- Separation and recovery of cellulose from Zoysia japonica by 1-allyl-3-methylimidazolium chloride
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We investigated the use of ionic liquid (IL) 1-allyl-3-methylimidazolium chloride (AMIMCl) for extracting cellulose from Zoysia japonica by using Fourier transform infrared spectroscopy, nuclear magnetic resonance, scanning electron microscopy and thermogravimetric analysis to analyze the IL and its effects on cellulose extraction. After water pretreatment at 121 °C for several minutes, cellulose extraction rate was 71% under optimized conditions, and the yield of cellulose was >99% by AMIMCl. The effectiveness of AMIMCl as an extraction agent can be attributed to the prevalence of intra- and inter-molecular hydrogen bonding in cellulose. By contrast, hemicelluloses were not recovered by AMIMCl because hemicelluloses in plant cell walls are connected to lignin by covalent bonding. Results also showed that the regenerated cellulose was exactly the same as untreated cellulose, except for the degree of crystallinity.
- Li, Wei-Zun,Ju, Mei-Ting,Wang, Yan-Nan,Liu, Le,Jiang, Yang
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- Catalytic conversion of fructose and sucrose to 5-hydroxymethylfurfural using simple ionic liquid/DMF binary reaction media
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The production of 5-hydroxymethylfurfural (HMF) from carbohydrates has been reported intensively in recent years. HMF is believed to be a versatile platform chemical and the focus of synthesizing it has especially been on the development of efficient catalysts, such as Lewis and Br?nsted Acids. On the contrary, herein, we report a novel catalytic system that consists of 1-allyl-3-methylimidazolium chloride ([AMIM]Cl) and N,N-Dimethylformamide (DMF) without any additional metal salts or acids, which leads to reasonable HMF yields (84.9%) and selectivities. In addition, the degradation mechanism of fructose catalyzed by [AMIM]Cl is also proposed in this communication.
- Shi, Jincai,Yang, Yan,Wang, Ningning,Song, Zhanxin,Gao, Haiyan,Xia, Yongmei,Li, Wei,Wang, Haijun
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- Task-specific ionic liquid for the depolymerisation of starch-based industrial waste into high reducing sugars
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Development of a simple route for the catalytic conversion of starch-based industrial waste (potato peels) and potato starch into reducing sugars was investigated in two ionic liquids for comparison - 1-allyl-3-methylimidazolium chloride [AMIM]Cl and 1-(4-sulfobutyl)-3-methylimidazolium chloride [SBMIM]Cl. Over a two hour period, a 20 wt% solution containing up to 43% and 98% of reducing sugars at low temperature in aqueous [SBMIM]Cl was achieved for the starch-based waste and the potato starch, respectively. In addition, the use of microwave and low frequency ultrasound to perform the depolymerisation of the raw starch-based material was explored and compared with conventional heating processes.
- Hernoux-Villière, Audrey,Lévêque, Jean-Marc,K?rkk?inen, Johanna,Papaiconomou, Nicolas,Lajunen, Marja,Lassi, Ulla
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- Successful application of an ionic liquid carrying the fluoride counter-ion in biomacromolecular chemistry: Microwave-Assisted acylation of cellulose in the presence of 1-allyl-3-methylimidazolium fluoride/DMSO mixtures
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The use of ionic liquids with fluoride anion (IL-F) is challenging because of side reactions. Neat 1-allyl-3-methylimidazolium fluoride (AlMeImF) is used as a solvent in microwave-assisted acylation of cellulose. The results are disappointing due to side reactions in the IL proper, and F--mediated hydrolysis of the produced ester. A dramatic improvement is observed, when AlMeImF/DMSO mixture is employed. The results are comparable to those obtained when pure 1-allyl-3-methylimidazolium chloride is employed. FTIR spectroscopy shows that dissolving a carboxylic acid anhydride in IL-F leads to the formation of acyl fluoride. Thus ILs are far from being "spectator" solvents. The new approach (use of IL-F/DMSO) is attractive because of its efficiency, low cost, and applicability to the derivatization of any polymer.
- Casarano, Romeu,El Seoud, Omar A.
