- Alendronic acid as ionic liquid: New perspective on osteosarcoma
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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.
- Branco, Luís C.,Costa-Rodrigues, Jo?o,Fernandes, Maria H.,Santos, Miguel M.,Teixeira, Sónia
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- Highly efficient green synthesis of the photochromic spironaphthoxazines using an eco-friendly choline hydroxide catalyst
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A greener route for the synthesis of the photochromic spironaphthoxazines employing a highly efficient, biodegradable and recyclable choline hydroxide catalyst in an aqueous medium has been described. This methodology offers diverse advantages such as mild reaction conditions, short reaction time (1 h), excellent yields (up to 91%), and operational simplicity that make it a useful and attractive option for the synthesis of the spironaphthoxazines. The choline hydroxide showed excellent catalytic performance until five recycles without significant loss of activity. The structures of synthesized spironaphthoxazines were deduced by their 1H NMR spectra and melting points.
- Vajekar, Shailesh N.,Shankarling, Ganapati S.
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- Synthesis and thermophysical properties of biocompatible cholinium-based amino acid ionic liquids
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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.
- Tao, Duan-Jian,Cheng, Zheng,Chen, Feng-Feng,Li, Zhang-Min,Hu, Na,Chen, Xiang-Shu
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- Functional ionic liquid from biorenewable materials: synthesis and application as a catalyst in direct aldol reactions
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A new room temperature ionic liquid (IL) (2-hydroxyethyl)-trimethyl-ammonium (S)-2-pyrrolidinecarboxylic acid salt ([Choline][Pro]) has been synthesized from biorenewable and nontoxic raw materials (choline chloride and l(-)-proline) in a simple and relative green route. The IL has been demonstrated to be the efficient catalyst of the direct aldol reactions between ketones and aromatic aldehydes in water at room temperature. The aldol products can be obtained with good yields and the IL in aqueous phase can be separated easily and reused.
- Hu, Suqin,Jiang, Tao,Zhang, Zhaofu,Zhu, Anlian,Han, Buxing,Song, Jinliang,Xie, Ye,Li, Wenjing
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- Biofriendly ionic liquids for starch plasticization: A screening approach
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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.
- Colomines,Decaen,Lourdin,Leroy
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- Environmentally benign synthesis of 4-aminoquinoline-2-ones using recyclable choline hydroxide
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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.
- Sanap, Anita Kailas,Shankarling, Ganapati Subray
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- The "neutral" hydrolysis of simple carboxylic esters in water and the rate enhancements produced by acetylcholinesterase and other carboxylic acid esterases
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Experiments at elevated temperatures permit the determination of rate constant and thermodynamic activation parameters for the neutral hydrolysis of the neurotransmitter acetylcholine in water. At 25 °C, the extrapolated rate constant for the uncatalyzed (or neutral) hydrolysis of acetylcholine is 3.9 × 10-7 s-1 at 25 °C (ΔH? = 20.0 kcal/mol; TΔS? = -6.1 kcal/mol). Acetylcholine is more susceptible to neutral and base-catalyzed hydrolysis than ethyl acetate but less susceptible to acid-catalyzed hydrolysis. For acetylcholinesterase from the electric eel, the catalytic proficiency [(kcat/K m)/kneutral] is 2 × 1016 M-1, comparable in magnitude with the catalytic proficiencies of aminohydrolases that act on peptides and nucleosides.
- Wolfenden, Richard,Yuan, Yang
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- Greener route for the synthesis of photo- and thermochromic spiropyrans using a highly efficient, reusable, and biocompatible choline hydroxide in an aqueous medium
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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.
- Pargaonkar, Jyotsna G.,Patil, Sanjay K.,Vajekar, Shailesh N.
