Renewable-based furan compounds derived from 2-formyl-5-(hydroxymethyl)furan (5-HMF) were successfully employed as catalysts to synthesize cyclic organic carbonates through the reaction of carbon dioxide with epoxides. The effects of temperature, reaction time, reagent ratios, and carbon dioxide pressure were optimized before evaluating various bio-based complexing agents in combination with different alkali metal halide salts. Among them, 2,5-bis(hydroxymethyl)tetrahydrofuran (BHTHF) showed the highest efficiency as a complexing agent when paired with sodium bromide (NaBr), enabling the production of industrially relevant cyclic carbonates in high yields (12 examples, achieving 94-99% epoxide conversion and 70-99% carbonate selectivity) under mild pressure conditions (carbon dioxide pressure of 1-10 bar, reaction time of 6 hours, and temperature of 120 °C). Additionally, the BHTHF/NaBr catalytic system demonstrated high stability, maintaining its performance over nine consecutive epoxide additions (8 mmol each) without any loss of efficiency.

2‐formyl‐5‐(hydroxymethyl)furan (HMF) derivatives as active complexing agent for CO2 insertion reaction

Fiorani, Giulia
Supervision
;
Bragato, Nicola
Writing – Original Draft Preparation
;
Annatelli, Mattia
Writing – Review & Editing
;
Bortoluzzi, Marco
Investigation
;
Calmanti, Roberto
Conceptualization
;
Perosa, Alvise
Membro del Collaboration Group
;
Selva, Maurizio
Membro del Collaboration Group
In corso di stampa

Abstract

Renewable-based furan compounds derived from 2-formyl-5-(hydroxymethyl)furan (5-HMF) were successfully employed as catalysts to synthesize cyclic organic carbonates through the reaction of carbon dioxide with epoxides. The effects of temperature, reaction time, reagent ratios, and carbon dioxide pressure were optimized before evaluating various bio-based complexing agents in combination with different alkali metal halide salts. Among them, 2,5-bis(hydroxymethyl)tetrahydrofuran (BHTHF) showed the highest efficiency as a complexing agent when paired with sodium bromide (NaBr), enabling the production of industrially relevant cyclic carbonates in high yields (12 examples, achieving 94-99% epoxide conversion and 70-99% carbonate selectivity) under mild pressure conditions (carbon dioxide pressure of 1-10 bar, reaction time of 6 hours, and temperature of 120 °C). Additionally, the BHTHF/NaBr catalytic system demonstrated high stability, maintaining its performance over nine consecutive epoxide additions (8 mmol each) without any loss of efficiency.
In corso di stampa
N/A
File in questo prodotto:
File Dimensione Formato  
Eur J Org Chem - 2025 - Fiorani - 2‐formyl‐5‐ hydroxymethyl furan HMF derivatives as active complexing agent for CO2.pdf

accesso aperto

Descrizione: Accepted manuscript
Tipologia: Documento in Post-print
Licenza: Accesso libero (no vincoli)
Dimensione 1.36 MB
Formato Adobe PDF
1.36 MB Adobe PDF Visualizza/Apri

I documenti in ARCA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10278/5092968
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? ND
social impact