Selectivity Control in the Oxidative Ring-Opening of Dimethylfuran Mediated by Zeolitic-Imidazolate Framework-8 Nanoparticles

The conversion of biomass-derived furans to synthetically valuable chemicals is highly desirable but it remains a formidable challenge with regard to product selectivity, particularly in oxidative reactions. For example, the oxidative ring-opening of 2,5-dimethylfuran (DMF) using hydrogen peroxide as the oxidant proceeds in a nonselective manner, resulting in a multicomponent mixture along with the target compound (3-hexene-2,5-dione). In this work, we address the selectivity issue with a simple and efficient approach using zeolitic-imidazolate framework-8 nanoparticles (ZIF-8 NPs) as selectivity mediators on the base of their unique ordered structure. A quantitative conversion of DMF with 85% of selectivity to the target 3-hexene-2,5-dione (in comparison to 27% selectivity in the blank reaction) was achieved in the presence of ZIF-8 NPs, and importantly, under mild conditions (60 °C, and methanol as solvent). Furthermore, computational studies based on the chemisorption models of ZIF-8 demonstrated a plausible explanation of the observed selectivity. This work may pave the way toward the development of alternative and cost-effective strategies to improve product selectivity in biomass conversion with a view of green and sustainable developments in the chemical industry. ©

Franco A.1 , Negi A.1, 2 , Luque R. 1, 3 , Carrillo-Carrión C.1
American Chemical Society
  • 1 Department of Organic Chemistry, University of Córdoba, Campus de Rabanales, Ctra. Nacional IV-A Km. 396, Córdoba, E-14014, Spain
  • 2 KelAda Pharmachem Ltd., A1.01, Science Centre South, Belfield, Dublin 4, Ireland
  • 3 Peoples Friendship University of Russia (RUDN University), 6 Miklukho Maklaya Str., Moscow, 117198, Russian Federation
Ключевые слова
furans; metal-organic framework (MOF); nanoscale MOF; ring-opening; selectivity; zeolitic-imidazolate framework-8 (ZIF-8)
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