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- Shape-selective production of zinc phosphate in aqueous and nonaqueous media using (2-hydroxyethyl) trimethylammonium hydroxide-assisted sonochemical route
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Zinc phosphatemolecular sieveswere synthesized using zinc chloride, phosphoric acid and (2-hydroxyethyl) trimethylammonium hydroxide as template, respectively. Synthesized samples were characterized by XRD, SEM and FT-IR techniques. The morphology and crystal size of the samples were investigated using ultrasonic during aging process. Large particle size (7.2 × 20.4 μm) was obtained by ultrasonication. Imperfect orthorhombic particles were obtained when the sample was mixed with magnetic stirrer; meanwhile, some rod-like particles were obtained when the mixture was stirred with ultrasonic. In addition, the rod-like b-Zn3(PO4)2· 4H2O phase was prepared using ethylene glycol as co-solvent. Iranian Chemical Society 2012.
- Samadi-Maybodi, Abdolraouf,Nejad-Darzi, Seyed Karim Hassani
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- Bifunctional Ionic Liquids Derived from Biorenewable Sources as Sustainable Catalysts for Fixation of Carbon Dioxide
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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.
- Saptal, Vitthal B.,Bhanage, Bhalchandra M.
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- Synthesis of phosphorous acid and its derivatives based on the reaction of elemental phosphorus (P4) and aqueous solution of choline in the presence of the hydroxides of earth alkali metals
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A nonchloric method for the synthesis of phosphorous acid and barium and calcium phosphites is proposed, involving the reaction of elemental phosphorus (P4) with aqueous barium and calcium hydroxides in the presence of quaternary ammonium base (choline). Conditions for the preparation of high-purity phosphorous acid based on the oxidation of the hypophosphite ion to the phosphite ion in a strong alkali medium were studied.
- Platova, Elena V.,Batyeva, Elvira S.,Kursheva, Lidiya I.,Sinyashin, Oleg G.
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- Synthesis of hydrotalcites from waste steel slag with [Bmim]OH intercalated for the transesterification of glycerol carbonate
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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.
- Liu, Guanhao,Xu, Xinru,Yang, Jingyi
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- Elucidation of the effect of some cholinium amino acid ionic liquids on the thermal and the conformational stability of insulin
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The major concerns about protein-based drugs are their stability i.e. maintaining the protein in the folded state throughout processing and storage, as well as the preparation of novel formulation. Stabilization of the monomeric form of insulin (In) under the condition of low pH has been a recent challenge. In our earlier investigation, we found that 1-butyl-3-methylimidazolium-based ionic liquids (ILs) containing acetate, trifluoroacetate or dicyanamide anions enhance In thermal stability and prevent protein aggregation. In the present study, six non-toxic ILs containing biocompatible cholinium cation [Chol] and an anion charged amino acid (asparginyl (Asp), glutaminyl (Glu), lysinyl (Lys) and arginyl (Arg)) were synthesized using a two-step procedure. Their effect of the ILs on the In secondary structures was evaluated using FTIR spectroscopy. Rearrangement in the protein molecules, an increase in the beta-structures on behalf of the α-helices, partial denaturation but no aggregation was observed in all In solutions containing ILs. Differential scanning calorimetry was applied to elucidate the effect of ILs on thermal stability of In. Interestingly, in presence of [Chol][Glu] and [Chol]2[Asp] the denaturation temperature of the In was shifted to higher temperatures with 9.6 and 4.1 °C, respectively.
- Guncheva,Ossowicz,Janus,Todinova,Yancheva
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- Design of environmentally friendly ionic liquid aqueous two-phase systems for the efficient and high activity extraction of proteins
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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.
