Third-generation ionic liquids with <i>N</i>-alkylated 1,4-diazabicyclo[2.2.2]octane cations and pelargonate anions

Turguła, Anna; Stęsik, Konrad; Materna, Katarzyna; Klejdysz, Tomasz; Praczyk, T.; Pernak, J.

doi:10.1039/d0ra00766h

Cited by 16 publications

(20 citation statements)

References 40 publications

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“…1055 [cm −1 ]. The vibration values were consistent with the literature data for the characteristic vibrations of functional groups in cations [18,41] and the anions [42] . Elemental analysis of CHN of compounds was carried out as well, which confirmed the purity of the ILs.…”

Section: Resultssupporting

confidence: 90%

“…[16] However, gemini ammonium tetracationic DABCO surfactants have the possibility to be used as stabilizers of liposomal formulations for transdermal drug delivery. [17] ILs with a monoalkylated derivative of 1,4-diazabicyclo[2.2.2]octane cations and 4-chloro-2-methylphenoxyacetate [14] or pelargonate [18] anions were focused on for their herbicidal or deterrent activity. DABCO's broad spectrum of activity encourages further research and exploration of other applications.…”

Section: Introductionmentioning

confidence: 99%

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Long‐Chain Ionic Liquids Based on Monoquaternary DABCO Cations and TFSI Anions: Towards Stable Electrolytes for Electrochemical Capacitors

et al. 2020

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The desirable properties of ionic liquids (ILs) enable their use in various branches of chemistry, through a wide range of applications, e. g. as organic electrolytes. In the present study, an efficient two‐step method was developed for the synthesis of long‐chain ionic liquids with alkyl derivatives of DABCO as cations and bis(trifluoromethane)sulfonimide as anions. ILs obtained with high yields (≥91 %) were solids with melting points that increased with the rise in the number of carbon atoms of the alkyl substituent in the bicyclic cation. The structure of the compounds was confirmed by spectroscopic methods and elemental analysis. All compounds were soluble in the main solvents except water and hexane. The solubility in organic solvents such as acetonitrile allowed the use of synthesized ILs in electrochemical capacitors. Electrochemical tests revealed that the ILs enhanced the conductivity of organic electrolytes. This phenomenon improved the cyclability and reduced the internal resistance of the electrochemical capacitors.

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Section: Resultssupporting

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Long‐Chain Ionic Liquids Based on Monoquaternary DABCO Cations and TFSI Anions: Towards Stable Electrolytes for Electrochemical Capacitors

et al. 2020

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“… 42 , 58 More recently, the field of bio-HILs was investigated, by searching for renewable or biodegradable cations (e.g., betaine, carnitine, d -glucose, choline, acetylcholine), 44 , 45 , 59 , 61 , 62 , 74 , 75 as well as anions (e.g., pelargonate). 33 , 34 , 53 , 76 , 77 Simultaneously, testing of various combinations of herbicidal anions and ammonium-based cations was in progress, resulting in numerous groups of their sources ( Figure 2 ).…”

Section: Current State Of Knowledgementioning

confidence: 99%

“… 23 This observation may be explained by the fact that in case of the quaternary cations, the risk of deprotonation and subsequent volatilization of both amine and acid does not exist. 34 Furthermore, the molecular mass of HILs should also be considered as a factor influencing their volatility. To date, it has been established that the increase in molecular mass of the active ingredient (by combination of 2,4-dichlorophenoxyacetic acid with amines substituted with different length of alkyls) decreased its volatility by reducing its saturated vapor pressure.…”

Section: Characterization Of Hilsmentioning

confidence: 99%

Herbicidal Ionic Liquids: A Promising Future for Old Herbicides? Review on Synthesis, Toxicity, Biodegradation, and Efficacy Studies

Wilms

Woźniak-Karczewska

Syguda

et al. 2020

J. Agric. Food Chem.

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The transformation of agrochemicals into herbicidal ionic liquids (HILs) has been suggested as a solution to problems associated with commercial forms of herbicides. The aim of this review was to summarize the latest progress in the field of HILs, including their synthesis as well as physicochemical and biological properties, and to address the areas that require further research in order to ensure their safe commercialization (e.g., data regarding biodegradability, toxicity, and environmental fate). The first part of the review provides an in-depth summary of the current state of knowledge regarding HILs, particularly the anions and cations used for their synthesis. The second part highlights the employed synthesis methods and elucidates their respective advantages and limitations. The third section is focused on the characterization of HILs with emphasis on the methods and factors that are significant in terms of their practical application. Subsequently, the issues associated with the biodegradation and toxic effects of HILs are discussed based on the relevant literature reports. All sections include comprehensively tabulated data in order to enable rapid comparison of utilized approaches. Finally, all the findings are critically analyzed in terms of crucial disadvantages (especially the lack of standardization), which allowed us to establish future recommendations and basic guidelines that are presented in the last section.

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“…Fatty acid ionic liquids were used successfully in various industries for different purposes, such as pharmaceutical [ 136 ], biorefining processes [ 137 ], solvents and co-solvents [ 138 , 139 , 140 ], dissolution and levulination of cellulose [ 141 ], formation of aqueous biphasic systems [ 142 ], CO 2 capture [ 143 , 144 ], catalyst [ 145 ], lubricant additives [ 146 ], plant protection products [ 147 ], and extraction agents [ 148 ]. Therefore, the demulsification potential of bio-based ionic liquids, as well as their human health effects, are worthy of further investigations in future.…”

Section: Challenges and Opportunitiesmentioning

confidence: 99%

Application of Ionic Liquids for Chemical Demulsification: A Review

Hassanshahi

2020

Molecules

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In recent years, ionic liquids have received increasing interests as an effective demulsifier due to their characteristics of non-flammability, thermal stability, recyclability, and low vapor pressure. In this study, emulsion formation and types, chemical demulsification system, the application of ionic liquids as a chemical demulsifier, and key factors affecting their performance were comprehensively reviewed. Future challenges and opportunities of ionic liquids application for chemical demulsification were also discussed. The review indicted that the demulsification performance was affected by the type, molecular weight, and concentration of ionic liquids. Moreover, other factors, including the salinity of aqueous phase, temperature, and oil types, could affect the demulsification process. It can be concluded that ionic liquids can be used as a suitable substitute for commercial demulsifiers, but future efforts should be required to develop non-toxic and less expensive ionic liquids with low viscosity, and the demulsification efficiency could be improved through the application of ionic liquids with other methods such as organic solvents.

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Third-generation ionic liquids with N-alkylated 1,4-diazabicyclo[2.2.2]octane cations and pelargonate anions

Abstract: Novel ionic liquids with cations based on alkyl derivatives of 1,4-diazabicyclo[2.2.2]octane (DABCO) and an anion derived from naturally occurring pelargonic acid possessed double biological functions: herbicidal and deterrent activity.

Cited by 16 publications

References 40 publications

Long‐Chain Ionic Liquids Based on Monoquaternary DABCO Cations and TFSI Anions: Towards Stable Electrolytes for Electrochemical Capacitors

Long‐Chain Ionic Liquids Based on Monoquaternary DABCO Cations and TFSI Anions: Towards Stable Electrolytes for Electrochemical Capacitors

Herbicidal Ionic Liquids: A Promising Future for Old Herbicides? Review on Synthesis, Toxicity, Biodegradation, and Efficacy Studies

Application of Ionic Liquids for Chemical Demulsification: A Review

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