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NEW JOURNAL OF CHEMISTRY · 2022 ·Vol. 46 ·期 38 ·18366-18373 · IF 3.925

A fluorescent sensor array based on three kinds of carbon dots for identification of hydroxybenzaldehyde and nitrobenzaldehyde isomers

Jinfa Yu,Xiangying Sun,Yiyang Chen

A fluorescent sensor array based on three kinds of carbon dots (CDs) were fabricated to discriminate hydroxybenzaldehyde and nitrobenzaldehyde isomers. Based on the Schiff base reaction, carbon dots with amino groups on the surface were designed. Fluorescence quenching of CDs occurred when hydroxybenzaldehyde and nitrobenzaldehyde isomers were combined with CDs. The sensor array showed different fluorescence patterns for each hydroxybenzaldehyde and nitrobenzaldehyde isomer in terms of fluorescence intensity change F/F0, which was further analyzed by principal component analysis (PCA). Finally, the fluorescent sensor array behaved well in differentiating and identifying hydroxybenzaldehyde and nitrobenzaldehyde isomers in aqueous solutions and distinguishing binary mixtures.

研究领域: 分析化学 · 材料科学
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CHINESE CHEMICAL LETTERS · 2010 · IF 0.643

Protecting-group-free amination of halogenated nitrobenzaldehyde with palladium catalyst

Jing Cao,Jun Xiang Feng,Yong Xiang Wu,Ya Ya Tuo

“One-step” method for the synthesis of secondary aliphatic amine substituted nitrobenzaldehyde was developed. In the presence of Pd catalyst, halogenated nitrobenzaldehyde could be smoothly coupled with secondary aliphatic amine to give the target product in hexamethylphosphamide (HMPT) media without the protection of aldehyde groups.

研究领域: 有机化学 · 药物化学
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FLUID PHASE EQUILIBRIA · 2015 · IF 2.2

Measurement and modeling for solubility of 3-hydroxybenzaldehyde and its mixture with 4-hydroxybenzaldehyde in supercritical carbon dioxide

Hao Wu,Jing Zhu,Yiwei Wang,Chengwei Chang,Junsu Jin

To understand the phase behavior of 3-hydroxybenzaldehyde (3-HBA) and the solubility effect of 3-HBA and 4-hydroxybenzaldehyde (4-HBA) on each other in supercritical carbon dioxide (SCCO 2 ), the equilibrium solubility of 3-HBA and its mixture with 4-HBA, was measured in SCCO 2 binary system (comprising of a solute and SCCO 2 ) and ternary system (comprising of two solutes and SCCO 2 ) at temperature and pressure given in range of 308–328 K and 11.0–21.0 MPa respectively. Comparing the solubility of 3-HBA and 4-HBA between in the binary system and ternary system, it was found that the equilibrium solubility of both 3-HBA and 4-HBA was enhanced in the ternary system due to the molecular interaction. The experimental data were correlated by Chrastil, Mendez-Santiago and Teja (M-S-T), Sovova, their modified models, and Zhu et al. model. Also a new model was deduced and established based on the Chemistry Association Theory and was verified by 636 groups of solubility data. The correlated results indicated that the new model obtained a less deviation than other models, including the modified Chrastil model, the modified M-S-T model, the modified Sovova model, and Zhu et al. model, all of which have same adjustable parameters.

CAS / MDL: 123-08-0 100-83-4
研究领域: 化学工程 · 物理化学
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APPLIED CATALYSIS A-GENERAL · 2023 · IF 5.5

Tuning the oxygen vacancy and acidity of V-Ag-Ce/TiO2 catalyst for selective gas-phase oxidation of toluene to benzaldehyde