- Li, Zhiyong,Liu, Xinxin,Pei, Yuanchao,Wang, Jianji,He, Mingyuan
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- Antimicrobial activities of highly bioavailable organic salts and ionic liquids from fluoroquinolones
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As the development of novel antibiotics has been at a halt for several decades, chemically enhancing existing drugs is a very promising approach to drug development. Herein, we report the preparation of twelve organic salts and ionic liquids (OSILs) from ciprofloxacin and norfloxacin as anions with enhanced antimicrobial activity. Each one of the fluoroquinolones (FQs) was combined with six different organic hydroxide cations in 93–100% yield through a buffer-assisted neutralization methodology. Six of those were isomorphous salts while the remaining six were ionic liquids, with four of them being room temperature ionic liquids. The prepared compounds were not toxic to healthy cell lines and displayed between 47-and 1416-fold more solubility in water at 25 and 37 ?C than the original drugs, with the exception of the ones containing the cetylpyridinium cation. In general, the antimicrobial activity against Klebsiella pneumoniae was particularly enhanced for the ciprofloxacin-based OSILs, with up to ca. 20-fold decreases of the inhibitory concentrations in relation to the parent drug, while activity against Staphylococcus aureus and the commensal Bacillus subtilis strain was often reduced. Depending on the cation–drug combination, broad-spectrum or strain-specific antibiotic salts were achieved, potentially leading to the future development of highly bioavailable and safe antimicrobial ionic formulations.
- Alves, Celso,Branco, Luís C.,Costa, Alexandra,Florindo, Catarina,Marrucho, Isabel M.,Pedrosa, Rui,Petrovski, ?eljko,Santos, Miguel M.,Silva, Joana
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- Deep eutectic solvent: A simple, environmentally benign reaction media for regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles
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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.
- Kalmode, Hanuman P.,Vadagaonkar, Kamlesh S.,Murugan, Kaliyappan,Prakash, Sattey,Chaskar, Atul C.
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- Greener [3+3] tandem annulation-oxidation approach towards the synthesis of substituted pyrimidines
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An economical and green synthesis of partly and fully substituted pyrimidines is described using α,β-unsaturated ketones and benzamidine hydrochloride using greener and recyclable choline hydroxide (ChOH) as both a catalyst and a reaction medium. The remarkable features of this method are mild reaction conditions, short reaction times, easy workup procedure, recyclability of the catalyst and excellent yields of the products. The reaction involves a [3+3] annulation-oxidation sequence and the protocol is useful for synthesizing a broad range of biologically significant pyrimidine derivatives.
- Vadagaonkar, Kamlesh S.,Kalmode, Hanuman P.,Prakash, Sattey,Chaskar, Atul C.
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- 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
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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.
- Liu, Lianglei,Sun, Danyu,Li, Fenfang,Ma, Shaoping,Tan, Zhijian
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- Choline and amino acid based biocompatible ionic liquid mediated transdermal delivery of the sparingly soluble drug acyclovir
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Transdermal delivery of drugs is more challenging for drugs that are insoluble or sparingly soluble in water and most organic solvents. To overcome this problem, ionic liquid (IL)-mediated ternary systems have been suggested as potential drug carriers. Here, we report potent ternary (IL–EtOH–IPM) systems consisting of biocompatible ILs, ethanol (EtOH), and isopropyl myristate (IPM) that can dissolve a significant amount of the sparingly soluble drug acyclovir (ACV). The ternary systems were optically transparent and thermodynamically stable with a wide range of IL pertinence. An in vitro drug permeation study showed that the ILs in the ternary systems dramatically enhanced ACV permeation into and across the skin. Fourier Transform Infrared spectroscopy of the stratum corneum (sc) after treatment with ternary systems showed that the skin barrier function was reduced by disturbance of the regularly ordered arrangement of corneocytes and modification of the surface properties of the sc during permeation. Histological analysis, and skin irritation studies using a reconstructed human epidermis model showed the safety profile of the ternary system, and there were no significant changes in the structures of the sc, epidermis, and dermis. Therefore, ternary systems containing biocompatible ILs are promising for transdermal delivery of insoluble or sparingly soluble drugs.
- Chowdhury, Md. Raihan,Goto, Masahiro,Islam, Md. Rafiqul,Kamiya, Noriho,Moniruzzaman, Muhammad,Tahara, Yoshiro,Wakabayashi, Rie
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- An efficient and reusable ionic liquid catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions
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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.
- Zhu, Anlian,Bai, Shukun,Jin, Wei,Liu, Ruixia,Li, Lingjun,Zhao, Yang,Wang, Jianji
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- Highly efficient green synthesis of α-hydroxyphosphonates using a recyclable choline hydroxide catalyst
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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.
