Hydrogenation Catalysis in Biobased Ionic Liquids

Hayouni, Safa; Ferlin, Nadège; Bouquillon, Sandrine

doi:10.5772/65448

Cited by 3 publications

(5 citation statements)

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“…Biosourced ionic liquids were prepared using an acid-base reaction between the tetrabutylammonium or -phosphonium hydroxides (TBAOH and TBPOH, respectively) or cholinium hydroxide ChOH with natural chiral amino acids (S-proline, R-proline, and trans-4-hydroxy-Sproline) (Scheme 3). The synthetic methodology was inspired by Ohno's work [51] in 2005 and previously reported works for some phosphonium or ammonium derivatives [38][39][40][41][42][43][44][45]. Nine ionic liquids were prepared easily with high yields and purity (Table 1), and the choliniumbased ionic liquids were synthesized following similar procedures previously used with ammonium or phosphonium-based ionic liquids.…”

Section: Resultsmentioning

confidence: 99%

“…Biosourced ionic liquids were prepared using an acid-base reaction between the tetrabutyl-ammonium or -phosphonium hydroxides (TBAOH and TBPOH, respectively) or cholinium hydroxide ChOH with natural chiral amino acids (S-proline, R-proline, and trans-4-hydroxy-S-proline) (Scheme 3). The synthetic methodology was inspired by Ohno's work [51] in 2005 and previously reported works for some phosphonium or ammonium derivatives [38][39][40][41][42][43][44][45].…”

Section: Resultsmentioning

confidence: 99%

“…As previously mentioned, we prepared some biobased ionic liquids with natural carboxylates and used these in hydrogenation and Heck couplings [38][39][40][41][42][43][44][45]. Among these ILs, we prepared tetrabutylphosphonium and tetrabutylammonium prolinate or hydroxyprolinate.…”

Section: Introductionmentioning

confidence: 99%

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Beneficial Contribution of Biosourced Ionic Liquids and Microwaves in the Michael Reaction

et al. 2020

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We developed a synthesis of chiral ionic liquids from proline and one of its derivatives. Nine chiral ionic liquids were synthesized with yields from 78% to 95%. These synthesized ionic liquids played two roles in Michael reactions, as solvents, and as basic catalysts, where the ionic phase could also be reused at least five times without loss of activity. The yields up to 99% were improved by increasing the amount of dimethylmalonate from 1.2 equivalents to 3 or 4 equivalents. Furthermore, the reaction time could be reduced from 24 h to 45 min through microwaves activation.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Beneficial Contribution of Biosourced Ionic Liquids and Microwaves in the Michael Reaction

et al. 2020

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“…Following the important trend of replacing artificial synthetic compounds with environmentally friendly counterparts, which are present in nature in large quantities and are relatively cheap, various bio-inspired ionic liquids (ILs) obtained from natural compounds, such as choline, betaine or amino acids, carnitine, carbohydrates, and various organic acids, − have been synthesized and utilized in industrial processes, including organic synthesis, catalysis, extraction, and separation. − The demand for synthetic schemes for such bio-derived ILs is related to high costs of production of common ILs, which are obtained from non-renewable sources. The production of ILs from cheap raw materials of plant origin is among the most crucial aims for a number of practical implementations. ,, …”

Section: Introductionmentioning

confidence: 99%

Biomass-Derived Ionic Liquids Based on a 5-HMF Platform Chemical: Synthesis, Characterization, Biological Activity, and Tunable Interactions at the Molecular Level

Seitkalieva

Vavina

Posvyatenko

et al. 2021

ACS Sustainable Chem. Eng.