Jiasheng Wang,Qingrong Wang,Mengdi Zhao,Ming Bao

Toluene gas-phase oxidation is a green, chlorine-free production process for benzaldehyde but its conversion efficiency is still unsatisfying due to the lack of highly efficient catalyst. Here the selective oxidation of toluene to benzaldehyde over V-Ag-Ce/TiO 2 under an air atmosphere was investigated. The catalyst was prepared by impregnation and characterized by scanning electron microscope (SEM), N 2 adsorption-desorption, X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Electron paramagnetic resonance (EPR), H 2 temperature programmed reduction (H 2 -TPR), O 2 temperature programmed desorption (O 2 -TPD), and NH 3 temperature programmed desorption (NH 3 -TPD). The amount of oxygen vacancy and acid of the catalyst can be tuned through adjusting the V:Ag:Ce ratio. Over the optimum catalyst (V:Ag:Ce = 4:2:1, molar ratio), 92% benzaldehyde selectivity with a 27% toluene conversion can be obtained at 550 °C. Medium amounts of oxygen vacancy (0.43) and acidity (0.10 mmol/g) are found to be conducive to the conversion of toluene to benzaldehyde. This study has important theoretical guiding significance for improving conversion efficiency from toluene to benzaldehyde by gas-phase aerobic oxidation.

研究领域: 催化化学 · 环境科学 · 材料科学
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2022 · IF 4.326

Selective Photooxidation of Benzyl Alcohol to Benzaldehyde via H-Abstraction by Bi2.15WO6 under Alkaline Conditions

Wen-Shuang Zhu,Dai Sun,Ling-Li Yu,Shao-Qi Zhi,Yu-Dong Shan,Yi-Fang Lu,Hai-Tao Ren,Song-Hai Wu,Yong Liu,Xu Han

In this study, Bi2.15WO6 with different morphologies was successfully synthesized and used for the selective photooxidation of benzyl alcohol to benzaldehyde in aqueous solutions. High conversion (85%) and selectivity (85%) can be simultaneously achieved under alkaline conditions by adding ethylenediamine to protect the produced benzaldehyde from overoxidation. In the oxidation process, ≡Bi–OO• and ≡Bi–OOH on Bi2.15WO6, instead of OH• and O2•–, are the primary oxidizing species to sequentially abstract two H (H+ + e–) from benzyl alcohol, accompanied by the formation of H2O2. Meanwhile, h+ and OH– also minorly contribute to the selective oxidation of benzyl alcohol via the H-abstraction pathway. This study enriches our understanding of the oxidizing species involved in the selective photooxidation of benzyl alcohol to benzaldehyde.

研究领域: 材料科学 · 催化化学 · 环境科学
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2024 · IF 3.8

Highly Selective Photooxidation of Benzyl Alcohol to Benzaldehyde by Bi–Mo/g-C3N4 in Aqueous Solution

Da Sheng,Qing He,Zhong-Hua Cao,Lun-Bo Chen,Song-Hai Wu,Yong Liu,Hai-Tao Ren,Xu Han

Although photooxidation of benzyl alcohol to benzaldehyde in aqueous solution is an important chemical process, its selectivity cannot be readily controlled due to the overoxidation of benzaldehyde. In this study, a series of Bi–Mo/CN photocatalysts are synthesized, and their reactivity in photooxidation of benzyl alcohol under visible light is compared. Bi–Mo/CN-2 exhibits high photocatalytic reactivity in the conversion of benzyl alcohol (51%) with a high selectivity toward benzaldehyde of 99.9%. In this process, the formed ≡Bi–OO• and ≡Bi–OOH selectively oxidize benzyl alcohol to benzaldehyde via the H-abstraction pathway after O2 is photoreduced on Bi–Mo/CN, accompanied by the formation of H2O2. Meanwhile, the doped Mo utilizes the produced H2O2 or ≡Bi–OOH to produce ≡Mo–O2 peroxo, which not only contributes to the selective oxidation of benzyl alcohol to benzaldehyde but also effectively prevents overoxidation of benzaldehyde. This work provides new insight into designing novel photocatalysts for selective oxidation of organic substrates.

研究领域: 化学 · 材料科学
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JOURNAL OF CHEMICAL AND ENGINEERING DATA · 2015 · IF 2.037

Solubilities of Benzoic Acid in Binary Methylbenzene + Benzyl Alcohol and Methylbenzene + Benzaldehyde Solvent Mixtures

