Using imidazolium-based ionic liquids as dual solvent-catalysts for sustainable synthesis of vitamin esters: inspiration from bio- and organo-catalysis

Tao, Yifeng; Dong, Ruijuan; Pavlidis, Ioannis V.; Chen, Biqiang; Tan, Tianwei

doi:10.1039/c5gc02557e

Cited by 60 publications

(48 citation statements)

References 68 publications

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“…[8] The rapid development of room-temperature ILs has led to extensives tudy of their use in esterificationo rt he synthesis of polyesters. [10] Althought he ILs used as reactionm edia can be recycled, they are still consumed in large amounts,a th igh cost. [10] Althought he ILs used as reactionm edia can be recycled, they are still consumed in large amounts,a th igh cost.…”

Section: Introductionmentioning

confidence: 99%

A Brønsted Acidic Ionic Liquid as an Efficient and Selective Catalyst System for Bioderived High Molecular Weight Poly(ethylene 2,5‐furandicarboxylate)

Jiang

Wang

et al. 2019

ChemSusChem

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Green synthesis of bioderived high‐molecular‐weight poly(ethylene 2,5‐furandicarboxylate) (PEF) over metal‐free catalysts is a significant challenge. This study focuses on PEF prepared from ethylene glycol and 2,5‐furandicarboxylic acid (FDCA) through a direct esterification method with ecofriendly metal‐free ionic liquids (ILs) as catalysts. The catalytic activities of a series of imidazolium cations in the presence of various anions are systematically investigated and found to be mainly governed by the anions. Among the ILs studied, 1‐ethyl‐3‐methylimidazolium tetrafluoroborate ([C2MIM]BF4) is identified as the best catalyst, showing excellent catalytic activity, selectivity, and stability, even at low catalyst loadings (0.1 mol % w.r.t. FDCA). Optimization of the polymerization parameters enables [C2MIM]BF4‐catalyzed production of PEF with a high number‐average molecular weight (Mn=5.25×104 g mol−1). The relationship between Brønsted acidity and catalytic activity is also investigated and the results show that the trend in catalytic activity is in good agreement with that in Brønsted acidity, as determined by the Hammett method. Additionally, on the basis of experimental results and density functional theory calculations, an electrophilic activation mechanism induced by hydrogen bonds is proposed. This strategy of adjustable acidity and anion structure in ILs provides an opportunity to develop other ILs for bio‐based polyesters through green synthesis pathways.

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Section: Introductionmentioning

confidence: 99%

A Brønsted Acidic Ionic Liquid as an Efficient and Selective Catalyst System for Bioderived High Molecular Weight Poly(ethylene 2,5‐furandicarboxylate)

Jiang

Wang

et al. 2019

ChemSusChem

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“…Although the interaction with 1 proceeded at much slower rate in this case, the addition of imidazole could improve the interaction rate (Figure d). This indicated the involvement of the imidazole group as a proton transfer catalyst in the overall sensing process . Nevertheless, the extent of spectral change observed in this case was less (ca.…”

Section: Resultsmentioning

confidence: 78%

Dual‐Mode Optical Sensing of Histamine at Nanomolar Concentrations in Complex Biological Fluids and Living Cells

Dey

Ali

Podder

et al. 2017

Chemistry A European J

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An easily synthesized fluorescein-based luminescent dye has been utilized for the dual-mode detection of histamine at nanomolar concentrations at pH 7.0 in water. The specific response to histamine was achieved by imidazole-catalyzed 'imine formation' reaction. The protocol was subsequently applied for the estimation of histamine in complex biological milieu such as human blood serum and urine samples. Furthermore, the dose-dependent cellular uptake of histamine and de novo synthesis (by thapsigargin treatment) was visualized in RAW 264.7, a mouse macrophage cell line. We have also developed portable paper strips for rapid, on-site detection of histamine without involving costly instruments.

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“…(a) Comparison of heat‐inactivated (120°C, 20 min) and original lipase catalysts for the esterification of α‐tocopherol in DMSO (TLIM: Thermomyces lanuginosus lipozyme, Novo435: immobilized lipase B from Candida antarctica , RMIM: Rhizomucor miehei lipozyme and CaLB: Candida antárctica lipase B) and (b) three strategies for the esterification of vitamin E with succinic anhydride …”

Section: Materials Chemicals and Fuels From Succinic Acidmentioning

confidence: 99%

“…Other Candida antárctica lipase B) and (b) three strategies for the esterifi cation of vitamin E with succinic anhydride. 99 works have also demonstrated the usefulness of SA or SAn for the bio-catalytic modifi cation of cellulose or starches ( Fig. 12(b)), 101,102 with a wide range of industrial applications (particularly as food additive).…”

Section: Bio-catalytic Conversion Of Succinic Acidmentioning

confidence: 99%

A review of progress in (bio)catalytic routes from/to renewable succinic acid

Mazière

Prinsen

García

et al. 2017

Biofuels Bioprod Bioref

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In the last decade, succinic acid has become a key platform chemical in the bio‐based industry. It is one of the few renewable chemicals that have proven to be competitive with the fossil‐derived production. Still, improvements can be made in terms of sustainability, especially in the usage of alternative carbon sources for advanced life cycles. Numerous catalytic routes have been developed for the conversion of bio‐succinate to a wide range of chemical compounds and bio‐based polymers. However, most of them have been demonstrated from pure isolated succinic acid, but the isolation and purification of succinic acid from fermentation broths is no mean task and requires a considerable amount of energy. Therefore, catalytic routes in aqueous phase have also been studied intensively to by‐pass isolation and purification steps. This review describes the recent developments published in this research field. © 2017 Society of Chemical Industry and John Wiley & Sons, Ltd

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Using imidazolium-based ionic liquids as dual solvent-catalysts for sustainable synthesis of vitamin esters: inspiration from bio- and organo-catalysis

Abstract: An efficient and sustainable approach using imidazolium-based ionic liquids as dual solvent-catalysts for synthesis of vitamin E ester was developed.

Cited by 60 publications

References 68 publications

A Brønsted Acidic Ionic Liquid as an Efficient and Selective Catalyst System for Bioderived High Molecular Weight Poly(ethylene 2,5‐furandicarboxylate)

A Brønsted Acidic Ionic Liquid as an Efficient and Selective Catalyst System for Bioderived High Molecular Weight Poly(ethylene 2,5‐furandicarboxylate)

Dual‐Mode Optical Sensing of Histamine at Nanomolar Concentrations in Complex Biological Fluids and Living Cells

A review of progress in (bio)catalytic routes from/to renewable succinic acid

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