{"title":"Ionic liquid-assisted approaches in the synthesis of nitrogen-containing heterocycles: A focus on 3- to 6-membered rings","authors":"Pravas Maity , Amrit Krishna Mitra","doi":"10.1016/j.jil.2025.100146","DOIUrl":"10.1016/j.jil.2025.100146","url":null,"abstract":"<div><div>Nitrogen-containing heterocyclic compounds represent one of the most significant groups in traditional organic chemistry. Many pharmaceuticals, designed to replicate the bioactivity of natural compounds, contain these nitrogen-based heterocyclic compounds. Organic chemists have invested substantial effort into creating these compounds, focusing on innovative and efficient synthetic methods. Ionic liquids (ILs) are highly valued in organic synthesis due to their unique characteristics, such as a wide liquid range, superior solvating properties, low vapour pressure, non-flammability, eco-friendliness, and high thermal stability. They also enhance reaction rates and are easily recyclable. Their dual role as both catalysts and reaction media has drawn significant attention from chemists. With about 4000 research papers published annually, ILs continue to be a major focus of scientific exploration, particularly in the synthesis of nitrogen-containing heterocyclic compounds. This review aims to portray the synthesis of nitrogen-containing heterocyclic compounds (3-membered to 6-membered) assisted by ionic liquids.</div></div>","PeriodicalId":100794,"journal":{"name":"Journal of Ionic Liquids","volume":"5 1","pages":"Article 100146"},"PeriodicalIF":0.0,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143768351","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Decomposition of ionic liquids with chloride anions: A combined study of the gas-phase dissociation of the isolated cations and pyrolysis of the bulk","authors":"Taofiq Abdulraheem, Amanda L. Patrick","doi":"10.1016/j.jil.2025.100149","DOIUrl":"10.1016/j.jil.2025.100149","url":null,"abstract":"<div><div>As the synthesis of diverse ionic liquids (ILs) proliferates and as (proposed) applications increase, there is growing concern about the possibility of finding IL components and degradation products in the environment, possibly as persistent and/or hazardous contaminants. Understanding IL stability and understanding what decomposition products arise when ILs do degrade will help us better understand potential environmental threats. While stability raises concern in terms of persistent environmental pollution, it is also one of the major strengths of ILs toward their many applications. From understanding degradation mechanisms that could be at play during use under extreme conditions to understanding the products that may form during incomplete incineration, a molecular-level understanding of IL thermal transformations is also desirable beyond the environmental concern. Ideally, such a molecular-level understanding could eventually lead to better predictions of thermal stability as a function of structure prior to synthesis and experimental characterization. In this work, the pyrolysis products of nine ILs, each with the chloride anion and various N-heterocyclic cations, were studied by gas chromatography-mass spectrometry and these results were compared to the unimolecular gas-phase dissociation behavior of the respective isolated cations. By comparing these two experimental approaches, differences between unimolecular decomposition pathways and bimolecular decomposition or transformation pathways could be explored. Further, these comparisons shed light on whether gas-phase dissociation of the isolated cation, which is a very straightforward experiment, could be used to provide any insights into bulk pyrolysis pathways. Overall trends, class-based trends, and behaviors specific to only certain species are identified and discussed. This work provides new molecular insights into the pyrolysis of ILs by studying an array of cations, including those with functionalized R-groups, and by integrating results from bulk pyrolysis with those from collision-induced dissociation of the isolated cation.</div></div>","PeriodicalId":100794,"journal":{"name":"Journal of Ionic Liquids","volume":"5 1","pages":"Article 100149"},"PeriodicalIF":0.0,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143760429","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Stephanie C. Jones , Devin J. Schwaibold , Grant Meadows , Brennan Shuler , Richard Sykora , Frank R. Fronczek , James H. Davis Jr , Benjamin F. Wicker
