Room‐Temperature Hydrogenation of Citral Catalyzed by Palladium–Silver Nanocrystals Supported on SnO<sub>2</sub>

Wang, Shuo; Shen, Rongan; Chen, Zheng; Wang, Dingsheng; Li, Yadong

doi:10.1002/ejic.201500057

Cited by 5 publications

(3 citation statements)

References 33 publications

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“…Generally, it has been observed that a high yield of menthol production via citral hydrogenation would possibly be produced with the use of selective, active, and recyclable bifunctional (metal–acid) catalysts with selective properties. Various catalytic-material-supported (metals), such as H-MCM-41, Al-MCM-41, H-Y zeolite, beta zeolite, activated carbon, Zr-zeolites, ionic liquid catalysts, nickel-supported metals [ 9 ], MOF-derived AgCo alloy nanoparticles [ 10 ], Pt/Sn [ 11 ], Ru-HY extrudates [ 12 ], Pt/SiO 2 [ 13 ] nano-composite catalysts [ 14 ], ruthenium nanoparticles [ 15 ], and SiO 2 -Al 2 O 3 , have been applied in citral hydrogenation reactions to obtain a higher yield of menthol [ 16 , 17 ]. Conversely, it has been observed that menthol selectivity would possibly be decreased due to the lack of active and selective catalyst designs that occur because of the formation of undesired/unrestrained hydrogenations, as well as cracking side reactions [ 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

Design of Nickel Supported Hierarchical ZSM-5/USY Zeolite Bifunctional Catalysts for One-Pot Menthol Synthesis via Liquid-Phase Citral Hydrogenation

Shah

et al. 2023

Molecules

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Nickel-supported hierarchical zeolite catalysts were prepared through a desilication reassembly process under optimized conditions and applied in one-pot menthol synthesis. In this work, the hierarchical zeolite-supported metal bifunctional catalysts were prepared with the help of desilication re-assembly and wetness impregnation techniques and applied in menthol synthesis via citral hydrogenation. The prepared catalysts were characterized using PXRD, BET, FE-TEM, NH3-TPD, H2-TPR, pyridine adsorption, and ICP-OES techniques. As a result, the physicochemical and acidic properties, such as mesopore surface area, metal dispersion, acidity, catalytic activity, and strong Lewis acid sites of pure microporous ZSM-5/USY zeolites, were significantly improved. Consequently, with the occurrence of superior physicochemical and acidic properties, the Ni/HZ-0.5 M catalyst exhibited outstanding catalytic activity (100% conversion, TOF 7.12 h−1) and menthol selectivity (83%, 4 h) with uniform stability at 100 °C, 1.0 MPa hydrogen. Similarly, the cracking rate decreased with the decrease in Bronsted acid sites.

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Section: Introductionmentioning

confidence: 99%

Design of Nickel Supported Hierarchical ZSM-5/USY Zeolite Bifunctional Catalysts for One-Pot Menthol Synthesis via Liquid-Phase Citral Hydrogenation

Shah

et al. 2023

Molecules

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“…Benefitting from their manifold compositions, valence states, and electron configurations, spinel compounds have attracted wide attention in magnetic, optical, electrical, and catalytic fields . In particular, for spinel nickel cobaltite (NiCo 2 O 4 ), the controllable composition, variable valence state, and easily constructed structure and morphology make it suitable for use as a catalyst or support for various catalytic reactions. − Palladium-based materials have higher CC multibond activation capacity than other precious metals such as platinum, rhodium, and ruthenium. , And supported Pd nanoparticles are considered to be highly efficient catalysts for the hydrogenation of α,β-unsaturated carbonyl compounds. − So NiCo 2 O 4 -supported Pd could be expected to show excellent selectivity and activity for the hydrogenation of α,β-unsaturated carbonyl compounds.…”

Section: Introductionmentioning

confidence: 99%

“…22−26 Palladium-based materials have higher CC multibond activation capacity than other precious metals such as platinum, rhodium, and ruthenium. 27,28 And supported Pd nanoparticles are considered to be highly efficient catalysts for the hydrogenation of α,βunsaturated carbonyl compounds. 29−33 So NiCo 2 O 4 -supported Pd could be expected to show excellent selectivity and activity for the hydrogenation of α,β-unsaturated carbonyl compounds.…”

Section: ■ Introductionmentioning

confidence: 99%

Defect Engineering in Pd/NiCo₂O_4–x for Selective Hydrogenation of α,β-Unsaturated Carbonyl Compounds under Ambient Conditions

Zhang

Wang

et al. 2020

ACS Sustainable Chem. Eng.

