123-41-1Relevant articles and documents
Alendronic acid as ionic liquid: New perspective on osteosarcoma
Branco, Luís C.,Costa-Rodrigues, Jo?o,Fernandes, Maria H.,Santos, Miguel M.,Teixeira, Sónia
, (2020)
Herein the quantitative synthesis of eight new mono-and dianionic Organic Salts and Ionic Liquids (OSILs) from alendronic acid (ALN) is reported by following two distinct sustainable and straightforward methodologies, according to the type of cation. The prepared ALN-OSILs were characterized by spectroscopic techniques and their solubility in water and biological fluids was determined. An evaluation of the toxicity towards human healthy cells and also human breast, lung and bone (osteosarcoma) cell lines was performed. Globally, it was observed that the monoanionic OSILs showed lower toxicity than the corresponding dianionic structures to all cell types. The highest cytotoxic effect was observed in OSILs containing a [C2OHMIM] cation, in particular [C2OHMIM][ALN]. The latter showed an improvement in IC50 values of ca. three orders of magnitude for the lung and bone cancer cell lines as well as fibroblasts in comparison with ALN. The development of OSILs with high cytotoxicity effect towards the tested cancer cell types, and containing an anti-resorbing molecule such as ALN may represent a promising strategy for the development of new pharmacological tools to be used in those pathological conditions.
Synthesis and thermophysical properties of biocompatible cholinium-based amino acid ionic liquids
Tao, Duan-Jian,Cheng, Zheng,Chen, Feng-Feng,Li, Zhang-Min,Hu, Na,Chen, Xiang-Shu
, p. 1542 - 1548 (2013)
Nowadays the knowledge of thermodynamic properties for amino acid ionic liquids (AAILs) has been paramount for the design of many chemical processes. In this present work, a series of cholinium-based AAILs ([Ch][AA]) were synthesized by neutralization of choline hydroxide solution with five amino acids and then were characterized by 1H NMR, Fourier transform infrared (FT-IR), elemental analysis, thermogravimetry, and differential scanning calorimetry (DSC) analysis. Physico-chemical properties such as density, viscosity, refractive index, and conductivity were measured and correlated with the empirical equations in a wide temperature range. The thermal expansion coefficient values were also calculated from the acquired experimental density values. From the experimental data, it was found that the density, viscosity, and refractive index decreased while conductivity increased with the increase of temperature. The correlation results were proposed to be in good agreement with the experimental data, and optimal fitting parameters were presented. In addition, the coefficient of thermal expansion was considered to be independent of temperature in the range of (298.15 to 353.15) K.
Biofriendly ionic liquids for starch plasticization: A screening approach
Colomines,Decaen,Lourdin,Leroy
, p. 90331 - 90337 (2016)
A series of cholinium cation-based bioionic liquids (BioILs) were synthetized with the aim of screening their performance as potential plasticizers of thermoplastic starch. To synthesize these BioILs, two easy and fast synthetic routes were selected: an ion exchange reaction, direct and economical, and a two-step acid-base reaction. Most of these BioILs allowed efficient plasticization of starch by film casting. The structure of the anion used significantly influences the thermo(hygro)mechanical and recrystallization behavior, making it possible to modulate the properties of the final material.
Environmentally benign synthesis of 4-aminoquinoline-2-ones using recyclable choline hydroxide
Sanap, Anita Kailas,Shankarling, Ganapati Subray
, p. 206 - 212 (2015)
Greener synthesis of 4-aminoquinoline-2-ones was achieved by intramolecular cyclization of 2-cyanophenylamide derivatives using biodegradable and recyclable choline hydroxide (ChOH). The reaction proceeds rapidly and affords the corresponding 4-aminoquinoline-2-ones with a good to excellent yield. The protocol has the advantage of easy workup, high yields, and an environmentally benign methodology compared to other reported methods. The simplicity of this method makes it an interesting alternative to other approaches.
Greener route for the synthesis of photo- and thermochromic spiropyrans using a highly efficient, reusable, and biocompatible choline hydroxide in an aqueous medium
Pargaonkar, Jyotsna G.,Patil, Sanjay K.,Vajekar, Shailesh N.
