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2001 Fiscal Year Final Research Report Summary

Novbel Desulfurization, Denitrogenation, and Demetalation Process for Fuel Oils Effected by Photochemical Reactions

Research Project

Project/Area Number 12555215
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field 化学工学一般
Research InstitutionOsaka University

Principal Investigator

HIRAI Takayuki  Osaka University, Research Center for Solar Energy Chemistry, Prorfessor, 太陽エネルギー化学研究センター, 教授 (80208800)

Co-Investigator(Kenkyū-buntansha) HINO Akira  Daihachi Chemical Co., Ltd., Engineer, 製造技術部主任(研究職)
NODA Hideo  Kansai Chemical Engineering, Co., Ltd., President, 取締役社長(研究職)
SHIRAISHI Yasuhiro  Osaka University, Research Center for Solar Energy Chemistry, Assistant Prorfessor, 太陽エネルギー化学研究センター, 助手 (70343259)
Project Period (FY) 2000 – 2001
KeywordsFuel oils / Desulfurization / Denitrogenation / Demetalation / Photochemical reaction / Chemical conversion / Upgrading / Clean Fuel
Research Abstract

Sulfur-, nitrogen-, and metal-containing compounds, present in fuel oils, are causes of air pollution and corrosion of combustion engine. These are removed presently by catalytic hydrorefining process. The present work developed novel desulfurization, denitrogenation, and demetalation processes, based on photochemicalconversion of the objective species.
1. Photochemical Desulfurization and Denitrogenation. Novel desulfurization and denitrogenation processes for heavy-middle distillate (light oils and vacuum gas oil), based on photoirradiation of oil/water and oil/acetonitrile systems, where sulfur and nitrogen compounds are photooxidized and removed successfully from oil. Alkyl-substituted DBTs, which is difficult to desulfurize by current hydrorefining process, is desulfurized easily by the present processes, and deep desulfurization is achieve successfully.
2. Photochemical Demetalation. Photochemical demetalation process for residue oils is developed based on photodecomposition of van … More adyl- and nickelporphyrins by UV irradiation in the presence of 2-propanol and subsequent extraction of the resulting metals by aqueous HC1 solution. By employing the process, almost all of the vanadium and nickel in atmospheric and vacuum residue oils can be removed successfully.
3. Desulfurization and Denitrogenation Based on Sulfonium Salts Formation. Novel desulfurization process for oils, based on alkylation of sulfur compounds and the subsequent precipitation of the resulting sulfonium salts, is developed. The sulfur content of light oil is decreased successfully to less than 0.005 wt % (ultra deep desulfurization level), where nitrogen compounds are also removed simultaneously.
4. Desulfurization Based on Sulfimides Formation. Novel desulfurization process for light oil, based on imidation of sulfur compounds and the subsequent adsorption of the resulting sulfimides, is developed.
5. Desulfurization and Denitrogenation Based on Chemical Oxidation. Novel desulfurization and denitrogenation process for light oil, based on chemical oxidation of sulfur and nitrogen compounds using hydrogen peroxide and acetic acid and the subsequent extraction of the resulting materials by aqueous acetonitrile solution, is developed. Less

  • Research Products

    (54 results)

All Other

All Publications (54 results)

