Tetraalkylammonium Ionic Liquids as Dual Solvents–Catalysts for Direct Synthesis of Sugar Fatty Acid Esters

Lin, Xiao‐Sheng; Zou, Yongjin; Zhao, Kai‐Hua; Yang, Tao-Xiang; Halling, Peter J.; Yang, Zhen

doi:10.1007/s11743-016-1798-7

Cited by 18 publications

(8 citation statements)

References 27 publications

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“…Both Lipozyme TLIM and Novozym 435 are able to catalyze the synthesis of glucose laurate, either through transesterification of glucose and vinyl laurate or through esterification of methyl glucoside and lauric acid. The product was identified as a mono-ester [27]. As no systematic research has been carried out regarding the use of IL or DES as solvents for these two specific reactions catalyzed by the two enzymes, respectively (Reactions 1 and 2 in Scheme 1), 14 different ILs were screened for the two reactions, and 14 DESs for the second reaction.…”

Section: Resultsmentioning

confidence: 99%

Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents

et al. 2016

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Sugar fatty acid esters (SFAEs) are biocompatible nonionic surfactants with broad applications in food, cosmetic, and pharmaceutical industries. They can be synthesized enzymatically with many advantages over their chemical synthesis. In this study, SFAE synthesis was investigated by using two reactions: (1) transesterification of glucose with fatty acid vinyl esters and (2) esterification of methyl glucoside with fatty acids, catalyzed by Lipozyme TLIM and Novozym 435 respectively. Fourteen ionic liquids (ILs) and 14 deep eutectic solvents (DESs) were screened as solvents, and the bisolvent system composed of 1-hexyl-3-methylimidazolium trifluoromethylsulfonate ([HMIm][TfO]) and 2-methyl-2-butanol (2M2B) was the best for both reactions, yielding optimal productivities (769.6 and 397.5 µmol/h/g, respectively) which are superior to those reported in the literature. Impacts of different reaction conditions were studied for both reactions. Response surface methodology (RSM) was employed to optimize the transesterification reaction. Results also demonstrated that as co-substrate, methyl glucoside yielded higher conversions than glucose, and that conversions increased with an increase in the chain length of the fatty acid moieties. DESs were poor solvents for the above reactions presumably due to their high viscosity and high polarity.

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Section: Resultsmentioning

confidence: 99%

Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents

et al. 2016

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“…also report these positive effects in hydrolysis reactions with the use of more hydrophobic protic ionic liquids. The literature has revealed that the performance of these ILs was dependent on both the cation and the anion . In this work, the same anion was studied, varying the cation of the ionic liquid.…”

Section: Resultsmentioning

confidence: 99%

Protic ionic liquids influence on immobilization of LipaseBurkholderia cepaciaon hybrid supports

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Santos

Fricks

et al. 2016

J. Chem. Technol. Biotechnol

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BACKGROUND This work aims to assess the use of protic ionic liquids (PIL), propanoate, butanoate and pentanoate of N‐methylmonoetanolamine (C3, C4 and C5), in the preparation of hybrid supports made of poly(3‐hydroxybutyrate‐co‐hydroxyvalerate) (PHBV) and silica for the immobilization of lipase of Burkholderia cepacia (BCL) by covalent binding. For immobilized biocatalysts (IBs), the performance was determined for immobilization and characterization (pH, temperature, stability thermal, operational and in solvents), with the best conditions being defined. For the supports and efficient IB, the morphological and physicochemical characterization (MEV, BET, FTIR and TGA) was evaluated. RESULTS For preparation of the hybrid support, the experiment using 3 g of PHBV presented a higher percentage of mass, around 50% recovery of the support in the granulometry used. The IBs total activity recovery yield (Ya) in hybrid supports modified with ionic liquids IB‐hybrid‐C3 (103%), IB‐hybrid‐C4 (120%) and IB‐hybrid‐C5 (133%) were above the results reported for the control (90%), with IB‐hybrid‐C5 being the most efficient, and presenting better thermal and operational stability. CONCLUSION Burkholderia cepacia lipase was immobilized successfully in a hybrid support (PHBV and silica) modified with protic ionic liquid by covalent binding, resulting in an improvement in the morphological and physicochemical characteristics, and consequently with greater Ya and good thermal and operational stability. © 2016 Society of Chemical Industry

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“…Reactions may be performed in the presence or absence of enzymes (Abdulmalek et al, 2012; Yang and Huang, 2012; Findrik et al, 2016). In chemical synthesis, ILs can act as both the catalyst and the solvent of the reaction (Forsyth et al, 2002; Lin et al, 2016). The choice of IL for enzymatic reactions is crucial, to ensure that the enzyme is not deactivated.…”

Section: Ionic Liquids For the Synthesis Of Sfaesmentioning

confidence: 99%

“…Lin et al described the synthesis of glucose monolaurate in ILs (Lin et al, 2015, 2016) with and without the use of enzymes. They studied the impact of the IL on SFAEs synthesis by enzymatic processes and they showed that better ester formation was achieved with ILs with a hydrophobic cation and a hydrophilic anion, such as [HMIm][TfO].…”

Section: Ionic Liquids For the Synthesis Of Sfaesmentioning

confidence: 99%

Atypical Reaction Media and Organized Systems for the Synthesis of Low-Substitution Sugar Esters

et al. 2019

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Sugar esters are non-ionic surfactants with amphiphilic properties of interest for the formulation of various products in the fields of detergents, foods, medicines, pharmaceuticals, agriculture, and cosmetics. The properties of sugar esters depend on their degree of substitution (we consider degrees of substitution between 1 and 3 here) which guides their use. Sugar esters are biodegradable and non-toxic, and the demand for these compounds is high and continuing to increase. Indeed, interest in these compounds stems from the natural origin of the raw materials, the synthetic processes involved and the performance of the final product. The choice of reaction medium is crucial, to facilitate contact between reactants and prevent hydrolysis of the products. In this review, we provide an overview of the processes and synthesis routes for sugar ester production, ionic liquids and deep eutectic solvent as non-usual media or with organized systems.

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Tetraalkylammonium Ionic Liquids as Dual Solvents–Catalysts for Direct Synthesis of Sugar Fatty Acid Esters

Cited by 18 publications

References 27 publications

Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents

Enzymatic Synthesis of Glucose-Based Fatty Acid Esters in Bisolvent Systems Containing Ionic Liquids or Deep Eutectic Solvents

Protic ionic liquids influence on immobilization of LipaseBurkholderia cepaciaon hybrid supports

Atypical Reaction Media and Organized Systems for the Synthesis of Low-Substitution Sugar Esters

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