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The highly selective hydrogenation of α,β-unsaturated carbonyl compounds is challenging and desirable in pharmaceutical manufacturing. Moreover, the ability to activate specific functional groups in complex starting materials is also in line with the concept of sustainable chemistry. Here, we use a simple room temperature chemical reduction strategy to implant defects into NiCo 2 O 4 while loading metal Pd. The synthesized Pd/ NiCo 2 O 4−x shows good catalytic performance for the selective (nearly 100%) hydrogenation of cinnamaldehyde to hydrocinnamaldehyde under mild conditions. Furthermore, the selectivity to hydrocinnamaldehyde can still be maintained by extending the reaction time and increasing the reaction temperature. Density functional theory calculations indicated that the C C bond of cinnamaldehyde is preferentially adsorbed on the surface of Pd nanoparticles than the CO bond. After hydrogenation of cinnamaldehyde to hydrocinnamaldehyde, the CO bonds of hydrocinnamaldehyde are strongly adsorbed by the oxygen defect of the NiCo 2 O 4−x . The adsorbed hydrocinnamaldehyde on oxygen defects will be erected on the surface of NiCo 2 O 4−x , which can impede the adsorption of hydrocinnamaldehyde on Pd nanoparticles. So, the further hydrogenation of hydrocinnamaldehyde is hindered. The present work provide new insights into highly selective hydrogenation of α,β-unsaturated carbonyl compounds and paves a new way for the defect engineering to design efficient catalytic materials and beyond.

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Manufacture of Citronellal by the Rhodium‐Catalyzed Homogeneous Hydrogenation of Neral

Holz

Doerfelt²,

Börner

2017

Adv Synth Catal

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Theh ighly chemoselective hydrogenation of neral affording citronellal is described. Ther eaction has been conducted with homogeneousr hodium complexes.A mong the set of ancillary diphosphane ligands tested, Xantphos was found to be superior. Ther elevant precatalyst hasb een generated from neutral metal sources such as Rh(acac)(CO) 2 or the carbon monoxide-free rhodium source Rh(acac)(cod) in the absence of anyb ase.Ahigh ac-tivity andchemoselectivity in favorofthe desired citronellal is achieved at 0.1 MPa and room temperature.U nder the same conditions,g eranial is also reduced to citronellal. Thea ddition of carbon monoxide to the hydrogen streama su sed in an industrial process is not necessary.Scheme 1. Synthesis of citronellal (2)b ythe chemoselective hydrogenation of citral isomers 1.

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Room‐Temperature Hydrogenation of Citral Catalyzed by Palladium–Silver Nanocrystals Supported on SnO₂

Cited by 5 publications

References 33 publications

Design of Nickel Supported Hierarchical ZSM-5/USY Zeolite Bifunctional Catalysts for One-Pot Menthol Synthesis via Liquid-Phase Citral Hydrogenation

Design of Nickel Supported Hierarchical ZSM-5/USY Zeolite Bifunctional Catalysts for One-Pot Menthol Synthesis via Liquid-Phase Citral Hydrogenation

Defect Engineering in Pd/NiCo₂O_4–x for Selective Hydrogenation of α,β-Unsaturated Carbonyl Compounds under Ambient Conditions

Manufacture of Citronellal by the Rhodium‐Catalyzed Homogeneous Hydrogenation of Neral

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Room‐Temperature Hydrogenation of Citral Catalyzed by Palladium–Silver Nanocrystals Supported on SnO2

Cited by 5 publications

References 33 publications

Design of Nickel Supported Hierarchical ZSM-5/USY Zeolite Bifunctional Catalysts for One-Pot Menthol Synthesis via Liquid-Phase Citral Hydrogenation

Design of Nickel Supported Hierarchical ZSM-5/USY Zeolite Bifunctional Catalysts for One-Pot Menthol Synthesis via Liquid-Phase Citral Hydrogenation

Defect Engineering in Pd/NiCo2O4–x for Selective Hydrogenation of α,β-Unsaturated Carbonyl Compounds under Ambient Conditions

Manufacture of Citronellal by the Rhodium‐Catalyzed Homogeneous Hydrogenation of Neral

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Room‐Temperature Hydrogenation of Citral Catalyzed by Palladium–Silver Nanocrystals Supported on SnO₂

Defect Engineering in Pd/NiCo₂O_4–x for Selective Hydrogenation of α,β-Unsaturated Carbonyl Compounds under Ambient Conditions