Journal of Oleo Science
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2021
·
IF 1.601
Hongli Yang,Xu Han,Ahmed S. M. Saleh,Chen Shao,Yumin Duan,Zhi-gang Xiao
In this study, Novozym 435-catalyzed interesterification of ethyl ferulate (EF) with phosphatidylcholine (PC) in a two-phase system consisting of an ionic liquid (IL) and toluene was optimized to prepare feruloylated lysophospholipids (FLPs). Optimum conditions for the interesterification process were found to be [Bmim][Tf2N]/toluene ratio of 1:1 (v/v), solvent volume of 4 mL, molecular sieves (4 Å) concentration of 80 mg/mL, reaction temperature of 55°C, substrate molar ratio of 5:1 (PC/EF), Novozym 435 concentration of 50 mg/mL. Under these conditions, two FLPs products (1-FLP and 2-FLP) with total conversion rate of 50.79% were obtained. Because the formation of 1-FLP was significantly higher than 2-FLP, 1-FLP was purified and characterized by LC-MS and NMR. In addition, 1-FLP showed DPPH scavenging activity comparable with those of EF and BHT. Therefore, this study provides a good method for transformation of ferulic acid to improve its solubility and promote its application as functional ingredient in the food and pharmaceutical industries.
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
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2021
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IF 3.764
Wei Chen,Yumiao Lu,Yanlei Wang,Feng Huo,Wei-Lu Ding,Li Wei,Hongyan He
The ability to tune structures and properties of interfacial ionic liquids (ILs) using electric fields lies at the heart of modern energy storage technologies, particularly for supercapacitors with ILs as electrolytes. Direct observation of the underlying structural change caused by charge injection is vitally important, but the data are extremely scarce. Here, we propose a general protocol to explore the dynamic structural response of interfacial ILs subjected to charge injection. The experimental results have revealed asymmetric structural evolution of interfacial ILs with a common feature of enhanced mobility during charge injection. Consequently, the surface ILs diffuse and agglomerate into various patterns, which depend critically on both the charge injection mode and initial structural feature. Slow and mild charge injection is advantageous in maintaining structural stability as well as regulating dielectric constants of interfacial ILs. Finally, we unveil the underlying energy conversion from electric energy to thermal energy that governs the structural evolution trend. Our current findings manifest a universal strategy for structural regulation of interfacial ILs via electric fields and open up opportunities for greatly accelerating charging efficiency of supercapacitors for energy storage and harvesting.
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2021
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IF 5.279
Pengfei Liu,Jiaojiao Zhang,Yan Qiao,Xianglin Hou,Yu Liu,Yingxiong Wang
Using environment-friendly catalysts to convert biomass into compounds with high values is one of the central topics of green chemistry. In this work, [Ch][Pro] (cholinium as the cation and l-proline as the anion) ionic liquid was synthesized and applied as a model catalyst in the production of deoxyfructosazine (DOF) and fructosazine (FZ) from d-glucosamine (GlcNH2). The 13C NMR chemical shift titration experiments and the diffusion-ordered NMR spectroscopy (DOSY) measurements showed that, when the [Ch][Pro] interacted with GlcNH2, the l-proline anion ([Pro]−) played a major catalytic role instead of cholinium cation ([Ch]+). The effects of the reaction temperature and the amount of [Ch][Pro] on the product yields were surveyed. The experimental results showed that the highest DOF yield (33.78%) was obtained after 30 min at 100 °C when the molar ratio of [Ch][Pro]/GlcNH2 was 1. Moreover, in situ1H NMR and in situ13C NMR experiments were applied to monitor the reaction process with [Ch][Pro] as the catalyst. The reactive intermediate, dihydrofructosazine, was clearly detected by these in situ techniques. Accordingly, a possible reaction pathway was proposed. By applying other amino acids as the anions, we also prepared five other [Ch][AA] ionic liquids, and they showed different catalytic activities and selectivity in the GlcNH2 self-condensation reaction.
