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Study on extraction of thiophene from model gasoline with br?nsted acidic ionic liquids

Xiaomeng WANG, Mingjuan HAN, Hui WAN, Cao YANG, Guofeng GUAN

《化学科学与工程前沿（英文）》 2011年第5卷第1期页码 107-112 doi: 10.1007/s11705-010-0539-0

摘要： Br?nsted acidic ionic liquids (ILs), -methylimidazole hydrogen sulfate ([HMIm]HSO ) and -methylpyrrolidone hydrogen sulfate ([HNMP]HSO ), are synthesized and employed as extractants to extract thiophene from model gasoline (thiophene dissolved in -octane). The effect of extraction temperature, extraction time and volume ratio of ILs to model gasoline on desulfurization rates is investigated. Then, the optimal desulfurization conditions are obtained: the ratio of ILs to model gasoline is 1∶1, extraction temperature is 50°C for [HMIm]HSO and 60°C for [HNMP]HSO , extraction time is 60 min. Meanwhile, the desulfurization rate of [HNMP]HSO for model gasoline is 62.8%, which is higher than that of [HMIm]HSO (55.5%) under optimal conditions. The reason is discussed on the basis of the interaction energy between thiophene and ILs at the B3LYP/6-311++ G(d,p) level. Furthermore, the total desulfurization rate of [HNMP]HSO and [HMIm]HSO reaches 96.4% and 94.4%, respectively, by multistage extraction. Finally, the used ILs can be reused by vacuum drying, and their desulfurization rates are not significantly decreased after recycling 7 times in single-stage desulfurization.

关键词： br?nsted ionic liquids model gasoline thiophene extraction density functional theory

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Ionic liquid mediated esterification of alcohol with acetic acid

Beilei ZHOU, Yanxiong FANG, Hao GU, Saidan ZHANG, Baohua HUANG, Kun ZHANG

《化学科学与工程前沿（英文）》 2009年第3卷第2期页码 211-214 doi: 10.1007/s11705-009-0054-3

摘要： Highly efficient esterification of alcohols with acetic acid by using a Br?nsted acidic ionic liquid, i.e., 1-methyl-2-pyrrolidonium hydrogen sulfate ([Hnmp]HSO ), as catalyst has been realized. The turnover numbers (TON) were able to reach up to 11000 and turnover frequency (TOF) was 846. The catalytic system is suitable for the esterification of long chain aliphatic alcohols, benzyl alcohol and cyclohexanol with good yields of esters. The procedure of separating the product and catalyst is simple, and the catalyst could be reused. [Hnmp]HSO had much weaker corrosiveness than H SO . The corrosive rate of H SO was 400 times more than that of [Hnmp]HSO to stainless steel.

关键词： ionic liquid Br?nsted acid esterification catalyst

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Benzenesulfonic acid-grafted UIO-66 with improved hydrophobicity as a stable Brønsted acid catalyst

《化学科学与工程前沿（英文）》 2023年第17卷第10期页码 1389-1398 doi: 10.1007/s11705-022-2285-5

摘要： Hydrothermal and catalytic stability of UIO-66 MOFs with defective structures are critical aspects to be considered in their catalytic applications, especially under the conditions involving water, moisture and/or heat. Here, we report a facile strategy to introduce the macromolecular acid group to UIO-66 to improve the stability of the resulting UIO-66−PhSO₃H MOF in aqueous phase catalysis. In detail, UIO-66−PhSO₃H was obtained by grafting benzenesulfonic acid on the surface of the pristine UIO-66 to introduce the hydrophobicity, as well as the Brønsted acidity, then assessed using catalytic hydrolysis of cyclohexyl acetate (to cyclohexanol) in water. The introduction of hydrophobic molecules to UIO-66 could prevent the material from being attacked by hydroxyl polar molecules effectively, explaining its good structural stability during catalysis. UIO-66−PhSO₃H promoted the conversion of cyclohexyl acetate at ca. 87%, and its activity and textural properties were basically intact after the cyclic stability tests. The facile modification strategy can improve the hydrothermal stability of UIO-66 significantly, which can expand its catalytic applications in aqueous systems.

关键词： metal−organic frameworks (MOFs) UIO-66 hydrolysis of cyclohexyl acetate hydrophobicity Brønsted acidity

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Oxidative desulfurization of fuels using ionic liquids: A review? ?

