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DEVELOPMENT OF SEPARATION AND OPTICAL RESOLUTION METHOD OF MATERIALS BY USING INCLUSION COMPOUND

Research Project

Project/Area Number 63840017
Research Category

Grant-in-Aid for Developmental Scientific Research

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionDEPARTMENT OF INDUSTRIAL CHEMISTRY, FACULTY OF ENGINEERING, EHIME UNIVERSITY, MATSUYAMA 790

Principal Investigator

TODA Fumio  DEPARTMENT OF INDUSTRIAL CHEMISTRY, FACULTY OF ENGINEERING, EHIME UNIVERSITY, PROFESSOR., 工学部, 教授 (50036232)

Co-Investigator(Kenkyū-buntansha) KITAMURA Mitsutaka  DEPARTMENT OF CHEMICAL TECHNOLOGY, FACULTY OF ENGINEERING, HIROSHIMA UNIVERSITY,, 工学部, 助手 (60127644)
NOHIRA Hiroyuki  DEPARTMENT OF INDUSTRIAL CHEMISTRY, FACULTY OF ENGINEERING, SAITAMA UNIVERSITY,, 工学部, 教授 (50008819)
Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥4,700,000 (Direct Cost: ¥4,700,000)
Fiscal Year 1989: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1988: ¥3,200,000 (Direct Cost: ¥3,200,000)
KeywordsOptical resolution / Isomer separation / Host-guest complex / Inclusion compound / Optically active host compound / Molecular design / Molecular recognition / Enantio recognition / ホストーゲスト錯体 / 分離 / 優先晶析
Research Abstract

1) Design and development of host compounds. Some optically active host compounds were derived from natural chiral source, tartaric acid. One of these is the amide derivative of tartaric acid. Compounds of other group are the host compounds which prepared by Grignard reaction of a ester derivative of tartaric acid with phenylmagnesium chloride. All of those showed a selective inclusion ability. By using the enantioselective inclusion ability of these hosts, some new other host compounds were resolved. For example, racemic 2,2'-dihydroxy- 1,1'-binaphthyl and 10,10'-dihydroxy-9,9'-biphenanthryl were resolved easily by optically active tartaric acid host.
2) Optical resolution and freezing of chirality. By using the hosts which derived from tartaric acid, following compounds were resolved efficiently. Bicyclic eneones, cyclic ketones, pantolactone, amines were resolved by this method. Details of the resolution have been reported in many publications. By using the optically active 2,2'-dihydroxy-1,1'binaphthyl, amine N-oxides, sulphoxides, selenoxides, arsine oxides, phosphine oxides, phosphinates were resolved efficiently.
3) Separation of materials. The inclusion method is very effective for a separation of isomers of the same or close boiling point. This is due to a recognition of molecular shape by the host. Many separations of material by this method have been carried out. Especially, separation of naphthalene derivatives were studied in detail.

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (30 results)

All Other

All Publications (30 results)

  • [Publications] Koichi Tanaka: "Separation and Optical Resolution by Using Inclusion Complex Formation" Nippon Kagaku Kaishi. 1643-1656 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumio Toda: "Optical Resolution of 2-Methylpiperazine by Complex Formation with Optically Active 1-Phenylー1-(o-chlorophenyl)prop-2-yn-1-ol" Chim.Lett.513-516 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumio Toda: "Optical Resolution of Amine N-Oxide by Diastereoisomeric Complex Formation with Optically Active Host Compound" Tetrahedron Lett.30. 1841-1844 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumio Toda: "Optical Resolution of Pantolactone by Inclusion Crystallization with (R,R)-(-)-2,3-Bis(diphenylhydroxymethyl)-1,4-dioxaspiro[4.5]decane" Chem.Lett.873-876 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Hiroyuki Nohira: "Optical Resolution of α-Ethylbenzylamine and Its Application as a Resolving Agent" Bull.Chem.Soc.Jpn.61. 1395-1396 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Mitsutaka Kitamura: "Polymorphism in the Crystallization of L-Glutamic Acid" J.Crystal Growth. 96. 541-546 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 戸田芙三夫監修: "包接化合物の基礎と応用" NTS.株式会社, 349 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 山中宏,野平博之,戸田芙三夫,他: "季刊化学総説「光学異性体の分離」" 日本化学会編・学会出版センタ-, 238 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Koichi Tanaka: "Separation and Optical Resolution by using Inclusion Complex Formation" Nippon Kagaku Kaishi. p. 1643-1656, 1988.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumio Toda: "Optical Resolution of 2-Methylpiperazine by Complex Formation with Optically Active 1-Phenyl-1-(o-chlorophenyl)prop-2-yn-1-ol" Chem. Lett. p. 513-516, 1988.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumio Toda: "Optical Resolution of Amine N-Oxide by Diastereomeric Complex Formation with Optically Active Host Compound" Tetrahedron Lett, 30. p. 1841-1844.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumio Toda: "Optical Resolution of Pantolactone by Inclusion Crystallization with (R,R)-(-)-2, 3-Bis(diphenylhydroxymethyl)-1, 4-dioxaspiro[4.5]decane" Chem. Lett. 873-876, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Hiroyuki Nohira: "Optical Resolution of alpha-Ethylbenzylamine and Its Application as a Resolving Agent" Bull. Chem. Soc. Jpn. 61. p. 1395-1396, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Mitsutaka Kitamura: "Polymorphisms in the Crystallization of L-Glutamic Acid" J. Crystal Growth, 96. p. 541-546, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumio Toda: "Fundamental and Application of Inclusion Compounds" J. Crystal Growth, 96. p. 1-349, 1989.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Hiroyuki Nohira and Fumio Toda: "Separation of Optical Isomers" J. Crystal Growth, 96. p. 1-238.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Koichi Tanaka: "Separation and Optical Resolution Using Inclusion Complex Formation" Nippon Kagaku Kaishi. 1643-1656 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Fumio Toda: "Optical Resolution of 2ーMethylpiperazine by Complex Formation with with Optically Active lーPhenylーlー(oーchlorophenyl)propー2ーynー1ーol" Chem.Lett.513-516 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Fumio Toda: "Optical Resolution of Amine NーOxide by Diastereoisomeric Complex Formation with Optically Active Host Compound" Tetrahedron Lett.30. 1841-1844 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Fumio Toda: "Optical Resolution of Pantolactone by Inclusion Crystallization with(R,R)ー(-)ー2,3ーBis(diphenylhydroxymethyl)ー1,4ーdioxaspiro[4.5]decane" Chem.Lett.873-876 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Hiroyuki Nohira: "Optical Resolution of alphaーEthylbenzylamine and Its Application as a Resolving Agent" Bull.Chem.Soc.Jpn.61. 1395-1396 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Mitsutaka Kitamura: "Polymorphism in Crystallization of LーGlutamic Acid" J.Crystal Growth. 96. 541-546 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 戸田芙三夫監修: "包接化合物の基礎と応用" NTS株式会社, 349 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 山中宏,野平博之,戸田芙三夫他: "季刊化学総説「光学異性体の分離」" 日本化学会編,学会出版センタ-, 238 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] F.Toda: J.Org.Chem.53. 308-312 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] F.Toda: Chem.Lett.513-516 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] F.Toda: J.Inclusion Phenomena. 6. 15-30 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] F.Toda: J.Org.Chem.53. 3607-3609 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] F.Toda: Chem.Lett.1755-1758 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] F.Toda: Chem.Lett.1997-2000 (1988)

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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