- Solvent extraction of lithium from aqueous solution using an ammonium ionic liquid
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A new functionalized ionic liquid (FIL), tetrabutylammonium 2-ethylhexyl hydrogen-2-ethylhexylphosphonate ([N4444][EHEHP]), was prepared and used in the extraction of lithium ion from aqueous solution. The factors affecting the extraction efficiencies, such as aqueous acidity, extractant concentration and temperature, were optimized. The mechanism involved in the extraction system was analyzed by slope analysis and FT-IR data. According to the Van't Hoff equation, the thermodynamic functions of the extraction reaction in ionic liquid system were obtained. Liquid/liquid extraction tests indicated that the ionic liquid system exhibited better selectivity towards lithium ions in the solution containing alkali metal ions. In addition, the quantitative stripping of lithium ions from the loaded ionic liquid phase was carried out and the effect of hydrochloric acid concentration on stripping rate was investigated in detail.
- Li, Hongxia,Liu, Bing,Qin, Yaru,Shi, Chenglong,Song, Guixiu
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- Hydrates of Organic Compounds. X. The Formation of Clathrate Hydrates of Tetrabutylammonium Alkanesulfonates
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The solid-liquid phase diagrams of binary mixtures of water with tetrabutylammonium alkanesulfonate (n-C4H9)4NO3SR(R=CH3-C5H11) and with tetrabutylammonium benzenesulfonate were examined in order to confirm the formation of clathrate-like hydrates.It has been found that (1) all the sulfonates examined can form clathrate-like hydrates with hydration numbers either around 30 or around 39; (2) these hydrates can be classified into three groups I, II, and III on the basis of the hydration numbers and melting points just as in the case of a series of tetrabutylammonium carboxylate hydrates; and (3) generally, the melting points of these sulfonate hydrates are lower than those of tetrabutylammonium carboxylate hydrates.The formation of clathrate-like hydrates of tetrabutylammonium hydrogensulfite and of tetrabutylammoniumsulfite has also been reported and is discussed in an appendix.
- Nakayama, Haruo,Usui, Hideyuki
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- Tartrate-based ionic liquids: Unified synthesis and characterisation
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A convenient and general preparative approach for tartrate-derived organic salts with bulky non-coordinating cations is described. This route is based on neutralisation of tartaric acid with cation hydroxides in aqueous solution. A series of 24 tartrate salts was prepared by systematic variation of the hemi- or bis-tartrate anion and the nature of the organic cation. Chirality of the anion was also explored as a vector for structural modification. Complete characterisation, including X-ray crystallography, was carried out. This comparative study of the physicochemical properties of these salts led to the identification of several informative trends useful for designing proper tartrate-based chiral ionic liquids.
- Rouch, Anne,Castellan, Tessa,Fabing, Isabelle,Saffon, Nathalie,Rodriguez, Jean,Constantieux, Thierry,Plaquevent, Jean-Christophe,Genisson, Yves
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- Preparation and application of highly efficient and reusable TBAPIL@Si(CH2)3@nano-silica-based nano-catalyst for preparation of benzoxanthene derivatives
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Tetrabutylammonium prolinate ionic liquid (TBAPIL) was prepared, and mesoporous silica nanoparticles (NPs) were synthesized. Both of these were linked through propyltriethoxysilane to prepare a reusable catalyst TBAPIL@Si(CH2)3@silica NPs (TBAPILS). The formation of TBAPIL was checked through Fourier-transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance (NMR) analysis. X-ray diffraction analysis confirmed the structure of silica NPs and linking of TBPAIL on it. Transmission electron microscopy proved the flourishing development of silica NPs. Scanning electron microscopy graphs exposed the altering in morphology of silica NPs and TBAPILS. FT-IR analysis also confirmed the formation of TBAPILS catalyst. Moreover, the effectiveness of the TBAPILS was also checked for the synthesis of various derivatives of tetrahydrobenzoxanthenes-11-ones. The formation and structure of obtained compounds were confirmed by FT-IR, elemental analysis, 1HNMR and 13C NMR spectral analysis. The catalyst TBAPILS was found to be used successfully up to five cycles without significant loss of activity.
