author(s)
      Naonobu Katada
    • Organizer
      17th Korea-Japan Symposium on Catalysis
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 活性点に関する確かな情報を得るための分析法2019

    • Author(s)
      片田直伸
    • Organizer
      第13回触媒道場
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] ゼオライトの触媒作用: 美しい構造と化学的性質の関係2019

    • Author(s)
      片田直伸
    • Organizer
      情報機構セミナー
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Catalytic Dealkylation of Alkyl Polycyclic Hydrocarbons Towards Innovation of Petroleum Refinery2019

    • Author(s)
      Naonobu Katada
    • Organizer
      ChemIndix2019
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Catalytic Dealkylation of Alkyl Polycyclic Hydrocarbons Towards Innovation of Petroleum Refinery,2019

    • Author(s)
      Naonobu Katada
    • Organizer
      29th Annual Saudi-Japan Symposium
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] YFI型ゼオライトの酸性質2019

    • Author(s)
      山本花菜, 窪田好浩, 稲垣怜史, 淺沼開, 中島一樹, 中村浩史郎, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第35回ゼオライト研究発表会
    • Related Report
      2019 Annual Research Report
  • [Presentation] テトラリン転換反応に対する*BEAゼオライト触媒への金属担持効果2019

    • Author(s)
      中島一樹, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第35回ゼオライト研究発表会
    • Related Report
      2019 Annual Research Report
  • [Presentation] アモルファスシリカアルミナによる減圧軽油中の塩基性含窒素化合物吸着の速度論的解析2019

    • Author(s)
      菅沼学史, 有田洸介, 辻悦司, 片田直伸
    • Organizer
      第49回石油・石油化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] イリジウム触媒を用いた高圧水素中でのデカリン開環反応2019

    • Author(s)
      金治弘樹, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第49回石油・石油化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 実減圧軽油中のアルキル多環芳香族の脱アルキル化に対するアルミノシリケート固体酸触媒の細孔特性と酸性質の影響2019

    • Author(s)
      中野史哉, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第124回触媒討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 高圧水素中での*BEAゼオライト触媒によるテトラリン転換反応2019

    • Author(s)
      中島一樹, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第124回触媒討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 石油中のアルキル多環芳香族脱アルキル化のためのシリカモノレイヤー触媒の合成2019

    • Author(s)
      胡摩智英, 中野史哉, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第13回触媒道場
    • Related Report
      2019 Annual Research Report
  • [Presentation] Selectivity and Durability of Silica Monolayer Catalyst for Dealkylation of Alkyl Polycyclic Aromatics in Vaccum Gas Oil2019

    • Author(s)
      Fumiya Nakano, Satoshi Suganuma, Etsushi Tsuji and Naonobu Katada
    • Organizer
      APCAT-8
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Influence of Acidic Priperty on Catalytic Activity for Tetralin Conversion over Zeolites2019

    • Author(s)
      Kazuki Nakajima, Satoshi Suganuma, Etsushi Tsuji and Naonobu Katada
    • Organizer
      IZC19
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Relationships among Local Geometry, Desorption Energy of Ammonia and Stretching Wavenumber of Broensted Acidic OH Group in Zeolite2019

    • Author(s)
      Naonobu Katada and Satoshi Suganuma
    • Organizer
      IZC19
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Ring Opening of Decalin in High Pressure Hydrogen over Iridium Catalyst2019

    • Author(s)
      金治弘樹, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第10回触媒科学研究発表会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 実減圧軽油中のアルキル多環芳香族の脱アルキル化に対するシリカモノレイヤー触媒の選択性と耐久性2019

    • Author(s)
      中野史哉, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      石油学会第68回研究発表会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ゼオライトの酸強度を決めるのは何か2018

    • Author(s)
      片田直伸
    • Organizer
      第2回ゼオライトセミナー
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] (特別講演)ゼオライト酸点の化学2018

    • Author(s)
      片田直伸
    • Organizer
      第25回ヤングセラミストミーティングin中四国
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] ゼオライトの酸性質2018

    • Author(s)
      片田直伸
    • Organizer
      キャラクタリゼーション講習会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] アモルファスシリカアルミナによる石油中の塩基性含窒素化合物の吸着除去2018

    • Author(s)
      菅沼学史*, 長野聡子, 衣笠圭祐, 辻悦司, 片田直伸
    • Organizer
      第48回石油・石油化学討論会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] ゼオライトの構造と酸性質のテトラリン開環に対する触媒活性への影響2018

    • Author(s)
      中島一樹*, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第122回触媒討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Reactions of Tetralin on Aluminosilicate-based Solid Acid Catalysts2018

    • Author(s)
      Kazuki Nakajima*, Satoshi Suganuma, Etsushi Tsuji and Naonobu Katada
    • Organizer
      ZMPC2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Factors Hidden in Activation Enthalpy-Entropy Relationship of Zeolite-Catalyzed Reactions2018

