Rational Study of DBU Salts for the CO<sub>2</sub> Insertion into Epoxides for the Synthesis of Cyclic Carbonates

Fanjul-Mosteirín, Noé; Jehanno, Coralie; Ruipérez, Fernando; Sardón, Haritz; Dove, Andrew P.

doi:10.1021/acssuschemeng.9b01300

Cited by 84 publications

(55 citation statements)

References 61 publications

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“…Using styrene oxide as substrate, a TON of 220 and a TOF of 14 h −1 were obtained with 1 (Table , entry 6). By comparison, DBU salts reported by Dove gave a TON of 9.6 and a TOF of 2.4 h −1 for the same substrate at 70 °C (Table , entry 7) . Similar results can also be achieved using covalent organic frameworks COF‐JLU7 in the presence of tetrabutylammonium bromide as a co‐catalyst, as reported by Liu (Table , entry 8) .…”

Section: Resultssupporting

confidence: 71%

A Thermomorphic Polyethylene‐Supported Imidazolium Salt for the Fixation of CO₂ into Cyclic Carbonates

Grollier

Onida

et al. 2020

Adv Synth Catal

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An imidazolium catalyst supported on thermomorphic polyethylene (PE) was prepared from 1methylimidazole and polyethylene iodide (PEÀ I). The catalyst was characterized by 1 H and 13 C NMR, SEC and MALDI-ToF mass spectrometry. Its catalytic activity was evaluated in the ring-opening of epoxides with carbon dioxide to give cyclic carbonates under solvent-free conditions. The catalyst proved to be active at low catalyst loading (down to 0.1 mol%) and allows the reaction to occur at low CO 2 pressure (1-5 bar) and moderate temperature (100°C). A range of terminal and internal epoxides was converted to the corresponding cyclic carbonates with high yields and selectivities. The recyclability of the catalyst was studied and no significant loss of activity was observed after 5 runs.

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Section: Resultssupporting

confidence: 71%

A Thermomorphic Polyethylene‐Supported Imidazolium Salt for the Fixation of CO₂ into Cyclic Carbonates

Grollier

Onida

et al. 2020

Adv Synth Catal

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“…A quite different mechanism was proposed by Liu, Wei, Dai and co-workers, whose paper is mentioned in entries 44-45 [85]. On the basis of their results, of some experiments with modified catalysts and DFT calculations they proposed the mechanism depicted in Scheme 3.…”

Section: Cyclic Carbonatesmentioning

confidence: 92%

Recent Advances in the Chemical Fixation of Carbon Dioxide: A Green Route to Carbonylated Heterocycle Synthesis

et al. 2019

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Carbon dioxide produced by human activities is one of the main contributions responsible for the greenhouse effect, which is modifying the Earth’s climate. Therefore, post-combustion CO2 capture and its conversion into high value-added chemicals are integral parts of today’s green industry. On the other hand, carbon dioxide is a ubiquitous, cheap, abundant, non-toxic, non-flammable and renewable C1 source. Among CO2 usages, this review aims to summarize and discuss the advances in the reaction of CO2, in the synthesis of cyclic carbonates, carbamates, and ureas appeared in the literature since 2017.

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“…The alkaline absorbents described in the literature as being capable of effectively absorbing CO 2 are different amines [28], including amidines such as 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) [28][29][30], guanidines such as 1,5,7-triazabicyclo[4.4.0]dec-5-enium (TBD) [28,29], and azaheterocycles such as pyridines and imidazoles [31,32], which are efficient for the chemisorption and activation of CO 2 .…”

Section: Catalytically Active Amines and Their Saltsmentioning

confidence: 99%

Utilization of CO2-Available Organocatalysts for Reactions with Industrially Important Epoxides

Weidlich

Kamenická

2022

Catalysts

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Recent knowledge in chemistry has enabled the material utilization of greenhouse gas (CO2) for the production of organic carbonates using mild reaction conditions. Organic carbonates, especially cyclic carbonates, are applicable as green solvents, electrolytes in batteries, feedstock for fine chemicals and monomers for polycarbonate production. This review summarizes new developments in the ring opening of epoxides with subsequent CO2-based formation of cyclic carbonates. The review highlights recent and major developments for sustainable CO2 conversion from 2000 to the end of 2021 abstracted by Web of Science. The syntheses of epoxides, especially from bio-based raw materials, will be summarized, such as the types of raw material (vegetable oils or their esters) and the reaction conditions. The aim of this review is also to summarize and to compare the types of homogeneous non-metallic catalysts. The three reaction mechanisms for cyclic carbonate formation are presented, namely activation of the epoxide ring, CO2 activation and dual activation. Usually most effective catalysts described in the literature consist of powerful sources of nucleophile such as onium salt, of hydrogen bond donors and of tertiary amines used to combine epoxide activation for facile epoxide ring opening and CO2 activation for the subsequent smooth addition reaction and ring closure. The most active catalytic systems are capable of activating even internal epoxides such as epoxidized unsaturated fatty acid derivatives for the cycloaddition of CO2 under relatively mild conditions. In case of terminal epoxides such as epichlorohydrin, the effective utilization of diluted sources of CO2 such as flue gas is possible using the most active organocatalysts even at ambient pressure.

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Rational Study of DBU Salts for the CO₂ Insertion into Epoxides for the Synthesis of Cyclic Carbonates

Cited by 84 publications

References 61 publications

A Thermomorphic Polyethylene‐Supported Imidazolium Salt for the Fixation of CO₂ into Cyclic Carbonates

A Thermomorphic Polyethylene‐Supported Imidazolium Salt for the Fixation of CO₂ into Cyclic Carbonates

Recent Advances in the Chemical Fixation of Carbon Dioxide: A Green Route to Carbonylated Heterocycle Synthesis

Utilization of CO2-Available Organocatalysts for Reactions with Industrially Important Epoxides

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Rational Study of DBU Salts for the CO2 Insertion into Epoxides for the Synthesis of Cyclic Carbonates

Cited by 84 publications

References 61 publications

A Thermomorphic Polyethylene‐Supported Imidazolium Salt for the Fixation of CO2 into Cyclic Carbonates

A Thermomorphic Polyethylene‐Supported Imidazolium Salt for the Fixation of CO2 into Cyclic Carbonates

Recent Advances in the Chemical Fixation of Carbon Dioxide: A Green Route to Carbonylated Heterocycle Synthesis

Utilization of CO2-Available Organocatalysts for Reactions with Industrially Important Epoxides

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Rational Study of DBU Salts for the CO₂ Insertion into Epoxides for the Synthesis of Cyclic Carbonates

A Thermomorphic Polyethylene‐Supported Imidazolium Salt for the Fixation of CO₂ into Cyclic Carbonates

A Thermomorphic Polyethylene‐Supported Imidazolium Salt for the Fixation of CO₂ into Cyclic Carbonates