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Friedel–Crafts反应
RSC Advances · 2018 ·Vol. 8 ·期 58 ·33217-33227 · IF 2.936

Facile preparation of hybrid porous polyanilines for highly efficient Cr(VI) removal

Wenjie Tang,Yue Wu,Tingting Gao,Yingqin Wei,Guowei Zhou

In the present work, leucoemeraldine-based hybrid porous polyanilines (LHPPs) have been synthesized by the Friedel–Crafts reaction of leucoemeraldine and octavinylsilsesquioxane (OVS) for Cr(VI) removal. The resulting LHPPs were characterized by Fourier transform infrared spectroscopy, powder X-ray diffraction, thermogravimetric analysis, scanning electron microscopy and N2 adsorption–desorption. The findings indiated that the LHPPs were amorphous, with apparent surface areas (SBET) in the range of 147 to 388 m2 g−1 and total volumes in the range of 0.13 to 0.44 cm3 g−1. Cr(VI) removal experiments displayed that the LHPPs exhibited highly efficient Cr(VI) removal performance. The maximum Cr(VI) removal capacity of LHPP-1 was 990.1 mg g−1 at 308 K and pH 1, which is higher than those of other reported polyaniline-based adsorbents. The adsorption process was a spontaneous, endothermic and chemical adsorption process. The adsorption behavior agreed well with Langmuir models and pseudo second-order equations. X-ray photoelectron spectroscopy and Fourier transformed infrared (FTIR) spectroscopy analysis revealed that the highly efficient Cr(VI) removal performance can be mainly attributed to the existence of numerous amine and imine groups on the surface of the LHPPs; these can function as adsorption active sites for Cr(VI) removal through electrostatic adsorption and reduction to Cr(III) under acidic conditions. Moreover, the LHPPs exhibited excellent adsorption selectivity for Cr(VI) despite the presence of other metal ions (K+, Cu2+, Mn2+) and anions (NO3−, SO42−). Therefore, the LHPPs have potential applications for Cr(VI) removal in industrial wastewater.

研究领域: 环境科学 · 材料科学
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POLYMER · 2018 · IF 3.483

Hypercrosslinked porous polycarbazoles from carbazolyl-bearing aldehydes or ketones

Rong-Rong Zhang,Qing Yin,Hai-Peng Liang,Qi Chen,Wei-Hua Luo,Bao-Hang Han

Hypercrosslinked polymers have drawn increasing interest due to their porous structure, large specific surface area, and excellent chemical and thermal stability. Using the carbonyl bearing carbazole monomers Cz-22∼27 , a series of hypercrosslinked porous polycarbazoles CPOP-22∼27 have been synthesized through oxidative coupling polymerization and Friedel–Crafts reaction in one-step promoted by FeCl 3 . The Brunauer–Emmett–Teller specific surface areas of CPOP-22∼27 are between 440 and 760 m 2  g −1 . Their dominant pore sizes vary from 0.99 to 1.06 nm, which indicating that the polymers are predominantly microporous . This work provides a new method to synthesis of hypercrosslinked porous polycarbazoles from carbonyl functionalized carbazoles. It is also found that parts of aldehyde groups can not react through the Friedel–Crafts alkylation when increasing the number of carbazole groups. The residual aldehyde groups in the polymer can even react with Tollens' reagent solution to form Ag nanoparticles composite.

研究领域: 材料科学 · 化学工程
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MICROPOROUS AND MESOPOROUS MATERIALS · 2017 · IF 3.615

POSS-based microporous polymers: Efficient Friedel-Crafts synthesis, CO2 capture and separation properties

Jun Liu,Yunfei Liu,Xiaowei Jiang,Yali Luo,Yinong Lyu

Two kinds of POSS-based microporous organic polymers (PMOPs) were prepared by cost-effective Friedel-Crafts reaction of octaphenylsilsesquioxanes with p -dimethoxybenzene (PMOP-1) or cyanuric chloride (PMOP-2). PMOP-1 with high surface area of 806 m 2  g −1 exhibited reasonable CO 2 adsorption (2.59 mmol g −1 , 273 K/1 bar) and selectivity, whereas PMOP-2 with lower surface area (559 m 2  g −1 ) showed a higher CO 2 /N 2 selectivity (30.0) and CO 2 /CH 4 selectivity (6.8) at 273 K/1 bar due to the high amount of nitrogen incorporated within the structure. The correlation between the performance of PMOPs in CO 2 capture/separation and their properties such as surface area, surface active sites, and heat of adsorption was investigated. The combination of a cost-effective method, high thermal stability, and reasonable selective adsorption make these materials potential candidates for application in CO 2 capture and separation technology.

研究领域: 材料科学 · 环境科学
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RSC Advances · 2015 ·Vol. 5 ·期 76 ·62241-62247 · IF 3.84

Durability enhanced ionic liquid catalyst for Friedel–Crafts reaction between benzene and 1-dodecene: insight into catalyst deactivation