- Kalla, Reddi Mohan Naidu,Zhang, Yu,Kim, Il
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- Favipiravir-Based Ionic Liquids as Potent Antiviral Drugs for Oral Delivery: Synthesis, Solubility, and Pharmacokinetic Evaluation
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Coronavirus disease 2019 (COVID-19) has spread across the world, and no specific antiviral drugs have yet been approved to combat this disease. Favipiravir (FAV) is an antiviral drug that is currently in clinical trials for use against COVID-19. However, the delivery of FAV is challenging because of its limited solubility, and its formulation is difficult with common organic solvents and water. To address these issues, four FAV ionic liquids (FAV-ILs) were synthesized as potent antiviral prodrugs and were fully characterized by nuclear magnetic resonance (NMR) spectroscopy, Fourier-transform infrared (FT-IR) spectrometry, powder X-ray diffraction (PXRD), thermogravimetric analysis (TGA), derivative thermogravimetry (DTG), and differential scanning calorimetry (DSC). The aqueous solubility and in vivo pharmacokinetic properties of the FAV-ILs were also evaluated. The FAV-ILs exhibited improved aqueous solubility by 78 to 125 orders of magnitude when compared with that of free FAV. Upon oral dosing in mice, the absolute bioavailability of the β-alanine ethyl ester FAV formulation was increased 1.9-fold compared with that of the control FAV formulation. The peak blood concentration, elimination half-life, and mean absorption time of FAV were also increased by 1.5-, 2.0-, and 1.5-fold, respectively, compared with the control. Furthermore, the FAV in the FAV-ILs exhibited significantly different biodistribution compared with the control FAV formulation. Interestingly, drug accumulation in the lungs and liver was improved 1.5-fold and 1.3-fold, respectively, compared with the control FAV formulation. These results indicate that the use of ILs exhibits potential as a simple, scalable strategy to improve the solubility and oral absorption of hydrophobic drugs, such as FAV.
- Moshikur, Rahman Md,Ali, Md. Korban,Wakabayashi, Rie,Moniruzzaman, Muhammad,Goto, Masahiro
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- Ionic Liquids and Salts from Ibuprofen as Promising Innovative Formulations of an Old Drug
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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.
- 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.
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- Preparation and characterization of new ionic liquid forms of 2,4-DP herbicide
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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.
- Niemczak, Micha?,Biedziak, Agnieszka,Czerniak, Kamil,Marcinkowska, Katarzyna
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- Nano-magnetic-iron Oxides@choline Acetate as a Heterogeneous Catalyst for the Synthesis of 1,2,3-Triazoles
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In this research, four cholines supported on core–shell iron oxides, Fe2O3@MgO@Ch.OAc (choline acetate), Fe2O3@MgO@Ch.OH (choline hydroxide), Fe3O4@Ch.OAc, Fe3O4@Ch.OH, were synthesized. The synthesized catalysts were tested in 1,2,3-triazoles synthesis by the reaction of nitromethane, aldehyde, and benzyl azide in EtOH as a green solvent. Among four synthesized heterogeneous catalysts, the Fe2O3@MgO@ch.OAc showed superior catalytic activity for the reaction and afforded the desired triazoles in good isolated yields under mild reaction conditions. Graphic Abstract: [Figure not available: see fulltext.]
- Heydari, Akbar,Mohammadkhani, Abolfazl
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- Choline hydroxide promoted sustainable one-pot three-component synthesis of 1H-pyrazolo[1,2-a]pyridazine-2-carbonitriles under solvent-free conditions
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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.
- Vajekar, Shailesh N.,Shankarling, Ganapati S.
