Quest for Green‐Solvent Design: From Hydrophilic to Hydrophobic (Deep) Eutectic Solvents

Florindo, Catarina; Branco, Luı́s C.; Marrucho, Isabel M.

doi:10.1002/cssc.201900147

Cited by 354 publications

(206 citation statements)

References 36 publications

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“…For this purpose, a hydrophobic DES consisting of (-)-menthol and decanoic acid was used for the synthesis of glucose monodecanoate for the first time. Hydrophobic DES are a new class of solvents that were described in 2015 for the first time [29]. (-)-menthol: decanoic acid DES was chosen as this DES can serve as solvent and substrate simultaneously, and low water solubility was reported, which is beneficial for reversed hydrolysis reactions [30,31].…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Synthesis of Glucose Monodecanoate in a Hydrophobic Deep Eutectic Solvent

Hollenbach

Ochsenreither

Syldatk

2020

IJMS

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Environmentally friendly and biodegradable reaction media are an important part of a sustainable glycolipid production in the transition to green chemistry. Deep eutectic solvents (DESs) are an ecofriendly alternative to organic solvents. So far, only hydrophilic DESs were considered for enzymatic glycolipid synthesis. In this study, a hydrophobic DES consisting of (-)-menthol and decanoic acid is presented for the first time as an alternative to hydrophilic DES. The yields in the newly introduced hydrophobic DES are significantly higher than in hydrophilic DESs. Different reaction parameters were investigated to optimize the synthesis further. Twenty milligrams per milliliter iCalB and 0.5 M glucose resulted in the highest initial reaction velocity for the esterification reaction, while the highest initial reaction velocity was achieved with 1.5 M glucose in the transesterification reaction. The enzyme was proven to be reusable for at least five cycles without significant loss of activity.

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Section: Introductionmentioning

confidence: 99%

Enzymatic Synthesis of Glucose Monodecanoate in a Hydrophobic Deep Eutectic Solvent

Hollenbach

Ochsenreither

Syldatk

2020

IJMS

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“…In the meantime, the group of Ribeiro proposed hydrophobic DESs based on dl ‐menthol and several carboxylic acids . Subsequently, hydrophobic DESs have been attracting increasing attention in applications of liquid‐phase microextraction and aqueous liquid–liquid extraction systems, such as extracting pesticides, metals, and contaminants from water samples; the capture of CO 2 ; and application as an eco‐friendly electrolyte medium in dye‐sensitized solar cells …”

Section: Introductionmentioning

confidence: 99%

Effective Release of Intracellular Enzymes by Permeating the Cell Membrane with Hydrophobic Deep Eutectic Solvents

Cao

Dong

et al. 2019

ChemBioChem

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An efficient and green method is crucial for the recovery of intracellular biological products. The major drawbacks of the conventional cell disruption method are nonselectivity and enzyme denaturation. The permeability of hydrophobic deep eutectic solvents (DESs) to the cell membrane was studied, for the first time, and then hydrophobic DESs were innovatively applied to release intracellular enzymes from recombinant Escherichia coli. After optimization, a DES suspension of l‐menthol/oleic acid (0.5 %, v/v) showed the highest release yield of intracellular enzyme. Compared with that released by sonication, a release yield of phospholipase D (PLD) of up to 114.58 % was achieved, and the specific activity was increased by 1.96 times. The microstructure of the cell membrane under different treatments was observed by using an electron microscope to understand the permeation of DESs to the cell membrane. The feasibility and applicability of the proposed release method in industrial applications were also demonstrated. The effective and green release method of intracellular enzymes developed herein has bright prospects for industrial application to replace traditional cell disruption methods. A preliminary study on the permeability of hydrophobic DESs to the cell membrane showed that there would be a potential application prospect of hydrophobic DESs not only in releasing intracellular contents, but also in seeking new green penetrating agents.

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“…Low-melting point binary or ternary mixtures based on small organic compounds or inorganic salts have attracted broad attention due to their possible use as a novel alternative to ionic liquids to be used use as media for chemical processes. [1][2][3][4][5][6] Due to the lack of strict definition, [4] the mixtures are commonly called deep eutectic solvents [1,7] (DESs), hydrophobic eutectic solvents, [6] natural deep eutectic solvents [3,8] (NADESs) or low-transition temperature viscous liquid is formed. The mixture shows no tendency to crystalize, presumably due to its high viscosity (13 000 mPa s at 21 °C, Table S1, Supporting Information).…”

mentioning

confidence: 99%

High‐Molecular‐Weight Polyampholytes Synthesized via Daylight‐Induced, Initiator‐Free Radical Polymerization of Renewable Itaconic Acid

Mielczarek

Łabanowska

Kurdziel

et al. 2020

Macromol. Rapid Commun.

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Herein, it is reported for the first time that when mixed with choline chloride, itaconic acid (IA), normally a low‐reactive vinyl monomer, undergoes initiator‐free radical polymerization under normal daylight. Furthermore, the process results in the formation of abnormally high‐molecular‐weight poly(itaconic acid) derivatives with Mw greater than ≈800 000 g mol−1. Detailed 1D/2D NMR studies indicate that the polymers have two types of ionizable moieties, that is, anionic carboxylic and cationic choline ester groups in an average molar ratio of 12:1. Potentiometric titration shows polyampholyte behavior of the polymers. Tentative mechanistic studies reveal that the daylight‐induced polymerization is initiated by species generated via interactions of near UV light with IA. However, EPR findings show that choline also participates in secondary radical reactions. The obtained polyampholytes are useful bio‐based materials for fast and straightforward fabrication of polymer–clay nanocomposite hydrogels with excellent mechanical properties.

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Quest for Green‐Solvent Design: From Hydrophilic to Hydrophobic (Deep) Eutectic Solvents

Cited by 354 publications

References 36 publications

Enzymatic Synthesis of Glucose Monodecanoate in a Hydrophobic Deep Eutectic Solvent

Enzymatic Synthesis of Glucose Monodecanoate in a Hydrophobic Deep Eutectic Solvent

Effective Release of Intracellular Enzymes by Permeating the Cell Membrane with Hydrophobic Deep Eutectic Solvents

High‐Molecular‐Weight Polyampholytes Synthesized via Daylight‐Induced, Initiator‐Free Radical Polymerization of Renewable Itaconic Acid

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