  • [Publications] Yasuhiro Shiraishi, Takayuki Hirai, Isao Komasawa: "Photochemical Desulfurization for Light Cycle Oil Using an Organic Two-Phase Extraction System"Solvent Extraction Research and Development, Japan. 7. 11-17 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Takayuki Hirai, Isao Komasawa: "A Novel Demetalation Process for Vanadyl-and Nickelporphyrins from Petroleum Residue by Photochemical Reaction and Liquid-Liquid Extraction"Industrial and Engineering Chemistry Research. 39(5). 1345-1355 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 白石康浩, 平井隆之, 駒沢 勲: "光化学反応と溶媒抽出を複合した燃焼油の深度脱硫プロセス"化学工学論文集. 26(4). 487-496 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Takayuki Hirai, Isao Komasawa: "Photochemical Denitrogenation Processes for Light Oils Effected by a Combination of UV Irradiation and Liquid-Liquid Extraction"Industrial and Engineering Chemistry Research. 39(8). 2826-2836 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Takayuki Hirai, Isao Komasawa: "Photochemical Desulfurization and Denitrogenation Process for Vacuum Gas Oil Using an Organic Two-Phase Extraction System"Industrial and Engineering Chemistry Research. 40(1). 293-303 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Yasuto Taki, Takayuki Hirai, Isao Komasawa: "A Novel Desulfurization Process for Fuel Oils Based on the Formation and Subsequent Precipitation of S-Alkylsulfonium Salts. 1. Light Oil Feedstocks"Industrial and Engineering Chemistry Research. 40(4). 1213-1224 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Kenya Tachibana, Takayuki Hirai, Isao Komasawa: "A Novel Desulfurization Process for Fuel Oils Based on the Formation and Subsequent Precipitation of S-Alkylsulfonium Salts. 2. Catalytic-Cracked Gasoline"Industrial and Engineering Chemistry Research. 40(4). 1225-1233 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Takayuki Hirai, Isao Komasawa: "Operability Study on a Photochemical Desulfurization Process for Light Oil Using an Organic Two-Phase Extraction System"Solvent Extraction Research and Development, Japan. 8. 165-171 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Kenya Tachibana, Takayuki Hirai, Isao Komasawa: "A Novel Desulfurization Process for Fuel Oils Based on the Formation and Subsequent Precipitation of S-Alkylsulfonium Salts. 3. Denitrogenation Behavior of Light Oil Feedstocks"Industrial and Engineering Chemistry Research. 40(15). 3390-3397 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Takayuki Hirai, Isao Komasawa: "A Novel Desulfurization Process for Fuel Oils Based on the Formation and Subsequent Precipitation of S-Alkylsulfonium Salts. 4. Desulfurization and Simultaneous Denitorogenation of Vacuum Gas Oil"Industrial and Engineering Chemistry Research. 40(15). 3398-3405 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Tomoko Naito, Takayuki Hirai, Isao Komasawa: "A Novel Methodology Towards Deep Desulfurization of Light Oil Effected by Sulfimides Formation"Chemical Communications. 1256-1257 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Kenya Tachibana, Takayuki Hirai, Isao Komasawa: "A Novel Desulfurization Process for Fuel Oils Based on the Formation and Subsequent Precipitation of S-Alkylsulfonium Salts. 5. Denitrogenation Reactivity of Basic and Neutral Nitrogen Compounds"Industrial and Engineering Chemistry Research. 40(22). 4919-4924 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Takayuki Hirai, Isao Komasawa: "Denitrogenation Behavior of Light Oils in a Desulfurization Process Based on Photosensitized Oxidation Using a Photosensitizer and Hydrogen Peroxide in an Oil/Water Two-Phase System"Solvent Extraction Research and Development, Japan. 9. 121-132 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Takayuki Hirai, Isao Komasawa: "Quantum Chemical Calculation on the Behavior of Sulfur Compounds in a Photochemical Deselfurization Process for Light Oils Using Organic Two-Phase Extraction"Solvent Extraction Research and Development, Japan. 9. 133-140 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Takayuki Hirai, Isao Komasawa: "TiO_2-Mediated Photocatalytic Desulfurization Process for Light Oils Using an Organic Two-Phase System"Journal of Chemical Engineering of Japan. 35(5). 489-492 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 白石康浩, 平井隆之, 駒沢 勲: "アレキル化沈澱法による燃料油の新規な脱硫・脱窒素プロセス"化学工学論文集. 28(3). 231-240 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Kenya Tachibana, Takayuki Hirai, Isao Komasawa: "Desulfurization and Denitrogenation Process for Light Oils Based on Chemical Oxidation followed by Liquid Extraction"Industrial and Engineering Chemistry Research. 