1,3-Bis(carboxymethyl)imidazolium Chloride as a Sustainable, Recyclable, and Metal-Free Ionic Catalyst for the Biginelli Multicomponent Reaction in Neat Condition
Ontology highlight
ABSTRACT:
SUBMITTER: Madivalappa Davanagere P
PROVIDER: S-EPMC8515400 | biostudies-literature |
REPOSITORIES: biostudies-literature
Similar Datasets
Project description:Unique tunable aryl imidazolium ionic liquids successfully catalyzed Friedel-Crafts acylation and thioesterification in sealed tubes. These reactions can form a C-C bond and a C-S bond with high atom economy. Ionic liquids exhibited high activity and catalyzed essential reactions with good to excellent yields while retaining their catalytic activities for recycling.
| S-EPMC7024267 | biostudies-literature
Project description:We describe the synthesis of silver loaded on zirconia and its use as an efficient catalyst for a one-pot three-component reaction to synthesize 11 indenopyrimidine derivatives, of which 7 are new compounds. The procedure involves substituted benzaldehydes, indane-1,3-dione, and guanidinium hydrochloride, with ethanol as solvent. The proposed green protocol at room temperature is simple and efficient, giving excellent yields (90?96%) in short reaction times (<30 min). The protocol works well according to the green chemistry principles with respect to high atom economy, no need for column separation, and reusability of the catalyst, which are attractive features. XRD, TEM, SEM, and BET analysis were used to characterize the catalyst materials.
| S-EPMC6100188 | biostudies-literature
Project description:Ionic Liquids are a broad group of salts with low melting points that can be specifically tuned for a broad range of applications. Despite being initially considered “green” solvents, their better environmental friendliness compared to traditional solvents has been increasingly challenged. In this study, we aimed to investigate the molecular effects of ILs exposure by using RNA-sequencing to study differential gene expression patterns. Thus, we exposed Daphnia magna to 1-ethyl-3-methylimidazolium chloride ([C2mim]Cl), 1-dodecyl chloride-3-methylimidazolium ([C12mim]Cl) and cholinium chloride ([Chol]Cl). Results suggest that the three ILs share several mechanisms of toxicity, including cellular membrane and cytoskeleton damage, oxidative stress, inhibition of antioxidant enzymes, mitochondrial affectation, changes in protein biosynthesis and energy production, DNA damage, and ultimately, programmed cell death and disease initiation. Overall, the dataset revealed that [C2mim]Cl and [C12mim]Cl were, respectively, the least and the most toxic ILs at the transcriptional level. Also, it is reinforced that [Chol]Cl is not devoid of environmental hazardous potential. Unique gene expression signatures could also be identified for each IL.
2021-08-13 | GSE156769 | GEO
Project description:A series of ionic (mono-/di-)phosphines (L2, L4, and L6) with structural similarity and their corresponding neutral counterparts (L1, L3, and L5) were applied to modulate the catalytic performance of RuCl3???3H2O. With the involvement of the ionic diphosphine (L4), in which the two phosphino-fragments were linked by butylene group, RuCl3???3H2O with advantages of low cost, robustness, and good availability was found to be an efficient and recyclable catalyst for the alkoxycarbonylation of aryl halides. The L4-based RuCl3???3H2O system corresponded to the best conversion of PhI (96?%) along with 99?% selectivity to the target product of methyl benzoate as well as the good generality to alkoxycarbonylation of different aryl halides (ArX, X=I and Br) with alcohols MeOH, EtOH, i-PrOH and n-BuOH. The electronic and steric effects of the applied phosphines, which were analyzed by the 31P NMR for 1 J 31 P- 77 Se 1 J measurement and single-crystal X-ray diffraction, were carefully co-related to the performance RuCl3???3H2O catalyst. In addition, the L4-based RuCl3???3H2O system could be recycled successfully for at least eight runs in the ionic liquid [Bmim]PF6.
| S-EPMC6356175 | biostudies-literature
Project description:In order to improve the total sulfur removal rate in coal combustion, an acidic ionic liquid (IL) 1-carboxymethyl-3-methylimidazolium hydrogen sulfate ([HOOCCH2mim][HSO4]) as the extractant combined with the oxidant 30% hydrogen peroxide (H2O2) was applied to reduce the total sulfur content, and its microscopic mechanism of desulfurization was analyzed. The experimental results show that the desulfurization rate of the [HOOCCH2mim][HSO4]-H2O2 (1:10) solution was 45.12% and the organic sulfur removal rate was 16.26%, which were significantly higher than those of only H2O2 or pure [HOOCCH2mim][HSO4]. Fourier-transform infrared (FTIR) spectroscopy and X-ray photoelectron spectroscopy analyses showed that the mercaptan -SH and disulfide -S-S- in coal decreased after being treated with IL-H2O2. In particular, the results of FTIR spectroscopy indicated that the relative proportion of -S-S-and -SH treated with IL-H2O2 (1:10) decreased by 31.9 and 27.2%, respectively, compared with that of a pure IL. This is due to H2O2 oxidation; -SH and -S-S- were oxidized to sulfoxide and then the sulfoxide transferred from the coal phase to the IL phase, which improved organic sulfur removal from coal. Therefore, the combination of an ionic liquid and H2O2 could increase the total desulfurization rate. In addition, the thermogravimetric analysis of coal is divided into four different stages; the weight loss during the combustion stage and the residues show that the IL-H2O2 could improve the coal combustion because of good previous swelling and destruction of bridge bonds and hydrogen bonding of coal. Besides, the fewer residues in IL-H2O2-treated coals also indicate that a less amount of inorganic substance is left in coal after IL-H2O2 desulfurization, which is consistent with the desulfurization results.