, p. 208 - 215 (2018)
Here, we report the synthesis of photo- and thermochromic spiropyrans promoted by a highly efficient, biocompatible, and reusable choline hydroxide (ChOH) in greener solvent water. This procedure provides several advantages such as simple workup, mild reaction conditions, short reaction time, and high yields of the products. Furthermore, the ChOH could be reused at least five times without significantly losing its catalytic activity. The structures of the synthesized spiropyran derivatives were confirmed by several characterization methods such as 1H NMR, 13C NMR, and mass spectra.
Bifunctional Ionic Liquids Derived from Biorenewable Sources as Sustainable Catalysts for Fixation of Carbon Dioxide
Saptal, Vitthal B.,Bhanage, Bhalchandra M.
, p. 1145 - 1151 (2017)
A series of highly efficient, bifunctional ionic liquids containing a quaternary alkyl ammonium cation and an amine anion were prepared from choline and amino acids, respectively. Nine ILs were synthesized, characterized, and applied as organocatalysts for the chemical fixation of carbon dioxide to form cyclic carbonates and quinazoline-2,4(1 H,3 H)-diones. A binary mixture of an IL and a co-catalysts generates deep eutectic solvents (DESs) and accelerates the rate of the cycloaddition reaction at atmospheric pressure and low temperature (70 °C). The presence of the hydroxyl functional group of choline and the free amine group of the amino acids in the ILs has a synergistic effect on the activation of the epoxide and carbon dioxide towards the cycloaddition reactions. These ILs are biodegradable and are synthesized from easily available biorenewable sources. Additionally, this catalytic method demonstrates ultimate environmental benignity because of the mild metal- and solvent-free conditions as well as the recyclability of the catalyst and co-catalyst.
Synthesis of hydrotalcites from waste steel slag with [Bmim]OH intercalated for the transesterification of glycerol carbonate
Liu, Guanhao,Xu, Xinru,Yang, Jingyi
, (2020)
Ca-Mg-Al hydrotalcites were prepared by coprecipitation from Type S95 steel slag of Shanghai Baosteel Group as supports of ionic liquid in this paper. Five basic ionic liquids [Bmim][CH3COO], [Bmim][HCOO], [Bmim]OH, [Bmim]Br and ChOH were prepared and their catalytic performance on the synthesis of glycerol carbonate by transesterification between dimethyl carbonate and glycerol was investigated. The characterization results indicated that [Bmim]OH is the best ionic liquid (IL) for the transesterification reaction of glycerol carbonate. The hydrotalcites before and after intercalation by ionic liquid were characterized by XRD, FTIR, SEM, EDS and the IL were characterized by FT-IR, 13C-NMR and basicity determination via the Hammett method. The analysis results implied that the dispersion of [Bmim]OH in hydrotalcites reduced the alkali density appropriately and facilitated the generation of glycerol carbonate. The yield of glycerol carbonate and the conversion rate of glycerol reached 95.0% and 96.1%, respectively, when the molar ratio of dimethyl carbonate and glycerol was 3:1, the catalyst dosage was 3 wt%, the reaction temperature was 75 ?C and the reaction time was 120 min. The layered structure of hydrotalcites increased the stability of ionic liquid intercalated in carriers, thus the glycerol conversion and the GC yield still remained 91.9% and 90.5% in the fifth reaction cycle.
