Continuous hydrogenation of 1-phenyl-1,2-propanedione under transient and steady-state conditions: Regioselectivity, enantioselectivity and catalyst deactivation

E. Toukoniitty, P. Mäki-Arvela, A. Kalantar Neyestanaki, T. Salmi, D. Yu Murzin*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

26 Citations (Scopus)

Abstract

Continuous enantioselective hydrogenation of 1-phenyl-1,2-propanedione was investigated at 25 °C and 5 bar H2 over a knitted Pt silica fiber catalyst modified with cinchonidine. The main reaction parameters were the reactant and modifier concentrations, the liquid space time and the pre-treatment of the catalyst. The initial hydrogen uptake rate decreased about 25-45% within 20 min time-on-stream. The catalyst deactivation was quantitatively described with a mechanistic model, which assumed that the deactivation is of first-order in reactant concentration. The amount of modifier did not affect the reaction rate. The steady-state regioselectivity of 1-hydroxy-1-phenylpropanone and enantioselectivity of the main product, (R)-1-hydroxy-1-phenylpropanone, were independent of reactant inlet concentration and space time. The enantioselectivity of the main product, (R)-1-hydroxy-1-phenylpropanone, increased from zero to the highest enantiomeric excess (ee = 60%) with increasing time-on-stream, after which it attained a steady-state value, dependent on the modifier concentration. Continuous feeding of the modifier was necessary to maintain a constant ee.

Original languageEnglish
Pages (from-to)125-138
Number of pages14
JournalApplied Catalysis A: General
Volume235
Issue number1-2
DOIs
Publication statusPublished - 30 Aug 2002
MoE publication typeA1 Journal article-refereed

Keywords

  • Continuous liquid-phase hydrogenation
  • Deactivation
  • Dione
  • Fibre catalyst

Fingerprint Dive into the research topics of 'Continuous hydrogenation of 1-phenyl-1,2-propanedione under transient and steady-state conditions: Regioselectivity, enantioselectivity and catalyst deactivation'. Together they form a unique fingerprint.

Cite this