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Microfluidic Chip Reactor and the Stereoselective Hydrogenation of Methylacetoacetate over (R)-Ru-BINAP in the [N8222][Tf2N]/Methanol/ Water Mixed Phase.

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    0474317 - ÚCHP 2018 RIV CH eng J - Článek v odborném periodiku
    Klusoň, Petr - Stavárek, Petr - Pěnkavová, Věra - Vychodilová, Hana - Hejda, Stanislav - Bendová, Magdalena
    Microfluidic Chip Reactor and the Stereoselective Hydrogenation of Methylacetoacetate over (R)-Ru-BINAP in the [N8222][Tf2N]/Methanol/ Water Mixed Phase.
    Chemical Engineering and Processing: Process Intensification. Roč. 115, May (2017), s. 39-46. ISSN 0255-2701
    Grant CEP: GA ČR GA15-04790S
    Institucionální podpora: RVO:67985858
    Klíčová slova: stereoselectivity * microfluidic chip * ionic liquids
    Kód oboru RIV: CI - Průmyslová chemie a chemické inženýrství
    Obor OECD: Chemical process engineering
    Impakt faktor: 2.826, rok: 2017

    Homogeneous asymmetric catalysts represented by organometallics of transition elements reveal very high activity and stereoselectivity in asymmetric hydrogenation of b-ketoesters. Recently, it appeared efficient to use ionic liquids of the [NR222][Tf2N] type for accommodation of the chiral catalytic complex. Even on the industrial scale it is becoming attractive to carry out hydrogenations with such immobilised complexes in a continuous regime in microreactors. Attention was paid to the stereoselective hydrogenation of methylacetoacetate (MAA) to isomeric (R)_(+) or (S)_(_)-methyl-3-hydroxybuta- noates over a chiral ([RuCl((R)-BINAP)(p-cymene)]Cl) complex immobilised in the mixed [N8222][Tf2N]/ methanol/water solvent phase, and performed inside of a microfluidic chip reactor. It was shown that the reaction could be successfully carried out in such an arrangement with a very high enantioselectivity (above 99%) and at very high conversion of MAA (above 97%). It was proven that the participation of a specific solvent (methanol or the mixture [N8222][Tf2N]/methanol/water) essentially influences the mechanism of the reaction. The solvents actively participate in the re-coordination of the catalytic complex in a series of reactions which is reflected in the values of reaction enthalpies. The specific process output was also evaluated.
    Trvalý link: http://hdl.handle.net/11104/0271418
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