Design of environmentally friendly ionic liquid aqueous two-phase systems for the efficient and high activity extraction of proteins
Li, Zhiyong,Liu, Xinxin,Pei, Yuanchao,Wang, Jianji,He, Mingyuan
, p. 2941 - 2950,10 (2012)
Ionic liquids (ILs) have numerous applications in industrial processes as a benign alternative to conventional volatile organic solvents. However, many of them are toxic to organisms and are poorly biodegradable. In this work, a series of environmentally friendly cholinium ILs have been designed and synthesized. It was found that these ILs could form aqueous two-phase systems (ATPSs) with polypropylene glycol 400 (PPG400) which is thermo-sensitive, non-toxic and biodegradable. In order to understand the phase formation processes and possible application of these ATPSs for extraction/separation of proteins, the binodal curves and tie lines of these ATPSs were measured at 25 °C, and the effects of anionic structure of the ionic liquids, nature of the proteins and difference in the concentration of top- and bottom-phases on the partitioning behavior of some typical proteins were investigated systematically. It was shown that bovine serum albumin (BSA), trypsin, papain and lysozyme could be enriched effectively into the ionic liquid-rich phase of the ATPSs, and single-step extraction efficiency could be as high as 86.4-99.9% under the optimized conditions. Furthermore, enzyme activity of the native trypsin in water and in aqueous ionic liquid solutions was determined by using N-a-benzoyl-l-arginine ethyl ester as a substrate, and activity increases to about 127% was observed after 13 months storage. In addition, PPG400 has been recovered simply by heating and reused in the next extraction processes. This avoids the non-sustainable issue of highly salty water produced in the application of the polyethylene glycol (PEG) + salt and ionic liquid + salt ATPSs.
Deep eutectic solvent: A simple, environmentally benign reaction media for regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles
Kalmode, Hanuman P.,Vadagaonkar, Kamlesh S.,Murugan, Kaliyappan,Prakash, Sattey,Chaskar, Atul C.
, p. 35166 - 35174 (2015)
Choline hydroxide has been successfully employed as an efficient base as well as reaction media for the synthesis of 2,3,4-trisubstituted 1H-pyrroles from methyl 2-isocyanoacetate and α,β-unsaturated ketones. The choline hydroxide used is inexpensive, non-toxic, recyclable and environmentally friendly. Mild reaction conditions and an easy workup procedure are the striking features of this protocol. This transformation proceeds through the 1,4-conjugate addition of methyl 2-isocyanoacetate with α,β-unsaturated ketones followed by intramolecular cyclization-oxidation reaction.
Enantioselective liquid-liquid extraction of valine enantiomers in the aqueous two-phase system formed by the cholinium amino acid ionic liquid copper complexes and salt
Liu, Lianglei,Sun, Danyu,Li, Fenfang,Ma, Shaoping,Tan, Zhijian
, (2019)
It was widely reported that the heterocyclic ionic liquids (ILs) had relatively high biotoxicity and the cholinium amino acid ionic liquids (ChAAILs) were much environmentally friendly. Therefore, the ChAAILs/salt aqueous two-phase systems (ATPSs) were developed for the chiral resolution of valine enantiomers in this study. The copper complexes were prepared by ChAAILs and Cu(Ac)2, which can be used as both the phase-forming components and the chiral selectors. A series of factors affecting the enantioseparation result were investigated, including type and concentration of ChAAILs, molar ratio of ChAAIL and Cu(Ac)2, type and concentration of salt, concentration of valine, and operation temperature. The valine enantiomers were preferentially recognized in the ChAAIL-rich phase (top phase) and the maximum e.e. value of 55.6% was obtained in the top phase. This ATPS used for the enantioseparation of valine enantiomers has the advantages of environmental friendliness, high enantioseparation efficiency and simple operation by one step extraction.
An efficient and reusable ionic liquid catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions
Zhu, Anlian,Bai, Shukun,Jin, Wei,Liu, Ruixia,Li, Lingjun,Zhao, Yang,Wang, Jianji
, p. 36031 - 36035 (2014)
In this work, it was found that acidic protic ionic liquid N,N-dimethylaminoethanol hydrosulfate ([DMEA][HSO4]) was an efficient and reusable catalyst for the one-pot synthesis of 14-aryl-14H-dibenzo[a,j] xanthenes under solvent-free conditions. This ionic liquid is very cheap, air and water stable, and can be easily recovered and reused for at least six cycles. The catalytic system described here is a green protocol since in the one-pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes, the yield of the target compounds is excellent, operation and work-up procedures are simple, and no volatile organic solvents have been used. It is suggested that the synergetic effect of the cation and the anion of this ionic liquid is the main reason for the high catalytic activity and high chemo-selectivity. Scale-up experiments also suggest that this catalytic system has potential in industrial application. This journal is the Partner Organisations 2014.
