Catalyst selection and solvent effects in the enantioselective hydrogenation of 1-phenyl-1,2-propanedione

E. Toukoniitty*, P. Mäki-Arvela, A. Kalantar Neyestanaki, T. Salmi, A. Villela, R. Leino, R. Sjöholm, E. Laine, J. Väyrynen, T. Ollonqvist

*Korresponderande författare för detta arbete

Forskningsoutput: TidskriftsbidragArtikelVetenskapligPeer review

12 Citeringar (Scopus)

Sammanfattning

1-Phenyl-1,2-propanedione was hydrogenated at 5 bar and 25 °C over Pt/Al2O3 catalysts in the presence of cinchonidine. The effect of four different solvents, ethyl acetate, toluene, ethanol and dichloromethane in the enantioselective hydrogenation of the dione was tested. The highest enantiomeric excess of (R)-1-hydroxy-1-phenyl-2-propanone, 65 %, was obtained in dichloromethane. Also toluene and ethyl acetate gave relatively high enantiomeric excesses. In ethanol, which highly interacts with Pt surface, the enantiomeric excess was only 12 %. Two different alumina supports and Pt-precursors were investigated using ethyl acetate as solvent. The highest enantiomeric excesses of (R)-1-hydroxy-1-phenyl-2-propanone were obtained with α-Al2O3 supported Pt catalyst prepared from hydrogen hexachloroplatinate(IV)hydrate precursor. The highest Pt loadings in the catalyst preferred enantiodifferentiation. Higher enantiomeric excesses were obtained by increasing the mean metal particle size of Pt.

OriginalspråkEngelska
Sidor (från-till)3363-3368
Antal sidor6
TidskriftStudies in Surface Science and Catalysis
Volym130 D
DOI
StatusPublicerad - 2000
MoE-publikationstypA1 Tidskriftsartikel-refererad

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