Enanntioselective hydrogenation using cinchona-modified Pt/y-Al2O3 catalyst: comparison of the reaction of ethyl pyruvate and buta-2,3-dione

L. Xiabao, N. F. Drummer, R. L. Jenkins, Richard Peter Kerwin Wells, P. B. Wells, D. J. Willock, S. H. Taylor, P. Johnston, G. J. Hutchings

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The enantioselective hydrogenation of buta-2,3-dione to 3-hydroxy-buta-2-one and ethyl pyruvate to ethyl lactate are compared using cinchona-modified Pt/gamma-Al2O3 catalysts. The reactions were carried out in a range of solvents and both reactants gave the same linear relationship between enantiomeric excess ( e. e.) and the dielectric constant of the solvent. The e. e. for the 3-hydroxybuta-2- one is lower than that for ethyl pyruvate. For both reactants there is an optimal concentration of the cinchona modi. er but the optimal concentration required for the hydrogenation of buta-2,3-dione is approximately an order of magnitude higher than that required for the hydrogenation of ethyl pyruvate. The hydrogenation of buta-2,3-dione in acetic acid as solvent leads to a suppression in the e. e. with an enhancement in rate, whereas the reaction of ethyl pyruvate in acetic acid leads to an enhancement in e. e. The e. e. for 3-hydroxy-buta-2-one formation is independent of conversion in the initial period of the reaction which contrasts markedly with the observed initial induction period for ethyl lactate formation. The results are discussed in terms of the interaction of the reactants with the cinchona alkaloid adsorbed on the Pt surface.

Original languageEnglish
Pages (from-to)147-151
Number of pages4
JournalCatalysis Letters
Volume96
DOIs
Publication statusPublished - 2004

Keywords

  • enantioselective hydrogenation
  • ethyl pyruvate
  • buta-2,3-dione
  • cinchonidine-modified Pt catalyst
  • cinchonine-modified Pt catalyst
  • INITIAL TRANSIENT PERIOD
  • PLATINUM SILICA EUROPT-1
  • ASYMMETRIC HYDROGENATION
  • HETEROGENEOUS CATALYSIS
  • ALPHA-KETOESTERS
  • NICKEL-CATALYST
  • OPTICAL YIELD
  • CONVERSION
  • PD
  • SELECTIVITY

Cite this

Enanntioselective hydrogenation using cinchona-modified Pt/y-Al2O3 catalyst: comparison of the reaction of ethyl pyruvate and buta-2,3-dione. / Xiabao, L.; Drummer, N. F.; Jenkins, R. L.; Wells, Richard Peter Kerwin; Wells, P. B.; Willock, D. J.; Taylor, S. H.; Johnston, P.; Hutchings, G. J.

In: Catalysis Letters, Vol. 96, 2004, p. 147-151.

Research output: Contribution to journalArticle

Xiabao, L. ; Drummer, N. F. ; Jenkins, R. L. ; Wells, Richard Peter Kerwin ; Wells, P. B. ; Willock, D. J. ; Taylor, S. H. ; Johnston, P. ; Hutchings, G. J. / Enanntioselective hydrogenation using cinchona-modified Pt/y-Al2O3 catalyst: comparison of the reaction of ethyl pyruvate and buta-2,3-dione. In: Catalysis Letters. 2004 ; Vol. 96. pp. 147-151.
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abstract = "The enantioselective hydrogenation of buta-2,3-dione to 3-hydroxy-buta-2-one and ethyl pyruvate to ethyl lactate are compared using cinchona-modified Pt/gamma-Al2O3 catalysts. The reactions were carried out in a range of solvents and both reactants gave the same linear relationship between enantiomeric excess ( e. e.) and the dielectric constant of the solvent. The e. e. for the 3-hydroxybuta-2- one is lower than that for ethyl pyruvate. For both reactants there is an optimal concentration of the cinchona modi. er but the optimal concentration required for the hydrogenation of buta-2,3-dione is approximately an order of magnitude higher than that required for the hydrogenation of ethyl pyruvate. The hydrogenation of buta-2,3-dione in acetic acid as solvent leads to a suppression in the e. e. with an enhancement in rate, whereas the reaction of ethyl pyruvate in acetic acid leads to an enhancement in e. e. The e. e. for 3-hydroxy-buta-2-one formation is independent of conversion in the initial period of the reaction which contrasts markedly with the observed initial induction period for ethyl lactate formation. The results are discussed in terms of the interaction of the reactants with the cinchona alkaloid adsorbed on the Pt surface.",
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AU - Xiabao, L.

