Hydrogenation of Phenol to Cyclohexanone over Bifunctional Pd/C-Heteropoly Acid Catalyst in the Liquid Phase

Liu, Shiwei; Han, Jing; Wu, Qiong; Bian, Bing; Li, Lü; Yu, Shitao; Song, Jié; Zhang, Cong; Ragauskas, Arthur J.

doi:10.1007/s10562-019-02852-1

Cited by 25 publications

(13 citation statements)

References 27 publications

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“…Just as our guesses, lower H 2 pressure and lower temperature slowed down the conversion rate of phenol (Figure , entries 7–10, and Figure S3). Although increasing these conditions can improve the conversion, higher hydrogen pressure or temperature will lead to excessive hydrogenation to generate cyclohexanol. , …”

Section: Resultsmentioning

confidence: 99%

“…Although increasing these conditions can improve the conversion, higher hydrogen pressure or temperature will lead to excessive hydrogenation to generate cyclohexanol. 49,50 Subsequently, it was applied to other phenolic substrates, and the results are shown in Table 1. It proved that the catalyst was also amenable to the hydrogenation of other phenols with good catalytic activity and selectivity for some hydrogenation products.…”

Section: Resultsmentioning

confidence: 99%

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Selective Hydrogenation of Phenol to Cyclohexanone over a Highly Stable Core-Shell Catalyst with Pd-Lewis Acid Sites

Yin

Xin

et al. 2021

J. Phys. Chem. C

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Cyclohexanone is widely used in coatings, pesticides, dyes, lubricants, and other industries due to its high solubility and low volatility, but designing highly active and stable heterogeneous catalysts for selective hydrogenation of phenol to cyclohexanone is a still challenge. In this paper, core-shell structure Pd@Al-mSiO 2 catalysts containing a Pd metal core and an Almodified mesoporous silica shell were design for hydrogenation of phenol to cyclohexanone. At 1 MPa, 1 h, and 100 °C, cyclohexanone with 98.5% of selectivity and 100% of phenol conversion was achieved over Pd@Al-mSiO 2 catalysts with trace aluminum modification. Pd cubes with (100) facets, as the hydrogenation active core, had higher cyclohexanone selectivity than nanoparticles with (111) facets, while mesoporous shells with abundant Lewis acid sites played an important role in activating aromatic rings and inhibiting carbonyl hydrogenation, and close metal−acid interfaces further enhance the synergy between multiple active sites. Moreover, owing to the protection of the shell, the catalyst could be repetitively used 5 times without any loss of catalytic activity.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Selective Hydrogenation of Phenol to Cyclohexanone over a Highly Stable Core-Shell Catalyst with Pd-Lewis Acid Sites

Yin

Xin

et al. 2021

J. Phys. Chem. C

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“…Pd metal on nitrogen‐containing supports such as mesoporous graphitic carbon nitride (Mpg‐C 3 N 4 ), polyaniline‐functionalized carbon‐nanofiber, carbon nitride, and N‐doped mesoporous carbon nanorods were employed for the conversion of phenolic compounds to cyclohexanone. The Pd supported on acidic and Ti‐based supports shows better yields of cyclohexanone under mild reaction conditions [64] . Ru, Pt, and Ni metals on moderate or highly acidic supports reported for high selectivity for cyclohexanes from phenols [60,65] …”

Section: Prior Art Of Hydrodeoxygenation/‐hydrogenation Of Lignin‐basmentioning

confidence: 99%

“…The PTA has a very strong Bronsted acidity which adsorbs phenol reactant easily through hydrogen bonding through hydroxyl group of phenol; which is partially hydrogenates to cyclohexanone. The heteropolyacid is low electron density; hence, accepts lone pair electron from carboxyl oxygen of cyclohexanone product and this interaction prevents further hydrogenation to cyclohexanol [64] . Another Pd metal catalyst supported on TiO 2 nano‐islands and N‐doped carbon (Pd@CN@TiO 2 ) was reported for highly selective (98‐99 %) synthesis of cyclohexanones from various phenols under relatively mild reaction conditions (Table 2, entry 12–18).…”

