Nicotine-derived ammonium salts as highly efficient catalysts for chemical fixation of carbon dioxide into cyclic carbonates under solvent-free conditions

Hajipour, Abdol R.; Heidari, Yasaman; Kozehgary, Gholamreza

doi:10.1039/c5ra08488a

Cited by 24 publications

(10 citation statements)

References 48 publications

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“…In contrast, non-nucleophilic anions such as NTf 2 − , PF 6 − or BF 4 − caused the loss of the catalytical activity of the studied BuDABCO salts. Interestingly, some of the attempts to boost the catalytic activity of onium salts constructing di-or tricationic ILs (Scheme 7) often fall flat (Figure 7) [66][67][68]. Surprisingly, when ILs containing activated CO 2 in their structures in N,N -di(alkyl)imidazolium-2-carboxylates were tested as CO 2 cycloaddition catalysts by Kayaki et al [65], the observed activity was quite low and a high CO 2 pressure was required to obtain satisfactory conversion (Table 13).…”

Section: Onium Salts As Catalystsmentioning

confidence: 99%

“…The hydrogen in position 2 on the imidazolium ring is, in all probability, important as an HBD for epoxide ring activation and substitution with -COO − causes a decrease in catalytic activity (Table 13). Interestingly, some of the attempts to boost the catalytic activity of onium salts constructing di-or tricationic ILs (Scheme 7) often fall flat (Figure 7) [66][67][68]. Interestingly, some of the attempts to boost the catalytic activity of onium salts constructing di-or tricationic ILs (Scheme 7) often fall flat (Figure 7) [66][67][68].…”

Section: Onium Salts As Catalystsmentioning

confidence: 99%

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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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Section: Onium Salts As Catalystsmentioning

confidence: 99%

Section: Onium Salts As Catalystsmentioning

confidence: 99%

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

Weidlich

Kamenická

2022

Catalysts

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“…[40][41][42] We have also reported the investigation of a series of nicotinebased ammonium salts as catalysts for chemical fixation of carbon dioxide into cyclic carbonates, and it was found that monobenzylnicotinium bromide showed a much higher activity than dibenzylnicotinium bromide. [43] In continuation of our recent studies on the development of eco-friendly catalytic protocols, [44,45] herein, we report the synthesis and characterization of a nicotine-functionalized silica supported Pd complex as a recyclable solid catalyst. This new catalyst system having a synergistic effect of coordination and electrostatic interactions was found to be efficient in palladium-catalyzed C-C bond formation.…”

Section: Introductionmentioning

confidence: 94%

“…Recently, we have used benzyl nicotinium chloride as the promoter in metal‐catalyzed C‐C and C‐S coupling reactions . We have also reported the investigation of a series of nicotine‐based ammonium salts as catalysts for chemical fixation of carbon dioxide into cyclic carbonates, and it was found that monobenzylnicotinium bromide showed a much higher activity than dibenzylnicotinium bromide …”

Section: Introductionmentioning

confidence: 99%

Nicotine functionalized‐silica palladium (II) complex: a highly efficient, environmentally benign and recyclable nanocatalyst for C‐C bond forming reactions under mild conditions

Hajipour

Tadayoni

Mohammadsaleh

2016

Applied Organom Chemis

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An environmentally friendly silica‐grafted nicotine‐based palladium(II) complex was successfully prepared and evaluated for the first time as novel and efficient nanocatalyst in C‐C bond forming reactions. Grafted‐nicotine in this catalytic system plays an important role, and as an effective ligand and a quaternary ammonium salt demonstrates an efficient stabilizing effect on the Pd(II) species by a synergistic effect of coordination and electrostatic interactions. The catalyst was well characterized by FT‐IR, CHN, XRD, TEM, SEM–EDX, ICP and TG analysis, and demonstrated a highly efficient catalytic activity in the reaction system under phosphine‐free and low Pd loading conditions, and the coupled products were produced in good to excellent yields. Furthermore, the catalyst can be easily recovered and reused without a significant loss of activity. Copyright © 2016 John Wiley & Sons, Ltd.

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“…Synthesis of biomass‐based protic ILs is usually achieved by pretreating or processing the respective biomass to yield primary, secondary, or tertiary amines, protonating them by strong acids, and exchanging the anion by metathesis reactions to the desired counterion . Similarly, by using quaternization reactions instead of strong acid treatment with the other reaction steps being the same, biomass‐based aprotic ionic liquids are available …”

Section: Electrolytes and Separatorsmentioning

confidence: 99%

Sustainable Battery Materials from Biomass

Liedel

2020

ChemSusChem

142

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Sustainable sources of energy have been identified as a possible way out of today's oil dependency and are being rapidly developed. In contrast, storage of energy to a large extent still relies on heavy metals in batteries. Especially when built from biomass‐derived organics, organic batteries are promising alternatives and pave the way towards truly sustainable energy storage. First described in 2008, research on biomass‐derived electrodes has been taken up by a multitude of researchers worldwide. Nowadays, in principle, electrodes in batteries could be composed of all kinds of carbonized and noncarbonized biomass: On one hand, all kinds of (waste) biomass may be carbonized and used in anodes of lithium‐ or sodium‐ion batteries, cathodes in metal–sulfur or metal–oxygen batteries, or as conductive additives. On the other hand, a plethora of biomolecules, such as quinones, flavins, or carboxylates, contain redox‐active groups that can be used as redox‐active components in electrodes with very little chemical modification. Biomass‐based binders can replace toxic halogenated commercial binders to enable a truly sustainable future of energy storage devices. Besides the electrodes, electrolytes and separators may also be synthesized from biomass. In this Review, recent research progress in this rapidly emerging field is summarized with a focus on potentially fully biowaste‐derived batteries.

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Nicotine-derived ammonium salts as highly efficient catalysts for chemical fixation of carbon dioxide into cyclic carbonates under solvent-free conditions

Abstract: Ammonium salts based on nicotine proved to be highly efficient and recyclable catalysts for the synthesis of cyclic carbonates from epoxides and CO2 without the utilization of any organic solvent and any additives.

Cited by 24 publications

References 48 publications

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

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

Nicotine functionalized‐silica palladium (II) complex: a highly efficient, environmentally benign and recyclable nanocatalyst for C‐C bond forming reactions under mild conditions

Sustainable Battery Materials from Biomass

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