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- Pretreatment of fibre sludge in ionic liquids followed by enzyme and acid catalysed hydrolysis
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Pretreatment of fibre sludge in ionic liquids and enzyme or acid catalysed hydrolysis of fibre sludge is studied. Ionic liquids, i.e. 1-allyl-3- methylimidazolium chloride ([AMIM]Cl) and 1-butyl-3-methylimidazolium chloride ([BMIM]Cl), are used in the pretreatment step. Effect of ionic liquid (IL) pretreatment on the acid and enzyme catalysed hydrolysis of fibre sludge is considered. Cellulose content of fibre sludge is more than 80 wt%, and therefore, reducing sugars obtained as a result of hydrolysis contain mostly glucose. To maximize the yield of reducing sugars during the enzymatic hydrolysis, the combinations of selective enzymes are required. Results also show that the use of ionic liquids in the pretreatment step before acid and enzyme hydrolysis increases significantly the yield of total reducing sugars.
- Holm, Jana,Lassi, Ulla,Romar, Henrik,Lahti, Riikka,K?rkk?inen, Johanna,Lajunen, Marja
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- Functional ionic liquids for hydrolysis of lignocellulose
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An efficient system for hydrolysis of lignocellulosic materials to prepare reducing sugar in a series of functional acidic ionic liquids with low synthetic cost and excellent dissolved and catalytic activity was established. High yield of reducing sugar was obtained with the use of 1-H-3-methylimidazolium chloride ([HMIM]Cl). The use of ionic liquid under ultrasound irradiation greatly improved the yield of total reducing sugar. The optimum reaction conditions were as follows: ratio of water/sample was 5 (w/w), ratio of IL/sample was 25 (w/w), 70 °C, 120 min and the yield of reducing sugar was up to 53.27 mg from 0.2 g of soybean straw and 50.03 mg from 0.2 g of corn straw.
- Hu, Xiaomei,Xiao, Yibo,Niu, Kun,Zhao, Yang,Zhang, Bixian,Hu, Baozhong
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- Dissolution of cellulose from AFEX-pretreated Zoysia japonica in AMIMCl with ultrasonic vibration
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In this study, 1-allyl-3-methylimidazolium chloride (AMIMCl), an ionic liquid, was synthesized and characterized by a series of test methods. Pretreatment of Zoysia japonica by ammonia fiber expansion (AFEX) was shown to reduce significantly the mass of hemicellulose and lignin in biomass, thereby breaking the lignocellulosic structure. Z. japonica samples pretreated with AFEX showed reasonable solubility in AMIMCl upon ultrasonic treatment. The rate of cellulose regeneration from Z. japonica samples pretreated with AFEX increased with increase in applied power of ultrasonication within a certain power range from 0 to 110 W. The regeneration rate of cellulose from AFEX-pretreated Z. japonica reached a maximum of 97% when the ultrasonic power was 110 W. Fourier transform infrared spectroscopy and nuclear magnetic resonance analyses indicated that the regenerated cellulose was similar to microcrystalline cellulose.
- Liu, Le,Ju, Meiting,Li, Weizun,Hou, Qidong
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- Dissolution of cellulose in 1-allyl-3-methylimizodalium carboxylates at room temperature: A structure-property relationship study
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The development of highly efficient cellulose solvents is imperative to the effective utilization of cellulose. In this work, ionic liquids (ILs) with the same 1-allyl-3-methylimidazolium cation ([Amim]+) but different carboxylate anions, such
- Zhang, Yajuan,Xu, Airong,Lu, Benlian,Li, Zhiyong,Wang, Jianji
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- Synthetic, spectroscopic and structural behavior of unsaturated functionalized N-heterocyclic carbene complexes of group 11
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A series of unsaturated functionalized silver(I) N-heterocyclic carbenes [{(κC-C7N2H10)AgCl}2] (1a), [{(κC-C8N2H12)2}2Ag][Ag2Cl4] (1b)
- González-Abrego, Daniel Omar,Zuno-Cruz, Francisco J.,Carpio-Granillo, Mariana,Andrade-López, Noemí,Cruz-Borbolla, Julián,Martínez-Macias, Claudia,Mendoza-Espinosa, Daniel,Rosales-Hoz, María J.,Leyva, Marco A.,Torres-Lubián, José R.,López-Jiménez, Jorge A.,Jancik, Vojtech,Sánchez-Cabrera, Gloria
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- Investigations about dissolution of cellulose in the 1-allyl-3- alkylimidazolium chloride ionic liquids
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In this work, the 1-allyl-3-alkylimidazolium chloride ionic liquids were synthesized and characterized by increasing carbon atoms (n ≤ 6) of alkyl chains on a cationic 3-imidazole ring. The results indicated that 1-allyl-3-alkylimidazolium chloride with asymmetrical structure on the two sides of a cationic 3-imidazole ring (i.e., n = 1, 2, 6) exhibited alkalinity and lower thermal stabilities, and showed better solubility to the cellulose samples at 60-120 °C than those with symmetrical structures (n = 3, 4). The cellulose samples treated by 20% (w/w) ethylenediamine solution showed better solubility in 1-allyl-3-ethyl, hexyl-imidazolium chloride ionic liquids than that treated with 20% (w/w) NaOH solution at 5 °C for 72 h. XRD and TG analysis indicated that 0 0 2 plane apparent crystallite size as well as thermal stability of the regenerated cellulose samples from the ionic liquids decreased significantly compared with the untreated cellulose samples.