Yibo He,Chao Wan,Qinghua Zhang,Xiaoli Zhan,Dang-guo Cheng,Fengqiu Chen

Friedel–Crafts alkylation of benzene with 1-dodecene, which is an important reaction of synthetic detergent, was studied using the catalyst [bmim][TFSI]/AlCl3 (1-butyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide/AlCl3). These ionic liquid catalysts show biphasic behaviors at a specific condition. Active site species and Lewis acidity were determined by NMR and acetonitrile probe FT-IR. NMR spectroscopy investigations indicated that “coordinated” and “uncoordinated” [TFSI]− existed in the ionic liquid catalyst system simultaneously, while tetrahedral 4-coordinate Al2Cl7− was the main active species for Friedel–Crafts alkylation. The complex [AlClx(TFSI)y]− tends to decompose and release 4-coordinated Al2Cl7− and [TFSI]−. The phase behavior study of the ionic liquid [bmim][TFSI]/AlCl3 demonstrated that the upper phase could be used as an efficient heterogeneous catalyst when AlCl3/IL ≥ 1.5. Due to the presence of the anion [TFSI]− around the active sites, especially [TFSI]− at the “uncoordinated” state, the ionic liquid formed a stable and hydrophobic chemical environment, which enhanced catalyst durability. The influence of various reaction conditions including catalyst reusability on the alkylation reaction was studied, and the potential reasons for catalyst deactivation were discussed. The highest 2-LAB selectivity was more than 50% when 1-dodecene conversion was nearly 100%. Compared with liquid or solid acid catalyst, ionic liquid catalysts have many advantages concerning energy and the environment.

CAS / MDL: 90076-65-6 85100-77-2
研究领域: 化学工程 · 催化化学
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MICROCHEMICAL JOURNAL · 2022 · IF 5.304

Convenient synthesis of a hyper-cross-linked polymer via knitting strategy for high-performance solid phase microextraction of polycyclic aromatic hydrocarbons

Zhengwang Wang,Yanjun Huang,Yalan Hu,Sheng Peng,Xiaoru Peng,Zhi-Wei Li,Juan Zheng,Fang Zhu,Gangfeng Ouyang

Precise quantifications of trace polycyclic aromatic hydrocarbons (PAHs) have been the focus in recent years due to the low concertation in environment and greatly potential damage on human health. The Rubrene (Rub) was used as the raw material to obtain a hyper-cross-linked polymer (HCP-Rub) via Friedel-Crafts reaction, which was further fabricated as a novel SPME coating. The abundant benzene rings on Rub could act as reactive sites, leading to the facile synthesis of HCP-Rub. Moreover, the as-prepared HCP-Rub possessed rich micropores, strong hydrophobicity and large conjugated structure, which made it an ideal candidate for the efficient enrichments of PAHs. The extraction efficiencies of HCP-Rub coated SPME fiber for PAHs were 1.5–16.4 times of the commercial PDMS fiber (100 μm), and 1.2–1.6 times of the commercial PDMS/DVB (65 μm) fiber, respectively. Under optimal conditions, the HCP-Rub coated fiber demonstrated high enhancement factors, ranging from 1331 to 3089. It was further coupled with gas chromatography-mass spectrometry (GC–MS) to establish an analytical method with wide linear ranges (5–1000 ng·L −1 ) and low detection limits (0.11–0.98 ng·L −1 ). Finally, the method was successfully applied to the determinations of trace PAHs in environmental water samples with good recoveries (83.7–108%).

研究领域: 环境科学 · 分析化学
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CURRENT ORGANIC SYNTHESIS · 2015 ·Vol. 12 ·期 1 ·71-75 · IF 2.117

Synthesis and Characterization of Bipolar Hosts Based on Triphenylamine and 4,5- Diazafluorene Through Friedel-Crafts Reaction

Nengquan Li,Kun Chen,Zhaokang Fan,Yiwu Quan,Qingmin Chen

A new family of bipolar hosts TPA-DAF, TPA-(DAF)2 and TPA-(DAF)3 based on triphenylamine and 4,5- diazafluorene moiety were synthesized through Friedel-Crafts reaction, and all of the three prepared hosts showed excellent thermal stability and exhibited blue fluorescence in solution.

研究领域: 有机电子学 · 光电材料 · 高分子化学 · 荧光材料 · 热稳定性研究
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CATALYSIS TODAY · 2016 · IF 4.312

Synthesis of efficient SBA-15 immobilized ionic liquid catalyst and its performance for Friedel–Crafts reaction

Yibo He,Qinghua Zhang,Xiaoli Zhan,Dang-guo Cheng,Fengqiu Chen

Friedel–Crafts alkylation of benzene with 1-dodecene, which is an important reaction of synthetic detergent, was studied via ionic liquid [bmim][TFSI]/AlCl 3 (1-butyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide/AlCl 3 ) immobilized on SBA-15 catalysts. XRD, BET, TEM, TG, ammonia TPD investigations were used to search insight into catalyst characteristic. The immobilized catalysts preserved ordered structure and presented high specific surface areas. The utilization of active sites was significantly improved by immobilization. Based on ammonia TPD, immobilized catalysts exhibited higher Lewis acidity than aluminum chloride grafted SBA-15. TG indicated that thermal stability of ionic liquid has been improved by immobilization. The influences of various reaction conditions including reaction time, benzene/1-dodecene ratio were studied. Immobilized ionic liquids have better performance of no matter 1-dodecene conversion or 2-linear alkyl benzene (2-LAB) selectivity, than bulk ionic liquid catalysts or aluminum chloride grafted mesoporous materials. 2-LAB selectivity can be increased from about 35% with bulk ionic liquid to more than 60% with immobilized catalysts. Under optimal condition, 2-LAB selectivity reached as high as 80%. The immobilized catalysts could be reused. And at 3th cycle of catalysts, 1-dodecene conversion could still reach more than 50%. The role of deactivation was proposed based on TEM, BET and TG investigations. By-products as oligomer , produced by oligomerization of olefin , blocked or covered the pores, led to deactivation of catalysts.

研究领域: 化学工程 · 催化材料科学
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