- Agrwal, Akansha,Kumar, Vipin,Kasana, Virendra
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p. 2583 - 2595
(2021/02/26)
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- Synthesis method of N-hydroxymethyl acrylamide
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The invention relates to a synthesis method of N-hydroxymethyl acrylamide. By taking solid acrylamide and paraformaldehyde as raw materials, adopting a supported quaternary ammonium base catalyst, and selectively activating an amino group in the acrylamide by controlling the size of a hydrocarbyl group connected with quaternary ammonium base and utilizing the steric effect of hydrocarbyl, the self-polymerization behavior in the production process of the N-hydroxymethyl acrylamide is reduced, and the N-hydroxymethyl acrylamide monomer is efficiently obtained. The supported quaternary ammonium alkali is used as the catalyst, the reaction condition is mild, the selectivity is high, system polymerization caused by the traditional inorganic alkali liquor reaction is effectively avoided, and the reaction system can realize high-efficiency conversion of raw materials without adding a large amount of water as a reaction solvent, so that the yield is improved; and the supported quaternary ammonium base catalyst has the characteristics of large specific surface area, high reaction activity and the like, greatly reduces the use amount of solvent water in the reaction process, is convenient to remove in the post-treatment process, and reduces sewage discharge.
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Paragraph 0038-0040
(2021/06/12)
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- Preparation of Acifluorfen-Based Ionic Liquids with Fluorescent Properties for Enhancing Biological Activities and Reducing the Risk to the Aquatic Environment
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In this work, 12 novel herbicidal ionic liquids (HILs) based on acifluorfen were prepared by pairing with the fluorescent hydrazides or different alkyl chains for increasing activities and reducing negative impacts on the aquatic environment. The results showed that the fluorescence of coumarin hydrazide in the HILs was applied as the internal and supplementary light source to meet the requirement of light wavelength range of acifluorfen, which improved the phytotoxicity of acifluorfen to weeds by enhancing singlet oxygen generation with increased sunlight utilization. The herbicidal activities of HILs were related positively with the length of chain of cation under high light intensity and depended mainly on the fluorescence characteristic of the cation under low light intensity, and the double salt IL forms of acifluorfen containing coumarin hydrazide and n-hexadecyltrimethylammonium had enhanced efficacies against broadleaf weeds in the field. Compared with acifluorfen sodium, HILs had lower water solubility, better surface activity, weaker mobility in soils, and higher decomposition temperature. These results demonstrated that HILs containing different cations provided a wider scope for fine-tuning of the physicochemical and biological properties of herbicides and established a promising way for the development of environmentally friendly herbicidal formulations.
- Cao, Yongsong,Li, Jianqiang,Niu, Junfan,Tang, Gang,Tang, Jingyue,Tang, Rong,Yang, Jiale,Zhang, Wenbing,Zhou, Zhiyuan
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p. 6048 - 6057
(2020/06/26)
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- Ionic Liquid Stabilized Niobium Oxoclusters Catalyzing Oxidation of Sulfides with Exceptional Activity
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We present here a new class of niobium oxoclusters that are stabilized effectively by carboxylate ionic liquids. These functionalized ILs are designated as [TBA][LA], [TBA][PA], and [TBA][HPA] in this work, in which TBA represents tetrabutylammonium and LA, PA, and HPA refer to lactate, propionate, 3-hydroxypropionate anions, respectively. The as-synthesized Nb oxoclusters have been characterized by use of elemental analysis, NMR, IR, XRD, TGA, HRTEM. It was found that [TBA][LA]-stabilized Nb oxoclusters (Nb?OC@[TBA][LA]) are uniformly dispersed with an average particle size of 2–3 nm and afforded exceptionally high catalytic activity for the selective oxidation of various thioethers. The turnover number with Nb?OC@[TBA][LA] catalyst was over 56 000 at catalyst loading as low as 0.0033 mol % (1 ppm). Meantime, the catalyst also showed the high activity for the epoxidation of olefins and allylic alcohols by using only 0.065 mol % of catalyst (50 ppm). The characterization of 93Nb NMR spectra revealed that the Nb oxoclusters underwent structural transformation in the presence of H2O2 but regenerated to their initial state at the end of the reaction. In particular, the highly dispersed Nb oxoclusters can absorb a large amount of polar organic solvents and thus were swollen greatly, which exhibited “pseudo” liquid phase behavior, and enabled the substrate molecules to be highly accessible to the catalytic center of Nb oxocluster units.
