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2012 Fiscal Year Final Research Report

Influences of humic acids on the degradation and toxicity of brominated flame retardants by oxidation catalysts

Research Project

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Project/Area Number 21310048
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Environmental technology/Environmental materials
Research InstitutionHokkaido University

Principal Investigator

FUKUSHIMA Masami  北海道大学, 大学院・工学研究院, 准教授 (40344113)

Co-Investigator(Kenkyū-buntansha) KURAMITZ Hideki  富山大学, 理工学研究部, 教授 (70397165)
NAGAO Seiya  金沢大学, 環日本海域環境研究センター, 教授 (20343014)
Project Period (FY) 2009 – 2012
Keywords環境技術 / 水質汚濁・土壌汚染防止・浄化 / 触媒・化学プロセス / 超分子化学
Research Abstract

Influences of humic acids on the catalytic oxidation of tetrabromobisphenol A (TBBPA) using iron(III)-porphyrin catalysts were investigated. The TBBPA was difficult to be oxidized and dehalogenated by the catalysts, compared to chlorinated phenols that had been investigated. In the catalytic oxidation of TBBPA, oxidative coupling reactions that can produce the oligomers were dominant. In the presence of humic acids, coupling compounds between oxidation intermediates from TBBPA and humic acid were mainly formed, and percents conversion of TBBPA to the coupling compounds were from 50 to 60%. The toxicity tests of the reaction mixtures in the absence and presence of humic acids by the inhibition of an algae (P.subcapitata) growth demonstrated that toxicity of TBBPA was reduced in the presence of humic acids.

  • Research Products

    (55 results)

All 2013 2012 2011 2010 2009 Other

All Journal Article (21 results) (of which Peer Reviewed: 21 results) Presentation (34 results)

  • [Journal Article] Effects of surfaceFe(III) oxides in a steel slag on the formation of humic-like dark-colored polymers by the polycondensation of humic precursors2013

    • Author(s)
      M. Fukushima
    • Journal Title

      Colloid Surf

      Volume: A 418 Pages: 117-123

    • DOI

      DOI:10.1016/j.colsurfa.2012.11.032

    • Peer Reviewed
  • [Journal Article] Electrochemical mutagenicity assay based on SOS/umu test using hydrodynamic voltammetry in a droplet.2012

    • Author(s)
      H. Kuramitz, M. Fukushima
    • Journal Title

      Sensors

      Volume: 12 Pages: 17414-17432

    • DOI

      DOI:10.3390/s121217414

    • Peer Reviewed
  • [Journal Article] Fe-loaded zeolites catalyze the formation of humic substance-like dark-colored polymers in polycondensation reactions of humic precursors2012

    • Author(s)
      M. Fukushima
    • Journal Title

      Clay Miner

      Volume: 47 Pages: 355-364

    • DOI

      DOI:10.1180/claymin.2012.047.3.06

    • Peer Reviewed
  • [Journal Article] Enhanced humification by carbonated basic oxygen furnace steel slag II. Process characterization and the role of inorganic components in the formation of humic-like substances.2012

    • Author(s)
      M. Fukushima
    • Journal Title

      Bioresource Technol

      Volume: 114 Pages: 637-643

    • DOI

      DOI:10.1016/j.biortech.2012. 03.064

    • Peer Reviewed
  • [Journal Article] Thermal treatment of rice bran by portion-wise addition in the presence of an organo-iron catalyst2012

    • Author(s)
      M. Fukushima
    • Journal Title

      J. Mater. Cycle Waste

      Volume: 14 Pages: 139-145

    • DOI

      DOI:10.1007/s10163-012-0049-x

    • Peer Reviewed
  • [Journal Article] Enhanced humification by carbonated basic oxygen furnace steel slag - I. Characterization ofhumic-like acids produced from humic precursors2012

    • Author(s)
      M. Fukushima
    • Journal Title

      Bioresource Technol.