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A new family of protic ammonium ionic liquids (ILs) with various inorganic anions was synthesized from bioderived 5-HMF. Starting with cellulose biomass, a complete preservation of the C 6 unit was achieved throughout the synthetic sequence (no carbon loss). Evaluation of green metrics showed a significant advantage of the developed bio-derived pathway to access ILs from a natural renewable source, depending on feasible routes to 5-HMF manufacturing. The reduced number of synthetic steps and availability of the starting materials were the key advantages. Experimental physicochemical and biological studies, as well as computational modeling revealed a unique multifunctional intrinsic organization of these bio-derived ILs. The nature of interactions between the cations and anions of the novel ILs was mapped at the molecular level. The substituents in the cationic core and the nature of the original building blocks had a prominent impact on cytotoxicity of the novel ILs. The obtained results suggest possible sustainable applications of the least toxic ILs, while the regulation of biological activity of the ILs via the corresponding structural adjustments can find biological and medicinal applications. The 5-HMF-derived IL with a sulfate anion demonstrated potentially useful properties in dissolution of microcrystalline cellulose.

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“…For several years, our group has developed a methodology to synthesize, with quantitative yields, tetrabutylammonium (TBA)- and tetrabutylphosphonium (TBP)- and cholinium (Cho)-based ILs associated with biosourced carboxylates (Scheme ). − …”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Betaine-Based Ionic Liquids by Using a “One-Pot” Amidation Process and Evaluation of Their Ecotoxicity through a New Method Involving a Hemocyte-Based Bioassay

Mbakidi

Barjhoux

Aguibi

et al. 2021

ACS Sustainable Chem. Eng.

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A new class of betaine-based ionic liquids (ILs) have been synthesized. Betaine is transformed into betaine amides with various anions. These amides were prepared at first through a classical four-step method; the synthesis was then improved by reducing the number of steps using a one-pot strategy for amidation. The final yields were good to high, and the various structures were fully characterized to valorize them in many domains such as catalysis, extraction, or dissolution of biopolymers. Next, to determine their ecotoxicity, a hemocyte-based bioassay was used. This new method to evaluate the ecotoxicity of ILs was also applied to other ILs [tetrabutylammonium (TBA), tetrabutyl-phosphonium (TBP), and betaine-and cholinium-based ILs] to prove its efficiency and its complementarity toward other ecotoxicological assessment methods. TBA-and TBP-based ILs induced limited effects on zebra mussel hemocytes, with TBP-ILs proving to be generally less toxic than TBA-based ones. On the contrary, betaine-and cholinium-based IL exposure led to more acute toxicity with a noticeable effect associated with the cation carbon chain length. Overall results also showed differential toxicity of ILs according to the nature of the anion in the assemblage, with lactate being the less biologically reactive anion. The results of this study thus reveal the importance of the nature of both cations and anions which constitute the IL structures and can strongly, sometimes synergistically, influence the IL toxicity. The possible interactions between the cationic and anionic parts reveal the complexity of IL toxicity prediction, thereby arousing interest in developing innovative strategies for the risk assessment of these molecular assemblages. In this context, the proposed hemocytebased bioassay proved its efficiency and sensitivity in scoring and ranking IL toxicity according to their effects in the immunocompetent cells of an environmentally sentinel bivalve. This alternative bioassay could represent a complementary tool to more traditional and standard bioassays to complete the toxicity screening of substances such as ILs or new chemicals synthesized under green chemistry principles and notably the limitation of environmental toxicity by investigating the acute and functional effects on a wild and relevant freshwater invertebrate species.

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Hydrogenation Catalysis in Biobased Ionic Liquids

Cited by 3 publications

References 79 publications

Beneficial Contribution of Biosourced Ionic Liquids and Microwaves in the Michael Reaction

Beneficial Contribution of Biosourced Ionic Liquids and Microwaves in the Michael Reaction

Biomass-Derived Ionic Liquids Based on a 5-HMF Platform Chemical: Synthesis, Characterization, Biological Activity, and Tunable Interactions at the Molecular Level

Synthesis of New Betaine-Based Ionic Liquids by Using a “One-Pot” Amidation Process and Evaluation of Their Ecotoxicity through a New Method Involving a Hemocyte-Based Bioassay

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