{"title":"Facile synthesis of tetraaryl phosphonium ionic liquids","authors":"Stephanie C. Jones , Devin J. Schwaibold , Grant Meadows , Brennan Shuler , Richard Sykora , Frank R. Fronczek , James H. Davis Jr , Benjamin F. Wicker","doi":"10.1016/j.jil.2025.100147","DOIUrl":"10.1016/j.jil.2025.100147","url":null,"abstract":"<div><div>The syntheses of triphenyl-2-pyridylphosphonium salts, [Mopyphos]A, where A<sup>-</sup> = BF<sub>4</sub><sup>-</sup>, B(C<sub>6</sub>H<sub>5</sub>)<sub>4</sub><sup>-</sup>, (CF<sub>3</sub>SO<sub>2</sub>)<sub>2</sub>N<sup>-</sup>, Sac<sup>-</sup>, and Ace<sup>-</sup>. (Sac<sup>-</sup> = saccharinate, Ace<sup>-</sup> = acesulfamate) are described. These salts can be synthesized on a multi-gram scale with good yields and have been characterized by NMR, single crystal XRD, and HRMS. Thermal analyses indicate that the bistriflimide (Tf<sub>2</sub>N<sup>-</sup> = (CF<sub>3</sub>SO<sub>2</sub>)<sub>2</sub>N<sup>-</sup>) salts are especially amenable towards high-temperature ionic liquid (IL) applications with decomposition temperatures above 450°C. The synthetic methods described herein can be utilized to generate several phosphonium bistriflimide ILs of the general formula [(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>P-Ar]Tf<sub>2</sub>N, where Ar = N-heteroaryl).</div></div>","PeriodicalId":100794,"journal":{"name":"Journal of Ionic Liquids","volume":"5 1","pages":"Article 100147"},"PeriodicalIF":0.0,"publicationDate":"2025-03-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143738367","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Graphene oxide based [EMIM]Cl ionanofluids in a tube and their heat transfer, and friction factor analyses under high Prandtl numbers: Experimental and ANN predictions","authors":"L. Syam Sundar","doi":"10.1016/j.jil.2025.100144","DOIUrl":"10.1016/j.jil.2025.100144","url":null,"abstract":"<div><div>In this study, the stable Graphene Oxide (GO) ionanofluids were prepared and investigated the thermophysical properties, heat transfer coefficient, and friction factor experimentally. These ionanofluids were prepared by dispersing the synthesized GO into the ionic liquid of 1-ethyl-3-methylimidazolium chloride [EMIM]Cl in the weight percentages of 0.05 %, 0.1 %, 0.3 % and 0.5 %, respectively. The obtained experimental data of Reynolds number, and weight percentage was used as input parameters, and heat transfer coefficient, Nusselt number, and friction factor was used as output parameters for the Artificial Neural Network- Scaled Conjugate Gradient (ANN-SCG) analysis. The results indicated that, the thermal conductivity is enhanced by 26.39 % at a temperature of 60°C, and the viscosity enhancement of 30.44 % at a temperature of 30°C, and at 0.5 % weight percentage. The results were also indicated that, the Nusselt number, heat transfer coefficient is enhanced by 32.27 %, and 41.96 %, with a friction factor penalty of 14.04 % at 0.5 % weight percentage and at a Reynolds number of 297.4, respectively, over base fluid. The ANN-SCG results are almost predicts high accuracy when compared with the experimental data. The correlation coefficient (R<sup>2</sup>) of Nusselt number, heat transfer coefficient, and friction factor are 0.9815, 0.9812, and 0.9918, respectively. Using the experimental data, a new Nusselt number and friction factor correlations were proposed.</div></div>","PeriodicalId":100794,"journal":{"name":"Journal of Ionic Liquids","volume":"5 1","pages":"Article 100144"},"PeriodicalIF":0.0,"publicationDate":"2025-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143735246","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Refilwe Mogale , Yuel W. Abraha , Marietjie Schutte-Smith , Hendrik.G. Visser , Elizabeth Erasmus
{"title":"Natural deep eutectic solvents (NADES) derived from choline chloride and indole-3-butyric acid for optimized CO2 utilization through cycloaddition with epichlorohydrin","authors":"Refilwe Mogale , Yuel W. Abraha , Marietjie Schutte-Smith , Hendrik.G. Visser , Elizabeth Erasmus","doi":"10.1016/j.jil.2025.100142","DOIUrl":"10.1016/j.jil.2025.100142","url":null,"abstract":"<div><div>The transition to a sustainable chemical industry necessitates the development of environmentally friendly solvents and catalysts. Carbon dioxide utilization reactions offer a promising avenue for reducing greenhouse gas emissions, but their commercialization depends on the availability of green catalysts and solvents. Traditional options often suffer from toxicity, volatility, and flammability, hindering their industrial application. Natural deep eutectic solvents (NADES) present a sustainable alternative. This study explores the potential of NADES derived from choline chloride (ChCl) and indole-3-butyric acid (IBA) as catalysts for the cycloaddition of CO<sub>2</sub> with epichlorohydrin. Nine NADES compositions were prepared and characterized using FTIR, NMR, DSC, and TGA. The [ChCl] : [IBA] (0.8 : 0.2) mixture exhibited the lowest melting point (4.4 °C) and the highest catalytic activity (TOF = 1091 h ¹). Under optimized conditions, the catalyst demonstrated excellent reusability, maintaining its activity over four catalytic cycles.</div></div>","PeriodicalId":100794,"journal":{"name":"Journal of Ionic Liquids","volume":"5 1","pages":"Article 100142"},"PeriodicalIF":0.0,"publicationDate":"2025-03-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143696910","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Muhamad Iqbal Ishak , Asiah Nusaibah Masri , Azad Anugerah Ali Rasol , Izni Mariah Ibrahim , Hasrinah Hasbullah
