Efficient selective hydrogenation of cinnamaldehyde over zeolite supported cobalt catalysts in water

Zhang, Xinbo; Zhang, Ya Juan; Chen, Feng; Xiang, Yizhi; Zhang, Bin; Li, Xu; Zhang, Tian Rui

doi:10.1007/s11144-015-0837-0

Cited by 15 publications

(15 citation statements)

References 21 publications

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“…The Pd/(SH)MSC catalyst can convert CAL in water. As a result, a high reaction rate along with undetectable byproducts (i.e., HCAL diethyl acetal) was achieved …”

Section: Resultsmentioning

confidence: 99%

Poison Tolerance to the Selective Hydrogenation of Cinnamaldehyde in Water over an Ordered Mesoporous Carbonaceous Composite Supported Pd Catalyst

Chen

et al. 2017

ACS Catal.

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A coordination-assisted pyrolysis procedure was adopted to encapsulate palladium (Pd) nanoparticles in a mesoporous carbonaceous matrix. X-ray diffraction and transmission electron microscopy measurements revealed that approximately 2.5 nm nanoparticles were highly dispersed inside the well-ordered porous framework. High-resolution TEM and temperature-programmed hydride decomposition analysis demonstrated the formation of interstitial carbon in the Pd lattice. Diffuse reflectance infrared Fourier transform spectroscopy indicated that carbon species could be deposited on low-coordinated surface sites of the Pd particles. This catalyst exhibited high activity in the selective hydrogenation of cinnamaldehyde (CAL) at 80 °C under an H2 pressure of 1.0 MPa (turnover frequency (TOF) of 2.4 s–1) to produce hydrocinnamyl aldehyde with high selectivity (HCAL; approximately 80%) in water and could be reused eight times with no clear activity loss. A trapping agent poisoning experiment using solid SH-SBA-15 revealed unobvious leaching of Pd into the solution. Exposure to thiourea with a S:Pd ratio of 0.1 resulted in slight activity and undetectable selectivity losses over the current catalyst in the selective hydrogenation of CAL at 80 °C under an H2 pressure of 1.0 MPa. However, a 50% activity loss was observed for commercial Pd/C. Even after an increase in the thiourea concentration to a S:Pd ratio of 3, the TOF remained at 1.9 s–1 with a negligible effect on the HCAL selectivity. Nearly complete deactivation of Pd/C occurred upon high exposure to thiourea. DFT calculations showed that the presence of surface or subsurface carbon can enhance the poison tolerance of the encapsulated Pd catalysts. The enhanced hydrogenation activity and strong poison tolerance are consistent with the interpretation that Pd nanoparticles are modified by carbonaceous deposits.

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“…The Pd/(SH)MSC catalyst can convert CAL in water. As a result, a high reaction rate along with undetectable byproducts (i.e., HCAL diethyl acetal) was achieved …”

Section: Resultsmentioning

confidence: 99%

Poison Tolerance to the Selective Hydrogenation of Cinnamaldehyde in Water over an Ordered Mesoporous Carbonaceous Composite Supported Pd Catalyst

Chen

et al. 2017

ACS Catal.

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“…Co, a transition metal element, has moderate activity. Generally, Co is used as a promoter in bimetallic catalysts, but it can also be an independent catalyst in the hydrogenation of CAL. , As shown in Table , some good results have been obtained, with the main product as COL over Co-based catalysts. Liu et al and Zhang et al reported the selective hydrogenation of CAL to COL over MOF-derived Co@CN-900 and MOF-derived Co x Si@C-N-2 (N-doped carbon) catalysts.…”

Section: Selective Hydrogenation Of Cal Over Non-noble Metal Catalystsmentioning

confidence: 97%

Recent Advances in Selective Hydrogenation of Cinnamaldehyde over Supported Metal-Based Catalysts

et al. 2020

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Selective hydrogenation of cinnamaldehyde (CAL) is an important reaction because the main products, cinnamic alcohol (COL) and hydrocinnamaldehyde (HCAL), are used in various fields, such as production of pharmaceutical intermediates, chemicals, perfumes, and fragrances. In recent years, numerous metal-based catalysts and significant study achievements have been reported. Thus, this Review focuses on selective hydrogenation of CAL to target products in terms of metal-based catalysts and summarizes recent developments in this reaction with different catalysts, including Pt-, Pd-, Ru-, Ni-, Co-, and Cu-based catalysts.In addition, the reaction mechanisms of different catalysts, the effects of catalyst substrates, the different catalyst structures, and the synergistic effects in bimetallic catalysts are discussed. Lastly, the limitations and barriers encountered for noble metal and non-noble metal catalysts in the current study as well as potential research trends are discussed.