- Liu, De-Tao,Xia, Kun-Feng,Cai, Wei-Hua,Yang, Ren-Dang,Wang, Li-Qin,Wang, Bin
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- Dissolution of feather keratin in ionic liquids
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Keratin from various livestock industries is currently a waste material that has potential as a source of polyamide polymers that could replace fossil fuel derived materials if processing methods can be developed. In this work we have investigated methods for the dissolution and regeneration of keratin. Dissolution of keratin (from turkey feather) in ionic liquids was conducted under nitrogen at 130 °C for 10 hours. It was found that [BMIM]Cl, [AMIM]Cl and [choline][thioglycolate] could dissolve turkey feather keratin without addition of solvent or other chemicals. A significant percentage of solubility was obtained, up to 45% by weight. A water insoluble fraction was recovered by addition of water to the solution (～50%). The structure and properties of this regenerated, water insoluble fraction were investigated. Compared to the starting material, the regenerated keratin shows structural changes rather than chemical changes within the polypeptide chains. The remaining fraction, consisting of water soluble fragments, was characterised by gel electrophoresis.
- Idris, Azila,Vijayaraghavan,Rana, Usman Ali,Fredericks, Dale,Patti,MacFarlane
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- Synthesis and characterization of nitrogen-based ionic liquids bearing allyl groups and examples of their application
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The syntheses and full spectral (NMR, MS, and IR), thermal (DSC) and ion chromatographic characterization of two series of amine-derived ionic liquids bearing allyl substituents and having chloride or bis(trifluoromethanesulfonyl)amide anions have been presented. The analysis of the dependence of the 1H NMR chemical shift values of the selected protons on the cation and anion structure has been conducted. DSC analysis records together with ion chromatography analysis results have been presented and interpreted. Moreover, a selection of obtained chloride ionic liquids have been transformed into the corresponding chlorocobaltates and chlorozincates or used as substrates in thiol-ene click reactions to indicate their potential as precursors of catalysts or various surface modifiers.
- Zajac, Adrian,Szpecht, Andrea,Szymanska, Anna,Zielinski, Dawid,Stolarska, Olga,Smiglak, Marcin,Maciejewski, Hieronim
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p. 12274 - 12288
(2020/07/30)
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- Understanding the efficiency of ionic liquids-DMSO as solvents for carbohydrates: use of solvatochromic- And related physicochemical properties
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The physical dissolution of carbohydrates (cellulose, chitin, and starch),i.e., without the formation of covalent bonds requires the solvent to possess certain physicochemical properties. Concentrating on cellulose, the solvent should act both as a Lewis acid and a Lewis base, and disrupt the present hydrophobic interactions, as the biopolymer exhibits amphiphilic characteristics. The quantification of the relative importance of these physicochemical properties helps in predicting the solvent structures, which are expected to be efficient as cellulose solvents. Ionic liquids (ILs) are extensively used as carbohydrate solvents because they disrupt the intramolecular-, intermolecular-, and hydrophobic interactions within the biopolymer structure, leading to its dissolution. Solvatochromic substances (probes) are especially sensitive to one or more of the above-mentioned biopolymer-solvent interactions. Consequently, they are used to predict and rationalize the solvent efficiency. The solvent parameters (descriptors) most widely employed are empirical polarity,ET(probe), Lewis acidity (SA); Lewis basicity (SB), dipolarity (SD), and polarizability (SP); S refers to the solvent. We synthesized 18 ILs, including derivatives of imidazole, 1,8-diazabicyclo[5.4.0]undec-7-ene, and tetramethylguanidine; the corresponding anions are carboxylates, chloride and dimethylphosphate. We used solvatochromic probes to calculate the descriptors of IL-DMSO (at fixed DMSO mole fraction of 0.6; 40 °C), and correlatedET(probe) with the other descriptors. We also tested the correlations by using a molar volume of the IL (VM) instead of SD, and the Lorentz-Lorenz refractive index functionf(n) of the IL-DMSO mixture instead of SP. The quality of the regression analysis increased noticeably when we limited the ILs correlated with those based on imidazole (13 ILs), and used (VM) andf(n). The regression coefficients showed that SA is the most important descriptor; the solvent empirical polarity is inversely dependent onVM. The value off(n) shows the importance of hydrophobic interactions. By using different probes, we showed that the observed small contribution of SB reflects the steric crowding around the positive nitrogen atoms in some probes. The results obtained help in selecting ILs as solvents for cellulose and other carbohydrates, based on the expected strength of their interactions with the biopolymers. Therefore, using solvatochromism for solvent efficiency screening saves labor and cost.
