Continuous enantioselective hydrogenation of activated ketones on a pt-cd chiral catalyst: Use of h-cube reactor system

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

The Pt-alumina-CD catalyzed enantioselective hydrogenations of ethylpyruvate (EP), ketopantolactone (KPL) and methyl benzoylformate (MBF) have been studied at first in an H-Cube flow hydrogenator in toluene and toluene + acetic acid. Based on the experience of previous studies carried out in batch-reactor and continuous flow systems, some parameters were kept constant (amount of catalyst, 380 mg; substrate concentration, 0.18 mol/L; temperature, 283 K), whereas others, namely chiral modifier (CD) concentration, hydrogen pressure and total liquid flow (TLF: substrate + modifier + solvent) were varied. In the course of enantioselective hydrogenation (R)-products were formed in excess: in the case of EP, KPL, MBF: 90, 60, 80 % enantioselectivities were obtained.

Original languageEnglish
Pages (from-to)391-398
Number of pages8
JournalReaction Kinetics and Catalysis Letters
Volume88
Issue number2
DOIs
Publication statusPublished - Aug 2006

Fingerprint

Toluene
Ketones
ketones
Hydrogenation
hydrogenation
toluene
reactors
catalysts
Catalysts
Aluminum Oxide
Enantioselectivity
liquid flow
Batch reactors
Substrates
acetic acid
Acetic acid
Acetic Acid
Hydrogen
Alumina
aluminum oxides

Keywords

  • Asymmetric
  • Enantioselective
  • Ethyl pyruvate
  • Fixed-bed reactor
  • Hydrogenation
  • Ketopantolactone
  • Methyl benzoylformate
  • Platinum-cinchonidine catalyst

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

@article{646ce0e3ce1f479087221ccb0ff3cef8,
title = "Continuous enantioselective hydrogenation of activated ketones on a pt-cd chiral catalyst: Use of h-cube reactor system",
abstract = "The Pt-alumina-CD catalyzed enantioselective hydrogenations of ethylpyruvate (EP), ketopantolactone (KPL) and methyl benzoylformate (MBF) have been studied at first in an H-Cube flow hydrogenator in toluene and toluene + acetic acid. Based on the experience of previous studies carried out in batch-reactor and continuous flow systems, some parameters were kept constant (amount of catalyst, 380 mg; substrate concentration, 0.18 mol/L; temperature, 283 K), whereas others, namely chiral modifier (CD) concentration, hydrogen pressure and total liquid flow (TLF: substrate + modifier + solvent) were varied. In the course of enantioselective hydrogenation (R)-products were formed in excess: in the case of EP, KPL, MBF: 90, 60, 80 {\%} enantioselectivities were obtained.",
keywords = "Asymmetric, Enantioselective, Ethyl pyruvate, Fixed-bed reactor, Hydrogenation, Ketopantolactone, Methyl benzoylformate, Platinum-cinchonidine catalyst",
author = "G. Sz{\"o}llősi and Be{\'a}ta Herm{\'a}n and F. F{\"u}l{\"o}p and M. Bart{\'o}k",
year = "2006",
month = "8",
doi = "10.1007/s11144-006-0076-5",
language = "English",
volume = "88",
pages = "391--398",
journal = "Reaction Kinetics, Mechanisms and Catalysis",
issn = "1878-5190",
publisher = "Springer Netherlands",
number = "2",

}

TY - JOUR

T1 - Continuous enantioselective hydrogenation of activated ketones on a pt-cd chiral catalyst

T2 - Use of h-cube reactor system

AU - Szöllősi, G.

AU - Hermán, Beáta

AU - Fülöp, F.

AU - Bartók, M.

PY - 2006/8

Y1 - 2006/8

N2 - The Pt-alumina-CD catalyzed enantioselective hydrogenations of ethylpyruvate (EP), ketopantolactone (KPL) and methyl benzoylformate (MBF) have been studied at first in an H-Cube flow hydrogenator in toluene and toluene + acetic acid. Based on the experience of previous studies carried out in batch-reactor and continuous flow systems, some parameters were kept constant (amount of catalyst, 380 mg; substrate concentration, 0.18 mol/L; temperature, 283 K), whereas others, namely chiral modifier (CD) concentration, hydrogen pressure and total liquid flow (TLF: substrate + modifier + solvent) were varied. In the course of enantioselective hydrogenation (R)-products were formed in excess: in the case of EP, KPL, MBF: 90, 60, 80 % enantioselectivities were obtained.

AB - The Pt-alumina-CD catalyzed enantioselective hydrogenations of ethylpyruvate (EP), ketopantolactone (KPL) and methyl benzoylformate (MBF) have been studied at first in an H-Cube flow hydrogenator in toluene and toluene + acetic acid. Based on the experience of previous studies carried out in batch-reactor and continuous flow systems, some parameters were kept constant (amount of catalyst, 380 mg; substrate concentration, 0.18 mol/L; temperature, 283 K), whereas others, namely chiral modifier (CD) concentration, hydrogen pressure and total liquid flow (TLF: substrate + modifier + solvent) were varied. In the course of enantioselective hydrogenation (R)-products were formed in excess: in the case of EP, KPL, MBF: 90, 60, 80 % enantioselectivities were obtained.

KW - Asymmetric

KW - Enantioselective

KW - Ethyl pyruvate

KW - Fixed-bed reactor

KW - Hydrogenation

KW - Ketopantolactone

KW - Methyl benzoylformate

KW - Platinum-cinchonidine catalyst

UR - http://www.scopus.com/inward/record.url?scp=33746035678&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33746035678&partnerID=8YFLogxK

U2 - 10.1007/s11144-006-0076-5

DO - 10.1007/s11144-006-0076-5

M3 - Article

AN - SCOPUS:33746035678

VL - 88

SP - 391

EP - 398

JO - Reaction Kinetics, Mechanisms and Catalysis

JF - Reaction Kinetics, Mechanisms and Catalysis

SN - 1878-5190

IS - 2

ER -