40(17). 4362-4375 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Tomoko Naito, Takayuki Hirai, Isao Komasawa: "A Desulfurization Process for Light Oils Based on the Formation and Subsequent Adsorption of N-Tosylsulfimides"Industrial and Engineering Chemistry Research. 41(17). 4376-4382 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Kenya Tachibana, Takayuki Hirai, Isao Komasawa: "A Novel Thermal Latent Cationic Initiator : S-Alkylsulfonium Salts Obtained by Desulfufrization of Light Oil"Industrial and Engineering Chemistry Research. 41(23). 5554-5557 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi Takayuki Hirai, Isao Komasawa: "Oxidative Desulfurization Process for Light Oil Using Titanium Silicate Molecular Sieve Catalysts"Journal of Chemical Engineering of Japan. 35(12). 1305-1311 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Kenya Tachibana, Takayuki Hirai, Isao Komasawa: "Photochemical Production of Biphenyls from Oxidized Sulfur Compounds Obtained by Oxidative Desulfurization of Light Oils"Energy and Fuels. 17(1). 95-100 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Takayuki Hirai, Isao Komasawa: "Polymer-Supported Sulfonium Salts Obtained by Desulfurization of Light Oil as Novel Phase Transfer Catalyst"Journal of Chemical Engineering of Japan. 36(2)(印刷中). (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Takayuki Hirai, Isao Komasazwa: "S-Methylsulfonium Salts Obtained by Desulfurization of Vacuum Gas Oil and Catalytic-Cracked Gasoline as Thermal Latent Polymerization Initiator"Journal of Chemical Eengineering of Japan. 36(3)(印刷中). (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yasuhiro Shiraishi, Takayuki Hirai, Isao Komasawa: "A Deep Desulfurization Process for Light Oil by Photochemical Reaction in an Organic Two-Phase Liquid-Liquid Extraction System"Solvent Extraction for the 21st Century, M. Cox, M. Hidalgo and M. Valiante (Editor), SCI, London. 1397-1401 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takayuki Hirai, Yasuhiro Shiraishi, Isao Komasawa: "Novel Refining Processes for Fuel Oil by Photochemical Reaction and Liquid-Liquid Extraction"Gratama Workshop 2000 Conference Report. 7. 87-89 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 白石康浩, 平井隆之, 駒沢 勲: "光化学反応と液液抽出法を利用する軽油の脱窒素プロセス"化学工学シンポジウムシリーズ. 76. 31-40 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 白石康浩, 平井隆之, 駒沢 勲: "スルフィミド形成反応による軽油の新規な深度脱流プロセス"ケミカルエンジニヤリング. 46(12). 956-961 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "Photochemical Desulfurization for Light Cycle Oil Using an Organic Two-Phase Extraction System"Solv. Extr. Res. Dev. Japan. 7. 11-17 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "A Novel Demetalation Process for Vanadyl- and Nickelporphyrins from Petroleum Residue by Photochemical Reaction and Liquid-Liquid Extraction"Ind. Eng. Chem. Res.. 39(5). 1345-1355 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Hirai and I. Komasawa: "Novel Deep Desulfurizatiion Processes for fuel Oils by Photochemical Reaction and Liquid-Liquid Extraction"Kagaku Kogaku Ronbunshu. 26(4). 487-496 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "Photochemical Denitrogenation Processes for Light Oils Effected by a Combination of UV Irradiation and Liquid-Liquid Extraction"Ind. Eng. Chem. Res.. 39(8). 2826-2836 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komawasa: "Photochemical Desulfurization and Denitrogenation Process for Vacuum Gas Oil Using an Organic Two-Phase Extraction System"Ind. Eng. Chem. Res.. 40(1). 293-303 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, Y. Taki, T. Hirai and I. Komasawa: "A Novel Desulfurization Process for Fuel Oils Based on the Formation and Subsequent Precipitatiion of S-Alkylsulfonium Salts. 1. Light Oil Feedstocks"Ind. Eng. Che. Res.. 40(4). 1213-1224 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, K. Tachibana, Yasuto Taki, T. Hirai and I. Komasawa: "A Novel Desulfurization Process for Fuel Oils Based on the Formation and Subsequent Precipitation of S-Alkylsulfonium Salts. 2. Catalytic-Cracked Gasoline"Ind. Eng. Chem. Res.. 40(4). 1225-1233 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "Operability Study on a Photochemical Desulfurization Process for Light Oil Using an Organic Two-Phase Extraction System"Solv. Extr. Res. Dev. Japan. 8. 165-171 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, K. Tachibana, T. Hirai and I. Komasawa: "A Novel Desulfurization Process for Fuel Oils Based on the Formation and Subsequent Precipitation of S-Alkylsulfonium Salts. 