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DEVELOPMENT OF C-C BOND FORMING FUNCTIONALIZATION

Research Project

Project/Area Number 08651013
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionKYUSHU UNIVERSITY

Principal Investigator

TANIGUCHI Yuki  KYUSHU UNIVERSITY FAC.OF ENGINEERING,DEPT OF CHEM.AND BIOCHEM., ASSISTANT PROFESSOR, 工学部, 助手 (50217139)

Co-Investigator(Kenkyū-buntansha) KITAMURA Tsugio  KYUSHU UNIVERSITY FAC.OF ENGINEERING,DEPT OF CHEM.AND BIOCHEM., ASSICIATE PROFES, 工学部, 助教授 (00153122)
FUJIWARA Yuzo  KYUSHU UNIVERSITY FAC.OF ENGINEERING,DEPT OF CHEM.AND BIOCHEM., PROFESSOR, 工学部, 教授 (10029481)
Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1997: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1996: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsCOPPER ACETATE / YTTERBIUM ACETATE / MANGANESE ACETATE / ALKANE / C-H BOND ACTIVATION / C-C BOND ACTIVATION / AMINOMETHYLATION / CARBOXYLATION / 酢酸イッテルビウム / メチルアミンN-オキシド / プロパン / エタン / メタン / トリフルオロ酢酸エステル
Research Abstract

(I)DeveIopment of Novel Synthetic Method for the Synthesis of Amines by Aminomethylation of AIkanes Catalyzed by Copper Acetate
Transition metal salts such as copper acetates catalyze the reaction of gaseous alkanes with N,N-dialkylmethylamine N-oxides in trifluoacetic acid (TFA) to afford N,N-dialkylaminomethylated alkanes in good yields. Aminomethylation reaction of propane with trimethylamine N-oxide gave N,N-dimethylisobutylamine as a single regioisomer together with isopropyl trifluoroacetate. Ethane reacts with trimethylamine N-oxide affording N,N-dimethylpropylamine as a sole product From the reaction of methane, methyl trifuoroacetate was obtained cxclusively.
(2)Acetic Acid Synthesis from Methane and Carbon Monoxide by Rare Earth Catalyst System
A new synthetic method of acetic acid in water has been developed from the carboxylation of methane with carbon monoxide using lanthanide catalysts. Ytterbium (III) acetate has been found to be the most active catalyst among the compounds of lanthanide series in the carboxylation reaction of methane with carbon monoxide. Sodium hypochlorite or hydrogen peroxide was used as oxidant in this reaction. Sodium hypochlorite exhibited the favorable activity than hydrogen peroxide in the reaction. The catalytic activity was improved by the addidon of transition metal salts such as manganese (II)acetate. The best result has been found at 0.1 ratio of manganese (II) acetate to ytterbium (III) acetate. The optimum reaction conditions (reaction temperature, 40. C ; time, 20h ; methane, 20atm ; carbon monoxide, 5atm) have been obtained.

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (11 results)

All Other

All Publications (11 results)

  • [Publications] Y.Fujiwara, K.Takaki, Y.Taniguchi: "Exploitation of Synthetic Reactions via C-H Bond Activation by Transition Metal Catalysis" Synlett. 1966. 591-599 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Y.Taniguchi, T.Kitamura, Y.Fujiwara, S.Horie, K.Takaki: "Copper(11) Catalyzed Reaction of Gaseous Alkanes with Amine N-Oxides" Catalysis Today. 36. 85-89 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] H.Asadullah, Y.Taniguchi, T.Kitamura, Y.Fujiwara: "Direct Carboxylation of Methane with CO by a Yb(OAc)_3/Mn(OAc)_2/NaClO/H_2O Catalytic System under Very Mild Conditions" Applied Organometalic Chemistry. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Y.FUJIWARA,K.TAKAKI,AND Y.TANIGUCHI: "EXPLOITATION OF SYNTHETIC REACTIONS VIA C-H BOND ACTIVATION BY TRANSITION METAL CATALYSTS" SYNLETT,VOL.1996. NO.7. 591-599 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Y.TANIGUCHI,T.KITAMURA,Y.FUJIWARA,S.HORIE,AND K.TAKAKI: "COPPER(II)-CATALYZED REACTION OF GASEOUS ALKANES WITH AMINE N-OXIDES" CATALYSIS TODAY. VOL.36. 85-89 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.ASADULLAH,Y.TANIGUCHI,T.KITAMURA,AND Y.FUZIWARA: "DIRECT CARBOXYLATION OF METHANE WITH CO BY A Yb(OAc)3/Mn(OAc)2/NaClO/H2O CATALYTIC SYSTEM UNDER VERY MILD CONDITIONs" APPLIED ORGANOMET.CHEM.IN PRESS.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Y.Fujiwara,K.Takaki,Y.Taniguchi: "Exploitation of Synthetic Reactions via C-H Bond Activation by Transition Metal Catalysts" Synlett. 1996・7. 591-599 (1996)

    • Related Report
      1997 Annual Research Report
  • [Publications] Y.Taniguchi,T.Kitamura,Y.Fujiwara,S.Horie,K.Takaki: "Copper(11)-catalyzed Reaction of Gaseous Alkanes with Amine N-Oxides" Catalysis Today. 36. 85-89 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Asodullah,Y.Taniguchi,T.Kitamura,Y.Fujiwara: "Direct Carboxylation of Methane with CO by a Yb(OAc)_3/Mn(OAc)_2/NaClO/H_2O Catalytic System under Very Mild Conditions." Applied.Organometallic Chemistry. (印刷中).

    • Related Report
      1997 Annual Research Report
  • [Publications] Y.Fujiwara,K.Takaki,Y.Taniguchi: "Exploitation of Synthetic Reactions via C-H Bond Activation by Transition Metal Catalysts." Synlett. 1996・7. 591-599 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Y.Taniguchi,T.Kitamura,Y.Fujiwara,S.Horie,K.Takaki: "Copper(11)-catalyzed Reaction of Gaseus Alkanes with Amine N-Oxides" Catalysis Today. (印刷中).

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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