| S-EPMC7450613 | biostudies-literature
Project description:Formic acid is a promising energy carrier for on-demand hydrogen generation. Because the reverse reaction is also feasible, formic acid is a form of stored hydrogen. Here we present a robust, reusable iridium catalyst that enables hydrogen gas release from neat formic acid. This catalysis works under mild conditions in the presence of air, is highly selective and affords millions of turnovers. While many catalysts exist for both formic acid dehydrogenation and carbon dioxide reduction, solutions to date on hydrogen gas release rely on volatile components that reduce the weight content of stored hydrogen and/or introduce fuel cell poisons. These are avoided here. The catalyst utilizes an interesting chemical mechanism, which is described on the basis of kinetic and synthetic experiments.
| S-EPMC4834634 | biostudies-literature
Project description:Environmental and health concerns force the search for sustainable super engineering plastics (SEPs) that utilise bio-derived cyclic monomers, e.g. isosorbide instead of restricted petrochemicals. However, previously reported bio-derived thermosets or thermoplastics rarely offer thermal/mechanical properties, scalability, or recycling that match those of petrochemical SEPs. Here we use a phase transfer catalyst to synthesise an isosorbide-based polymer with a high molecular weight?>100?kg?mol-1, which is reproducible at a 1-kg-scale production. It is transparent and solvent/melt-processible for recycling, with a glass transition temperature of 212?°C, a tensile strength of 78?MPa, and a thermal expansion coefficient of 23.8 ppm K-1. Such a performance combination has not been reported before for bio-based thermoplastics, petrochemical SEPs, or thermosets. Interestingly, quantum chemical simulations show the alicyclic bicyclic ring structure of isosorbide imposes stronger geometric restraint to polymer chain than the aromatic group of bisphenol-A.
| S-EPMC6565616 | biostudies-literature
Project description:The microwave-assisted three-component reactions of 3,5-bis(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones, acenaphthenequinone and cyclic ?-amino acids in an ionic liquid, 1-butyl-3-methylimidazolium bromide, occurred through a domino sequence affording structurally intriguing diazaheptacyclic cage-like compounds in excellent yields.
| S-EPMC6273701 | biostudies-other
Project description:We disclose the unprecedented hybrid-ruthenium catalysis for distal meta-C-H activation. The hybrid-ruthenium catalyst was recyclable, as was proven by various heterogeneity tests, and fully characterized with various microscopic and spectroscopic techniques, highlighting the physical and chemical stability. Thereby, the hybrid-ruthenium catalysis proved broadly applicable for meta-C-H alkylations of among others purine-based nucleosides and natural product conjugates. Additionally, its versatility was further reflected by meta-C-H activations through visible-light irradiation, as well as para-selective C-H activations.
| S-EPMC7756437 | biostudies-literature
Project description:Biological properties of ionic liquids (ILs) have been usually tested with the help of standard biodegradation or ecotoxicity tests. So far, several articles on the identification of intermediate metabolites of microbiological decay of ILs have been published. Simultaneously, the number of novel ILs with unrecognized characteristics regarding biodegradability and effect on organisms and environment is still increasing. In this work, seven imidazolium ionic liquids of different chemical structure were studied. Three of them are 1-alkyl-3-methyl-imidazolium bromides, while the other four are tetra- or completely substituted imidazolium iodides. This study focused on the identification of intermediate metabolites of the aforementioned ionic liquids subjected to biodegradation in a laboratory activated sludge system. Both fully substituted ionic liquids and 1-ethyl-3-methyl-imidazolium bromide were barely biodegradable. In the case of two of them, no biotransformation products were detected. The elongation of the alkyl side chain made the IL more susceptible for microbiological decomposition. 1-Decyl-3-methyl-imidazolium bromide was biotransformed most easily. Its primary biodegradation up to 100 % could be achieved. Nevertheless, the cleavage of the imidazolium ring has not been observed.
| S-EPMC4637002 | biostudies-literature