3. Denitrogenation Behavior of Light Oil Feedstocks"Ind. Eng. Chem. Res.. 40(15). 3390-3397 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "A Novel Desulfurization Process for Fuel Oils Based on the Formation and Subsequent Precipitation of S-Alkylsulfonium Salts. 4. Desulfurization and Simultaneous Denitorogenation of Vacuum Gas Oil"Ind. Eng. Chem. Res.. 40(15). 3398-3405 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Naito, T. Hirai and I. Komasawa: "A Novel Methodology Towards Deep Desulfurizatio of Light Oil Effected by Sulfimides Formation"Chem. Commun.. 1256-1257 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, K. Tachibana, T. Hirai and I. Komasawa: "A Novel Desulfurization Process for Fuel Oils Based on the Formation and Subsequent Precipitation of S-Alkylsulfonium Salts. 5. Denitrogenation Reactivity of Basic and Neutral Nitrogen Compounds"Ind. Eng. Chem. Res.. 40(22). 4919-4924 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "Denitrogenation Behavior of Light Oils in a Desulfurization Process Based on Photosensitized Oxidation Using a Photosensitizer and Hydrogen Peroxide in an Oil/Water Two-Phase System"Solv. Extr. Res. Dev. Japan. 9. 121-132 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "Quantum chemical Calculation on the Behavior of Sulfur Compounds in a Photochemical Desulfurization Process for Light Oils Using Organic Two-Phase Extraction"Solv. Extr. Res. Dev. Japan. 9. 133-140 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "TiO_2-Mediated Photocatalytic Desulfurization Process for Light Oils Using an Organic Two-Phase System"J. Chem. Eng. Japan. 35(5). 489-492 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "Novel Desulfurization and Simultaneous Denitrogenation Processes for Fuel Oils by Alkylation and Precipitation"Kagaku Kogaku Ronbunshu. 28(3). 231-240 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, K. Tachibana, T. Hirai and I. Komasawa: "Desulfurization and Denitrogenation Procdess for Light Oils Based on Chemical Oxidation followed by Liquid-Liquid Extraction"Ind. Eng. Chem. Res.. 41(17). 4362-4375 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Naito, T. Hirai and I. Komasawa: "A Desulfurization Process for Light Oils Based on the Formation and Subsequent Adsorption of N-Tosylsulfimides"Ind. Eng. Chem. Res.. 41(17). 4376-4382 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, K. Tachibana, T. Hirai and I. Komasawa: "A Novel Thermal Latent Cationic Initiator : S-Alkylsulfonium Salts Obtained by Desulfurization of Light Oil"Ind. Eng. Chem. Res.. 41(23). 5554-5557 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "Oxidative Desulfurization Process for Light Oil Using Titanium Silicate Molecular Sieve Catalysts"J. Chem. Eng. Japan. 35(12). 1305-1311 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, K. Tachibana, T. Hirai and I. Komasawa: "Photochemical Production of Biphenyls from Oxidized Sulfur Compounds Obtained by Oxidative Desulfurization of Light Oils"Energy and Fuels. 17(1). 95-100 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "Polymer-Supported Sulfonium Salts Obtained by Desulfurization of Light Oil as Novel Phase Transfer Catalyst"J. Chem. Eng. Japan. 36(2). 220-224 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "S-Methylsulfonium Salts Obtained by Desulfurization of Vacuum Gas Oil and Catalytic-Cracked Gasoline as Thermal Latent Polymerization Initiator"J. Chem. Eng. Japan. 36(3)(in press). (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "A Deep Desulfurization Process for Light Oil by Photochemical Reaction in an Organic Two-Phase Liquid-Liquid Extraction System"Solvent Extraction for the 21st Century, M. Cox, M. Hidalgo and M. Valiante (Editor). (SCI, London). 1397-1401 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Hirai Y. Shiraishi and I. Komasawsa: "Novel Refining Processes for Fuel Oil by Photochemical Reaction and Liquid-Liquid Extraction"Gratama Workshop 2000 Conference Report. 87-89 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "A Novel Denitrogenation Process for Light Oils by Photochemical Reaction and Liquid-Liquid Extraction"Chemical Engineering Symposium Series. 76. 31-40 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Shiraishi, T. Hirai and I. Komasawa: "A Novel Deep Desulfurization Process for Light Oils Based on the Formation of N-Tosylsulfimides"Chemical Engineering. 46(12). 956-961 (2001)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2003-09-17  

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