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CHINESE JOURNAL OF CHEMICAL ENGINEERING
·
2021
·
IF 3.171
Xiaocheng Lin,Youjie Huang,Ling Li,Changshen Ye,Jie Chen,Ting Qiu
A series of polymeric ionic liquids (PILs) used as effective heterogeneous catalysts for biodiesel production via esterification of free fatty acids (FFAs) were effectively prepared by the reaction of poly (ethylene imine) (PEI) polymers with different molecular weight and 1,3-propanesultone, followed by the further acidification with differential effective acids, i.e. H 2 SO 4 , CF 3 SO 3 H, CH 3 SO 3 H or p -toluenesulfonic acid ( p -TSA). Ultrahigh acidity and catalytic performance were achieved and could be fine-tuned by simply adjusting the molecular weight of PEI and by further treatment of acids. Specifically, under the optimal conditions ( i.e. reaction temperature was 70 °C, reaction time was 2.0 h, catalyst dosage was 3.15% (mass), and alcohol/acid molar ratio was 14:1) acquired through the Box-BEHNKEN response surface methodology, a high oleic acid conversion of 98.42% could be obtained over the optimal PIL, PEI(70000)-PS- p -TSA. Additionally, our PILs also showed high generality for esterification of other FFAs, with general high conversion over 90% noted in each case even under much milder reaction conditions compared to other conventional catalysts.
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JOURNAL OF MOLECULAR LIQUIDS
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2020
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IF 5.065
Lei Yuan,Hongshuai Gao,Haiyan Jiang,Shaojuan Zeng,Tao Li,Baozeng Ren,Xiangping Zhang
A novel type of dual-functionalized pyridinium-based ionic liquids (ILs) with acidic protons and hydroxyl groups , were designed and synthesized for ammonia (NH 3 ) absorption. The NH 3 absorption isotherms in dual-functionalized pyridinium-based ILs at temperatures from 303.15 to 343.15 K and pressures up to 600 kPa were computed using gas-liquid equilibrium method. It revealed that 4-pyridinemethanol bis(trifluoromethane)sulfonamide [4-MeOHPy][NTf 2 ] showed the maximum NH 3 solubility of 3.43 mol NH 3 /mol IL at 313.15 K and atmospheric pressure, surpassing any nonmetallic ILs previously reported. Furthermore, the characteristics of isotherms under low pressures behaved an obvious chemical reaction between ILs and NH 3 , and all experimental solubilities were regulated by a reaction equilibrium thermodynamic model (RETM). The thermodynamic properties were further obtained to better understand the NH 3 absorption process. The results indicated that this model endorses the 1:1 (NH 3 -IL) mole ratio of chemical reaction mechanism and the reaction enthalpy is main driving force of NH 3 absorption in ILs.
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RENEWABLE ENERGY
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2020
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IF 6.274
Dongren Cai,Guowu Zhan,Jingran Xiao,Shu-Feng Zhou,Ting Qiu
Biodiesel produced from non-edible oils has received intensive attention in recent years. Herein, a series of novel amphipathic ionic liquids (ILs) based on the 4-dimethylaminopyridine (DMAP) were prepared for the transesterification of soapberry oil and methanol. The structures of the prepared ILs were systematically characterized by both Fourier transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance (NMR, 1 H NMR and 13 C NMR). In addition, the effects of side-chain length of cation and the number of active site (H + ) of ILs on the biodiesel yield were investigated, and the results suggested that 1-dodecyl-(4-dimethylammonium)-pyridinium bisulfate ([C12-DMAPH][HSO 4 ] 2 ) exhibited the highest catalytic efficiency. Meanwhile, [C12-DMAPH][HSO 4 ] 2 was proven to be amphipathic, and the corresponding catalytic mechanism was proposed. Under the catalysis of [C12-DMAPH][HSO 4 ] 2 , the optimum operating conditions of transesterification of soapberry oil and methanol were explored via the combination of single factor experiment and response surface methodology , obtaining the high biodiesel yield of (98.02 ± 0.36)% under the optimum operating conditions. Importantly, [C12-DMAPH][HSO 4 ] 2 exhibited high stability in the transesterification of soapberry oil and methanol in five consecutive runs. Furthermore, the catalytic activities of [C12-DMAPH][HSO 4 ] 2 towards other transesterification of non-edible oils and lower alcohols were also investigated, which indicated a general applicability of the prepared IL.
