Browsing by Author "Nayak, M.K."

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    Efficient Preparation of the Esters of Biomass-Derived Isohexides by Base-Catalyzed Transesterification under Solvent-Free Conditions
    (American Chemical Society, 2023) Bhat, N.S.; Vinod, N.; Tarafder, K.; Nayak, M.K.; Jana, A.; Mal, S.S.; Dutta, S.
    The monoesters and diesters of glucose-derived isosorbide (IS) have potential applications as sustainable dispersants, surfactants, emulsifiers, monomer units for polymers, and plasticizers. This work reports a solvent-free, high-yielding, and scalable pathway for producing the monoesters and diesters of IS by a transesterification reaction using K2CO3 as an efficient, inexpensive, and recyclable base catalyst. In the case of monoesters, the selectivity toward the exo-monoester of IS was found higher than that toward the endo-monoester. The methodology was successfully extended to synthesize the monoesters and diesters of isomannide and isoidide. The gram-scale preparation of alkyl, vinyl, and aryl esters of isohexides was optimized on the reaction temperature, duration, equivalence of the ester reagent, and catalyst loading. Under optimized conditions (50 mol % K2CO3, 180 °C, 6 h), various aryl and alkyl esters of the isohexides were isolated in satisfactory yields. The unsymmetrical diesters of the isohexides were conveniently synthesized by stepwise transesterification. © 2023 American Chemical Society.