Order in the chaos: the secret of the large negative entropy of dissolving 1-alkyl-3-methylimidazolium chloride in trihexyltetradecylphosphonium chloride

2015 ◽  
Vol 17 (6) ◽  
pp. 4034-4037 ◽  
Author(s):  
Stefan Zahn ◽  
Annegret Stark
Keyword(s):  
Ionic Liquids ◽  
Ion Dynamics ◽  
Negative Entropy ◽  
Alkyl Chains ◽  
Ion Cluster

A large symmetric ion cluster cage is formed if 1-alkyl-3-methylimidazolium chloride ionic liquids with short alkyl chains are added to trihexyltetradecylphosphonium chloride which results in a large negative entropy of dissolution and an unexpected ion dynamics.

scholarly journals Synthesis, antibiotic structure–activity relationships, and cellulose dissolution studies of new room-temperature ionic liquids derived from lignin

2021 ◽  
Vol 14 (1) ◽  
Author(s):  
Shihong Liu ◽  
Michael Gonzalez ◽  
Celine Kong ◽  
Scott Weir ◽  
Aaron M. Socha
Keyword(s):  
Antibacterial Activity ◽  
Ionic Liquids ◽  
Room Temperature ◽  
Oxidation Products ◽  
Cellulose Dissolution ◽  
Melting Points ◽  
E Coli ◽  
Alkyl Chains ◽  
Renewable Feedstocks ◽  
Commodity Chemicals

Abstract Background Ionic liquids (ILs) are promising pretreatment solvents for lignocellulosic biomass, but are largely prepared from petroleum precursors. Benzaldehydes from depolymerized lignin, such as vanillin, syringaldehyde, and 4-methoxy benzaldehyde, represent renewable feedstocks for the synthesis of ionic liquids. We herein report syntheses of novel lignin-derived ionic liquids, with extended N-alkyl chains, and examine their melting points, cellulose dissolution capacities, and toxicity profiles against Daphnia magna and E. coli strain 1A1. The latter organism has been engineered to produce isoprenol, a drop-in biofuel and precursor for commodity chemicals. Results The new N,N-diethyl and N,N-dipropyl methyl benzylammonium ILs were liquids at room temperature, showing 75–100 °C decreased melting points as compared to their N,N,N-trimethyl benzylammonium analog. Extension of N-alkyl chains also increased antibacterial activity threefold, while ionic liquids prepared from vanillin showed 2- to 4-fold lower toxicity as compared to those prepared from syringaldehyde and 4-methoxybenzaldehyde. The trend of antibacterial activity for anions of lignin-derived ILs was found to be methanesulfonate < acetate < hydroxide. Microcrystalline cellulose dissolution, from 2 to 4 wt% after 20 min at 100 °C, was observed in all new ILs using light microscopy and IR spectroscopy. Conclusions Ionic liquids prepared from H-, S- and G-lignin oxidation products provided differential cytotoxic activity against E. coli and D. magna, suggesting these compounds could be tailored for application specificity within a biorefinery.

scholarly journals Voltammetric sensor based on long alkyl chain tetraalkylammonium ionic liquids comprising ascorbate anion for determination of nitrite

2021 ◽  
Vol 188 (2) ◽  
Author(s):  
Tomasz Rębiś ◽  
Michał Niemczak ◽  
Patrycja Płócienniczak ◽  
Juliusz Pernak ◽  
Grzegorz Milczarek
Keyword(s):  
Ionic Liquids ◽  
Electrostatic Interactions ◽  
Film Surface ◽  
Modified Electrodes ◽  
Voltammetric Sensor ◽  
Nitrite Oxidation ◽  
Alkyl Chains ◽  
Modified Surface ◽  
Influence Of Ph

AbstractAn electrochemical sensor was fabricated utilizing ionic liquids possessing cations with long alkyl chains such as trimethyl octadecylammonium and behenyl trimethylammonium and ascorbate anion. The ionic liquids were drop-coated onto the electrode. Thin modifying layers were prepared. Cyclic voltammetric investigations revealed electrostatic interactions between the electrochemical probes and the modified surface, proving that a positive charge was established at the film surface. Hence, negatively charged species such as nitrite can be pre-concentrated on the surface of presented modified electrodes. The fabricated electrodes have been used as a voltammetric sensor for nitrite. Due to the electrostatic accumulation properties of long alkyl cation, the assay exhibits a remarkable improvement in the voltammetric response toward nitrite oxidation. The influence of pH on the electrode response was thoroughly investigated, and the mechanism of the electrode was established. The developed sensor showed a linear electrochemical response in the range 1.0–50 μM with a detection limit of 0.1 μM. The electrode revealed good storage stability, reproducibility, and anti-interference ability. The determination of nitrite performed in curing salts brought satisfactory results. Graphical abstract

scholarly journals Enhancement of Functional Properties of Liquid Electrolytes for Lithium‐Ion Batteries by Addition of Pyrrolidinium‐Based Ionic Liquids with Long Alkyl‐Chains