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CHEMICAL PHYSICS LETTERS
·
2020
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IF 2.029
Xiuxiu Wang,Lijuan Guo,Shaokui Cao,Weizhen Zhao
In this work, we proposed an effective route of introducing poly(ionic liquid) (PIL) gel as electrolyte to suppress dimer formation of viologen radical cation during switching in electrochromic devices (ECDs). The ECDs were fabricated based on ion gels consisting of various viologens, PIL and ferrocene (Fc). We found that incorporation of PIL contributed to the suppression of dimer production. The suppression of dimer formation can provide ECDs with improved colouration efficiencies, faster switching times, longer cycle lives, and potentially reduced costs. The results showed that an excellent cyclic stability over 96% of initial transmittance change after 4000 cycles of switching.
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CATALYSIS LETTERS
·
2020
·Vol. 150
·期 9
·2549-2557
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IF 2.482
Wang Yun,Chen Xin-Yi,Liang Xin-Yi,Liang Zhi-Hui,Cheng Hong,Li Xiang,Li Li-Ling
Abstract Pepsin was found to catalyze asymmetric cross aldol reactions of aromatic and polycyclicaromatic aldehydes with cyclic ketones in ionic liquids and deep eutectic solvents for the first time. Pepsin exhibited high catalytic activity and excellent stereoselectivity in ionic liquids and deep eutectic solvents in the presence of moderate water. High yields of up to 93.1%, excellent enantioselectivities of up to 96% ee, and good diastereoselectivities of up to 5:95 dr were achieved. Graphic Abstract
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Green Energy & Environment
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2020
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IF 6.395
Meichen Li,Jie Chen,Ling Li,Changshen Ye,Xiaocheng Lin,Ting Qiu
Biodiesel is an attractive alternative to fossil fuels due to the energy and environmental concerns. In this paper, seven different multi –SO 3 H functionalized ILs based on the low-cost less-substituted amines, which contained massive sites for functionalization of sulfonic acid groups and further treatment of sulfonate-based anions, were prepared as catalysts with high acidity and desirable catalytic activity for the synthesis of biodiesel from the esterification of oleic acid with methanol. The physicochemical properties of these acidic ILs were characterized by a variety of analytical techniques such as FT-IR, EA, TGA, and the Brønsted acidity was well determined by UV–vis. Among the ILs prepared, [EDA-PS][P-TSA] showed the highest catalytic activity for esterification due to its high acidity and appropriate miscibility with reactants, with an ultrahigh 97.58% conversion of oleic acid under the optimum conditions (i.e. reaction time, 1.8 h; catalyst amount, 3 wt%; alcohol/acid molar ratio, 13:1, temperature 70 °C) acquired from the Box–Behnken response surface methodology. With the novel strategy of multi –SO 3 H modification on ILs, our catalyst had an approaching or even superior oleic acid conversion rate compared to other reported catalysts with considerably lower catalyst dosage and shorter reaction time. More importantly, it also exhibited high generality for converting various FFA feedstocks into biodiesel with considerable conversion within 93.59–94.33% under a rather lower catalyst dosage, which showed the valuable potential for converting low-cost oils into biodiesel from an economic and environmental perspective.