- Bioni, Thaís A.,de Oliveira, Mayara L.,Dignani, Marcella T.,El Seoud, Omar A.
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p. 14906 - 14914
(2020/09/23)
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- Olefin-tethered organoruthenium carbene complexes: Synthesis, X-ray structure and catalytic insights on hydrogenation of esters
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A series of Ru(II) complexes encompassing imidazolylidene olefin arm have been designed. The newly synthesized ligands and complexes were fully characterized by 1H, 13C NMR, and elemental analyses. Structural geometry for one of the envoy Ru(II) carbene complexes 3a was confirmed by single-crystal X-ray diffraction studies. The complexes acquired a distorted octahedral geometry. The highly active [Ru(II)-NHC] complex 3b, showed excellent catalytic performance for the hydrogenation of esters in 1,4-dioxane medium. The effects of solvent, base, wingtip substituents, time and catalyst loading were also investigated. The reported catalyst performed exceptionally well for a range of esters and furnishes very good yield of hydrogenated products.
- Nirmala, Muthukumaran,Murugan, Kaliyappan,Vijayapritha, Subbarayan,Viswanathamurthi, Periasamy,Bertani, Roberta,Malecki, Jan Grzegorz
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- Direct catalytic conversion of glucose and cellulose
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Biomass product 5-hydroxymethylfurfural (5-HMF) can be used to synthesize a broad range of value added compounds currently derived from petroleum. Thus, the effective conversion of glucose or cellulose (the major components of biomass) into fuels and chemical commodities has been capturing increasing attention. Previous studies have been extensively focused on a two-step process for producing 5-HMF from glucose or cellulose, i.e., the isomerization of glucose into fructose and then the dehydration of fructose. We herein discovered that heterogeneous sulfonated poly(phenylene sulfide) (SPPS) containing strong Br?nsted acid sites is able to convert glucose and cellulose into 5-HMF with a high yield in ionic liquids (ILs). The optimal activity of glucose conversion to 5-HMF achieves a yield of 87.2% after 4 h reaction at 140 °C. For direct cellulose conversion, a 5-HMF yield of 68.2% can be achieved. The reaction mechanism over the SPPS catalyst in ILs was studied by DFT calculations, and the results indicated that the SO3H group of SPPS plays a crucial role in glucose conversion into 5-HMF, and it acts as a proton donor as a Br?nsted acid and functions as a proton acceptor as the conjugate base. Furthermore, the anions and cations of ILs together with SO3H-SPPS helped in stabilizing the reaction intermediates and transition states, which also resulted in glucose facile conversion into 5-HMF. The new catalyst system highlights new opportunities offered by optimizing the production of 5-HMF directly from glucose and cellulose.
- Li, Zhenhuan,Su, Kunmei,Ren, Jun,Yang, Dongjiang,Cheng, Bowen,Kim, Chan Kyung,Yao, Xiangdong
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supporting information
p. 863 - 872
(2018/03/05)
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- Zinc-based imidazole type ion liquid for liquid sealing and preparation method thereof
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The invention relates to zinc-based imidazole type ion liquid for liquid sealing. The proper intermediates and zinc salts can be selected according to the concrete density requirements or materials requirements of required liquid sealing; then, the proportion of the required intermediates and the zinc salts is calculated according to the concrete density, the intermediates and the zinc salt density of the required liquid sealing media; the preparation is performed to obtain ion liquid used for liquid sealing. The zinc-based imidazole type ion liquid has the following beneficial effects of non-volatile performance, non-combustibility, no combustion and explosion risk, high safety performance, wide liquid path range, applicability at 0 to 250 DEG C, physical and chemical stability and intermiscibility with various materials; through the design and the synthesis of novel ion liquid, the wider application range can be realized. The ion liquid density is higher than or equal to 1.2g/ml; the density is higher than that of ordinary media; the ion liquid can be applicable various special occasions; through the design synthesis, the ion liquid density can be changed; the density is adjustable in a 1.2 to 2.0 g/ml; homogeneous materials are used, and the particle suspension problem does not exist.
