Continuous flow Meerwein-Ponndorf-Verley reduction of HMF and furfural using basic zirconium carbonate

Author(s)

Marcon, Henrique Magri ; Pastre, Julio Cezar

• Document type: Journal article
• Source: RSC ADVANCES; v. 12, n. 13, p. 10-pg., 2022-03-08.

Abstract

Continuous Flow Microreactors and Green Chemistry are areas with promising applications, especially when allied. In this scenario, the main goal of this study was to develop new strategies for the synthesis of bio-based compounds under a flow regime. We worked towards the flow synthesis of furfuryl alcohol and DHMF (dihydroxymethylfuran), from their respective aldehydes, through a Meerwein-Ponndorf-Verley reaction with iso-propanol catalysed by basic zirconium carbonate. Furfuryl alcohol was prepared in essentially quantitative yield with productivities as high as 67 mg min(-1). Efforts towards DHMF synthesis were performed and the process was also optimized using design of experiments. The optimal conditions were defined for DHMF at 0.25 M and were determined to be 120 degrees C and 50 s of residence time, giving yields of up to 99% and productivity of 50 mg min(-1). The use of a FT-IR device for the in-line continuous monitoring was pivotal for the fast optimization of the processes, securing steady-state operations, and design of experiments ensured a greater understanding of the effect of temperature, residence time and concentration, alongside their interactions in yield, selectivity and productivity. (AU)

• FAPESP's process: 14/26378-2 - Development of methodologies and synthetic processes employing a new technological platform: micro and meso reactor assisted synthesis of natural products and derivatives with potential pharmacological activity
• Grantee: Júlio Cezar Pastre
• Support Opportunities: Research Grants - Young Investigators Grants
• FAPESP's process: 18/25233-1 - Continuous flow synthesis of biomass-derivatives
• Grantee: Henrique Magri Marçon
• Support Opportunities: Scholarships in Brazil - Master
• FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
• Grantee: Carlos Roque Duarte Correia
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 20/11578-7 - Enabling technologies allied to green chemistry: synthesis of high value-added compounds from biomass derivatives
• Grantee: Júlio Cezar Pastre
• Support Opportunities: Program for Research on Bioenergy (BIOEN) - Regular Program Grants