1. HOME
  2. Transesterification Catalysts (La(III))

Transesterification Catalysts (La(III))

  • 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

A facile, atom-economical, and chemoselective esterification is crucial in modern organic synthesis, particularly in the areas of pharmaceutical, polymer, and material science. We developed a highly active dinuclear La(III) catalyst, which is prepared in situ from lanthanum(III) isopropoxide and 2-(2-methoxyethoxy)ethanol. This catalyst is effective for the practical transesterification of methyl carboxylates, ethyl acetate, weakly reactive dimethyl carbonate, and much less-reactive methyl carbamates with primary, secondary, and tertiary alcohols. As the second generation, nearly neutral lanthanum(III) nitrate alkoxide has been developed. This catalyst is prepared in situ from inexpensive, stable, low-toxic lanthanum(III) nitrate hydrate and methyltrioctylphosphonium methyl carbonate, and is highly useful in the non-epimerized transesterification of alpha-substituted chiral carboxylic esters. Large-scale synthesis without the need for inconvenient work-up or careful purification procedures can be realized.

Novelty and originality of this research

Our lanthanum(III) catalysts could be used for not only carboxylic esters but also dimethyl carbonates and methyl carbamates. Moreover, our lanthanum(III) catalysts could be used for much less reactive tertiary alcohols rather than primary and secondary alcohols. Our lanthanum(III) catalysts have no toxicity and no problem of coloration. Recovery and reuse of catalysts can be realized.

Application and research area for Industry collaboration

Syntheis of acrylates, urethane, and polyesters

Key Takeaway

Lanthanun(III)-catalyzed efficient ester synthesis

Keywords

ester, alcohol, lanthanam, 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.