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supporting information
p. 1147 - 1158
(2020/03/30)
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- Synthesis and antibacterial activity of ionic liquids and organic salts based on penicillin g and amoxicillin hydrolysate derivatives against resistant bacteria
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The preparation and characterization of ionic liquids and organic salts (OSILs) that contain anionic penicillin G [secoPen] and amoxicillin [seco-Amx] hydrolysate derivatives and their in vitro antibacterial activity against sensitive and resistant Escherichia coli and Staphylococcus aureus strains is reported. Eleven hydrolyzed β-lactam-OSILs were obtained after precipitation in moderate-to-high yields via the neutralization of the basic ammonia buffer of antibiotics with different cation hydroxide salts. The obtained minimum inhibitory concentration (MIC) data of the prepared compounds showed a relative decrease of the inhibitory concentrations (RDIC) in the order of 100 in the case of [C2OHMIM][seco-Pen] against sensitive S. aureus ATCC25923 and, most strikingly, higher than 1000 with [C16Pyr][seco-Amx] against methicillin-resistant Staphylococcus aureus (MRSA) ATCC 43300. These outstanding in vitro results showcase that a straightforward transformation of standard antibiotics into hydrolyzed organic salts can dramatically change the pharmaceutical activity of a drug, including giving rise to potent formulations of antibiotics against deadly bacteria strains.
- Branco, Luís C.,Dias, Ana Rita,Dias, Vitorino,Ferraz, Ricardo,Noronha, Jo?o Paulo,Petrovski, ?eljko,Pinheiro, Luís,Prudêncio, Cristina,Santos, Miguel M.,Silva, Dário
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- FOLATE SALTS
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The invention relates to crystalline folate salts. The salt consists of a folate anion and an organic cation. The folate anion is 5-methyl-(6S)-tetrahydrofolic acid, and the cation is an organic compound which is an alkanolamine selected from the group consisting of choline, N-methylaminoethanol, 2-amino-2-methylpropanol and 2-dimethylaminoethanol.
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Paragraph 0030
(2020/05/28)
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- Choline hydroxide: An efficient and biodegradable catalyst for the synthesis of 2-amino-3-nitro-4H-chromene derivatives in an aqueous medium
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An expedient, eco-friendly and efficient procedure for the synthesis of novel 2-amino-3-nitro-4H-chromene derivatives has been developed through the reaction of various 2-hydroxybenzaldehydes and (E)-N-methyl-1-(methylthio)-2-nitroethenamine in the presence of the basic ionic liquid catalyst (choline hydroxide (ChOH)) at room temperature an aqueous medium. The advantageous of this method is a biodegradable and recyclable catalyst, mild, environmentally friendly and high products yields (83-96%) in short reaction times.
- Krishnammagari, Suresh Kumar,Lim, Kwon Taek,Cho, Byung Gwon,Tae Jeong, Yeon
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supporting information
p. 574 - 581
(2018/09/25)
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- Rapid and highly efficient synthesis of thioureas in biocompatible basic choline hydroxide
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A straightforward and convenient synthesis of symmetrical thiourea derivatives by the reaction of primary amines and carbon disulfide in biocompatible basic choline hydroxide is presented. A variety of biologically important thiourea derivatives can be obtained in good to excellent yields without a tedious work-up under mild reaction conditions. A series of primary aliphatic and aromatic amines with different substituted functional groups have been converted to thiourea derivatives under milder reaction conditions and short reaction times.
- Azizi, Najmedin,Farhadi, Elham
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p. 548 - 554
(2017/09/27)
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- A choline hydroxide catalyzed synthesis of 2,3-dihydroquinazolin-4(1: H)-ones in an aqueous medium
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A simple, metal and ligand-free protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives using choline hydroxide (ChOH) as an effective catalyst in an aqueous medium has been developed. The good to high yield of the desired product is obtained, with a low environmental factor and high atom economy. ChOH was found to be recyclable up to six consecutive runs without significant loss in its activity. The use of water as an environmentally benign solvent, ease of work up and efficient recyclability of the catalyst makes this process more advantageous and greener.
