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Transesterification Catalysts (Onium Salts)

  • School of Engineering/Graduate School of Engineering
  • Department of Molecular and Macromolecular Chemistry
  • Research Group of Molecular Chemistry
  • (Laboratory of Catalysis in Organic Synthesis)

Kazuaki Ishihara [Professor]

http://www.ishihara-lab.net/english/

  • School of Engineering/Graduate School of Engineering
  • Department of Molecular and Macromolecular Chemistry
  • Research Group of Molecular Chemistry
  • (Laboratory of Catalysis in Organic Synthesis)

Manabu Hatano [Associate Professor]

Outline of Seeds

We found trioctylmethylammonium methyl carbonate as a highly active catalyst for the transesterification during the development of our previous lanthanum nitrate-onium salt catalysts. In particular, this ammonium salt catalyst was highly effective for the transesterification of chelatable esters and alcohols. As a result, the ammonium salt catalyst showed higher catalytic activity than the previous lanthanum nitrate-onium salt catalysts and conventional acid or base catalysts for chelatable substrates, and the desired products were obtained in high yields.

Novelty and originality of this research

Our onium methyl carbonate salt catalysts can be used for highly chelatable substrates, which would usually deactivate the catalysts. These catalysts are metal free, non-toxic, and no coloration. General solvents can be used for the transesterifucation. Therefore, our metal free onium methyl carbonate salt catalysts are highly suitable for green catalysis.

Application and research area for Industry collaboration

Syntheis of acrylates and polyesters

Key Takeaway

Metal-free onim salts-catalyzed efficient ester synthesis

Keywords

ester, alcohol, ammonium salt, phosphonum salt

Technologies

  • Synthetic method of esters

Patents

  • JP5167483
  • JP5804472

Monographs, Papers and Articles

  • Manabu Hatano, Yoshiro Furuya, Takumi Shimmura, Katsuhiko Moriyama, Sho Kamiya, Toshikatsu Maki, Kazuaki Ishihara:Org. Lett. 2011, 13(3), 426–429.
  • Manabu Hatano, Sho Kamiya, Katsuhiko Moriyama, Kazuaki Ishihara:Org. Lett. 2011, 13(3), 430–433.
  • Manabu Hatano, Kazuaki Ishihara:Chem. Commun. 2013, 49(20), 1983-1997.