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Paragraph 0030
(2017/04/25)
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- Succinic anhydride-modified cellulose-based drug controlled-release carrier and preparation method thereof
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The invention discloses a succinic anhydride-modified cellulose-based drug controlled-release carrier and a preparation method thereof. Succinic anhydride-modified cellulose is applied to controlled-release domperidone, and a carboxy group can be combined with secondary amine hydrogen and carbonyl oxygen in the domperidone to generate a hydrogen bond, so that the domperidone can be loaded on the succinic anhydride-modified cellulose; and meanwhile, sites for hydrogen bond interaction formed between the succinic anhydride-modified cellulose and the domperidone are increased through the carboxy group and an esteryl group and the drug-loading stability of the succinic anhydride-modified cellulose is strengthened, so that release of the domperidone is retarded.
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Paragraph 0050; 0051
(2017/08/31)
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- Application of mild autohydrolysis to facilitate the dissolution of wood chips in direct-dissolution solvents
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Wood is not fully soluble in current non-derivatising direct-dissolution solvents, contrary to the many reports in the literature quoting wood 'dissolution' in ionic liquids. Herein, we demonstrate that the application of autohydrolysis, as a green and economical wood pre-treatment method, allows for a massive increase in solubility compared to untreated wood. This is demonstrated by the application of two derivitising methods (phosphitylation and acetylation), followed by NMR analysis, in the cellulose-dissolving ionic liquids 1-allyl-3-methylimidazolium chloride ([amim]Cl) and 1,5-diazabicyclo[4.3.0]non-5-enium acetate ([DBNH][OAc]). In addition, the non-derivitising tetrabutylphosphonium acetate ([P4444][OAc]) : DMSO-d6 electrolyte also allowed for dissolution of the autohydrolysed wood samples. By combination of different particle sizes and P-factors (autohydrolysis intensity), it has been clearly demonstrated that the solubility of even wood chips can be drastically increased by application of autohydrolysis. The physiochemical factors affecting wood solubility after autohydrolysis are also discussed.
- Deb, Somdatta,Labafzadeh, Sara R.,Liimatainen, Unna,Parviainen, Arno,Hauru, Lauri K. J.,Azhar, Shoaib,Lawoko, Martin,Kulomaa, Tuomas,Kakko, Tia,Fiskari, Juha,Borrega, Marc,Sixta, Herbert,Kilpel?inen, Ilkka,King, Alistair W. T.
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supporting information
p. 3286 - 3294
(2016/06/15)
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- Synthesis and hypergolic activity evaluation of some new ammonium-imidazolium based ionic liquids
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In this study, a new class of dicyanamide-based ionic liquids containing mono and dicationic counterparts was synthesized and characterized. Results demonstrate that the physical properties of these salts, including thermal stability, melting point, density and viscosity, are highly dependent on the structure of cation and type of anion. It was observed that the thermal stability of dicationic ionic liquids is higher for the monocationic ones. Furthermore, droplet tests were used to investigate the hypergolic properties of these ionic liquids. All of the synthesized compounds showed hypergolic activity upon contact with white fuming nitric acid, suggesting that some may have potential for application as bipropellants or energetic additives.
- Fareghi-Alamdari, Reza,Ghorbani-Zamani, Faezeh,Zekri, Negar
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p. 26386 - 26391
(2016/03/25)
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- Regeneration of cello-oligomers via selective depolymerization of cellulose fibers derived from printed paper wastes
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Cellulose extracted from printed paper wastes were selectively depolymerized under controlled conditions into cello-oligomers of controllable chain lengths via dissolution in an ionic liquid, 1-allyl-3-methylimidazolium chloride (AMIMCl), and in the presence of an acid catalyst, Amberlyst 15DRY. The depolymerization process was optimized against reaction temperature, concentration of acid catalyst, and reaction time. Despite rapid initial depolymerization process, the rate of cellulose depolymerization slowed down gradually upon prolonged reaction time, with 75.0 wt% yield of regenerated cello-oligomers (mean Viscosimetric Degree of Polymerization value of 81) obtained after 40 min. The depolymerization of cellulose fibers at 80 °C appeared to proceed via a second-order kinetic reaction with respect to the catalyst concentration of 0.23 mmol H3O+. As such, the cellulose depolymerization process could afford some degree of control on the degree of polymerization or chain lengths of cello-oligomers formed.