      Volume: 104 Pages: 497-502

    • DOI

      DOI:10.1016/j.biortech.2011.11.021

    • Peer Reviewed
  • [Journal Article] Influence of halogen substituents on the catalytic oxidation of 2,4,6-halogenated phenols by Fe(III)-tetrakis(p-hydroxyphenyl) porphyrins and potassium monopersulfate.2012

    • Author(s)
      M. Fukushima, Y. Mizutani, S. Maeno, Q.Zhu, H. Kuramitz, S. Nagao
    • Journal Title

      Molecules

      Volume: 17 Pages: 48-60

    • DOI

      DOI:10.3390/molecules17010048

    • Peer Reviewed
  • [Journal Article] 腐植 物質と疎水性有害有機物質との相互作用とその土壌浄化への活用(総説)2011

    • Author(s)
      福嶋正巳 , 寺島元基, 藪田ひかる
    • Journal Title

      分析化学

      Volume: 60 Pages: 895-909

    • URL

      URL: https://www.jstage.jst.go.jp/browse/bunsekikagaku/60/0/_contents

    • Peer Reviewed
  • [Journal Article] Effect of different fractions of weathered pumice in the formation of humic-like substances.2011

    • Author(s)
      M. Fukushima
    • Journal Title

      Clay Miner

      Volume: 46 Pages: 637-648

    • DOI

      DOI:10.1180/claymin.2011.046.4.637

    • Peer Reviewed
  • [Journal Article] egradation of pentachlorophenol in a contaminated soil suspension using hybrid catalysts prepared via urea-formaldehyde polycondensation between tetrakis (hydroxyphenyl) porphineirn(III) and humic acid.2011

    • Author(s)
      M. Fukushima, S. Shigematsu, S. Nagao
    • Journal Title

      Environ. Chem. Lett

      Volume: 9 Pages: 223-228

    • DOI

      DOI:10.1007/s10311-009-0269-z

    • Peer Reviewed
  • [Journal Article] Characterization of humic acids in sediments from dam reservoirs by pyrolysis-gas chromatography/mass spectrometry using tetramethylammonium hydroxide: Influence of the structural features of humic acids on iron(II) binding capacity2011

    • Author(s)
      M. Fukushima
    • Journal Title

      J. Anal. Appl.

      Volume: Pyrol. 91 Pages: 323-331

    • DOI

      DOI:10.1016/j.jaap.2011.03.008

    • Peer Reviewed
  • [Journal Article] Optimization of conditions for thermal treatment of rice bran using an accelerator including an organo-iron compound2011

    • Author(s)
      H. Kanno, N. Tachibana, M. Fukushima
    • Journal Title

      Bioresource Technol

      Volume: 102 Pages: 3430-3436

    • DOI

      DOI:10.1016/j.biortech.2010.10.039

    • Peer Reviewed
  • [Journal Article] Spectroscopic investigations of humic-like acids formed via polycondensation reactions between glycine, catechol and glucose in the presence of natural zeolites2011

    • Author(s)
      M. Fukushima
    • Journal Title

      J. Mol. Struct

      Volume: 982 Pages: 181-186

    • DOI

      DOI:10.1016/j.molstruc.2010.08.032

    • Peer Reviewed
  • [Journal Article] Characterization of an adsorbed humin-like substance on an allophanic soil formed via catalyticpolycondensation between catechol and glycine, and its adsorption capability to pentachlorophenol.2011

    • Author(s)
      M. Fukushima
    • Journal Title

      Chemosphere

      Volume: 83 Pages: 1502-1506

    • DOI

      DOI:10.1016/j.chemosphere.2011.01.053

    • Peer Reviewed
  • [Journal Article] Oxidative degradation of 2,6-dibromophenol using an anion-exchange resin supported supramolecular catalysts of iron(III)-5,10,15,20-tetrakis(p-hydroxyphenyl)porph yrin bound to humic acid prepared via formaldehyde and urea-formaldehyde polycondensation.2011

    • Author(s)
      S. Shigematsu, M. Fukushima, S. Nagao
    • Journal Title

      J. Environ. Sci. Heal

      Volume: A45 Pages: 1536-1542

    • DOI

      DOI:10.1080/10934529.2010.506110

    • Peer Reviewed
  • [Journal Article] Pattern of oxidation products derived from tetrabromobisphenol A in a catalytic system comprised of iron(III)-tetrakis(p-sulfophenyl)porphyrin, KHSO5 and humic acids2011

    • Author(s)
      M. Fukushima, Y. Ishida, S. Shigematsu, H.Kuramitz, S. Nagao
    • Journal Title

      Chemosphere

      Volume: 80 Pages: 860-865

    • DOI

      DOI:10.1016/j.chemosphere.2010.05.041

    • Peer Reviewed
  • [Journal Article] Influence of humic acid type on theoxidation products of pentachlorophenol using hybrid catalysts prepared by introducing iron(III)-5,10,15,20-tetrakis (p-hydroxyphenyl)porphyrin into hydroquinone-derived humic acids2010