- Zhou, Qingqing,Ye, Man,Ma, Wenbao,Li, Difan,Ding, Bingjie,Chen, Manyu,Yao, Yefeng,Gong, Xueqing,Hou, Zhenshan
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p. 4206 - 4217
(2019/03/26)
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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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p. 7315 - 7325
(2017/11/27)
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- Method of manufacturing tetrabuthyl ammonium acetate (by machine translation)
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PROBLEM TO BE SOLVED: use raw material, and the solvent through the proper selection of a simple and easy process suitable for the manufacture of solubility of cellulose tet love chill ammonium acetate. SOLUTION: and a starting material by tributylamine, tributylamine in polar aprotic organic solvent and by the reaction of halogenated butyl tetrabuthyl ammonium halide and a process for obtaining, in tetrabuthyl ammonium halide vopo and [...] by the reaction of an alkali metal hydroxide and a process for obtaining, in [...] vopo tetrabuthyl ammonium acetate and acetic acid tetrabuthyl by reaction of the process and to obtain. Selected drawing: fig. 1 (by machine translation)
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- Novel ionic liquid with peroxyniobate-radical negative ions and preparing method thereof
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The invention relates to novel ionic liquid with peroxyniobate-radical negative ions and a preparing method thereof. The ionic liquid comprises imidazolium salt positive ions, quaternary ammonium salt positive ions and the peroxyniobate-radical negative ions. The preparing method of the ionic liquid includes the steps that 1, alkyl-replacing N-methylimidazole hydrochloride is prepared from N-methylimidazole; 2, alkyllimidazolium salt chloride and quaternary ammonium salt halogenide are subjected to ion exchange to obtain corresponding ethanol solutions of hydroxide; 3, ammonium peroxyniobate is prepared from commercial niobium pentoxide with the document method; 4, the brand-new-structure ionic liquid with the peroxyniobate-radical negative ions is obtained with the ion exchange (acid-base neutralization) method. According to the novel ionic liquid with the peroxyniobate-radical negative ions and the preparing method thereof, the ionic liquid is prepared for the first time, the preparing method is simple, the yield is high, and the characteristics of a niobium element can be fully used to carry out a certain catalytic oxidation reaction.
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Page/Page column 7
(2016/12/01)
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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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- METHOD FOR PRODUCING COMPOSITE GEL BY CROSS-LINKING HYALURONIC ACID AND HYDROXYLPROPYL METHYLCELLULOSE
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A method for covalently cross-linking hyaluronic acid (HA) and hydroxypropyl methylcellulose (HPMC) by a diepoxide crosslinking agent. The method includes the following steps: a) mixing HA and HPMC in water; b) adding an alkali as a catalyst and a diepoxide as a crosslinking agent; c) neutralizing with hydrochloric acid and dehydrating with ethanol and acetone; and d) drying in vacuum and redissolving in water to obtain an HA-HPMC composite gel.
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Paragraph 0048
(2016/11/14)
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- Extractant and Method for Extracting and Separating Yttrium
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An extractant and a method for the extraction and separation of yttrium are disclosed in the invention. Cations of said extractant are selected from the group of quaternary phosphonium or quaternary ammonium, and the anion is sec-octylphenoxy acetate. The extractant has a simple composition, the formulated organic phase has stable properties and can be recycling used without significantly decreased concentration. The present invention used a mixed organic phase consisting of an extractant and a diluent to extract a rare earth feed liquid containing yttrium, and then washed and back extracted it with deionized water so that the consumption of acid and alkali in all the processes of extraction, washing and back extraction was avoided. Therefore, the extraction is carried out under a low acidity and a high extraction efficiency was ensured. The organic phase can be recycling used without saponification, so that no ammonia wastewater was produced in the processes.
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Paragraph 0068
(2016/12/22)
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- Quaternary ammonium salt type perrhenate ionic liquid and synthetic method and application thereof
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The invention discloses quaternary ammonium salt type perrhenate ionic liquid and a synthetic method and application thereof. The method comprises the steps that alkyl ammonium bromide and KOH are reacted to obtain quaternary ammonium base, the quaternary ammonium base and perrhenate (NH4ReO4) metal salt are subjected to a replacement reaction, and quaternary ammonium salt type perrhenate ionic liquid is obtained. The synthesized quaternary ammonium salt type perrhenate ionic liquid is a pollution-free catalyst, has catalysis activity for lignocellulose, can be used as the catalyst for degrading lignocellulose to prepare reducing sugar, and the high yield is obtained.
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Paragraph 0025
(2017/06/02)
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- Synthesis of Conjugates of hyaluronic and nicotinic acids
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Conjugates with nicotinic acid of hyaluronic acid carboxylic and hydroxyl groups were synthesized and exhibited polyampholyte properties.