- Voon, Lee Ken,Pang, Suh Cem,Chin, Suk Fun
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- Preparation method of 1-allyl-3-methylimidazole chloride
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The invention discloses a preparation method of 1-allyl-3-methylimidazole chloride. The compound, 1-allyl-3-methylimidazole chloride, which has a complex structure, is synthesized with N-methylimidazole, chloropropene and the like raw materials. The product is high in yield, is good in crystallization effect, is high in purity and can be used as high-purity reference products and standard samples for follow-up chemical and biological experiments.
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Paragraph 0011; 0012; 0013; 0014
(2016/11/24)
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- Efficient ionic liquid synthesis method
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The invention relates to an efficient ionic liquid synthesis method. The efficient ionic liquid synthesis method is characterized in that an ultrasonic and microwave synergistic heating manner is adopted in an ionic liquid synthesis process. Through the new method adopting the ultrasonic and microwave synergistic heating manner to synthetize the ionic liquid, the reaction time is shortened, the reaction temperature is reduced, the energy consumption is reduced, and the obtained target product, namely the ionic liquid, is high in purity and less in by-product, and has a potential possibility of large scale popularization.
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Paragraph 0025; 0026; 0027; 0028
(2017/01/02)
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- Cyanoborohydride-based ionic liquids as green aerospace bipropellant fuels
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In propellant systems, the most common bipropellants are composed of two chemicals, a fuel (or reducer) and an oxidizer. Currently, the choices for propellant fuels rely mainly on hydrazine and its methylated derivatives, even though they are extremely toxic, highly volatile, sensitive to adiabatic compression (risk of detonation), and, therefore, difficult to handle. With this background, the search for alternative green propellant fuels has been an urgent goal of space science. In this study, a new family of cyanoborohydride-based ionic liquids (ILs) with properties and performances comparable to hydrazine derivatives were designed and synthesized. These new ILs as bipropellant fuels, have some unique advantages including negligible vapor pressure, ultra-short ignition delay (ID) time, and reduced synthetic and storage costs, thereby showing great application potential as environmentally friendly fuels in bipropellant formulations.
- Zhang, Qinghua,Yin, Ping,Zhang, Jiaheng,Shreeve, Jean'Ne M.
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p. 6909 - 6914
(2014/06/09)
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- Nonaborane and decaborane cluster anions can enhance the ignition delay in hypergolic ionic liquids and induce hypergolicity in molecular solvents
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The dissolution of nido-decaborane, B10H14, in ionic liquids that are hypergolic (fuels that spontaneously ignite upon contact with an appropriate oxidizer), 1-butyl-3-methylimidazolium dicyanamide, 1-methyl-4-amino-1,2,4-triazolium dicyanamide, and 1-allyl-3-methylimidazolium dicyanamide, led to the in situ generation of a nonaborane cluster anion, [B9H14]-, and reductions in ignition delays for the ionic liquids suggesting salts of borane anions could enhance hypergolic properties of ionic liquids. To explore these results, four salts based on [B10H13]- and [B9H 14]-, triethylammonium nido-decaborane, tetraethylammonium nido-decaborane, 1-ethyl-3-methylimidazolium arachno-nonaborane, and N-butyl-N-methyl-pyrrolidinium arachano-nonaborane were synthesized from nido-decaborane by reaction of triethylamine or tetraethylammonium hydroxide with nido-decaborane in the case of salts containing the decaborane anion or via metathesis reactions between sodium nonaborane (Na[B9H 14]) and the corresponding organic chloride in the case of the salts containing the nonaborane anion. These borane cluster anion salts form stable solutions in some combustible polar aprotic solvents such as tetrahydrofuran and ethyl acetate and trigger hypergolic reactivity of these solutions. Solutions of these salts in polar protic solvents are not hypergolic.
- McCrary, Parker D.,Barber, Patrick S.,Kelley, Steven P.,Rogers, Robin D.
