Ruthenium‐Catalyzed Selective Hydrogenation of Benzene to Cyclohexene in the Presence of an Ionic Liquid

Schwab, Frederick; Lucas, Martin; Claus, Peter

doi:10.1002/anie.201104959

Cited by 82 publications

(66 citation statements)

References 20 publications

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“…催化剂上 Ru 的分散度(dispersion)和粒径(d Ru )采用 CO 化学吸附在美国 Micromeritics 2750 型化学吸附仪上测定. 将约 100 mg 样品装入样品管中, 在 Ar (99.999%) 气氛中于 473 K 下预处理 1 h, 然后降温至 298 K. 在该温度下 CO (99.999%)脉冲进样 [24] , 至热导检测器(TCD) 检测的峰面积恒定为止, 即达到饱和吸附. 根据 CO 吸附面积, 采用文献提供的方法计算 S Ru 和 Ru 的分散度, 假定吸附 CO 与金属 Ru 的化学计量比(CO/Ru)为 0.5, 且 Ru 的表面原子密度为 1.63×10 19 atoms•m -2 [33] .…”

Section: 引言unclassified

Pore Size Effect of Ru-Zn/ZrO₂ Catalyst on Partial Hydrogenation of Benzene to Cyclohexene

周功兵¹,

Wang²,

裴燕³

et al. 2017

Acta Chim. Sinica

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Partial hydrogenation of benzene to cyclohexene is an important industrial process and features exceptional superiority to processes such as dehydration of cyclohexanol, dehydrogenation of cyclohexane, and the Birch reduction in terms of inexpensive feedstock, succinct reaction route and consequently, improved operational simplicity. In this work, the pore size effect on the partial hydrogenation of benzene to cyclohexene over the Ru-Zn/ZrO 2 catalysts was studied for the first time. Three ZrO 2 supports with the same tetragonal crystallographic form (t-ZrO 2 ) but different pore sizes were synthesized by the precipitation and the solvothermal methods. Using these ZrO 2 samples, the Ru-Zn/ZrO 2 catalysts were prepared by the deposition-precipitation method followed by reduction in ZnSO 4 •7H 2 O aqueous solution. The supports and catalysts were characterized by powder X-ray diffraction (XRD), N 2 physisorption, inductively coupled plasma-atomic emission spectroscopy (ICP-AES), CO chemisorption, X-ray photoelectron spectroscopy (XPS), X-ray absorption near-edge structure (XANES), temperature-programmed reduction of H 2 (H 2 -TPR), and transmission electron microscopy (TEM). It is identified that the Ru nanoparticles (NPs) on these catalysts had similar size and chemical state. In the partial hydrogenation of benzene to cyclohexene, a pronounced pore size effect of the catalyst was identified. With the increase in the pore size, while the turnover frequency (TOF) of benzene was essentially unchanged, the initial selectivity (S 0 ) to cyclohexene increased steadily. The Ru-Zn/ZrO 2 (11.7) catalyst with the ZrO 2 support having the pore size of 11.7 nm exhibited the highest S 0 (88%) and yield (54%) of cyclohexene. On the basis of the characterization results, the similarity in the TOFs of benzene on the

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Section: 引言unclassified

Pore Size Effect of Ru-Zn/ZrO₂ Catalyst on Partial Hydrogenation of Benzene to Cyclohexene

周功兵¹,

Wang²,

裴燕³

et al. 2017

Acta Chim. Sinica

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“…It has been proved that the modifiers, which are dissolved in water, can improve the cyclohexene selectivity effectively. 9 Various substances have been used as the modifiers, including inorganic salts, 10 organic compounds, 11,12 ionic liquids, 13 etc. Struijk et al 10 studied the effect of a variety of inorganic salts on the reaction.…”

Section: Introductionmentioning

confidence: 99%

“…Fan et al 11 and Sun et al 12 investigated the effect of organic modifiers on the reaction. Schwab et al 13 utilized small amounts ( ppm range) of ionic liquid with [N(CN) 2 ] − as the modifier to block the consecutive hydrogenation to cyclohexane. It has also been reported that adding some alkaline agents into the reaction system, especially sodium hydroxide (NaOH), enhances the selectivity to cyclohexene.…”

Section: Introductionmentioning

confidence: 99%

Ru–Zn supported on hydroxyapatite as an effective catalyst for partial hydrogenation of benzene

Zhang,

Wu,

Jiang

et al. 2013

Green Chem.