Hui Wang,Qinbo Wang,Zhenhua Xiong,Chuxiong Chen,Binwei Shen

By using the synthetic method, the solubilities of benzoic acid in binary methylbenzene + benzyl alcohol solvent mixtures at (301.05 to 355.65) K and in binary methylbenzene + benzaldehyde solvent mixtures at (301.05 to 354.45) K were determined at atmospheric pressure. The studied mass fractions of benzyl alcohol and benzaldehyde in the corresponding binary solvent mixtures range from 0.0 to 1.0. It was found that the measured solubilities increase with the increase of temperature at constant solvent composition. For the ternary system benzoic acid + methylbenzene + benzyl alcohol, the results show that the binary methylbenzene + benzyl alcohol solvent mixture with the mass fraction of benzyl alcohol at 0.80 has the best dissolving capacity for benzoic acid at constant temperature. However, for the ternary system benzoic acid + methylbenzene + benzaldehyde, the results show that the binary methylbenzene + benzaldehyde solvent mixture with the mass fraction of benzaldehyde of 0.20 has the best dissolving capacity for benzoic acid at constant temperature. The experimental data were correlated by both the nonrandom two-liquid (NRTL) and the Apelblat equations, and the correlated solubilities agree satisfactorily with the experimental observations. By coupling the Apelblat equation with the Clark and Glew equation, the thermodynamic functions for the two studied solid–liquid equilibrium systems, including dissolution enthalpy, entropy, Gibbs energy, and isobaric heat capacity, were calculated and discussed.

研究领域: 物理化学 · 热力学
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SENSORS AND ACTUATORS B-CHEMICAL · 2018 · IF 5.667

Discrimination and detection of benzaldehyde derivatives using sensor array based on fluorescent carbon nanodots

Yingying Li,Xue Liu,Qiuhua Wu,Jie Yi,Guolin Zhang

Excessive residual benzaldehyde derivatives in environment can cause severe ecological problems. There are currently less simple, rapid, sensitive and low-cost methods available to detect benzaldehyde derivatives. In this study, fluorescent nano-probes based on carbon nanodots (CDs) were developed for the determination of benzaldehyde derivatives in aqueous solution. Three kinds of classical CDs with different structure and photoluminescence characteristic were randomly chosen and prepared by using different carbon source and synthetic methods Static fluorescent quenching occurred to CDs in the presence of benzaldehyde derivatives. The concentration detection range covered from μM level to mM level, and the minimum detection limit reached 0.3 μM. Benzaldehyde derivatives with various structures and functional groups contributed differential fluorescent quenching degrees to CDs through the donor-acceptor electronic effect. On this basis, sensor array based on CDs was constructed for the discrimination and determination of benzaldehyde derivatives. Two principal components contributing 99.22% of the total variability were extracted by using principal component analysis method (PCA). PCA scattergraph was plotted and applied to descriminate five benzaldehyde derivatives intuitively, including 2,4-dihydroxybenzaldehyde, salicylaldehyde, m-hydroxybenzaldehyde, benzaldehyde and m-methylbenzaldehyde. Experimental results confirmed the practical utility and stability of the CD array for the assay of benzaldehyde derivatives.

研究领域: 环境科学 · 分析化学
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CHEMICAL ENGINEERING RESEARCH & DESIGN · 2018 · IF 2.795

The synergistic effect of benzyl benzoate on the selective oxidation of toluene to benzaldehyde

Chen Lu,Jiaming Hu,Yuning Meng,Aidong Zhou,Feng Zhang,Zhibing Zhang

To resolve the defects of acetic acid solvents for the liquid-phase oxidation of toluene to benzaldehyde with oxygen, a low-corrosive and green method was developed by introducing benzyl benzoate into the reaction. It was found that compared with the case of acetic acid, benzyl benzoate showed gratifying effect on the oxidation of toluene to benzaldehyde. The reaction was more active in the initial stage of oxidation, and the generated benzaldehyde was protected from further oxidation due to the synergistic effect of benzyl benzoate along with toluene-derived products benzyl alcohol and benzyl bromide. Benzyl benzoate inhibited the esterification of benzyl alcohol, while benzyl bromide promoted the formation of benzyl alcohol. Therefore, considerable benzyl alcohol concentration could be maintained and high benzaldehyde selectivity could be achieved under high toluene conversion.