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p. 4770 - 4776
(2014/05/20)
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- On the solubility of wood in non-derivatising ionic liquids
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Norway spruce wood was mechanically pulverized to varying degrees. The solubility of the wood samples, in a range of common ionic and molecular solvents, was quantified using a novel 31P NMR technique. The results show that intact wood is not soluble under mild treatment conditions, in cellulose-dissolving or swelling solvents.
- Kylloenen, Lasse,Parviainen, Arno,Deb, Somdatta,Lawoko, Martin,Gorlov, Mikhail,Kilpelaeinen, Ilkka,King, Alistair W. T.
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supporting information
p. 2374 - 2378
(2013/09/12)
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- Electrodeposition of zinc coatings from the solutions of zinc oxide in imidazolium chloride/urea mixtures
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To solve the inherent disadvantages in conventional processes for electrodeposition of zinc, it's necessary to develop more high-efficiency and environmentally friendly electrolytes. In this work, it was found that the dissolution of ZnO was remarkably enhanced in some imidazolium chloride by the addition of urea, and the solubility of ZnO in 1:1 [Amim]Cl/urea mixture was as high as 8.35 wt% at 373.2 K. Electrochemical measurements showed that zinc could be readily electrodeposited from the solutions of ZnO. Bright, dense and well adherent zinc coatings with good purity were obtained from 0.6 M solution of ZnO in 1:1 [Amim]Cl/urea at 323.2?343.2 K. It's expected that the solutions of ZnO in imidazolium chloride/urea mixtures have the potential to replace the traditional electrolytes, especially toxic zinc chloride-based ones for zinc electroplating, as well as preparation of zinc materials. Science China Press and Springer-Verlag Berlin Heidelberg 2012.
- Zheng, Yong,Dong, Kun,Wang, Qian,Zhang, Suo Jiang,Zhang, Qin Qin,Lu, Xing Mei
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p. 1587 - 1597
(2012/11/07)
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- Thermal stability of 1,3-disubstituted imidazolium tetrachloroferrates, magnetic ionic liquids
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Thermal stability of synthesized magnetic liquids, tetrachloroferrates of 1,3-disubstitued derivatives of imidazolium, was examined. An effect of the cation structure on thermal stability of ionic liquids was considered and a mechanism of thermal destruction was suggested.
- Zhuravlev,Verolainen,Voronchikhina
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experimental part
p. 1158 - 1164
(2011/11/30)
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- Thermo-solvatochromism in binary mixtures of water and ionic liquids: On the relative importance of solvophobic interactions
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The thermo-solvatochromism of 2,6-dibromo-4-[(E)-2-(1-methylpyridinium-4- yl)ethenyl] phenolate, MePMBr2, has been studied in mixtures of water, W, with ionic liquids, ILs, in the temperature range of 10 to 60 °C, where feasible. The objectives of the study were to test the applicability of a recently introduced solvation model, and to assess the relative importance of solute-solvent solvophobic interactions. The ILs were 1-allyl-3-alkylimidazolium chlorides, where the alkyl groups are methyl, 1-butyl, and 1-hexyl, respectively. The equilibrium constants for the interaction of W and the ILs were calculated from density data; they were found to be linearly dependent on NC, the number of carbon atoms of the alkyl group; van't Hoff equation (log K versus 1/T) applied satisfactorily. Plots of the empirical solvent polarities, ET (MePMBr2) in kcal mol-1, versus the mole fraction of water in the binary mixture, χw, showed non-linear, i.e., non-ideal behavior. The dependence of ET (MePMBr2) on χw, has been conveniently quantified in terms of solvation by W, IL, and the "complex" solvent IL-W. The non-ideal behavior is due to preferential solvation by the IL and, more efficiently, by IL-W. The deviation from linearity increases as a function of increasing NC of the IL, and is stronger than that observed for solvation of MePMBr2 by aqueous 1-propanol, a solvent whose lipophilicity is 12.8 to 52.1 times larger than those of the ILs investigated. The dependence on NC is attributed to solute-solvent solvophobic interactions, whose relative contribution to solvation are presumably greater than that in mixtures of water and 1-propanol.
- Sato, Bruno M.,De Oliveira, Carolina G.,Martins, Clarissa T.,El Seoud, Omar A.
