Enantioselective hydrogenation of (E)-2-methyl-2-butenoic acid over cinchonidine modified Pd catalyst. Effect of the structure of achiral amine additives

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Abstract

The effect of the structure of the achiral primary amine additive on the enantioselective heterogeneous catalytic hydrogenation of (E)-2-methyl-2- butenoic acid over cinchonidine modified Pd/Al2O3 was studied. It was found that a variety of amines increase the enantioselectivity, which was always accompanied by decrease in the initial rate of the hydrogenations. Based on these results, the participation of the amine additive in the formation of the intermediate complex responsible for enantioselection was suggested. A decrease in the reaction temperature resulted in further increase in the optical purity of the product up to 67%, the highest value reported in the hydrogenation of unsaturated aliphatic acids in this heterogeneous catalytic system so far.

Original languageEnglish
Pages (from-to)319-325
Number of pages7
JournalReaction Kinetics and Catalysis Letters
Volume96
Issue number2
DOIs
Publication statusPublished - Apr 2009

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Crotonates
Hydrogenation
hydrogenation
Amines
amines
catalysts
acids
Catalysts
Acids
Enantioselectivity
purity
Fatty Acids
products
cinchonidine
Temperature
temperature

Keywords

  • (E)-2-methyl-2- butenoic acid
  • Amine additive
  • Cinchonidine
  • Enantioselective catalytic hydrogenation
  • Palladium

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

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title = "Enantioselective hydrogenation of (E)-2-methyl-2-butenoic acid over cinchonidine modified Pd catalyst. Effect of the structure of achiral amine additives",
abstract = "The effect of the structure of the achiral primary amine additive on the enantioselective heterogeneous catalytic hydrogenation of (E)-2-methyl-2- butenoic acid over cinchonidine modified Pd/Al2O3 was studied. It was found that a variety of amines increase the enantioselectivity, which was always accompanied by decrease in the initial rate of the hydrogenations. Based on these results, the participation of the amine additive in the formation of the intermediate complex responsible for enantioselection was suggested. A decrease in the reaction temperature resulted in further increase in the optical purity of the product up to 67{\%}, the highest value reported in the hydrogenation of unsaturated aliphatic acids in this heterogeneous catalytic system so far.",
keywords = "(E)-2-methyl-2- butenoic acid, Amine additive, Cinchonidine, Enantioselective catalytic hydrogenation, Palladium",
author = "G. Sz{\"o}llősi and Zsolt Makra and M. Bart{\'o}k",
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T1 - Enantioselective hydrogenation of (E)-2-methyl-2-butenoic acid over cinchonidine modified Pd catalyst. Effect of the structure of achiral amine additives

AU - Szöllősi, G.

AU - Makra, Zsolt

AU - Bartók, M.

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N2 - The effect of the structure of the achiral primary amine additive on the enantioselective heterogeneous catalytic hydrogenation of (E)-2-methyl-2- butenoic acid over cinchonidine modified Pd/Al2O3 was studied. It was found that a variety of amines increase the enantioselectivity, which was always accompanied by decrease in the initial rate of the hydrogenations. Based on these results, the participation of the amine additive in the formation of the intermediate complex responsible for enantioselection was suggested. A decrease in the reaction temperature resulted in further increase in the optical purity of the product up to 67%, the highest value reported in the hydrogenation of unsaturated aliphatic acids in this heterogeneous catalytic system so far.

AB - The effect of the structure of the achiral primary amine additive on the enantioselective heterogeneous catalytic hydrogenation of (E)-2-methyl-2- butenoic acid over cinchonidine modified Pd/Al2O3 was studied. It was found that a variety of amines increase the enantioselectivity, which was always accompanied by decrease in the initial rate of the hydrogenations. Based on these results, the participation of the amine additive in the formation of the intermediate complex responsible for enantioselection was suggested. A decrease in the reaction temperature resulted in further increase in the optical purity of the product up to 67%, the highest value reported in the hydrogenation of unsaturated aliphatic acids in this heterogeneous catalytic system so far.

KW - (E)-2-methyl-2- butenoic acid

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KW - Cinchonidine

KW - Enantioselective catalytic hydrogenation

KW - Palladium

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