研究领域: 化学工程 · 环境科学
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2023 · IF 4.2

Highly Selective Oxidation of Toluene to Benzaldehyde in Alkaline Systems

Huaxun Luo,Weida Chen,Jiaming Hu,Feng Zhang,Xingbang Hu

For the selective oxidation of toluene to benzaldehyde, the biggest challenge is to prevent the further oxidation of benzaldehyde as toluene conversion increases. Using benzyl benzoate as the solvent and adding benzoate to adjust the alkalinity of the system, the formation of the benzoyl radical can be well inhibited, but the oxidation of toluene is weakened. The decomposition of benzyl benzoate to benzaldehyde can activate the reaction at the initial stage, and the negative influence of alkalinity is avoided to some extent. Therefore, by using atmospheric air as an oxidant, a high selectivity and yield of benzaldehyde can be obtained in a benzyl benzoate catalytic system with alkali as an additive. The mechanism of alkaline regulation and selective oxidation of toluene was investigated by in situ infrared (IR) spectroscopy experiments. The benzaldehyde capacity is defined to characterize the tolerance of benzaldehyde in the system. Catalysts and alkaline regulators can be easily reused with high-boiling solvents, making it a convenient process for product separation and catalyst–alkaline solvent recycling.

研究领域: 化学工程 · 催化化学
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ACS Sustainable Chemistry & Engineering · 2025 · IF 7.3

Multidimensional Utilization of Kraft Lignin: Upgrading Glycerol to Sustainable Fuel Additives Using Lignin-Derived Benzaldehyde over Lignin-Based Acid Catalyst

Chi Zhang,Xueru Sheng,Haiyuan Jia,Na Li,Jian Zhang,Bing Wang,Haiqiang Shi,Qingwei Ping,Ning Li

This study aims to explore a lignin-based catalyst for the green synthesis of sustainable fuel additive using lignin-derived benzaldehyde and glycerol, byproducts from the paper industry and biodiesel preparation, respectively. This sustainable fuel additive can be refilled into biodiesel to improve the carbon atom economy, promoting resource efficiency and environmental sustainability. Kraft lignin was modified with phosphoric acid and sulfuric acid to prepare solid acid catalysts KL-HP-SO3H. A series of characterization techniques showed that phosphorylation can markedly enhance the specific surface area, while sulfonation can notably increase the acid sites and acid strength. The synergistic physical–chemical effect of phosphorylation and sulfonation collectively enhances the activity of the KL-HP-SO3H catalyst. In addition, ball milling and thermal catalysis were compared and analyzed in this study. The results show that the ball milling technology offers an advantage: it achieves a high product yield within only 15 min. The ball milling process consumes less energy than the hydrothermal reactor (21.3 vs 493.8 kWh·mol–1). From a long-term investment perspective, the ball milling process is economically superior. This study contributes an efficient catalyst strategy to green chemical synthesis while providing multifunctional utilization of lignin.

CAS / MDL: 76-59-5
研究领域: 化学工程 · 可再生资源利用
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JOURNAL OF CHEMICAL AND ENGINEERING DATA · 2017 · IF 2.323

Solubility of Benzoin in Six Monosolvents and in Some Binary Solvent Mixtures at Various Temperatures

Yang Yang,Weiwei Tang,Xiaona Li,Dandan Han,Yumin Liu,Shichao Du,Teng Zhang,Shiyuan Liu,Junbo Gong

The solubility of benzoin in monosolvents (acetone, ethyl acetate, methanol, ethanol, 1-propanol, and 1-butanol) and binary solvent mixtures (ethyl acetate + methanol, ethyl acetate + ethanol) was measured using UV–vis spectroscopy at temperatures ranging from 283.15 K to 323.15 K. It can be seen from the data that the solubility of benzoin increases expectedly as temperature increases in a given solvent or solvent mixture, the solubility in acetone is maximum among six monosolvents which could be well explained by the existence of strong H-bonds, rather than the “like dissolves like” rule. In binary solvent mixtures, the solubility reaches maximum when the mole fraction of methanol is 0.1 in ethyl acetate + methanol mixed solvents, while the maximum exhibits at 0.2 of mole fraction of ethanol in ethyl acetate + ethanol. The solubility parameter was interpreted as the cosolvency of benzoin solubility in binary solvent mixtures. The solubility data were correlated by modified Apelbalt equation, CNIBS/R-K equation, λh equation, Jouyban–Acree model, and Van’t–JA equation. Mixing thermodynamic properties were further calculated and discussed regarding their roles in dissolution and solubility.

CAS / MDL: 69-72-7
研究领域: 化学 · 药学
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