Section: Catalytic Conversion Of Lignin‐model Phenolics Into Cyclohexmentioning

confidence: 99%

Recent Catalytic Approaches for the Production of Cycloalkane Intermediates from Lignin‐Based Aromatic Compounds: A Review

Gundekari

Karmee

2021

ChemistrySelect

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Lignin is one of the primary components of lignocellulosic biomass. It is an alternative and sustainable source for aromatic and cyclic hydrocarbons. Lignin is obtained in large quantities as a co‐product in sugar, paper‐pulp, and bioethanol industries. Hydrodeoxygenation/‐hydrogenation of lignin‐based phenolic compounds is an important route to synthesize new generation products. This review focuses on recent catalytic methods for selective conversion of phenolics into cyclohexa(nol/none/ne); which are precursors for emerging polymers and fuels. Furthermore, effect of metal catalysts, supports, and parameters on different reactions were discussed along with possible industrial applications of obtained cycloalkanes. In addition, limitations, advantages, and future scope of hydrodeoxygenation/‐hydrogenation of monolignols are also described.

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“…Hydrogenation of phenol to cyclohexanone was used as a model for this catalyst. The reaction is very important in the industry to produce cyclohexanone, which is a raw material for nylon industries [28,29]. It is very difficult to obtain excellent cyclohexanone selectivity at high phenol conversion since the desired product (cyclohexanone) is very active and can be easily hydrogenated to undesired product (cyclohexanol) as shown in Equation (1).…”

Section: Introductionmentioning

confidence: 99%

Polarized Catalytic Polymer Nanofibers

2019

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Molecular scale modifications were achieved by spontaneous polarization which is favored in enhancements of β-crystallization phase inside polyvinylidene fluoride (PVDF) nanofibers (NFs). These improvements were much more effective in nano and submicron fibers compared to fibers with relatively larger diameters. Metallic nanoparticles (NPs) supported by nanofibrous membranes opened new vistas in filtration, catalysis, and serving as most reliable resources in numerous other industrial applications. In this research, hydrogenation of phenol was studied as a model to test the effectiveness of polarized PVDF nanofiber support embedded with agglomerated palladium (Pd) metallic nanoparticle diameters ranging from 5–50 nm supported on polymeric PVDF NFs with ~200 nm in cross-sectional diameters. Scanning Electron Microscopy (SEM), Transmission Electron Microscopy (TEM), Atomic Force Microscopy (AFM), Energy Dispersive X-Ray Spectroscopy (EDX), Fourier Transform Infrared Spectroscopy (FTIR) and other analytical analysis revealed both molecular and surface morphological changes associated with polarization treatment. The results showed that the fibers mats heated to their curie temperature (150 °C) increased the catalytic activity and decreased the selectivity by yielding substantial amounts of undesired product (cyclohexanol) alongside with the desired product (cyclohexanone). Over 95% phenol conversion with excellent cyclohexanone selectivity was obtained less than nine hours of reaction using the polarized PVDF nanofibers as catalytic support structures.

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Hydrogenation of Phenol to Cyclohexanone over Bifunctional Pd/C-Heteropoly Acid Catalyst in the Liquid Phase

Cited by 25 publications

References 27 publications

Selective Hydrogenation of Phenol to Cyclohexanone over a Highly Stable Core-Shell Catalyst with Pd-Lewis Acid Sites

Selective Hydrogenation of Phenol to Cyclohexanone over a Highly Stable Core-Shell Catalyst with Pd-Lewis Acid Sites

Recent Catalytic Approaches for the Production of Cycloalkane Intermediates from Lignin‐Based Aromatic Compounds: A Review

Polarized Catalytic Polymer Nanofibers

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