Selective Oxygenation of 3,4‐Dihydro‐2H‐Pyran to 5,6‐Dihydro‐2H‐Pyran‐2‐One With Pd/C Catalyst and Molecular Oxygen
Naoki Kawabata, Mizuho Yabushita, Keiichi Tomishige, Yoshinao Nakagawa
TL;DR
Scientists developed a method to efficiently convert a compound from plant material into a valuable chemical using a reusable catalyst and oxygen.
Contribution
A reusable Pd/C catalyst with base addition was found to selectively produce 5,6-dihydro-2H-pyran-2-one from lignocellulose-derived furfural with 52% yield.
Findings
Pd/C catalyst with NaHCO3 base achieved 52% yield of 5,6-dihydro-2H-pyran-2-one.
Catalyst activity was recoverable after heat treatment under H2.
Radical scavenger reduced DHPO formation, indicating radical intermediates in the reaction.
Abstract
The oxidation of 3,4‐dihydro‐2H‐pyran (DHP), which can be produced from lignocellulose‐derived furfural, was investigated with various catalysts and molecular oxygen as an oxidant in a H2O solvent. 5,6‐Dihydro‐2H‐pyran‐2‐one (DHPO) was obtained in moderate yield with a carbon black‐supported Pd catalyst (Pd/C). The addition of base (NaHCO3) suppressed the side reaction of DHP (i.e., hydration of DHP) and increased DHPO yield up to 52%. The activity of the catalyst was slightly decreased after three‐time use but recovered by the heat‐treatment under H2. Through the investigation of various Pd/support catalysts, the catalysts with low valent and stable Pd0 phase during the reaction, such as Pd/C and Pd/BN, showed high activity in DHPO formation. Positive and almost zero reaction orders were observed with respect to O2 pressure and DHP concentration, respectively, indicating the…
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Taxonomy
TopicsCatalysis for Biomass Conversion · Lignin and Wood Chemistry · Oxidative Organic Chemistry Reactions