{"title":"Amino Acid Deep Eutectic Solvents (AADES) in Oil Purification: An Overview of Properties, Applications, and Future Directions","authors":"Muhamad Iqbal Ishak , Asiah Nusaibah Masri , Azad Anugerah Ali Rasol , Izni Mariah Ibrahim , Hasrinah Hasbullah","doi":"10.1016/j.jil.2025.100143","DOIUrl":"10.1016/j.jil.2025.100143","url":null,"abstract":"<div><div>Amino Acid Deep Eutectic Solvents (AADES) are emerging as a promising sustainable alternative to conventional organic solvents, particularly in oil purification processes. This review explores the unique properties of AADES, including their environmental benefits, biocompatibility, and high extraction efficiency. Given the limited availability of published studies specifically on AADES for oil purification, this work references research on deep eutectic solvents (DES) containing amino acids, as well as DES with mechanisms that could be applicable to AADES. The article highlights the potential role of AADES in enhancing oil purification techniques, offering a greener and more efficient approach to industrial applications. However, challenges remain, particularly regarding their scalability, long-term stability, and the lack of direct comparative studies with traditional solvents. By integrating insights from existing DES studies, this review underscores the need for further research to optimize AADES formulations for specific contaminants and improve their performance in large-scale applications. Additionally, understanding the mechanisms governing their interactions with biomolecules and oil-based contaminants is crucial for advancing their industrial viability. Addressing these gaps will support the broader adoption of AADES, contributing to more sustainable and effective oil purification processes while promoting environmental conservation efforts.</div></div>","PeriodicalId":100794,"journal":{"name":"Journal of Ionic Liquids","volume":"5 1","pages":"Article 100143"},"PeriodicalIF":0.0,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143725627","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis and properties of GABA-based ionic liquids and deep eutectic solvents","authors":"Satoshi Kitaoka , Natsuko Shimaike , Yuhei Kubo , Yukino Isshiki , Anju Furukawa , Kaoru Nobuoka","doi":"10.1016/j.jil.2025.100141","DOIUrl":"10.1016/j.jil.2025.100141","url":null,"abstract":"<div><div>GABA-based ionic liquids (ILs) and deep eutectic solvents (DESs) were synthesized and their properties compared with those of ILs and DESs with similar structures. In ILs, using GABA as the anion, [N<sub>4444</sub>][GABA], [N<sub>2224</sub>][GABA] and [N<sub>4446</sub>][GABA] in combination with ammonium, [C<sub>2</sub>mim][GABA] in combination with imidazolium and [Ch][GABA] in combination with the biological substance choline were synthesized. Among the ILs under investigation, [N<sub>2224</sub>][GABA], [N<sub>4446</sub>][GABA] and [C<sub>2</sub>mim][GABA] were liquid at room temperature. In DESs, GABA was used as the hydrogen bond donor and three GABA-based DESs were prepared by combining [Ch][Cl], [L-Car][Cl], and [DL-Car][Cl] as hydrogen bond acceptors. Among these DESs, [L-Car][Cl] : GABA (1:1) and [DL-Car][Cl] : GABA (1:1) were shown to be liquid at room temperature. Comparing the viscosities of the prepared liquids showed that DESs was significantly higher than ILs. The viscosity increase was suggested to be due to the hydrogen bond acceptors of [L-Car][Cl] : GABA (1:1) and [DL-Car][Cl] : GABA (1:1) having carboxyl groups. The toxicity of GABA-based ILs and DESs was investigated using HeLa cells, which showed that their cytotoxicity was similar to or lower than that of GABA alone in HeLa cells.</div></div>","PeriodicalId":100794,"journal":{"name":"Journal of Ionic Liquids","volume":"5 1","pages":"Article 100141"},"PeriodicalIF":0.0,"publicationDate":"2025-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143642978","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Saba Goharshenas Moghadam, Gelareh Momen, Reza Jafari
{"title":"Navigating ice-free Horizons: A Review on the Role of Ionic liquids and Deep eutectic solvents in Anti-icing Technologies","authors":"Saba Goharshenas Moghadam, Gelareh Momen, Reza Jafari","doi":"10.1016/j.jil.2025.100139","DOIUrl":"10.1016/j.jil.2025.100139","url":null,"abstract":"<div><div>This review investigates the unexplored potential of ionic liquids (ILs) and deep eutectic solvents (DESs) as innovative solutions for advancing anti-icing technologies, particularly in harsh sub-freezing conditions, with a focus on coating applications. Despite limited exploration, ILs and DESs stand out due to their remarkable properties—low melting points, excellent hydrogen-bond donor capabilities, thermal stability, and the formation of quasi-liquid layers that drastically reduce ice adhesion. While research on IL-based coatings for ice mitigation is still in its infancy, the