Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/royal-society-of-chemistry/kinetics-and-catalyst-deactivation-in-the-enantioselective-LR15DNtkGI
References (31)
-
T. Mallát, M. Bodmer, A. Baiker (1997)
Enantioselective hydrogenation of trifluoroacetophenone over cinchonidine-modified platinumCatalysis Letters, 44
-
M. Sutyinszki, Kornel Szoeri, K. Felföldi, M. Bartók (2002)
Heterogeneous Asymmetric Reactions. 29. Enantioselective Hydrogenation of Ethyl Benzoylformate over Dihydrocinchonidine-Modified Platinum–Alumina Catalyst in Acetic AcidCatalysis Letters, 81
-
M. Sutyinszki, Kornél Szőri, K. Felföldi, M. Bartók (2002)
98% Enantioselectivity in the asymmetric synthesis of a useful chiral building block by heterogeneous method: Enantioselective hydrogenation of ethyl-benzoylformate over cinchona modified Pt/Al2O3 catalysts in the acetic acidCatalysis Communications, 3
-
M. Bartók, K. Felföldi, B. Török, T. Bartók (1998)
A new cinchona-modified platinum catalyst for the enantioselective hydrogenation of pyruvate: the structure of the 1:1 alkaloid–reactant complexChemical Communications
-
E. Toukoniitty, B. Ševčíková, P. Mäki-Arvela, J. Wärnå, T. Salmi, D. Murzin (2003)
Kinetics and modeling of 1-phenyl-1,2-propanedione hydrogenationJournal of Catalysis, 213
-
Zhen Ma, F. Zaera (2005)
Role of the solvent in the adsorption-desorption equilibrium of cinchona alkaloids between solution and a platinum surface: correlations among solvent polarity, cinchona solubility, and catalytic performance.The journal of physical chemistry. B, 109 1
-
E. Toukoniitty, P. Mäki-Arvela, Narendra Kumar, T. Salmi, D. Murzin (2003)
Influence of mass transfer on regio- and enantioselectivity in hydrogenation of 1-phenyl-1,2-propanedione over modified Pt catalystsCatalysis Today, 79
-
Erik Schmidt, C. Bucher, Gianluca Santarossa, T. Mallát, R. Gilmour, A. Baiker (2012)
Fundamental insights into the enantioselectivity of hydrogenations on cinchona-modified platinum and palladiumJournal of Catalysis, 289
-
H. Lieske, G. Lietz, H. Spindler, J. Völter (1983)
Reactions of platinum in oxygen- and hydrogen-treated Ptγ-Al2O3 catalysts: I. Temperature-programmed reduction, adsorption, and redispersion of platinumJournal of Catalysis, 81
-
H. Blaser, H. Jalett, M. Garland, M. Studer, H. Thies, Amina Wirth-Tijani (1998)
Kinetic Studies of the Enantioselective Hydrogenation of Ethyl Pyruvate Catalyzed by a Cinchona Modified Pt/Al2O3CatalystJournal of Catalysis, 173
-
A. Baiker (1997)
Progress in asymmetric heterogeneous catalysis: Design of novel chirally modified platinum metal catalystsJournal of Molecular Catalysis A-chemical, 115
-
D. Murzin (1997)
Kinetic modeling of enantioselective hydrogenationIndustrial & Engineering Chemistry Research, 36
-
M. Schürch, O. Schwalm, T. Mallát, J. Weber, A. Baiker (1997)
Enantioselective Hydrogenation of KetopantolactoneJournal of Catalysis, 169
-
U. Böhmer, F. Franke, K. Morgenschweis, T. Bieber, W. Reschetilowski (2000)
Enantioselective hydrogenation of ethyl pyruvate: Long-term performance of chirally modified Pt/zeolite catalystsCatalysis Today, 60
-
H. Blaser, H. Jalett, J. Wiehl (1991)
Enantioselective hydrogenation of α-ketoesters with cinchona-modified platinum catalysts : effect of acidic and basic solvents and additivesJournal of Molecular Catalysis, 68
-
M. Arx, T. Mallát, A. Baiker (2000)
First enantioselective hydrogenation of a trifluoro-β-ketoester with cinchona-modified platinumJournal of Catalysis, 193
-
H. Blaser, H. Jalett, M. Muller, M. Studer (1997)
Enantioselective hydrogenation of α-ketoesters using cinchona modified platinum catalysts and related systems: A reviewCatalysis Today, 37
-
W.-R. Huck, T. Bürgi, T. Mallát, A. Baiker (2003)
Asymmetric hydrogenation on platinum: nonlinear effect of coadsorbed cinchona alkaloids on enantiodifferentiationJournal of Catalysis, 216
-
Lyndsey Baldyga (2012)