- Borase, Pravin N.,Thale, Pranila B.,Shankarling
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p. 63078 - 63083
(2016/07/16)
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- Biodegradable choline hydroxide promoted environmentally benign thiolysis of epoxides
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An environmentally benign and rapid thiolysis of epoxides using a biodegradable, choline-based task-specific ionic liquid has been developed. The ring opening reaction of aryl and alkyl epoxides proceeded rapidly and afforded the corresponding β-hydroxysulfides in high yields with excellent regioselectivity. The protocol has the advantages of easy work-up, short reaction times, high yields, and a biodegradable catalyst.
- Azizi, Najmedin,Edrisi, Mahtab
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supporting information
p. 525 - 528
(2016/01/20)
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- BIOCATALYST SOLVENT USING IONIC LIQUID, AND BIOCATALYST SOLUTION CONTAINING THE SOLVENT AND BIOCATALYST
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PROBLEM TO BE SOLVED: To provide: a biocatalyst solvent that can be stored for a long period of time and that can dissolve a high concentration of a biocatalyst from low temperatures to high temperatures while retaining the activity of the biocatalyst; and a biocatalyst solution using the biocatalyst solvent. SOLUTION: The biocatalyst solvent is composed of an ionic liquid containing anions and quaternary ammonium cations represented by the following formula (1), where each Ra independently represents: a hydroxyalkyl group which has at least one hydroxyl group, in which the alkyl moiety is in a C1-10 straight-chained or branched state, and in which the alkyl moiety may contain an oxygen atom; a carboxyalkyl group which has at least one carboxy group, in which the alkyl moiety is in a C1-10 straight-chained or branched state, and in which the alkyl moiety may contain an oxygen atom; or a hydroxy-carboxyalkyl group which has at least one each of a hydroxyl group and a carboxy group, in which the alkyl moiety is in a C1-10 straight-chained or branched state, and in which the alkyl moiety may contain an oxygen atom and where each Rb independently represents a hydrogen atom or a C1-5 straight-chained or branched alkyl group. n represents an integer of 1-4. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0142; 0143
(2016/10/10)
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- PROCESS FOR THE PRODUCTION OF CHOLINE HYDROXIDE
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A continuous process for the production of choline hydroxide includes reacting ethylene oxide, trimethylamine, and water in a reaction zone to form a reaction mixture and extracting heat from the reaction mixture. Subsequently, phase separation of the s reaction mixture is induced to obtain a choline hydroxide phase and an organic liquid phase comprising trimethylamine. A choline hydroxide solution (e.g., at a concentration of about 40% to 50% by weight, based on total weight of the choline hydroxide solution) is obtained from the choline hydroxide phase.
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Paragraph 0044
(2015/02/19)
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- Choline Hydroxide: An Efficient and Biocompatible Basic Catalyst for the Synthesis of Biscoumarins Under Mild Conditions
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In this work, choline hydroxide is found to be an efficient and green catalyst for the synthesis of biscoumarins through the Domino Knoevenagel-Michael reaction of a series of aldehydes with 4-hydroxylcoumarin under mild conditions. A series of aldehydes with different substituted functional groups, especially those which are sensitive to acid, have been converted to biscoumarins with good to excellent isolated yields, and the reactions can be easily scaled up to multigrams. The target products can be simply separated by filtration, and the aqueous solution of choline hydroxide (as filtrate) can then be reused for the next run reaction.
- Zhu, Anlian,Bai, Shukun,Li, Lingjun,Wang, Mingyue,Wang, Jianji
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p. 1089 - 1093
(2015/02/05)
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- Free-radical polymerization of itaconic acid in the presence of choline salts: Mechanism of persulfate decomposition
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Kinetics of decomposition of persulfate activated by choline in aqueous solution has been studied. Additionally, the products of choline degradation were analyzed by 1H NMR spectroscopy, and betaine aldehyde was identified as the main oxidation product. Thus, radical-chain redox mechanism is postulated to explain experimental results. The mechanism was successfully verified using kinetic modeling approach. Moreover, it was found that due to formation of complex of itaconic acid and choline chloride, the salt solubility of the acid in water was increased. Finally, free-radical polymerization of itaconic acid initiated by persulfate in aqueous solution of the choline salt yielded poly(itaconic acid) with higher molecular weight and increased polydispersity.