Highly efficient green synthesis of α-hydroxyphosphonates using a recyclable choline hydroxide catalyst
Kalla, Reddi Mohan Naidu,Zhang, Yu,Kim, Il
, p. 5373 - 5379 (2017)
Choline hydroxide has been found to be an efficient basic ionic liquid catalyst for the synthesis of α-hydroxyphosphonates. Hydrophosphonylation of aldehydes was performed via the nucleophilic addition of diethylphosphite to aldehydic carbonyl compounds, in the presence of choline hydroxide under neat as well as solvent conditions. A wide array of substrates, including aromatic, fused aromatic, and heterocyclic aldehydes, were efficiently converted to their corresponding products in good yields. This protocol provides an alternative method for the straightforward synthesis of α-hydroxyphosphonates in high yields.
Ionic Liquids and Salts from Ibuprofen as Promising Innovative Formulations of an Old Drug
Santos, Miguel M.,Raposo, Luís R.,Carrera, Gon?alo V. S. M.,Costa, Alexandra,Dionísio, Madalena,Baptista, Pedro V.,Fernandes, Alexandra R.,Branco, Luís C.
, p. 907 - 911 (2019)
Herein we report the synthesis of novel ionic liquids (ILs) and organic salts by combining ibuprofen as anion with ammonium, imidazolium, or pyridinium cations. The methodology consists of an acid–base reaction of neutral ibuprofen with cation hydroxides, which were previously prepared by anion exchange from the corresponding halide salts with Amberlyst A-26(OH). In comparison with the parent drug, these organic salts display higher solubility in water and biological fluids and a smaller degree of polymorphism, which in some cases was completely eliminated. With the exception of [C16Pyr][Ibu] and [N1,1,2,2OH1][Ibu], the prepared salts did not affect the viability of normal human dermal fibroblasts or ovarian carcinoma (A2780) cells. Therefore, these ibuprofen-based ionic liquids may be very promising lead candidates for the development of effective formulations of this drug.
Preparation and characterization of new ionic liquid forms of 2,4-DP herbicide
Niemczak, Micha?,Biedziak, Agnieszka,Czerniak, Kamil,Marcinkowska, Katarzyna
, p. 7315 - 7325 (2017)
In this study, a series of new 2-(2,4-dichlorophenoxy)propionate-based herbicidal ionic liquids (HILs), incorporating well-known, commercially available tetraalkylammonium cations, were synthesized in high yield (≥89%) via a simple two-step procedure. Generally, at room temperature, the products comprising at least one long alkyl substituent in the cation were viscous liquids. All the synthesized salts maintained biological activity against the selected dicotyledonous weeds (common lambsquarters and cornflower). Among the tested salts, the HILs with dodecyltrimethylammonium, trimethyl(tetradecyl)ammonium and trimethyl(octadecyl)ammonium cations were characterized by the highest herbicidal efficacy against both plants. The spray solutions of the prepared HILs revealed their good surface-activation and wetting properties (contact angle = 43–63° and surface tension = 27–29 mN m?1), justifying an enhancement of the biological activity caused by the facilitated penetration of the active substance into the interior of the plant. The values of the octanol–water partition coefficient of the new salts indicate their low potential for bioaccumulation in the soil.
Choline hydroxide promoted sustainable one-pot three-component synthesis of 1H-pyrazolo[1,2-a]pyridazine-2-carbonitriles under solvent-free conditions
Vajekar, Shailesh N.,Shankarling, Ganapati S.
supporting information, p. 1147 - 1158 (2020/03/30)
A sustainable one-pot three-component synthesis of novel 1H-pyrazolo[1,2-a]pyridazine-2-carbonitrile derivatives employing a highly efficient, biodegradable, and recyclable choline hydroxide catalyst under solvent-free conditions is demonstrated. The salient features of this protocol are simple workup, mild reaction conditions, short reaction time (10 min), excellent yields (up to 97%), high atom economy, column chromatography-free protocol, and eco-friendliness. Interestingly, the choline hydroxide was recycled up to five cycles without any considerable loss of efficiency. The structures of the products were deduced by their 1H NMR, 13C NMR, and HRLC-MS spectra.