promising synergy between DESs and ILs paves the way for creating highly effective ice-resistant surfaces. DESs, recognized for their eco-friendly and straightforward preparation, have been primarily studied for anti-freezing resilience, leaving their potential as ice growth inhibitors largely unexplored. This review presents DESs as effective ice growth inhibitors and highlights their synergistic combination with ILs, functioning as dynamic interface melting agents, for enhanced ice mitigation performance. Furthermore, the review consolidates current studies, emphasizing the need for further investigation into ILs and DESs for combating ice formation. It also proposes future research directions, such as exploring diverse IL chemistries, enhancing the stability of ILs, and investigating novel matrix materials to improve mechanical durability. The review provides a broad perspective on integrating these materials into various industrial and environmental applications, offering fresh insights into their transformative potential in anti-icing systems.</div></div>","PeriodicalId":100794,"journal":{"name":"Journal of Ionic Liquids","volume":"5 1","pages":"Article 100139"},"PeriodicalIF":0.0,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143600764","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Molecular interactions of 1-butyl-2,3-dimethylimidazolium chloride ionic liquid in aqueous L-alanine solutions through volumetric and compressibility approaches","authors":"Vandana Patel, Anuja Jain, Sangesh P. Zodape","doi":"10.1016/j.jil.2025.100140","DOIUrl":"10.1016/j.jil.2025.100140","url":null,"abstract":"<div><div>The interactions of 1-Butyl-2,3-dimethylimidazolium chloride ionic liquid i.e. [BMMIm][Cl] with <span>l</span>-alanine as a function of temperature and concentration have been inspected. The density and speed of sound values for the [BMMIm][Cl] in different concentrations (0.05 mol·kg<sup>-1</sup> and 0.10 mol·kg<sup>-1</sup>) of aqueous <span>l</span>-alanine solutions within the concentration range of 0.01 to 0.13 mol·kg<sup>-1</sup> at <em>T</em> = (288.15, 293.15, 298.15, 303.15, 308.15, 313.15 and 318.15) K and atmospheric pressure have been measured. The apparent molar volume of solute, limiting apparent molar volume of solute, and transfer limiting apparent molar volume of solute for [BMMIm][Cl] in aqueous <span>l</span>-alanine solutions have been calculated using density data. The apparent molar isentropic compression of solute, limiting apparent molar isentropic compression of solute, and transfer limiting apparent molar isentropic compression of solute have been assessed utilizing speed of sound data. The expansivity parameter and its derivative with respect to temperature, and the pair and triplet interaction coefficients were evaluated. The findings of the study have been analyzed in terms of solute-solute and solute-solvent interactions in ternary systems.</div></div>","PeriodicalId":100794,"journal":{"name":"Journal of Ionic Liquids","volume":"5 1","pages":"Article 100140"},"PeriodicalIF":0.0,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143686621","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Algae cultivation in Ultra-high concentration Amino acid based ionic liquids","authors":"Yuchao Li , Yuli Kou , Jide Wang , Yansong Zhao","doi":"10.1016/j.jil.2025.100138","DOIUrl":"10.1016/j.jil.2025.100138","url":null,"abstract":"<div><div>Liquid water is an important solvent for carbon-based life, due to its special structure and hydrogen bond engaging the biochemical reactions and energy transformations in the cell. However, the liquid window of water is narrow, within 0–100 °C at 1 atm. When water is partly replaced using ionic liquids (ILs) to transfer energy and nutrition, life activities may happen at a wide temperature range and a wide pressure range on earth, in the solar system and the universe. Aqueous Gly-based ILs were employed as a culture medium for the cultivation of algae. Four different kinds of Gly-based ILs were first synthesized by neutral reaction. Structure of synthesized ILs was confirmed by FT-IR and NMR. Furthermore, effect of Gly-based ILs concentration on algae growth was investigated. Growth rate of algae was tested by microscope and UV–vis according to the absorption of chlorophyll. The Gly-based IL presented higher biological compatibility of algae than previous work. The highest concentration of glycine phosphate suit for algae cultivation is 15 % and the algae could reproduce for 30 days without obvious inhibition. This research is promising work in the context of the cultivation of algae in amino acid IL based culture medium and exploring the life activity restricted zone on earth.</div></div>","PeriodicalId":100794,"journal":{"name":"Journal of Ionic Liquids","volume":"5 1","pages":"Article 100138"},"PeriodicalIF":0.0,"publicationDate":"2025-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143552207","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}