Bio ionic liquids and water mixtures: a structural study

Gontrani, Lorenzo; Scarpellini, Eleonora; Caminiti, Ruggero; Campetella, Marco

doi:10.1039/c6ra28545g

Cited by 16 publications

(9 citation statements)

References 63 publications

(61 reference statements)

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“…11 Their unabated popularity is related to the fact that these compounds are usually less harmful to the environment and are more readily biodegradable than the ILs obtained from synthetic substrates. 12,13 Naturally occurring L-carnitine, choline, or betaine cations are used to synthesize the majority of the bio-ILs, 14,15 while derivatives of fatty acids and carboxylic acids, such as acetic or formic acid, are often utilized as the source of the anion. 10,16,17 Bio-ILs derived from amino acids or sugars have also recently been described in the literature.…”

Section: ■ Introductionmentioning

confidence: 99%

Ionic Liquids Derived from Vitamin C as Multifunctional Active Ingredients for Sustainable Stored-Product Management

Niemczak

Kaczmarek

Klejdysz

et al. 2018

ACS Sustainable Chem. Eng.

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This study is focused on the utilization of naturally occurring ascorbic acid (vitamin C) in the synthesis of biologically inspired ionic liquids with attractive application potential. The ionic liquids with the ascorbate anion were obtained in high yield (>90%) via a simple, "green" two-step procedure using well-known, cost-effective, and commercially available alkyltrimethylammonium, dialkyldimethylammonium, and alkylmethylbis(2hydroxyethyl)ammonium cations. Three positive ions in this group used for syntheses are derived from renewable resources, such as vegetable oil or animal fat. The study confirmed the strong influence of the chemical structure of the cation on the stability of the compounds obtained in the air, as well as in aqueous solutions. In addition, the synthesized ionic forms of vitamin C exhibited very good antibacterial and antifungal properties against different microorganisms, including pathogens. The tests also revealed the excellent or good deterrent activity toward common stored-grain insects (granary weevil, confused flour beetle, and khapra beetle), reaching the values determined for azadirachtin, known as the reference antifeedant. The best results were achieved with products containing two long alkyl substituents in the cation (dimethyldioctylammonium and didecyldimethylammonium) that proved to be extremely effective against all the organisms tested. The results of the biological activity indicate that the products synthesized belong to the third generation of ionic liquids. In conclusion, ascorbate-based ionic liquids with multifunctional (antibacterial, antifungal, antifeedant, and antioxidant) properties have substantial potential to be used in the storage of crop protection products.

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Section: ■ Introductionmentioning

confidence: 99%

Ionic Liquids Derived from Vitamin C as Multifunctional Active Ingredients for Sustainable Stored-Product Management

Niemczak

Kaczmarek

Klejdysz

et al. 2018

ACS Sustainable Chem. Eng.

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“…As disccused previously, the controllable friction behavior enabled in a wide range of humidity is attributed to the plentiful hydrogen bond donors and acceptors found in [Cho][Pro]. More importantly, Gontrani and coworkers found that the types of hydrogen bonds in Choline‐based IL/water mixtures could be determined by the water content, based on their molecular simulation and experimental studies . As schematically shown in Figure b, the water molecules prefer to establish H‐bonds with the cations and anions in the case of lower water content.…”

Section: Resultsmentioning

confidence: 74%

“…More importantly, Gontrani and coworkers found that the types of hydrogen bonds in Choline-based IL/water mixtures could be determined by the water content, based on their molecular simulation and experimental studies. [56,57] As schematically shown in Figure 6b, the water molecules prefer to establish H-bonds with the cations and anions in the case of lower water content. With the water concentration increase, IL pair formation decreases and H-bonds between water and water form, as shown in Figure 6c.…”

Section: Resultsmentioning

confidence: 99%

Controllable Friction of Green Ionic Liquids via Environmental Humidity

et al. 2020

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Intelligent control of friction is an attractive but challenging topic. In this work, it is investigated if it would be possible to adjust friction in a lubricated contact by controlling environmental humidity. By exploiting the ability to adjust the environmental humidity by various saturated salt solutions, friction behavior of contacts lubricated with Choline l‐Proline ([Cho][Pro]) is modulated in a wide range of relative humidity (RH). The friction increases when the environmental humidity is increased and decreases when water is partially evaporated to a lower RH. It is thus possible to control friction by environmental humidity. The addition of water in ionic liquids (ILs) causes a decrease in viscosity, but as the tests are calculated to be performed in boundary lubrication the viscosity change is not the main factor for the change in friction. The friction sensitivity of RH can be explained by the effect of adhesion on the water uptake from humid air by [Cho][Pro]. Furthermore, the reversible changes of H‐bond types determined by the water content could be another explanation to the altered friction.

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“…Analogous approaches based on a combined experimental and MD study by Gontrani et al ( 2017 ) have elucidated, using different degrees of water dilution in the IL, the behavior of hydrogen bonding between opposite- and like-charge dimers and the intercalation structure of the final solutions. These findings agree with what was found by Shyama and Lakshmipathi ( 2020 ) where 8 [EMIM][AA] ILs were investigated by DFT calculations.…”

Section: Structure and Computational Studiesmentioning

confidence: 99%

Cholinium amino acid-based ionic liquids

Donne

Bodo

2021

Biophys Rev

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Boosted by the simplicity of their synthesis and low toxicity, cholinium and amino acid-based ionic liquids have attracted the attention of researchers in many different fields ranging from computational chemistry to electrochemistry and medicine. Among the uncountable IL variations, these substances occupy a space on their own due to their exceptional biocompatibility that stems from being entirely made by metabolic molecular components. These substances have undergone a rather intensive research activity because of the possibility of using them as greener replacements for traditional ionic liquids. We present here a short review in the attempt to provide a compendium of the state-of-the-art scientific research about this special class of ionic liquids based on the combination of amino acid anions and cholinium cations.

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Bio ionic liquids and water mixtures: a structural study

Abstract: In this study we have explored, by means of ab initio molecular dynamics, a subset of three different water/cho+–phe− mixtures.

Cited by 16 publications

References 63 publications

Ionic Liquids Derived from Vitamin C as Multifunctional Active Ingredients for Sustainable Stored-Product Management

Ionic Liquids Derived from Vitamin C as Multifunctional Active Ingredients for Sustainable Stored-Product Management

Controllable Friction of Green Ionic Liquids via Environmental Humidity

Cholinium amino acid-based ionic liquids

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