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Enantioselective synthesis of D-lactic acid via chemocatalysis using MgO: Experimental and molecular-based rationalization of the triose's reactivity and preliminary insights with raw biomass

Applied Catalysis B: Environmental, ISSN: 0926-3373, Vol: 292, Page: 120145
2021
  • 56
    Citations
  • 0
    Usage
  • 12
    Captures
  • 0
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    56
    • Citation Indexes
      56
  • Captures
    12

Article Description

The widespread applications of d -lactic acid (D-LaA) significantly prompted the research of its synthesis from renewable biomass via chemo-catalysis. Herein, we developed a robust but simple MgO- d -LaA system without using extra chiral ligand, achieving the highest LaA yield ∼90 % with ∼75 % enantiomeric excess (ee) value to d -LaA from dihydroxyacetone, glyceraldehyde, and pyruvaldehyde. The experimental and quantum chemistry computational results revealed that MgO and d -LaA presented a pronounced synergetic effect, where pre-added d -LaA provided suitable pH to promote [Mg(OH)(H 2 O) 3 ] + formation, acting as the active species to facilitate the production of pyruvaldehyde, from dihydroxyacetone and glyceraldehyde. d -LaA interacted with Mg II species forming a chiral pocket-like complex, Mg II -2(D-Lactate), which combined to pyruvaldehyde giving the transition state with lower strain energy due to the smaller steric repulsion, thus enabling 1, 2-H shift of hydrated-pyruvaldehyde preferentially via si -face attack, leading to d -LaA. The catalytic system could also be applied for the conversion of raw corn stover.

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