Efficiency in Carbon Dioxide Fixation into Cyclic Carbonates: Operating Bifunctional Polyhydroxylated Pyridinium Organocatalysts in Segmented Flow Conditions

Lorenzo Poletti; Caterina Rovegno; Graziano Di Carmine; Filippo Vacchi; Daniele Ragno; Arianna Brandolese; Alessandro Massi; Paolo Dambruoso

doi:10.3390/molecules28041530

Efficiency in Carbon Dioxide Fixation into Cyclic Carbonates: Operating Bifunctional Polyhydroxylated Pyridinium Organocatalysts in Segmented Flow Conditions

Lorenzo Poletti, Caterina Rovegno, Graziano Di Carmine, Filippo Vacchi, Daniele Ragno, Arianna Brandolese, Alessandro Massi^*, Paolo Dambruoso^*

^*Corresponding author for this work

Chemistry

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Abstract

Novel polyhydroxylated ammonium, imidazolium, and pyridinium salt organocatalysts were prepared through N-alkylation sequences using glycidol as the key precursor. The most active pyridinium iodide catalyst effectively promoted the carbonation of a set of terminal epoxides (80 to >95% yields) at a low catalyst loading (5 mol%), ambient pressure of CO₂, and moderate temperature (75 °C) in batch operations, also demonstrating high recyclability and simple downstream separation from the reaction mixture. Moving from batch to segmented flow conditions with the operation of thermostated (75 °C) and pressurized (8.5 atm) home-made reactors significantly reduced the process time (from hours to seconds), increasing the process productivity up to 20.1 mmol_(product) h⁻¹ mmol_(cat)⁻¹, a value ~17 times higher than that in batch mode.

Original language	English
Article number	1530
Number of pages	16
Journal	Molecules
Volume	28
Issue number	4
DOIs	https://doi.org/10.3390/molecules28041530
Publication status	Published - 4 Feb 2023

Bibliographical note

Funding Information:
This research was funded by the NATO Science for Peace and Security Programme (NATO SPS, Grant No. MYP G5885, project acronym: TANGO).

Publisher Copyright:
© 2023 by the authors.

Keywords

carbon dioxide
cyclic carbonates
flow chemistry
mass transfer
organocatalysis

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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PolettiL2023EfficiencyFinal published version, 3.18 MBLicence: Creative Commons: Attribution (CC BY)

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title = "Efficiency in Carbon Dioxide Fixation into Cyclic Carbonates: Operating Bifunctional Polyhydroxylated Pyridinium Organocatalysts in Segmented Flow Conditions",

abstract = "Novel polyhydroxylated ammonium, imidazolium, and pyridinium salt organocatalysts were prepared through N-alkylation sequences using glycidol as the key precursor. The most active pyridinium iodide catalyst effectively promoted the carbonation of a set of terminal epoxides (80 to >95% yields) at a low catalyst loading (5 mol%), ambient pressure of CO2, and moderate temperature (75 °C) in batch operations, also demonstrating high recyclability and simple downstream separation from the reaction mixture. Moving from batch to segmented flow conditions with the operation of thermostated (75 °C) and pressurized (8.5 atm) home-made reactors significantly reduced the process time (from hours to seconds), increasing the process productivity up to 20.1 mmol(product) h−1 mmol(cat)−1, a value ~17 times higher than that in batch mode.",

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author = "Lorenzo Poletti and Caterina Rovegno and {Di Carmine}, Graziano and Filippo Vacchi and Daniele Ragno and Arianna Brandolese and Alessandro Massi and Paolo Dambruoso",

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AU - Poletti, Lorenzo

AU - Rovegno, Caterina

AU - Di Carmine, Graziano

AU - Vacchi, Filippo

AU - Ragno, Daniele

AU - Brandolese, Arianna

AU - Massi, Alessandro

AU - Dambruoso, Paolo

N1 - Funding Information: This research was funded by the NATO Science for Peace and Security Programme (NATO SPS, Grant No. MYP G5885, project acronym: TANGO). Publisher Copyright: © 2023 by the authors.

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N2 - Novel polyhydroxylated ammonium, imidazolium, and pyridinium salt organocatalysts were prepared through N-alkylation sequences using glycidol as the key precursor. The most active pyridinium iodide catalyst effectively promoted the carbonation of a set of terminal epoxides (80 to >95% yields) at a low catalyst loading (5 mol%), ambient pressure of CO2, and moderate temperature (75 °C) in batch operations, also demonstrating high recyclability and simple downstream separation from the reaction mixture. Moving from batch to segmented flow conditions with the operation of thermostated (75 °C) and pressurized (8.5 atm) home-made reactors significantly reduced the process time (from hours to seconds), increasing the process productivity up to 20.1 mmol(product) h−1 mmol(cat)−1, a value ~17 times higher than that in batch mode.

AB - Novel polyhydroxylated ammonium, imidazolium, and pyridinium salt organocatalysts were prepared through N-alkylation sequences using glycidol as the key precursor. The most active pyridinium iodide catalyst effectively promoted the carbonation of a set of terminal epoxides (80 to >95% yields) at a low catalyst loading (5 mol%), ambient pressure of CO2, and moderate temperature (75 °C) in batch operations, also demonstrating high recyclability and simple downstream separation from the reaction mixture. Moving from batch to segmented flow conditions with the operation of thermostated (75 °C) and pressurized (8.5 atm) home-made reactors significantly reduced the process time (from hours to seconds), increasing the process productivity up to 20.1 mmol(product) h−1 mmol(cat)−1, a value ~17 times higher than that in batch mode.

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Efficiency in Carbon Dioxide Fixation into Cyclic Carbonates: Operating Bifunctional Polyhydroxylated Pyridinium Organocatalysts in Segmented Flow Conditions

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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