Study of the role of alkaline sodium additive in selective hydrogenation of phenol

Chen, Yuzhuo; Kong, Xiangqian; Mao, Shanjun; Wang, Zhe; Gong, Yutong; Wang, Yong

doi:10.1016/s1872-2067(19)63386-3

Cited by 32 publications

(19 citation statements)

References 73 publications

(88 reference statements)

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“…Only 12.5% conversion of phenol is achieved with Pd–chitin-150(HCl) as catalyst (Table , entry 19). This result indicates that sodium ions in catalyst play important function in phenol hydrogenation as in other reports . Sodium can not only enhance the catalytic activity due to its electron-donating property but also improve the selectivity of phenol hydrogenation to cyclohexanone by promoting the dissociation of H atom of phenolic hydroxyl of phenol.…”

Section: Resultssupporting

confidence: 72%

“…This result indicates that sodium ions in catalyst play important function in phenol hydrogenation as in other reports. 38 Sodium can not only enhance the catalytic activity due to its electron-donating property but also improve the selectivity of phenol hydrogenation to cyclohexanone by promoting the dissociation of H atom of phenolic hydroxyl of phenol. In comparison with other catalytic system (Table S2), the support is natural biomass and the preparation process of Pd−chitin-150 is more facile and green.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Palladium Nanoparticles Anchored on Sustainable Chitin for Phenol Hydrogenation to Cyclohexanone

Zhao

Zhang

Liu

et al. 2020

ACS Sustainable Chem. Eng.

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A kind of natural, sustainable, and abundant biomass, chitin, is used as support to load palladium nanoparticles catalyst (Pd−chitin) for the transfer hydrogenation of phenolic compounds to ketones in HCOONa solution. The appropriate reduction temperature in hydrogen atmosphere is a key factor to improve the coordination between oxygen-containing groups and palladium nanoparticle, which prevents palladium nanoparticles leaching during the reaction so that Pd−chitin-150 exhibits good recycling stability. More importantly, Pd−chitin-150 can be fabricated into a PTFE tube with 2 mm inner diameters as a kind of monolithic catalyst, achieving the continuous production of cyclohexanone by feeding the mixture of phenol and HCOONa solution. The functions of sodium introduced during the preparation of catalyst are researched by H 2 -TPR, CO−DRIFT, and DFT calculations, which facilitate the reduction of palladium and increase the catalytic activity for phenol hydrogenation and selectivity to cyclohexanone.

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Section: Resultssupporting

confidence: 72%

Section: ■ Results and Discussionmentioning

confidence: 99%

Palladium Nanoparticles Anchored on Sustainable Chitin for Phenol Hydrogenation to Cyclohexanone

Zhao

Zhang

Liu

et al. 2020

ACS Sustainable Chem. Eng.

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“…Especially, the realization of high chemoselectivity is increasingly challenging as the reducibility of the competing functional groups increases. 6,7 Haloanilines (HANs), for instance, as the vital organic intermediate widely used in the production of polymers, pharmaceuticals, herbicides, dyes, etc., are usually obtained through the selective reduction of the corresponding halonitrobenzenes (HNBs). 8 A range of noble-metal-based heterogeneous catalysts such as Pt, 9,10 Pd, 11,12 Ru, 13,14 and Au 15,16 have been studied for HNBs hydrogenation.…”

Section: Introductionmentioning

confidence: 99%

Insight into Single-Atom-Induced Unconventional Size Dependence over CeO2-Supported Pt Catalysts

Wang

Mao

Wang

et al. 2020

Chem

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Identification of the structure-performance relationship at the atomic level is vital for getting a deep understanding of the size-dependence behavior of metal catalysts. Here, an unconventional size dependence of Pt toward selective hydrogenation of p-chloronitrobenzene has been extensively investigated over CeO 2 support. An upturned volcanic curve toward the selectivity of p-chloroaniline was found by decreasing the size of Pt from nanoparticles to single atoms. Differences on predominant orbitals among diverse coordination-environment Pt sites were identified to be the key factors influencing the modes of interaction with the C-Cl bond of p-chloroaniline. Specifically, electrostatic repulsion between nonbonding orbitals of Cl and predominant orbitals of Pt sites with high steric hindrance were speculated to be responsible for the suppression of dehalogenation and the high selectivity. This strategy to build correlation between the valence orbitals of active sites and their catalytic behavior could well be expanded to other structure-sensitive reactions and atomically dispersed catalysts.

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“…35 KOH played the role of promoting the adsorption of hydrogen donors on the surface of the catalyst. 36 Furthermore, hydrogen dissociation from the hydroxy group of the EG was promoted by the presence of KOH base. 37 The catalytic performance of CuNi NPs was analyzed thoroughly by taking nitrobenzene as an example.…”

Section: Resultsmentioning

confidence: 99%

“…In this work, EG was used as a hydrogen donor, which was very likely to lose hydrogen during the reaction and become glycolaldehyde . KOH played the role of promoting the adsorption of hydrogen donors on the surface of the catalyst . Furthermore, hydrogen dissociation from the hydroxy group of the EG was promoted by the presence of KOH base …”

Section: Results and Discussionmentioning

confidence: 99%

Magnetic CuNi Alloy Nanoparticles for Catalytic Transfer Hydrogenation of Nitroarene

Shi

Dai

Liu

et al. 2021

Ind. Eng. Chem. Res.

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Magnetic CuNi alloy nanoparticles (CuNi NPs) for the catalytic transfer hydrogenation (CTH) of nitroarene were successfully prepared by the facile thermal decomposition of copper formate (Cuf) and nickel formate (Nif) simultaneously. Liquid paraffin served as solvent, and oleylamine (OAM) acted as both complexing agent and stabilizer. The particle size and Cu/Ni composition of CuNi NPs could be controlled by adjusting the amount of OAM and the Cu/Ni ratio of the precursor. The average diameter of the prepared CuNi NPs ranged from 10.2 to 56.9 nm. It had been confirmed that CuNi NPs were an alloy of Cu and Ni and effectively resistant to oxidation. The prepared CuNi NPs could be separated under an external magnetic field without any energy consumption since they were superparamagnetic. Among the prepared CuNi NPs with different compositions, the Cu3Ni7 NPs were the best catalyst for catalytic transfer hydrogenation of nitrobenzene with ethylene glycol (EG) as the hydrogen donor, giving a nitrobenzene conversion of 99% and an aniline yield of >97%. The conversion and yield remained above 95% and 80% respectively after 10 cycles of NOBF4-treated Cu3Ni7 NPs, demonstrating good reusability for the CTH reaction. This work reported a novel method for preparing magnetic CuNi NPs and also provided a new approach for the hydrogenation of nitroarene catalyzed by non-noble metals in a green environment.

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Study of the role of alkaline sodium additive in selective hydrogenation of phenol

Cited by 32 publications

References 73 publications

Palladium Nanoparticles Anchored on Sustainable Chitin for Phenol Hydrogenation to Cyclohexanone

Palladium Nanoparticles Anchored on Sustainable Chitin for Phenol Hydrogenation to Cyclohexanone

Insight into Single-Atom-Induced Unconventional Size Dependence over CeO2-Supported Pt Catalysts

Magnetic CuNi Alloy Nanoparticles for Catalytic Transfer Hydrogenation of Nitroarene

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