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

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

12 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3363-3368
Number of pages6
JournalStudies in Surface Science and Catalysis
Volume130 D
DOIs
Publication statusPublished - 2000
MoE publication typeA1 Journal article-refereed

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