- Bednarz, Szczepan,B?aszczyk, Alicja,B?azejewska, Diana,Bogda?, Dariusz
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p. 297 - 304
(2015/02/19)
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- PROCESS FOR THE PRODUCTION OF CHOLINE HYDROXIDE
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A continuous process for the production of choline hydroxide includes reacting ethylene oxide, trimethylamine, and water in a reaction zone to form a reaction mixture and extracting heat from the reaction mixture. Subsequently, phase separation of the reaction mixture is induced to obtain a choline hydroxide phase and an organic liquid phase comprising trimethylamine. A choline hydroxide solution (e.g., at a concentration of about 40% to 50% by weight, based on total weight of the choline hydroxide solution) is obtained from the choline hydroxide phase.
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Page/Page column 12
(2013/07/19)
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- PROCESS FOR PREPARING CHOLINE HYDROXIDE FROM TRIMETHYLAMINE AND ETHYLENE OXIDE
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Processes for preparing N,N,N-trimethylethanolammonium hydroxide (choline hydroxide) and the choline hydroxide produced are described. These processes minimize the production of byproduct mono-ethoxylated and di-ethyoxylated choline in the product choline hydroxide. The processes generally include feeding ethylene oxide, trimethylamine, and water into a first reactor to create a first reactor product under temperature controlled conditions. The product of the first reactor is fed into a second reactor to form a second reactor product under uncontrolled, adiabatic, conditions. Finally, any unreacted to trimethylamine in the second reactor product is removed to form a final product comprising choline hydroxide. Additional reactors can be used for the ethylene oxide and trimethylamine reaction.
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Paragraph 0036; 0037; 0041; 0042
(2013/07/31)
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- STABILIZED CHOLINE SOLUTIONS AND METHODS FOR PREPARING THE SAME
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A method for the stabilization of an aqueous choline hydroxide solution includes, optionally adding a first stabilizer of a dithionite salt and/or a dialkylhydroxylamine to an aqueous solution containing reactants that will produce an aqueous choline hydroxide solution; and after the aqueous choline hydroxide solution is formed, adding a second stabilizer which comprises a dialkylhydroxylamine to the aqueous choline hydroxide solution. The stabilized choline hydroxide solution may include choline hydroxide, water, and a dialkylhydroxylamine and optionally a dithionite salt as a stabilizer present in an amount of from about 50 ppm to less than about 5000 ppm by weight relative to the total weight of the stabilized choline hydroxide solution.
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Page/Page column 18
(2013/06/06)
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- STABILIZED CHOLINE SOLUTIONS AND METHODS FOR PREPARING THE SAME
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A method for the stabilization of an aqueous choline hydroxide solution includes optionally, adding a first stabilizer of a dithionite salt or a dialkylhydroxylamine to an aqueous solution containing reactants that will produce an aqueous choline hydroxide solution; and after the aqueous choline hydroxide solution is formed, adding a second stabilizer of a dithionite salt or a dialkylhydroxylamine to the aqueous choline hydroxide solution. The stabilized choline hydroxide solution may include choline hydroxide, water, and a dithionite salt and/or a dialkylhydroxylamine as a stabilizer present in an amount of about 100 ppm to about 2000 ppm by weight of the stabilized choline hydroxide solution.
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Page/Page column 12
(2013/06/06)
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- Dual functions of N,N-dimethylethanolamnium-based ionic liquids for the Knoevenagel reactions at room temperature
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In this work, the hydrogen bond formation ability of cation and anion of the ILs was determined by using the solvatochromic method and was found to be responsible for their catalytic activity in the Knoevenagel reactions. The enhancement in the hydrogen bond donor ability of the cations and the hydrogen bond acceptor ability of the anions can both lead to the increase in the catalytic activity of the ILs. From the proposed reaction mechanism, it was deduced that the cations of the ILs can form hydrogen bond with aldehyde to activate the CO bond as electrophile, and the anions of the ILs can promote active methylene compound to produce carboanion as nucleophile, showing dual function activation effect in the catalytic processes. In addition, the optimized N,N-dimethylethanolamnium acetate as dual function activator for the Koevenagel reactions benefits from wide substrates tolerance, ambient reaction temperature, easy work-up procedure, and easy reuse of the IL.