Hua Zhao,Gary A. Baker

《化学科学与工程前沿（英文）》 2015年第9卷第3期页码 262-279 doi: 10.1007/s11705-015-1528-0

摘要： Extractive oxidation, wherein aromatic sulfur-containing compounds are extracted and subsequently oxidized to their corresponding sulfones, has proven to be one of the most effective desulfurization methods for producing ultra-low sulfur content fuels. As non-volatile and highly designable solvents, ionic liquids (ILs) have attracted considerable attention for the oxidative desulfurization of fuels. In this review, we systematically discuss the utility of ILs in catalytic and extractive oxidation, including their role as extractant, catalyst, or both. We also discuss the challenges facing the use of ILs in this regard, including their relatively high cost and excessive viscosity, as well as their efficiency and stability as catalyst.

关键词： oxidative desulfurization ionic liquids extraction fuels petroleum polyoxometalates

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Latest advances in ionic liquids promoted synthesis and application of advanced biomass materials

《化学科学与工程前沿（英文）》 2023年第17卷第7期页码 798-816 doi: 10.1007/s11705-023-2316-x

摘要： The utilization of sustainable resources provides a path to relieving the problem of dependence on fossil resources. In this context, biomass materials have become a feasible substitute for petroleum-based materials. The development of biomass materials is booming and advanced biomass materials with various functional properties are used in many fields including medicine, electrochemistry, and environmental science. In recent years, ionic liquids have been widely used in biomass pretreatments and processing owing to their “green” characteristics and adjustable physicochemical properties. Thus, the effects of ionic liquids in biomass materials generation require further study. This review summarizes the multiple roles of ionic liquids in promoting the synthesis and application of advanced biomass materials as solvents, structural components, and modifiers. Finally, a prospective approach is proposed for producing additional higher-quality possibilities between ionic liquids and advanced biomass materials.

关键词： biomass materials functional materials ionic liquids synthesis structure-property relationship

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Electrocatalytic reduction of NO to NH in ionic liquids by P-doped TiO nanotubes

《化学科学与工程前沿（英文）》 2023年第17卷第6期页码 726-734 doi: 10.1007/s11705-022-2274-8

摘要： Designing advanced and cost-effective electrocatalytic system for nitric oxide (NO) reduction reaction (NORR) is vital for sustainable NH₃ production and NO removal, yet it is a challenging task. Herein, it is shown that phosphorus (P)-doped titania (TiO₂) nanotubes can be adopted as highly efficient catalyst for NORR. The catalyst demonstrates impressive performance in ionic liquid (IL)-based electrolyte with a remarkable high Faradaic efficiency of 89% and NH₃ yield rate of 425 μg·h⁻¹·mg_cat.⁻¹, being close to the best-reported results. Noteworthy, the obtained performance metrics are significantly larger than those for N₂ reduction reaction. It also shows good durability with negligible activity decay even after 10 cycles. Theoretical simulations reveal that the introduction of P dopants tunes the electronic structure of Ti active sites, thereby enhancing the NO adsorption and facilitating the desorption of *NH₃. Moreover, the utilization of IL further suppresses the competitive hydrogen evolution reaction. This study highlights the advantage of the catalyst−electrolyte engineering strategy for producing NH₃ at a high efficiency and rate.

关键词： nitric oxide reduction reaction electrcatalysis ammonia production phosphorus-doped titania

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Benzene alkylation with long chain olefins catalyzed by ionic liquids: a review

QIAO Congzhen, CAI Yonghong, GUO Quanhui

《化学科学与工程前沿（英文）》 2008年第2卷第3期页码 346-352 doi: 10.1007/s11705-008-0045-9

摘要： The introduction of ionic liquids to alkylation process gives a choice for “green production” in the petrochemical and detergent industry. A lot of papers and patents have been published using chloroaluminate ionic liquid as a novel catalyst for alkylation with high reactivity and easy separation from reactants. These included the acidity, characterization, determination and catalysis technologies in batch and continuous operation mode for different scales. According to published data and several results of pilot alkylation,including the authors’ experience,the prospect of chloroaluminate ionic liquids for commercials was also discussed. It has been pointed out that there still are many difficulties and challenges to be overcome for commercial application of the ionic liquid catalyst.

