Hydrogen-free ring hydrogenation of phenol to cyclohexanol over a rhodium-loaded titanium(IV) oxide photocatalyst

Kinoshita, Atsufumi; Nakanishi, Kousuke; Yagi, Ryosuke; Tanaka, Atsuhiro; Hashimoto, Keiji; Kominami, Hiroshi

doi:10.1016/j.apcata.2019.04.001

Cited by 19 publications

(7 citation statements)

References 30 publications

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“…The main pathways can be classified into two groups, gaseous [9] and liquid phase [10]. In the gaseous phase, a variety of supported noble metals, such as Pd [11,12], Pt [13,14], Ru [15,16], Rh [17,18], have been reported to be effective in the hydrogenation system. For example, Wang et al reported a hierarchically porous ZSM-5 zeolite with micropore and b-axis-aligned mesopore-supported Ru nanoparticles (Ru/HZSM-5-OM), which were highly effective for the hydrogenation of both phenol and its derivatives to the corresponding cyclohexane [15].…”

Section: Introductionmentioning

confidence: 99%

Selective Hydrogenation of Phenol to Cyclohexanol over Ni/CNT in the Absence of External Hydrogen

et al. 2020

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Transfer hydrogenation is a novel and efficient method to realize the hydrogenation in different chemical reactions and exploring a simple heterogeneous catalyst with high activity is crucial. Ni/CNT was synthesized through a traditional impregnation method, and the detailed physicochemical properties were performed by means of XRD, TEM, XPS, BET, and ICP analysis. Through the screening of loading amounts, solvents, reaction temperature, and reaction time, 20% Ni/CNT achieves an almost complete conversion of phenol after 60 min at 220 °C in the absence of external hydrogen. Furthermore, the catalytic system is carried out on a variety of phenol derivatives for the generation of corresponding cyclohexanols with good to excellent results. The mechanism suggests that the hydrogenation of phenol to cyclohexanone is the first step, while the hydrogenation of cyclohexanone for the generation of cyclohexanol takes place in a successive step. Moreover, Ni/CNT catalyst can be magnetically recovered and reused in the next test for succeeding four times.

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Section: Introductionmentioning

confidence: 99%

Selective Hydrogenation of Phenol to Cyclohexanol over Ni/CNT in the Absence of External Hydrogen

et al. 2020

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“…As an important chemical raw material, cyclohexanone is widely used in many fields such as medicine, pesticides, coatings, dyes, paints, rubber, and printing [1,2] . Especially for the caprolactam and adipic acid monomers used in the manufacture of nylon 6 and nylon 66 [3–6] . An attractive route for the production of cyclohexanone is selective hydrogenation of phenol in the liquid phase by a one‐step process because of the high efficiency [6–8] .…”

Section: Introductionmentioning

confidence: 99%

“…[1,2] Especially for the caprolactam and adipic acid monomers used in the manufacture of nylon 6 and nylon 66. [3][4][5][6] An attractive route for the production of cyclohexanone is selective hydrogenation of phenol in the liquid phase by a one-step process because of the high efficiency. [6][7][8] However, because cyclohexanone still contains unsaturated bonds, it is easy to further hydrogenate to produce by-product cyclohexanol in the selective hydrogenation process.…”

Section: Introductionmentioning

confidence: 99%

Hybrid Nano‐Structured Pd Catalyst for Selective Hydrogenation of Phenol and the Insights of Deactivation Mechanism

Zhang

Zhou

2022

ChemistrySelect

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A catalyst composed of La2O3/AC and Pd nanoparticles is constructed for precise synthesis of cyclohexanone from phenol hydrogenation with high conversion (>99 %) and selectivity (>95 %). The special structure and the synergistic effect remarkably facilitate the high conversion of phenol. The stability test results of the used Pd/@‐La2O3/AC catalyst showed that the phenol conversion decreased from 100 % to 24.5 %. The deactivation reason for the used catalyst was the agglomeration of Pd nanoparticles and the adsorption of organics. Three treatment methods, heat treatment, ethanol wash, and water wash, were regenerated the catalytic activity of the used Pd/@‐La2O3/AC catalyst. The regenerated method of water wash solved the problem of organic matter blockage and residue to a certain extent, but still can not fully recover its high activity. This deactivation mechanism provides important guidance to develop high stable Pd‐based catalyst for the selective hydrogenation of phenol.

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“…By contrast, rhodium is considered as a highly active catalyst for the hydrogenation of aromatic ring under mild conditions. , However, only a few studies focus on the phenol selective hydrogenation over rhodium catalysts due to the relatively low selectivity of cyclohexanone. In these studies, on the one hand, some are concentrated on different supports to anchor or encage Rh nanoparticles, including SBA-15, TiO 2 , and hollow mesoporous silica, yet the main product is cyclohexanol. On the other hand, three main strategies have been proposed for improving the selectivity of cyclohexanone over Rh catalysts.…”

Section: Introductionmentioning

confidence: 99%

Tailoring Locations and Electronic States of Rh Nanoparticles in KL Zeolite by Varying the Reduction Temperature for Selective Phenol Hydrogenation

Liu

Zhu

Liu

et al. 2021

Ind. Eng. Chem. Res.

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In this study, we employed a top-down strategy, which entailed first the in situ encapsulation of Rh species within the one-dimensional KL channels and then the reduction of catalysts at different temperatures, to tailor the locations and electronic states of the Rh nanoparticles in KL channels for selective phenol hydrogenation under mild conditions. Kinetic studies revealed that with the reduction temperature increasing from 100 to 300 °C, Rh catalysts showed improved activity, while they demonstrated similar time profiles. The cyclohexanone selectivity of 82.4% could be obtained at the phenol conversion of 72.2%, which remained unchanged after recycling seven times. X-ray photoelectron spectroscopy (XPS) and in situ CO adsorption Fourier transform infrared spectroscopy (FT-IR) analyses indicated that the improved activity might be attributed to the more electron-rich chemical state of Rh nanoparticles as there were more probabilities to accept electrons from potassium when Rh nanoparticles migrated from the central location to the edge or surface of the KL zeolite.

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Hydrogen-free ring hydrogenation of phenol to cyclohexanol over a rhodium-loaded titanium(IV) oxide photocatalyst

Cited by 19 publications

References 30 publications

Selective Hydrogenation of Phenol to Cyclohexanol over Ni/CNT in the Absence of External Hydrogen

Selective Hydrogenation of Phenol to Cyclohexanol over Ni/CNT in the Absence of External Hydrogen

Hybrid Nano‐Structured Pd Catalyst for Selective Hydrogenation of Phenol and the Insights of Deactivation Mechanism

Tailoring Locations and Electronic States of Rh Nanoparticles in KL Zeolite by Varying the Reduction Temperature for Selective Phenol Hydrogenation

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