New phenomenon in competitive hydrogenation of binary mixtures of activated ketones over unmodified and cinchonidine-modified Pt/alumina catalyst

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Abstract

Competitive hydrogenations of eight binary mixtures of ethyl pyruvate (EP), methyl benzoylformate (MBF), ketopantolactone (KPL), pyruvic aldehyde dimethyl acetal (PA) and trifluoroacetophenone (TFAP) on platinum/alumina catalysts unmodified (racemic hydrogenation) and modified by cinchonidine (chiral hydrogenation) were studied under the experimental conditions of the Orito reaction. Reaction rates of chiral and racemic hydrogenations were determined and relative adsorption coefficients were calculated. In the competitive chiral hydrogenation of EP + MBF, EP + TFAP and KPL + MBF binary mixtures a new phenomenon was observed: namely the EP and KPL are hydrogenated faster than MBF and TFAP, whereas in racemic one the MBF and TFAP are hydrogenated faster than EP or KPL. Effects of the activated ketones structure on their reactivity and the stability of the surface complexes are discussed. It was found that differences in rate enhancement are caused by the differences both in the adsorptivity and in the reactivity of adsorbed substrates and adsorbed intermediate complexes.

Original languageEnglish
Pages (from-to)1410-1414
Number of pages5
JournalCatalysis Communications
Volume12
Issue number15
DOIs
Publication statusPublished - Sep 15 2011

Fingerprint

Aluminum Oxide
Binary mixtures
Ketones
Hydrogenation
Alumina
Catalysts
Pyruvaldehyde
Platinum
Aldehydes
Reaction rates
ethyl pyruvate
cinchonidine
phenylglyoxylic acid
Adsorption
keto-pantoyllactone
Substrates

Keywords

  • Activated ketones
  • Binary mixtures
  • Cinchonidine
  • Competitive hydrogenation
  • Enantioselective
  • Platinum

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Chemistry(all)

Cite this

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title = "New phenomenon in competitive hydrogenation of binary mixtures of activated ketones over unmodified and cinchonidine-modified Pt/alumina catalyst",
abstract = "Competitive hydrogenations of eight binary mixtures of ethyl pyruvate (EP), methyl benzoylformate (MBF), ketopantolactone (KPL), pyruvic aldehyde dimethyl acetal (PA) and trifluoroacetophenone (TFAP) on platinum/alumina catalysts unmodified (racemic hydrogenation) and modified by cinchonidine (chiral hydrogenation) were studied under the experimental conditions of the Orito reaction. Reaction rates of chiral and racemic hydrogenations were determined and relative adsorption coefficients were calculated. In the competitive chiral hydrogenation of EP + MBF, EP + TFAP and KPL + MBF binary mixtures a new phenomenon was observed: namely the EP and KPL are hydrogenated faster than MBF and TFAP, whereas in racemic one the MBF and TFAP are hydrogenated faster than EP or KPL. Effects of the activated ketones structure on their reactivity and the stability of the surface complexes are discussed. It was found that differences in rate enhancement are caused by the differences both in the adsorptivity and in the reactivity of adsorbed substrates and adsorbed intermediate complexes.",
keywords = "Activated ketones, Binary mixtures, Cinchonidine, Competitive hydrogenation, Enantioselective, Platinum",
author = "K. Bal{\'a}zsik and K. Sz{\"o}ri and G. Sz{\"o}llősi and M. Bart{\'o}k",
year = "2011",
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language = "English",
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T1 - New phenomenon in competitive hydrogenation of binary mixtures of activated ketones over unmodified and cinchonidine-modified Pt/alumina catalyst

AU - Balázsik, K.

AU - Szöri, K.

AU - Szöllősi, G.

AU - Bartók, M.

PY - 2011/9/15

Y1 - 2011/9/15

N2 - Competitive hydrogenations of eight binary mixtures of ethyl pyruvate (EP), methyl benzoylformate (MBF), ketopantolactone (KPL), pyruvic aldehyde dimethyl acetal (PA) and trifluoroacetophenone (TFAP) on platinum/alumina catalysts unmodified (racemic hydrogenation) and modified by cinchonidine (chiral hydrogenation) were studied under the experimental conditions of the Orito reaction. Reaction rates of chiral and racemic hydrogenations were determined and relative adsorption coefficients were calculated. In the competitive chiral hydrogenation of EP + MBF, EP + TFAP and KPL + MBF binary mixtures a new phenomenon was observed: namely the EP and KPL are hydrogenated faster than MBF and TFAP, whereas in racemic one the MBF and TFAP are hydrogenated faster than EP or KPL. Effects of the activated ketones structure on their reactivity and the stability of the surface complexes are discussed. It was found that differences in rate enhancement are caused by the differences both in the adsorptivity and in the reactivity of adsorbed substrates and adsorbed intermediate complexes.

AB - Competitive hydrogenations of eight binary mixtures of ethyl pyruvate (EP), methyl benzoylformate (MBF), ketopantolactone (KPL), pyruvic aldehyde dimethyl acetal (PA) and trifluoroacetophenone (TFAP) on platinum/alumina catalysts unmodified (racemic hydrogenation) and modified by cinchonidine (chiral hydrogenation) were studied under the experimental conditions of the Orito reaction. Reaction rates of chiral and racemic hydrogenations were determined and relative adsorption coefficients were calculated. In the competitive chiral hydrogenation of EP + MBF, EP + TFAP and KPL + MBF binary mixtures a new phenomenon was observed: namely the EP and KPL are hydrogenated faster than MBF and TFAP, whereas in racemic one the MBF and TFAP are hydrogenated faster than EP or KPL. Effects of the activated ketones structure on their reactivity and the stability of the surface complexes are discussed. It was found that differences in rate enhancement are caused by the differences both in the adsorptivity and in the reactivity of adsorbed substrates and adsorbed intermediate complexes.

KW - Activated ketones

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KW - Competitive hydrogenation

KW - Enantioselective

KW - Platinum

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