    • Author(s)
      M. Fukushima, S. Shigematsu, S. Nagao
    • Journal Title

      Chemosphere

      Volume: 78 Pages: 1155-1159

    • DOI

      DOI:10.1016/j.chemosphere.2009.12.010

    • Peer Reviewed
  • [Journal Article] Studies of structural alterations of humic acids from conifer bark residue during composting by pyrolysis-gas chromatography/mass spectrometry using tetramethylammonium hydroxide (TMAH-py-GC/MS).2009

    • Author(s)
      M. Fukushima
    • Journal Title

      J. Anal. Appl. Pyr

      Volume: 86 Pages: 200-206

    • DOI

      DOI:10.1016/j.jaap.2009.06.005

    • Peer Reviewed
  • [Journal Article] マイクロスケール藻類生長阻害試験を用いた銅の毒性に対する溶存有機物質に含まれる抑制成分の探索.2009

    • Author(s)
      倉光英樹
    • Journal Title

      水環境学会誌

      Volume: 32 Pages: 309-314

    • URL

      URL: https://www.jstage.jst.go.jp/browse/jswe/32/6/_contents/-char/ja/

    • Peer Reviewed
  • [Journal Article] Oxidative degradation of2,4,6-trichlorophenol and pentachlorophenol in contaminated soil suspension using a supramolecular catalyst prepared via formaldehyde polycondensation between tetrakis(p-hydroxyphenyl)porphineiron(III) and humic acid2009

    • Author(s)
      M. Fukushima, S. Shigematsu, S. Nagao
    • Journal Title

      J. Enviro. Sci. Heal

      Volume: A 44 Pages: 1088-1097

    • DOI

      DOI:10.1080/10934520903005053

    • Peer Reviewed
  • [Journal Article] Evaluation of the toxicity of tetrabromobisphenol A and some of its oxidation products using a microscale algal growth inhibition test

    • Author(s)
      M Fukushima, H. Kuramitz
    • Journal Title

      Toxicol. Environ. Chem

      Volume: (in press)

    • DOI

      DOI:10.1080/02772248.2013.775290

    • Peer Reviewed
  • [Presentation] Sorption of pentachlorophenol to organo-clay complexes prepared by polycondensation reactions of humic precursors.2013

    • Author(s)
      M. Fukushima
    • Organizer
      The 16th Meeting of the International Humic Substances Society
    • Place of Presentation
      浙江大学(杭州)、中国.
    • Year and Date
      20130909-14
  • [Presentation] SBA-15に担持した鉄ポルフィリン触媒による臭素系難燃剤の酸化分解2013

    • Author(s)
      福嶋正巳
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(草津)
    • Year and Date
      20130321-24
  • [Presentation] イオン交換樹脂に担持した鉄ポルフィリン触媒によるテトラブロモビスフェノール A の酸化分解2013

    • Author(s)
      福嶋正巳
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(草津)
    • Year and Date
      20130321-24
  • [Presentation] シリカに坦持した鉄フタロシアニン触媒による臭素系難燃剤の酸化分解挙動2013

    • Author(s)
      福嶋正巳
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(草津)
    • Year and Date
      20130321-24
  • [Presentation] イオン交換樹脂に担持した鉄ポルフィリン触媒によるテトラブロモビスフェノールAの酸化に及ぼす腐植酸の影響2013

    • Author(s)
      福嶋正巳
    • Organizer
      化学系学協会北海道支部冬季研究発表会
    • Place of Presentation
      北海道大学(札幌)
    • Year and Date
      20130129-30
  • [Presentation] 陽イオン交換樹脂に担持した鉄ポルフィリン触媒によるテトラブロモビスフェノールAの酸化:腐植酸の影響2012

    • Author(s)
      福嶋正巳
    • Organizer
      第28回腐植物質学会講演会
    • Place of Presentation
      首都大学東京(八王子).
    • Year and Date
      20121121-22
  • [Presentation] Influences of a humic acid on potassium monopersulfate oxidation of 2,4,6-tribromophenol by a SiO2-supported iron(III)-porphyrin catalyst2012

    • Author(s)
      M. Fukushima
    • Organizer
      The 16th Meeting of the International HumicSubstances Society
    • Place of Presentation
      浙江大学(杭州)、中国.
    • Year and Date
      20120909-14
  • [Presentation] 鉄をドープしたゼオライト触媒による不均一フェントン反応系における 2,4,6-トリブロモフェノールの酸化分解に及ぼす有機酸の添加効果2012

    • Author(s)
      福地茂樹、西本遼、 福嶋正巳
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学(横浜)
    • Year and Date
      2012-03-27
  • [Presentation] 担持型鉄ポルフィリン触媒によるテトラブロモビスフェノールAの酸化分解に及ぼす腐植酸の影響2012