关键词： different petrochemical characterization introduction chloroaluminate

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Deep eutectic ionic liquids based on DABCO-derived quaternary ammonium salts: A promising reaction medium

Muhammad Faisal, Azeem Haider, Quret ul Aein, Aamer Saeed, Fayaz Ali Larik

《化学科学与工程前沿（英文）》 2019年第13卷第3期页码 586-598 doi: 10.1007/s11705-018-1788-6

摘要： Owing to the directional H-bonding, coordination and -stacking abilities, terpyridines have been widely used as supramolecular tectons in molecular architectures, skeletons in molecular devices and metallopolymers, and are gaining importance in medicinal chemistry. In this paper, we have synthesized, characterized and applied deep eutectic ionic liquids (DEILs) based on 1,4-diazabicyclo[2.2.2]octane; triethylenediamine (DABCO)-derived quaternary ammonium salts for the preparation of terpyridines. These DEILs were synthesized through -alkylation of DABCO with haloalkanes (1-bromopentane or 1-bromoheptane) followed by mixing and heating with methanol or polyethylene glycol as a hydrogen bond donor. The synthesized DEILs were structurally characterized by IR and NMR. The formation of deep eutectic solvent was confirmed by freezing point depression, it composition was investigated through phase diagram, and its thermal stability was determined through differential scanning calorimetry, derivative thermogravimetry and thermal gravimetric analysis studies. Further, theseDEILswereinvestigatedfor theireffectivenesstowards synthesis of 2,2′:6′,2″-terpyridine, 3,2′:6′,3″-terpyridineand 4,2′:6′,4″-terpyridinederivatives through Kröhnke reaction. The results show that these three types of terpyridines can be obtained in reasonable yields (80% 97%) by the one-pot reaction of 2-, 3- or 4-acetylpyridine with a variety of aromatic aldehydes in the presence of DEIL as a reaction medium, sodium hydroxide as a base and ammonium acetate as a cyclizing agent. This methodology is highly efficient and cost-effective for synthesis of symmetrical as well as unsymmetrical terpyridines. Importantly, these DEILs can be reused several times without an obvious loss of activity and are non-toxic, low-volatile, biodegradable and highly thermally stable. Therefore, these DEILs as a non-conventional reaction medium for the synthesis of terpyridines provides appealing opportunities to be investigated in the domain of green synthesis.

关键词： terpyridine deep eutectic solvent ionic liquid Kröhnke reaction DABCO

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Preparation of Ni/SiO catalyst in ionic liquids for hydrogenation

FAN Qingming, LIU Yingxin, ZHENG Yifan, YAN Wei

《化学科学与工程前沿（英文）》 2008年第2卷第1期页码 63-68 doi: 10.1007/s11705-008-0013-4

摘要： A series of silica supported nickel catalysts were prepared from nickel nitrate and tetraethyl orthosilicate by the sol-gel method with the imidazolium type ionic liquids as solvents. The catalysts were characterized by means of X-ray diffraction (XRD), scanning electron microscopy (SEM) and energy dispersive X-ray spectroscopy (EDS). Their catalytic performances for the selective hydrogenation of cinnamaldehyde to hydrocinnamaldehyde were investigated. The results show that the Ni/SiO catalyst prepared with 1-(2-hydroxyethyl)-3-methyl-imidazole tetrafluoroborate ionic liquid as solvent exhibits the highest catalytic activity for the reaction. Under the optimal conditions of catalyst dosage (based on the mass of cinnamaldehyde used) 10%, reaction pressure 2 MPa, temperature 373 K and reaction time 2 h, the conversion of cinnamaldehyde and the selectivity to hydrocinnamaldehyde can reach 97.6% and 98.8%, respectively.

关键词： dispersive conversion catalytic 2-hydroxyethyl catalytic activity

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Measurement of activity coefficients at infinite dilution for hydrocarbons in imidazolium-based ionicliquids and QSPR model

ZHU Jiqin, YU Yanmei, CHEN Jian, FEI Weiyang

《化学科学与工程前沿（英文）》 2007年第1卷第2期页码 190-194 doi: 10.1007/s11705-007-0035-3

摘要： The separations of olefin/paraffin, aromatic/aliphatic hydrocarbons or olefin isomers using ionic liquids instead of volatile solvents have interested many researchers. Activity coefficients γ at infinite dilution of a solute in ionic liquid are generally used in the selection of solvents for extraction or extractive distillation. In fact, the measurement of γ by gas-liquid chromatography is a speedy and cost-saving method. Activity coefficients at infinite dilution of hydrocarbon solutes, such as alkanes, hexenes, alkylbenzenes, styrene, in 1-allyl-3-methylimidazolium tetrafluoroborate ([AMIM][BF]) and 1-butyl-3-methyl imidazolium hexafluorophosphate ([BMIM][PF6]), 1-isobutenyl-3-methylimidazolium tetrafluoroborate ([MPMIM][BF]) and [MPMIM][BF]-AgBF have been determined by gas-liquid chromatography using ionic liquids as stationary phase. The measurements were carried out at different temperatures from 298 to 318 K. The separating effects of these ionic liquids for alkanes/hexane, aliphatic hydrocarbons/benzene and hexene isomers have been discussed. The hydrophobic parameter, dipole element, frontier molecular orbital energy gap and hydration energy of these hydrocarbons were calculated with the PM3 semi-empirical quantum chemistry method. The quantitative relations among the computed structure parameters and activity coefficients at infinite dilution were also developed. The experimental activity coefficient data are consistent with the correlated and predicted results using QSPR models.