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Design and preparation of efficient and greener catalytic systems for partial hydrogenation of benzene to cyclohexene is an interesting topic in green chemistry. In this work, Ru and Ru-Zn catalysts supported on hydroxyapatite (HAP), which is nontoxic and abundant in nature, were prepared via the simple ionexchange method. The catalysts were characterized by powder X-ray diffraction (XRD), transmission electron spectroscopy (TEM), X-ray photoelectron spectroscopy (XPS) and nitrogen adsorption-desorption methods. The influences of Ru/Zn molar ratio, reaction temperature, pressure, reaction time, and amount of modifier NaOH on the partial hydrogenation of benzene were studied in detail. It was demonstrated that metallic nanoparticles of less than 2 nm were dispersed uniformly on the surface of the HAP, and the bimetallic Ru-Zn/HAP catalysts showed high activity and selectivity. The yield of cyclohexene could reach 33% over Ru-Zn/HAP at the optimized conditions, and the catalyst could be reused at least four times without obvious loss of the activity and selectivity.

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“…Another example for selective hydrogenation is the highly interesting conversion of benzene to cyclohexene in the presence of Ru-NPs in [C 4 C 1 Im][PF 6 ] ( Table 2: Entry C, Fig. 7) [57,93]. Moreover, Ru-NPs in ILs are suitable for the hydrogenation of biomass-derived organic molecules based on 5-hydroxymethylfurfural (HMF) and furfural, which can be obtained in turn from hexoses and pentoses (Scheme 6) [76].…”

Section: Hydrogenation Reactionsmentioning

confidence: 99%

Ruthenium Nanoparticles in Ionic Liquids – A Saga

Campbell

Prechtl²,

Santini³

et al. 2013

COC

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Ionic liquids (ILs) are excellent media for the generation and stabilisation of metallic nanoparticles (NPs). Their ionic character coupled with 3-D structural pre-organisation in the liquid state, serves to direct the growth of transition metal NPs generated in situ, and to subsequently protect and stabilise them. Until now, many different NPs have been successfully synthesised within these media, however much attention has been paid to Ru-NPs. These have been prepared with small sizes and narrow size distributions by reduction of organometallic compounds with molecular hydrogen as well as decomposition of transition-metal complexes in the zero-valent state. These stable Ru-NPs immobilised in the ILs have proven to be efficient green catalysts for several reactions in multiphase conditions, including important energy-related processes such as biomass refinement. Furthermore, they present potential novel materials for use in the production of smarter electronic devices. In this review, the synthesis, stabilisation and size-control of Ru-NPs via various methods in different ILs is discussed, followed by their varied application in catalysis and potential in new fields.

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Ruthenium‐Catalyzed Selective Hydrogenation of Benzene to Cyclohexene in the Presence of an Ionic Liquid

Cited by 82 publications

References 20 publications

Pore Size Effect of Ru-Zn/ZrO₂ Catalyst on Partial Hydrogenation of Benzene to Cyclohexene

Pore Size Effect of Ru-Zn/ZrO₂ Catalyst on Partial Hydrogenation of Benzene to Cyclohexene

Ru–Zn supported on hydroxyapatite as an effective catalyst for partial hydrogenation of benzene

Ruthenium Nanoparticles in Ionic Liquids – A Saga

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Ruthenium‐Catalyzed Selective Hydrogenation of Benzene to Cyclohexene in the Presence of an Ionic Liquid

Cited by 82 publications

References 20 publications

Pore Size Effect of Ru-Zn/ZrO2 Catalyst on Partial Hydrogenation of Benzene to Cyclohexene

Pore Size Effect of Ru-Zn/ZrO2 Catalyst on Partial Hydrogenation of Benzene to Cyclohexene

Ru–Zn supported on hydroxyapatite as an effective catalyst for partial hydrogenation of benzene

Ruthenium Nanoparticles in Ionic Liquids – A Saga

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Pore Size Effect of Ru-Zn/ZrO₂ Catalyst on Partial Hydrogenation of Benzene to Cyclohexene

Pore Size Effect of Ru-Zn/ZrO₂ Catalyst on Partial Hydrogenation of Benzene to Cyclohexene