    • Author(s)
      福嶋正巳
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学(横浜).
    • Year and Date
      2012-03-27
  • [Presentation] 鉄フタロシアニン触媒によるテトラブロモビスフェノールAの酸化分解に及ぼす腐植酸の影響2012

    • Author(s)
      福嶋正巳
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学(横浜).
    • Year and Date
      2012-03-27
  • [Presentation] 有害化学物質と腐植物質の相互作用に関する分析化学的研究(依頼講演)2012

    • Author(s)
      福嶋正巳
    • Organizer
      化学系学協会北海道支部冬季研究発表会
    • Place of Presentation
      北海道大学(札幌).
    • Year and Date
      2012-02-01
  • [Presentation] 鉄(III)-フタロシアニン触媒によるテトラブロモビスフェノールAの酸化分解挙動2012

    • Author(s)
      福嶋正巳
    • Organizer
      化学系学協会北海道支部冬季研究発表会
    • Place of Presentation
      北海道大学(札幌).
    • Year and Date
      2012-02-01
  • [Presentation] 鉄ポルフィリン‐腐植酸超分子触媒によるハロゲン化フェノールの酸化2011

    • Author(s)
      福嶋正巳
    • Organizer
      生成物の解析、日本腐植物質学会第27回講演会
    • Place of Presentation
      金沢大学(金沢)
    • Year and Date
      2011-11-17
  • [Presentation] ベントナイト層間に形成した人工ヒューミンへのペンタクロロフェノールの吸着能2011

    • Author(s)
      福嶋正巳
    • Organizer
      日本分析化学会第60年会
    • Place of Presentation
      名古屋大学(名古屋)
    • Year and Date
      2011-09-16
  • [Presentation] 水溶性鉄ポルフィリン触媒によるハロゲン化ビスフェノールAの酸化分解生成物の解析2011

    • Author(s)
      水谷祐介、前野翔平、福嶋正巳
    • Organizer
      日本分析化学会第60年会
    • Place of Presentation
      名古屋大学(名古屋).
    • Year and Date
      2011-09-14
  • [Presentation] 鉄ポルフィリン触媒によるハロゲン化ビスフェノールAの酸化分解に及ぼす腐植酸の影響2011

    • Author(s)
      水谷祐介、福嶋正巳
    • Organizer
      化学系学協会北海道支部冬季研究発表会
    • Place of Presentation
      北海道大学学術交流会館(札幌)
    • Year and Date
      2011-02-02
  • [Presentation] △14C values of dissolved humic and fulvic acids in the Tokachi River system2010

    • Author(s)
      S. Nagao
    • Organizer
      The third Asian and Oceanic Congress on Radiation Protection
    • Place of Presentation
      タワーホール船堀(千葉)
    • Year and Date
      20100523-28
  • [Presentation] Size selective complexation for Am with groundwater humic and fulvic acids2010

    • Author(s)
      S. Nagao
    • Organizer
      The 6th International Conference on Interfaces against pollution
    • Place of Presentation
      Bejing Frendship Hotel (北 京)、 中国
    • Year and Date
      20100516-19
  • [Presentation] 蛍光検出-藻類生長阻害試験の検討と腐植物質存在下におけるテトラブロモビスフェノールAの毒性評価2010

    • Author(s)
      倉光英樹、福嶋正巳
    • Organizer
      第26回日本腐植物質学会講演会
    • Place of Presentation
      筑波大学(つくば)
    • Year and Date
      2010-11-30
  • [Presentation] 鉄ポルフィリン-腐植酸超分子触媒によるハロゲン化フェノールの酸化挙動2010

    • Author(s)
      福嶋正巳、水谷祐介、倉光英樹、長尾誠也
    • Organizer
      第26回日本腐植物質学会講演会
    • Place of Presentation
      筑波大学(つくば)
    • Year and Date
      2010-11-30
  • [Presentation] カテコールとグリシンの縮重合生成物とベントナイトとの複合体に対するペンタクロロフェノールの吸着挙動2010

    • Author(s)
      福嶋正巳
    • Organizer
      第26回日本腐植物質学会講演会
    • Place of Presentation
      筑波大学(つくば)
    • Year and Date
      2010-11-29
  • [Presentation] N. Hata, and S.Taguchi, Development of mutagenic assay based on hydrodynamic voltammetry in a droplet.2010