关键词： cost-saving consistent coefficient measurement separating

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Biodiesel production by the transesterification of cottonseed oil by solid acid catalysts

CHEN He, PENG Baoxiang, WANG Dezheng, WANG Jinfu

《化学科学与工程前沿（英文）》 2007年第1卷第1期页码 11-15 doi: 10.1007/s11705-007-0003-y

摘要： Methyl esters (biodiesel) were produced by the transesterification of cottonseed oil with methanol in the presence of solid acids as heterogeneous catalysts. The solid acids were prepared by mounting HSO on TiO · nHO and Zr(OH), respectively, followed by calcining at 823K. TiO-SO and ZrOSO showed high activity for the transesterification. The yield of methyl esters was over 90% under the conditions of 230°C, methanol/oil mole ratio of 12:1, reaction time 8 h and catalyst amount (catalyst/oil) of 2% (w). The solid acid catalysts showed more better adaptability than solid base catalysts when the oil has high acidity. IR spectral analysis of absorbed pyridine on the samples showed that there were Lewis and BrØnsted acid sites on the catalysts.

关键词： BrØnsted reaction presence cottonseed biodiesel

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离子液体在金属离子萃取中的研究进展

刘利梅,苏永庆,李琮,贺飞,何永福,钟云

《中国工程科学》 2007年第9卷第11期页码 187-190

摘要：

介绍了离子液体的定义，发展历史，性质等，重点阐述用于金属离子萃取的离子液体的性质、合成方法和发展方向。

关键词：离子液体萃取金属离子绿色溶剂

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Effects of support acidity on the reaction mechanisms of selective catalytic reduction of NO by CH

Shicheng XU, Junhua LI, Dong YANG, Jiming HAO

《环境科学与工程前沿（英文）》 2009年第3卷第2期页码 186-193 doi: 10.1007/s11783-009-0016-5

摘要： The reaction mechanisms of selective catalytic reduction (SCR) of nitric oxide (NO) by methane (CH ) over solid superacid-based catalysts were proposed and testified by DRIFTS studies on transient reaction as well as by kinetic models. Catalysts derived from different supports would lead to different reaction pathways, and the acidity of solid superacid played an important role in determining the reaction mechanisms and the catalytic activities. Higher ratios of Br?nsted acid sites to Lewis acid sites would lead to stronger oxidation of methane and then could facilitate the step of methane activation. Strong Br?nsted acid sites would not necessarily lead to better catalytic performance, however, since the active surface NO species and the corresponding reaction routes were determined by the overall acidity strength of the support. The reaction routes where NO moiety was engaged as an important intermediate involved moderate oxidation of methane, the rate of which could determine the overall activity. The reaction involving NO moiety was likely to be determined by the step of reduction of NO. Therefore, to enhance the SCR activity of solid superacid catalysts, reactions between appropriate couples of active NO species and activated hydrocarbon intermediates should be realized by modification of the support acidity.

关键词： selective catalytic reduction (SCR) nitric oxide (NO) methane support acidity Br?nsted acid sites NO_y species

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微波辐射下离子液体［RMIm］PF6（R=P, B, C6）的合成及其电导率研究

何永福

《中国工程科学》 2008年第10卷第9期页码 92-95

摘要： justify;">在微波辐射下，1－甲基咪唑分别与有机卤盐(1－溴丙烷、1－溴丁烷、1－溴己烷)在80 ℃回流加热10 min，可制得咪唑类离子液体的中间体溴代1－丁基－3－甲基咪唑（［BMIm］Br）、溴代1－丙基－3－甲基咪唑（［PMIm］Br）、溴代1－己基－3－甲基咪唑（［C6MIm］Br），进一步与HPF6在室温搅拌反应4 h，制得憎水性的咪唑类离子液体［BMIm］PF6，［PMIm］PF6

关键词：离子液体微波辐射电导率 [BMIm]PF6 [PMIm]PF6 [C6MIm]PF6