This paper reports a new sustainable protocol for the microwave-assisted catalytic conversion of levulinic acid into N-substituted pyrrolidones over tailor-made mono (Pd, Au) or bimetallic (PdAu) catalysts supported on either highly mesoporous silica (HMS) or titania-doped HMS, exploiting the advantages of dielectric heating. MW-assisted reductive aminations of levulinic acid with several amines were first optimized in batch mode under hydrogen pressure (5 bar) in solvent-free conditions. Good-to-excellent yields were recorded at 150 degrees C in 90 min over the PdTiHMS and PdAuTiHMS, that proved recyclable and almost completely stable after six reaction cycles. Aiming to scale-up this protocol, a MW-assisted flow reactor was used in combination with different green solvents. Cyclopentyl methyl ether (CPME) provided a 99 % yield of N-(4-methoxyphenyl) pyrrolidin-2-one at 150 degrees C over PdTiHMS. The described MW-assisted flow synthesis proves to be a safe procedure suitable for further industrial applications, while averting the use of toxic organic solvents.Microwave-assisted batch and flow syntheses of pyrrolidones from levulinic acid have been exploited under neat conditions and using CPME as green solvent.image

Batch and Flow Green Microwave-Assisted Catalytic Conversion Of Levulinic Acid to Pyrrolidones

Calcio Gaudino, Emanuela;Manzoli, Maela;Grillo, Giorgio;Cravotto, Giancarlo;Acciardo, Elisa;Tabasso, Silvia
2023-01-01

Abstract

This paper reports a new sustainable protocol for the microwave-assisted catalytic conversion of levulinic acid into N-substituted pyrrolidones over tailor-made mono (Pd, Au) or bimetallic (PdAu) catalysts supported on either highly mesoporous silica (HMS) or titania-doped HMS, exploiting the advantages of dielectric heating. MW-assisted reductive aminations of levulinic acid with several amines were first optimized in batch mode under hydrogen pressure (5 bar) in solvent-free conditions. Good-to-excellent yields were recorded at 150 degrees C in 90 min over the PdTiHMS and PdAuTiHMS, that proved recyclable and almost completely stable after six reaction cycles. Aiming to scale-up this protocol, a MW-assisted flow reactor was used in combination with different green solvents. Cyclopentyl methyl ether (CPME) provided a 99 % yield of N-(4-methoxyphenyl) pyrrolidin-2-one at 150 degrees C over PdTiHMS. The described MW-assisted flow synthesis proves to be a safe procedure suitable for further industrial applications, while averting the use of toxic organic solvents.Microwave-assisted batch and flow syntheses of pyrrolidones from levulinic acid have been exploited under neat conditions and using CPME as green solvent.image
2023
1
8
CPME; continuous flow process; levulinic acid; microwaves; pyrrolidones
Calcio Gaudino, Emanuela; Manzoli, Maela; Testa, Maria Luisa; La Parola, Valeria; Grillo, Giorgio; Cravotto, Giancarlo; Acciardo, Elisa; Tabasso, Silvia
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/1970090
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