- Ponedel'kina,Sal'nikova,Lukina,Tyumkina,Odinokov
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experimental part
p. 189 - 193
(2012/09/08)
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- Influence of alkyl chain length and temperature on thermophysical properties of ammonium-based ionic liquids with molecular solvent
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Mixing of ionic liquids (ILs) with molecular solvent can expand the range of structural properties and the scope of molecular interactions between the molecules of the solvents. Exploiting of these phenomena essentially require a basic fundamental understanding of mixing behavior of ILs with molecular solvents. In this context, a series of protic ILs possessing tetra-alkyl ammonium cation [R4N]+ with commonly used anion hydroxide [OH]- were synthesized and characterized by temperature dependent thermophysical properties. The ILs [R4N]+[OH]- are varying only in the length of alkyl chain (R is methyl, ethyl, propyl, or butyl) of tetra-alkyl ammonium on the cationic part. The ILs used for the present study included tetramethyl ammonium hydroxide [(CH3) 4N]+[OH]- (TMAH), tetraethyl ammonium hydroxide [(C2H5)4N]+[OH]- (TEAH), tetrapropyl ammonium hydroxide [(C3H7)4N] +[OH]- (TPAH) and tetrabutyl ammonium hydroxide [(C 4H9)4N]+[OH]- (TBAH). The alkyl chain length effect has been analyzed by precise measurements such as densities (ρ), ultrasonic sound velocity (u), and viscosity (η) of these ILs with polar solvent, N-methyl-2-pyrrolidone (NMP), over the full composition range as a function of temperature. The excess molar volume (VE), the deviation in isentropic compressibility (Δκs) and deviation in viscosity (Δη) were predicted using these properties as a function of the concentration of ILs. Redlich-Kister polynomial was used to correlate the results. A qualitative analysis of the results is discussed in terms of the ion-dipole, ion-pair interactions, and hydrogen bonding between ILs and NMP molecules. Later, the hydrogen bonding features between ILs and NMP were also analyzed using a molecular modeling program with the help of HyperChem 7.
- Kavitha,Attri, Pankaj,Venkatesu, Pannuru,Devi, R. S. Rama,Hofman
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experimental part
p. 4561 - 4574
(2012/07/02)
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- Metal or ammonium alginates as Lewis base catalysts for the 1,2-addition of silyl nucleophiles to carbonyl compounds
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Several metal (Na+, Ca2+) or ammonium (n-Bu 4N+) derivatives of alginic acid, an abundant bio-polymer obtained from the cell walls of brown algae, were synthesized. Their potential to act as organocatalysts to catalyze the 1,2-addition of various silyl derivatives to carbonyl compounds was evaluated for the first time. Ammonium alginate 1h is able to promote the reaction in modest to good isolated yields (up to 98%) affording access to a large range of substrates (β-cyano alcohols or ester, β-substituted methylacrylate or acrylonitrile, and cyanohydrin) by using only 5 mol % of catalyst.
- Verrier, Cécile,Oudeyer, Sylvain,Dez, Isabelle,Levacher, Vincent
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supporting information; experimental part
p. 1958 - 1960
(2012/05/19)
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- Distinguishing between pathways for transmetalation in Suzuki-Miyaura reactions
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We report a systematic study of the stoichiometric reactions of isolated arylpalladium hydroxo and halide complexes with arylboronic acids and aryltrihydroxyborates to evaluate the relative rates of the two reaction pathways commonly proposed to account for transmetalation in the Suzuki-Miyaura reaction. On the basis of the relative populations of the palladium and organoboron species generated under conditions common for the catalytic process and the observed rate constants for the stoichiometric reactions between the two classes of reaction components, we conclude that the reaction of a palladium hydroxo complex with boronic acid, not the reaction of a palladium halide complex with trihydroxyborate, accounts for transmetalation in catalytic Suzuki-Miyaura reactions conducted with weak base and aqueous solvent mixtures.
- Carrow, Brad P.,Hartwig, John F.