- Zhu, Anlian,Liu, Ruixia,Li, Lingjun,Li, Liangyun,Wang, Lan,Wang, Jianji
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- One-pot synthesis of 3,4-dihydro-2(H)-pyrimidinones catalyzed by reusable acidic choline-based ionic liquids
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A series of choline-based ionic liquids (CIL) have been synthesized in this work. The results suggested that both the cations and the anions have significant influences on their properties such as thermostabilities, acidities and their performances for the synthesis of 3,4-dihydro-2(H)-pyrimidinones. The optimized catalytic system based on the CIL [DMEA][HSO4] for the Biginelli reactions benefits from the wide substrates tolerance, benign reaction conditions, easy work-up procedures, and the feasible reusability of the ionic liquid. Graphical Abstract: The thermostabilities, acidities, and the catalytic activities for the Biginelli reactions are all follows the sequence of [DMEA][HSO4] > [Choline] [HSO4] > [DMEA][H 2PO4] > [Choline] [H2PO4][Figure not available: see fulltext.].
- Zhu, Anlian,Li, Qianqian,Li, Lingjun,Wang, Jianji
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p. 463 - 468
(2013/08/23)
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- FIRE RESISTANT GLAZINGS
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An additive for alkali metal silicate solutions, comprising a quaternary ammonium compound having the general formula (1) R1R2R3R4N+OH?, wherein R1, R2, R3 and R4 which may be the same or different represent alkyl groups, hydroxy-substituted alkyl groups, alkaryl groups, hydroxy-substituted alkaryl groups comprising from 1 to 12 carbon atoms, or groups having the general formula —[CH2]n-N+R5R6R7 wherein n is an integer having a value of from 1 to 12, the group —[CH2]n may be hydroxy-substituted, and R5, R6 and R7 which may be the same or different represent alkyl groups, hydroxy-substituted alkyl groups, alkaryl groups or hydroxy-substituted alkaryl groups comprising from 1 to 12 carbon atoms; with the proviso that at least one of the groups R1, R2, R3, R4, R5, R6 and R7 represents a hydroxy-substituted alkyl group or a hydroxy-substituted alkaryl group comprising at least 2 carbon atoms wherein the hydroxy substituent is not located on a carbon atom which is bonded to a nitrogen atom.
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Page/Page column 5-6
(2012/10/23)
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- COMPOSITION COMPRISING CHOLINE HYDROXIDE AND PROCESS FOR PREPARING THE SAME
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The present invention relates to a composition comprising choline hydroxide, a solvent, and one or more stabilizers selected from the group consisting of a hydride and choline sulfite.
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Page/Page column 7; 8
(2008/06/13)
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- METHOD FOR PRODUCING QUATERNARY AMMONIUM COMPOUNDS
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The inventive method for producing quaternary ammonium compounds consists in reacting compounds containing an sp3 hybridised nitrogen atom with dialkyl sulphate or trialkyl phosphate and in exposing the thus obtained ammonium compound to an ion-exchange.
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Page/Page column 23-24
(2008/06/13)
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- TRIGGER - ONE STATIONARY STATE BIFURCATIONS INDUCED BY INHIBITORS IN THE ACETYLCHOLINESTERASE REACTION
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Basing on the experimental dependence of the rate of hydrolysis of acetylcholine by acetylcholinesterase the bifurcation: 3 stationary states - 1 stationary state is shown to occur if some critical concentration of inhibitor is exceeded.The calculations were performed for chosen allosteric and competitive inhibitors as well as for irreversible ones.These calculations point out that the bifurcation is induced by trace quantities of inhibitors.This raises hopes that the occurrence of this bifurcation can be used as a very sensitive analytical method.
- Kawczynski, Andrzej Lech
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p. 533 - 540
(2007/10/02)
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