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“…Dioxane was the first solvent used, in order to avoid the formation of acetal by-products usually produced in alcohols from the acid-catalyzed condensation reaction between CAL (or HCAL) and the solvent. 38 In Figure 2 and Table 1 we report the catalytic performances of the catalysts tested. Despite the lower geometric specific surface area of hcp-CoNR (89.2 m 2 .g -1 ) as compared to -CoNP 104 m 2 .g -1 ), the hcp-CoNR were more active than the -CoNP, but the selectivity towards COL (at iso-conversion 40%) was higher for the -CoNP (86.8 % versus 66.7% for hcp-CoNR).…”

Section: Scheme 1 Outline Of the Synthesis And The Isolation Of The C...mentioning

confidence: 99%

“…[26][27][28][29] Nevertheless, when employed alone, while more selective, it is not a viable catalyst because of its low activity. Thus, examples of cobaltbased catalysts for the selective hydrogenation of  -unsaturated alcohols are rather scarce and among them, only very few concern pure Co. [30][31][32][33][34][35][36][37][38][39][40][41] The development of a stable, active and COL-selective pure cobalt catalyst would thus, be a major breakthrough in the field. Size-, shape-and crystal structure-controlled cobalt nanostructures have been synthesized by some of us by the reduction by H2 of [Co{N(SiMe3)2}2(thf)] in the presence of lauric acid (LA) and hexadecylamine (HDA).…”

Section: Introductionmentioning

confidence: 99%

“…Among the cost-effective metals, cobalt has been used as a COL selectivity promoter of Pt-based catalysts. − Nevertheless, when employed alone, while more selective to COL, it is not a viable catalyst because of its low activity. Thus, examples of cobalt-based catalysts for the selective hydrogenation of α,β-unsaturated alcohols are rather scarce and among them, only a very few concern pure Co. − The development of a stable, active, and COL-selective pure cobalt catalyst would thus be a major breakthrough in the field.…”

Section: Introductionmentioning

confidence: 99%

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Epsilon Cobalt Nanoparticles as Highly Performant Catalysts in Cinnamaldehyde Selective Hydrogenation

Min

Muzzi

et al. 2022

ACS Appl. Nano Mater.

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Epsilon cobalt nanoparticles are under-explored in catalysis due to the fact that they are accessible only through wet-chemical approaches which employ ligands as stabilizing agents.Ligands may play a significant role in determining the structure and the catalytic performances of nanoparticles, which complicates their comparison in catalysis. Here we present the catalytic performances in cinnamaldehyde hydrogenation, of freestanding and few-layer graphenesupported ε-Co nanoparticles and hcp-Co nanorods which are stabilized by the same ligands.We show that while hcp-Co nanorods exposing a majority of {11-20} type facets are the most active, the supported spherical ε-Co nanoparticles combine high activity and excellent selectivity for the selective hydrogenation of cinnamaldehyde to cinnamyl alcohol. The concentration dependent ligand conformation on the surface of the nanostructures influences their catalytic performances with higher concentrations favoring both activity and selectivity to cinnamyl alcohol. These results should incite the interest in the implementation of ε-Co nanoparticles in other catalytic reactions where the cobalt crystal structure may play an important role.

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Efficient selective hydrogenation of cinnamaldehyde over zeolite supported cobalt catalysts in water

Cited by 15 publications

References 21 publications

Poison Tolerance to the Selective Hydrogenation of Cinnamaldehyde in Water over an Ordered Mesoporous Carbonaceous Composite Supported Pd Catalyst

Poison Tolerance to the Selective Hydrogenation of Cinnamaldehyde in Water over an Ordered Mesoporous Carbonaceous Composite Supported Pd Catalyst

Recent Advances in Selective Hydrogenation of Cinnamaldehyde over Supported Metal-Based Catalysts

Epsilon Cobalt Nanoparticles as Highly Performant Catalysts in Cinnamaldehyde Selective Hydrogenation

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