AU - Drummer, N. F.

AU - Jenkins, R. L.

AU - Wells, Richard Peter Kerwin

AU - Wells, P. B.

AU - Willock, D. J.

AU - Taylor, S. H.

AU - Johnston, P.

AU - Hutchings, G. J.

PY - 2004

Y1 - 2004

N2 - The enantioselective hydrogenation of buta-2,3-dione to 3-hydroxy-buta-2-one and ethyl pyruvate to ethyl lactate are compared using cinchona-modified Pt/gamma-Al2O3 catalysts. The reactions were carried out in a range of solvents and both reactants gave the same linear relationship between enantiomeric excess ( e. e.) and the dielectric constant of the solvent. The e. e. for the 3-hydroxybuta-2- one is lower than that for ethyl pyruvate. For both reactants there is an optimal concentration of the cinchona modi. er but the optimal concentration required for the hydrogenation of buta-2,3-dione is approximately an order of magnitude higher than that required for the hydrogenation of ethyl pyruvate. The hydrogenation of buta-2,3-dione in acetic acid as solvent leads to a suppression in the e. e. with an enhancement in rate, whereas the reaction of ethyl pyruvate in acetic acid leads to an enhancement in e. e. The e. e. for 3-hydroxy-buta-2-one formation is independent of conversion in the initial period of the reaction which contrasts markedly with the observed initial induction period for ethyl lactate formation. The results are discussed in terms of the interaction of the reactants with the cinchona alkaloid adsorbed on the Pt surface.

AB - The enantioselective hydrogenation of buta-2,3-dione to 3-hydroxy-buta-2-one and ethyl pyruvate to ethyl lactate are compared using cinchona-modified Pt/gamma-Al2O3 catalysts. The reactions were carried out in a range of solvents and both reactants gave the same linear relationship between enantiomeric excess ( e. e.) and the dielectric constant of the solvent. The e. e. for the 3-hydroxybuta-2- one is lower than that for ethyl pyruvate. For both reactants there is an optimal concentration of the cinchona modi. er but the optimal concentration required for the hydrogenation of buta-2,3-dione is approximately an order of magnitude higher than that required for the hydrogenation of ethyl pyruvate. The hydrogenation of buta-2,3-dione in acetic acid as solvent leads to a suppression in the e. e. with an enhancement in rate, whereas the reaction of ethyl pyruvate in acetic acid leads to an enhancement in e. e. The e. e. for 3-hydroxy-buta-2-one formation is independent of conversion in the initial period of the reaction which contrasts markedly with the observed initial induction period for ethyl lactate formation. The results are discussed in terms of the interaction of the reactants with the cinchona alkaloid adsorbed on the Pt surface.

KW - enantioselective hydrogenation

KW - ethyl pyruvate

KW - buta-2,3-dione

KW - cinchonidine-modified Pt catalyst

KW - cinchonine-modified Pt catalyst

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KW - PLATINUM SILICA EUROPT-1

KW - ASYMMETRIC HYDROGENATION

KW - HETEROGENEOUS CATALYSIS

KW - ALPHA-KETOESTERS

KW - NICKEL-CATALYST

KW - OPTICAL YIELD

KW - CONVERSION

KW - PD

KW - SELECTIVITY

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DO - 10.1023/B:CATL.0000030112.70608.a0

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VL - 96

SP - 147

EP - 151

JO - Catalysis Letters

JF - Catalysis Letters

SN - 1011-372X

ER -