    • Author(s)
      K. Sazawa, H. Kuramitz
    • Organizer
      The 17th Asian Symposium on Ecotechnology(ASET17)
    • Place of Presentation
      宇奈月国際会館(黒部).
    • Year and Date
      2010-11-12
  • [Presentation] Shigematsu, Influences of humic acids on the pattern of oxidation products of tetrabromobisphenol A derived from a catalytic system using iron(III)-tetrakis(p-sulfophenyl)porphyrinand KHSO52010

    • Author(s)
      M. Fukushima,Y. Ishida, S.
    • Organizer
      15th Meeting of theInternational Humic Substances Society
    • Place of Presentation
      Tenerife - Canary Islands, Spain.
    • Year and Date
      2010-07-01
  • [Presentation] 鉄ポルフィリン-腐植酸超分子触媒の陰イオン交換樹脂への担持とその触媒活性評価2010

    • Author(s)
      福嶋正巳、重松聡子
    • Organizer
      第71回分析化学討論会
    • Place of Presentation
      島根大学(松江).
    • Year and Date
      2010-05-11
  • [Presentation] イオン交換樹脂に担持した鉄ポルフィリン‐腐植酸超分子 触媒による 2,6-ジブロモフェノールの酸化分解2010

    • Author(s)
      重松聡子、 福嶋正巳
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学(大阪)
    • Year and Date
      2010-03-27
  • [Presentation] 腐植物質の機能による有機ハロゲン化物の無害化(依頼講演)2010

    • Author(s)
      福嶋正巳
    • Organizer
      日本化 学会第90 春季年会
    • Place of Presentation
      近畿大学(大阪)
    • Year and Date
      2010-03-26
  • [Presentation] 水溶性鉄ポルフィリンビスフェノール A の酸化生成物に及ぼす腐植酸の影響2010

    • Author(s)
      石田洋輔、重松聡子、福嶋正巳
    • Organizer
      化学系学協会北海道支部2010冬季研究発表会
    • Place of Presentation
      北海道大学(札幌).触媒によるテトラブロモ
    • Year and Date
      2010-01-27
  • [Presentation] 水溶性鉄ポルフィリン触媒によるテトラブロモビスフェノールAの酸化分解挙動に及ぼす腐植酸の影響2009

    • Author(s)
      福嶋正巳,石田洋輔,重松聡子,倉光英樹
    • Organizer
      第25回日本腐植物質学会講演会
    • Place of Presentation
      兵庫県立大学(姫路)
    • Year and Date
      2009-11-26
  • [Presentation] 液滴試料の対流ボルタンメトリーによるイムノアッセイとバイオアッセイの高度化(依頼講演)2009

    • Author(s)
      倉光英樹
    • Organizer
      第40回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      岐阜大学(岐阜).
    • Year and Date
      2009-11-07
  • [Presentation] 新規電気化学的変異原性試験法を用いた土壌・底質中の有害汚染物質の毒性変化2009

    • Author(s)
      倉光英樹
    • Organizer
      日本分析化学会第58年会
    • Place of Presentation
      北海道大学(札幌).
    • Year and Date
      2009-09-24
  • [Presentation] Development of microscaled algal growth inhibition test and assessment for mitigating effect of dissolved humic substances on various environmental pollutants toxicity2009

    • Author(s)
      H. Kuramitz
    • Organizer
      Asia Young Analytical Chemist Session (AYACS) 2009
    • Place of Presentation
      Putra World Trade Center (Kuala Lumpur), Malaysia.
    • Year and Date
      2009-08-10
  • [Presentation] 有機汚染物質の無害化促進に有用な腐植物質の機能解明(依頼講演)2009

    • Author(s)
      福嶋正巳
    • Organizer
      第27回九州分析化学会若手の会夏季セミナー
    • Place of Presentation
      宮崎観光ホテル(宮崎).
    • Year and Date
      2009-07-30
  • [Presentation] 対流ボルタンメトリーを用いた変異原性試験法の開発2009

    • Author(s)
      倉光英樹
    • Organizer
      第70回分析化学討論会
    • Place of Presentation
      和歌山大学(和歌山).
    • Year and Date
      2009-05-17
  • [Presentation] Introduction of tetra(p-hydroxyphenyl) porphine iron (III) into humic acid via covalent binding to retard its self-degradation.2009

    • Author(s)
      M. Fukushima
    • Organizer
      The 3rd INTERNATIONAL WORKSHOP AND CONFERENCE ON EARTH RESOURCES TECHNOLOGY
    • Place of Presentation
      北海道大学 (札幌)
    • Year and Date
      2009-05-13

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Published: 2014-08-29  

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