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experimental part
p. 1764 - 1771
(2010/09/05)
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- Salting-out effect of ionic liquids on poly(propylene glycol) (PPG): Formation of PPG + ionic liquid aqueous two-phase systems
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In the present work, aqueous poly(propylene glycol) (PPG) solution was separated into aqueous two-phase systems (ATPSs) in the presence of ionic liquid 1-allyl-3-methylimidazolium chloride ([Amim]Cl), 1-butyl-3-methylimidazolium acetate ([C4mim]Ac), or 1-butyl-3-methylimidazolium chloride ([C 4mim]Cl). The top phase was PPG-rich, whereas the bottom phase was ionic liquid (IL)-rich. Liquid-liquid equilibrium data for the ATPSs and the salting-out coefficients of the ILs have been determined at 298.15 K and atmospheric pressure. It was shown that the binodal curves and the tie-lines could be described by a three-parameter equation and the Othmer-Tobias and Bancroft equations, respectively. The salting-out ability of the ILs on PPG was found to follow the order: [Amim]Cl > [C4mim]Ac > [C 4mim]Cl > [C4mim][BF4]. Since PPG is a thermo-sensitive polymer and can be recovered simply by heating, these novel ATPSs are expected to have applications in the recycling and/or enrichment of hydrophilic ILs from aqueous solutions.
- Wu, Changzeng,Wang, Jianji,Pei, Yuanchao,Wang, Huiyong,Li, Zhiyong
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experimental part
p. 5004 - 5008
(2011/08/22)
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- Dissolution of wood in ionic liquids
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The present paper demonstrates that both hardwoods and softwoods are readily soluble in various imidazolium-based ionic liquids (ILs) under gentle conditions. More specifically, a variety of ionic liquids can only partially dissolve wood chips, whereas ionic liquids such as 1-butyl-3-methylimidazolium chloride and 1-allyl-3-methylimidazolium chloride have good solvating power for Norway spruce sawdust and Norway spruce and Southern pine thermomechanical pulp (TMP) fibers. Despite the fact that the obtained solutions were not fully clear, these ionic liquids provided solutions which permitted the complete acetylation of the wood. Alternatively, transparent amber solutions of wood could be obtained when the dissolution of the same lignocellulosic samples was attempted in 1-benzyl-3-methylimidazolium chloride. This realization was based on a designed augmented interaction of the aromatic character of the cation of the ionic liquid with the lignin in the wood. After dissolution, wood can be regenerated as an amorphous mixture of its original components. The cellulose of the regenerated wood can be efficiently digested to glucose by a cellulase enzymatic hydrolysis treatment. Furthermore, completely acetylated wood was found to be readily soluble in chloroform, allowing, for the first time, detailed proton nuclear magnetic resonance (NMR) spectra and NMR diffusion measurements to be made. It was thus demonstrated that the dissolution of wood in ionic liquids now offers a variety of new possibilities for its structural and macromolecular characterization, without the prior isolation of its individual components. Furthermore, considering the relatively wide solubility and compatibility of ionic liquids with many organic or inorganic functional chemicals or polymers, it is envisaged that this research could create a variety of new strategies for converting abundant woody biomass to valuable biofuels, chemicals, and novel functional composite biomaterials.
- Kilpelaeinen, Ilkka,Xie, Haibo,King, Alistair,Granstrom, Mari,Heikkinen, Sami,Argyropoulos, Dimitris S.
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experimental part
p. 9142 - 9148
(2009/09/25)
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- Preparation of functionalized imidazolium salts under microwave irradiation
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A direct alkylation of a substituted imidazole to prepare the corresponding functionalized ionic liquid has been developed in excellent yields under microwave irradiation. Copyright Taylor & Francis Group, LLC.
- Fu, Shih-Kang,Liu, Shiuh-Tzung
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p. 2059 - 2067
(2007/10/03)
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- 14N NMR and two-dimensional suspension 1H and 13C HAMAS NMR spectroscopy of ionic liquids immobilized on silica
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A variety of popular ionic liquids have been synthesized and characterized, including by optimized 14N NMR spectroscopy of the neat and dissolved ionic liquids. Ionic liquids incorporating Si(OEt)3 groups have been immobilized on silica in a well-defined manner with the imidazolium moiety remaining intact. This has been proved by optimized one- and two-dimensional 1H and 13C HRMAS NMR spectroscopy of the materials suspended in suitable solvents.
- Brenna, Stefano,Posset, Tobias,Furrer, Julien,Bluemel, Janet
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p. 2880 - 2888
(2008/02/03)
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