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CHINESE JOURNAL OF CHEMICAL ENGINEERING
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2020
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IF 2.627
Jinghang Li,Huimin Zang,Shun Yao,Zicheng Li,Hang Song
In recent years, ionic liquids (ILs) have been widely used in extraction, synthesis, electrochemistry and other fields. Meanwhile, the environmental impact of ILs has been attracting a lot of attention, and eco-friendly treatment for ILs is becoming a necessary subject. In this study, photocatalytic degradations of benzothiazole ILs catalyzed by titanium dioxide (TiO 2 ) and silver-loaded titanium dioxide (Ag/TiO 2 ) were studied for the first time. The degradation of benzothiazole hexafluorophosphate ([C 4 Bth]PF 6 ) could reach more than 99% within 240 min with the catalysis of TiO 2 . To improve catalytic efficiency, Ag/TiO 2 was synthesized and characterized by UV–Vis diffuse reflectance absorption spectra (DRS) and X-ray photoelectron spectroscopy (XPS). The degradation of [C 4 Bth]PF 6 could reach more than 99% within 120 min in the degradation catalyzed by Ag/TiO 2 . The photodegradation products of benzothiazole ILs are composed of inorganic substances or organic substances with simpler structures, which are easier to decompose and less toxic. The degradation system proposed by this study could provide a simple, green, safe, and economical method for the efficient treatment of benzothiazole ILs.
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SEPARATION AND PURIFICATION TECHNOLOGY
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2020
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IF 5.774
Yan Li,Jian-Ying Dai,Zhi-Long Xiu
The salting-out extraction (SOE) systems based on ionic liquids (ILs) have attracted extensive attention in the separation of bio-based products, in which imidazolium ILs were widely studied. However, the high cost and toxicity have hindered their further industrial application. Hydroxylammonium ILs have the characteristics of cheap raw material, simple synthesis process and low toxicity, but are rarely used in the SOE systems. In this work, five hydroxylammonium ILs (2 cations and 4 carboxylate anions) were synthesized and used in SOE of bio-chemicals. The phase forming abilities of ILs with K 3 PO 4 and H 2 O were affected by the hydrophilicity of anions and cations. With the increase of carbon chain length, phase forming abilities of ILs increased, while the temperature had little influence. The partition behaviors of acetoin, ILs and 2,3-butandiol, and the selectivity of acetoin to organic acids were investigated and compared at different concentrations of ethanolammonium butyrate (EOAB) and K 3 PO 4 . In a SOE system consisted of 6% EOAB-38% K 3 PO 4 (w/w), the recovery of acetoin, IL and 2,3-butandiol was 92.7%, 76.0% and 86.0%, respectively, and the selectivity of acetoin to lactic acid and acetic acid was 16.46 and 3.85, respectively. The ATR-IR spectra showed the hydrogen bonds formed between acetoin and O-H, N-H, –COO – of hydroxylammonium IL played an important role in the efficient extraction of acetoin from fermentation broths.
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FUEL
·
2021
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IF 6.609
Guokai Cui,Shuzhen Lyu,Huiyong Wang,Zhiyong Li,Ruina Zhang,Jianji Wang
A series of pyridinolate anion-functional ionic liquids (ILs) containing different kinds of cations were designed and prepared, including tri- n -hexyltetradecylphosphonium [P 66614 ], tri- n -butylethylphosphonium [P 4442 ], and 1,1,3,3-tetramethylguandinium [TMG] cations and pyridinolate [PyO] anions with different N positions. Densities and viscosities at different temperatures were measured because of their importance for the absorption of SO 2 . Effect of different structures on the absorption of SO 2 was studied, including the type and the alkyl chain length of cations, and the N positions of [PyO] anions (2-, 3-, and 4-). Additionally, effects of SO 2 concentration and temperature for absorption were investigated. Especially, up to 6.00 and 2.53 mol SO 2 per mole IL could be obtained by [P 66614 ][4-PyO] at 1 bar and 0.1 bar of SO 2 , respectively, when absorptions performed at 20 °C. The results indicate that (1) the aprotic cations weakened the cation⋯anion interaction and resulted in the released active sites on the anions, and (2) N position has an influence on charge distribution of [PyO] anions and resulted in the tunable absorption of SO 2 . Reversible SO 2 absorption and [P 66614 ][4-PyO] regeneration could be performed several times without losing efficiency. Furthermore, the mechanism of absorption was studied through FT-IR and NMR methods and the results showed that the absorption of SO 2 by [P 66614 ][4-PyO] includes physisorption and chemisorption.
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