2020 ◽  
Vol 3 (10) ◽  
pp. 1059-1068 ◽  
Author(s):  
Arcangelo Celeste ◽  
Laura Silvestri ◽  
Marco Agostini ◽  
Matthew Sadd ◽  
Stefano Palumbo ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Lithium Ion Batteries ◽  
Functional Properties ◽  
Lithium Ion ◽  
Alkyl Chains ◽  
Liquid Electrolytes

scholarly journals Evaluating the Toxicity of Ionic Liquids on Shewanella sp. for Designing Sustainable Bioprocesses

2020 ◽  
Vol 7 ◽  
Author(s):  
Hakima Kebaili ◽  
Antonia Pérez de los Ríos ◽  
María José Salar-García ◽  
Víctor Manuel Ortiz-Martínez ◽  
Mostefa Kameche ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Chemical Structure ◽  
Marine Bacterium ◽  
Diffusion Test ◽  
Disk Diffusion Test ◽  
Alkyl Chains ◽  
Key Factor ◽  
Wide Group ◽  
Separation Media ◽  
The Relationship

Ionic liquids (ILs) are widely used as reaction and separation media in many technologies due to their unique and advantageous physicochemical properties. Thus, further studies approaching the study of the toxicity of these materials are required. Moreover, they are utilized in devices in which microorganisms such as Shewanella sp. act as biocatalysts. Thus, in this work, the toxicity of 69 ILs on the marine bacterium Shewanella sp. was tested. Specifically, the ILs analyzed were based on the cations imidazolium, pyridinium, pyrrolidinium, piperidinium, morpholinium, oxazolinium, phosphonium, ammonium, and sulfonium, in combination with different anions. The toxicities of this wide group of ILs on Shewanella sp. were determined using two methods: 1) the agar disk-diffusion test and 2) the growth inhibition test in liquid media. The relationship between toxicity and IL chemical structure was elucidated. A decrease in the hydrophobicity of the alkyl chain length was found to be a key factor to reduce IL toxicity. On the other hand, phosphonium-based ILs containing long alkyl chains were shown to be largely incompatible with Shewanella sp.

scholarly journals Vapor pressures of 1,3-dialkylimidazolium bis(trifluoromethylsulfonyl)imide ionic liquids with long alkyl chains

2014 ◽  
Vol 141 (13) ◽  
pp. 134502 ◽  
Author(s):  
Marisa A. A. Rocha ◽  
João A. P. Coutinho ◽  
Luís M. N. B. F. Santos
Keyword(s):  
Ionic Liquids ◽  
Vapor Pressures ◽  
Alkyl Chains

scholarly journals The impact of ionic liquid fluorinated moieties on their thermophysical properties and aqueous phase behaviour

2014 ◽  
Vol 16 (39) ◽  
pp. 21340-21348 ◽  
Author(s):  
Catarina M. S. S. Neves ◽  
Kiki A. Kurnia ◽  
Karina Shimizu ◽  
Isabel M. Marrucho ◽  
Luís Paulo N. Rebelo ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Aqueous Phase ◽  
Thermophysical Properties ◽  
Phase Behaviour ◽  
Alkyl Chains ◽  
The Impact

The presence of fluorinated alkyl chains in ionic liquids is quite relevant regarding their thermophysical properties and aqueous phase behaviour.

Molecular dynamics study of mesophase transitions upon annealing of imidazolium-based ionic liquids with long-alkyl chains

2018 ◽  
Vol 20 (15) ◽  
pp. 9796-9805 ◽  
Author(s):  
Hailong Peng ◽  
Momoji Kubo ◽  
Hayato Shiba
Keyword(s):  
Molecular Dynamics ◽  
Ionic Liquid ◽  
Ionic Liquids ◽  
Alkyl Chains ◽  
Different Temperatures ◽  
Long Time

The isotropic to mesophase transition upon the long-time annealing of a 1-dodecyl-3-methylimidazolium hexafluorophosphate ionic liquid at different temperatures is illustrated.

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