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1989 Fiscal Year Final Research Report Summary

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
KeywordsOptical resolution / Isomer separation / Host-guest complex / Inclusion compound / Optically active host compound / Molecular design / Molecular recognition / Enantio recognition
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.

  • Research Products

    (16 results)

All Other

All Publications (16 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 1993-03-26  

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