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supporting information; experimental part
p. 2116 - 2119
(2011/04/23)
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- Spiro(imidazo[1,2-a]pyrano[2,3-c]pyridine-9-indenes) as inhibitors of gastric acid secretion
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Asymmetric and symmetric spiro(imidazo[1,2-a]pyrano[2,3-c]pyridine-9-indenes) were prepared using a synthetic approach that comprised a cross-metathesis reaction and an acid-catalyzed cycloisomerisation as key steps. The target compounds constitute potent inhibitors of the gastric proton pump enzyme with inhibitory activity comparable to potassium-competitive acid blockers (P-CABs) belonging to the known 9-aryl-7H-8,9-dihydropyrano[2,3-c]imidazo[1,2-a]pyridine series. Spiro(imidazo[1,2-a]pyrano[2,3-c]pyridine-9,2′-indenes) represent the first example for P-CABs, in which the distance between the heterocyclic scaffold and the aryl residue has been modified, and are promising candidates for further development as anti-ulcer drugs.
- Palmer, Andreas Marc,Chrismann, Sandra,Muench, Gabriela,Brehm, Christof,Zimmermann, Peter Jan,Buhr, Wilm,Senn-Bilfinger, Joerg,Feth, Martin Philipp,Simon, Wolfgang Alexander
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experimental part
p. 368 - 384
(2011/02/26)
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- Quaternary ammonium arylspiroborate esters as organo-soluble, environmentally benign wood protectants
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As part of a larger project aimed at the development of leach resistant boron-based wood preservatives, the anti-fungal and termiticidal activities, and the resistance to leaching from timber, of three related tetra-n-butylammonium spiroborates, tetra-n-butylammonium bis(ortho-hydroxymethylphenolato)borate 2, tetra-n-butylammonium bis[catecholato(2?)-O,O?]borate 3, and tetra-n-butylammonium bis[salicylato(2-)-O,O']borate 4, have been examined. All three borates are found to be active against test organisms, with the following orders of activity being observed: 2 > 3 > 4 > boric acid against wood decay fungi, and 2 > 3 ? 4 > boric acid against termites. The most active compound in both assays 2 also has the highest calculated lipophilicity. In a test for permanence in wood, the following order of leach resistance is observed: 4 >> 3 ? 2 > boric acid. This order appears to correlate more closely with the stability constants of the borate esters, as determined using 11B NMR spectroscopy, rather than calculated lipophilicities. CSIRO 2005.
- Carr, Jenny M.,Duggan, Peter J.,Humphrey, David G.,Platts, James A.,Tyndall, Edward M.
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p. 901 - 911
(2007/10/03)
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- USE OF NAFION MEMBRANES IN LABORATORY ORGANIC ELECTROSYNTHESIS
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Electrolysis of quarternary ammonium bromides and iodides in a divided cell with a Nafion membrane yields quarternary polyhalogenides at a carbon anode in water-ethanolic anolytes.The electrodialysis of tetrabutylammonium iodide in a cell with a Nafion membrane enables generation of tetrabutylammonium hydroxide.In electrolytic reduction of nitrobenzene in presence of 1,3-dibromopropane, N-phenylisoxazolidine results in approx. 60percent yield.This electrosynthesis takes place in dimethylformamide with tetrabutylammonium bromide at a glassy-carbon cathode in a divided cell.In the electroreduction of lobelanine hydrogensulfate in a divided cell in acid water-ethanolic media at a lead cathode prevalently lobelanidine has been obtained.
- Hlavaty, Jaromir,Volke, Jiri
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p. 3164 - 3170
(2007/10/02)
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- Proximate Charge Effects. 6. Anion-Cation-Zwitterion Triplets in Solution
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The reaction of p-nitrophenol with tetra-n-butylammonium taurinate in 95.3 mol percent dioxane-water was found to give an anion-cation-zwitterion triplet which then dissociates to a zwitterion and to an ion pair.The equilibrium constants for the formation of this triplet, Kf, and for dissociation, Kd, were found to be Kf = 3.57 L1/2 mol-1/2 and Kd = 1.73 x 10-7 mol L-1.
- Haberfield, Paul,Cincotta, Joseph J.
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p. 4188 - 4192
(2007/10/02)
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- COSTANTE DE L'EQUILIBRE ACIDO-BASIQUE DU TRIPHENYLSILANOL AVEC L'HYDROXYDE DE TETRABUTYLAMMONIUM EN MILIEU ACETONITRILE-EAU A 25 DEG C
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The equilibrium constant of the acid-base reaction of triphenylsilanol with tetrabutylammonium hydroxide is determined from kinetic measurements of the inhibiting effect of silanol upon the basic condensation of triphenylsilane.Within the utilized range of water contents (1.09 mol-1 H2O -1), pK decreases linearily with the logarithm of mole fraction of water.
- Borghese, Alfio,Tondeur, Jean-Jacques
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