    • Author(s)
      Naonobu Katada*, Koshiro Nakamura, Etsushi Tsuji and Satoshi Suganuma
    • Organizer
      ZMPC2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Dealkylation of Alkyl Polycyclic Aromatic Hydrocarbons in Vacuum Gas Oil2018

    • Author(s)
      Fumiya Nakano*, Keisuke Kinugasa, Satoshi Suganuma, Etsushi Tsuji and Naonobu Katada
    • Organizer
      TOCAT8
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 減圧軽油中のアルキル多環芳香族脱アルキル化での反応条件の最適化2018

    • Author(s)
      中野史哉*, 衣笠圭祐, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      石油学会第67回研究発表会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 減圧軽油中のアルキル多環芳香族脱アルキル化での反応条件の最適化2018

    • Author(s)
      中野史哉, 衣笠圭祐, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      石油学会第67回研究発表会
    • Related Report
      2017 Annual Research Report
  • [Presentation] (Keynote Lecture) Advances in Analysis of Acidic Properties of Zeolites2018

    • Author(s)
      Naonobu Katada
    • Organizer
      18th Kuwait / Japan Joint Symposium "Advancement in Petroleum Industries"
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 固体酸を吸着剤として用いる石油中の塩基性含窒素化合物の効率的な除去2017

    • Author(s)
      菅沼学史, 竹田一貴, 佐藤大地, 長野聡子, 辻悦司, 片田直伸
    • Organizer
      第47回石油・石油化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 減圧軽油中のアルキル多環芳香族脱アルキル化のための塩基性物質の除去と触媒再生2017

    • Author(s)
      衣笠圭祐, 竹田一貴, 橋本瀬那, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第47回石油・石油化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 減圧軽油中のアルキル多環芳香族の脱アルキル化反応における阻害物質の特定2017

    • Author(s)
      中野史哉, 衣笠圭祐, 竹田一貴, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      2017年日本化学会中国四国支部大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 減圧軽油中の塩基性物質の除去がアルキル多環芳香族の脱アルキル化に与える影響2017

    • Author(s)
      衣笠圭祐, 竹田一貴, 佐藤大地, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Principles Found in Acidic Properties of Aluminosilicates Including Zeolites2017

    • Author(s)
      Naonobu Katada
    • Organizer
      Catalyst R&D Workshop
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] (Plenary Lecture) Principles and Questions about What Controls Brønsted Acid Strength of Aluminosilicate2017

    • Author(s)
      Naonobu Katada
    • Organizer
      ABC-8, 8th International Symposium on Acid-Base Catalysis
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 酸性イオン交換樹脂による石油中の塩基性物質除去とその再生2017

    • Author(s)
      竹田一貴, 佐藤大地, 菅沼学史, 辻悦司, 片田直伸
    • Organizer
      石油学会第66回研究発表会
    • Place of Presentation
      石油学会第66回研究発表会
    • Related Report
      2016 Annual Research Report
  • [Presentation] シリカモノレイヤー触媒によるアルキル多環芳香族の脱アルキル化2016

    • Author(s)
      片田直伸*, 松岡卓, 川口侑亮, 竹田一貴, 藤原翔平, 衣笠圭祐, 菅沼学史
    • Organizer
      石油学会第65回研究発表会
    • Place of Presentation
      東京, タワーホール船堀
    • Related Report
      2016 Annual Research Report
  • [Presentation] Effect of nitrogen-containing compounds on dealkylation of alkylnaphthalene catalyzed by silica monolayer2016

    • Author(s)
      Kazuki Takeda*, Taku Matsuoka, Yusuke Kawaguchi, Shohii Fujiwara, Keisuke Kinugasa, Satoshi Suganuma and Naonobu Katada
    • Organizer
      16th International Catalysis Congress
    • Place of Presentation
      Beijing, China National Convention Center
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] シリカモノレイヤー触媒の高温焼成によるアルキルナフタレンの脱アルキル化活性の変化2016

    • Author(s)
      衣笠圭祐*, 川口侑亮, 竹田一貴, 菅沼学史, 片田直伸
    • Organizer
      第118回触媒討論会
    • Place of Presentation
      盛岡, 岩手大学
    • Related Report
      2016 Annual Research Report
  • [Presentation] 減圧軽油中のアルキル多環芳香族の脱アルキル化反応―シリカモノレイヤー触媒の再生―2016

    • Author(s)
      竹田一貴*, 衣笠圭祐, 佐藤大地, 菅沼学史, 片田直伸
    • Organizer
      第46回石油・石油化学討論会
    • Place of Presentation
      京都, 京都リサーチパーク
    • Related Report
      2016 Annual Research Report

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Published: 2016-04-21   Modified: 2022-01-27  

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