Effect of Platinum Particle Size on the Sulfur Deactivation of Hydrogenation Catalysts -
N. Kuenzle, A. Szabó, M. Schürch, Guozhi Wang (1998)
Enantioselective hydrogenation of a cyclic imidoketone over chirally modified Pt/Al2O3Chemical Communications
-
V. Morawsky, U. Prüße, L. Witte, K. Vorlop (2000)
Transformation of cinchonidine during the enantioselective hydrogenation of ethyl pyruvate to ethyl lactateCatalysis Communications, 1
-
E. Toukoniitty, P. Mäki-Arvela, M. Kuzma, A. Villela, A. Neyestanaki, T. Salmi, R. Sjöholm, R. Leino, E. Laine, D. Murzin (2001)
Enantioselective Hydrogenation of 1-Phenyl-1,2-propanedioneJournal of Catalysis, 204
-
M. Bartók, K. Balázsik, G. Szöllösi, T. Bartók (2001)
Solvent and support effects in the case of acetic acid and alumina: Oxonium cations in asymmetric hydrogenation of ethyl pyruvate over dihydrocinchonidine modified platinumCatalysis Communications, 2
-
C. LeBlond, Jian Wang, J. Liu, A. Andrews, Yong-kui Sun (1999)
Highly Enantioselective Heterogeneously Catalyzed Hydrogenation of α-Ketoesters under Mild ConditionsJournal of the American Chemical Society, 121
-
M. Schürch, N. Kuenzle, T. Mallát, A. Baiker (1998)
Enantioselective Hydrogenation of Ketopantolactone: Effect of Stereospecific Product Crystallization during ReactionJournal of Catalysis, 176
-
A. Tokarev, A. Kirilin, E. Murzina, K. Eränen, L. Kustov, D. Murzin, J. Mikkola (2010)
The role of bio-ethanol in aqueous phase reforming to sustainable hydrogenInternational Journal of Hydrogen Energy, 35
-
M. Studer, S. Burkhardt, H. Blaser (1999)
Enantioselective hydrogenation of α-keto acetals with cinchona modified Pt catalystChemical Communications
-
E. Toukoniitty, J. Wärnå, D. Murzin, T. Salmi (2010)
Modelling of transient kinetics in catalytic three-phase reactors: Enantioselective hydrogenationChemical Engineering Science, 65
-
J. Wehrli, A. Baiker, D. Monti, H. Blaser (1990)
Enantioselective hydrogenation of α-ketoesters : preparation and catalytic behavior of different alumina-supported platinum catalysts modified with cinchonidineJournal of Molecular Catalysis, 61
-
M. Bartók, G. Szöllösi, K. Balázsik, T. Bartók (2002)
Heterogeneous asymmetric reactions: Part 25. On the pretreatment and prehydrogenation of Pt-alumina catalyst in the hydrogenation of ethyl pyruvate☆Journal of Molecular Catalysis A-chemical, 177
-
Q. Shao, Liangliang Huang, Jian Zhou, Linghong Lu, Luzheng Zhang, Xiaohua Lu, Shaoyi Jiang, K. Gubbins, Yudan Zhu, Wenfeng Shen (2007)
Molecular dynamics study on diameter effect in structure of ethanol molecules confined in single-walled carbon nanotubesJournal of Physical Chemistry C, 111
- Publisher
- Royal Society of Chemistry
- Copyright
- This journal is © The Royal Society of Chemistry
- ISSN
- 2044-4753
- eISSN
- 2044-4761
- DOI
- 10.1039/c3cy00548h
- Publisher site
- See Article on Publisher Site
Abstract
The enantioselective hydrogenation of ethyl benzoylformate (EBF) to (R)-ethyl mandelate over (−)-cinchonidine (CD)-modified Pt/Al2O3 catalyst in toluene in a semi-batch reactor was studied as a function of modifier concentration, reaction temperature, stirring rate and catalyst particle size. The kinetic results showed higher enantioselectivity and lower initial rates tending asymptotically to a constant value as the amount of modifier increased. The maximum enantiomeric excess (ee) and the initial hydrogenation rate or turnover frequency obtained under optimized conditions with an initial concentration of 5.6 mmol L−1 EBF at 25 °C over 5% (w/w) Pt/Al2O3 were 85% (modifier-to-surface Pt of 1.28) and 109 h−1 (modifier-to-surface Pt of 0.16), respectively. Additionally, catalyst deactivation due to the presence of impurities in the feed was prominent in some cases; therefore activated carbon was used as a cleaning agent of the raw material to remove impurities prior to catalyst addition.
Journal
Catalysis Science & Technology – Royal Society of Chemistry
Published: Dec 4, 2013