The effect of surface acidic and basic properties on the hydrogenation of aromatic rings over the supported nickel catalysts

Chen, Hui; Xue, Mingwei; Hu, Shenghua; Shen, Jianyi

doi:10.1016/j.cej.2010.05.019

Cited by 77 publications

(58 citation statements)

References 89 publications

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“…The main byproducts of Ni/MgO are 2‐MeOCHol and phenol (5 %), whereas no cycloalkanes were formed (Table 1, entry 7). The low activity of Ni/MgO in this study agrees with a recent study by Shen et al., who found a similar low activity for the hydrogenation of aromatics 29…”

Section: Resultssupporting

confidence: 93%

Selective Nickel‐Catalyzed Conversion of Model and Lignin‐Derived Phenolic Compounds to Cyclohexanone‐Based Polymer Building Blocks

et al. 2015

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Valorization of lignin is essential for the economics of future lignocellulosic biorefineries. Lignin is converted into novel polymer building blocks through four steps: catalytic hydroprocessing of softwood to form 4-alkylguaiacols, their conversion into 4-alkylcyclohexanols, followed by dehydrogenation to form cyclohexanones, and Baeyer-Villiger oxidation to give caprolactones. The formation of alkylated cyclohexanols is one of the most difficult steps in the series. A liquid-phase process in the presence of nickel on CeO2 or ZrO2 catalysts is demonstrated herein to give the highest cyclohexanol yields. The catalytic reaction with 4-alkylguaiacols follows two parallel pathways with comparable rates: 1) ring hydrogenation with the formation of the corresponding alkylated 2-methoxycyclohexanol, and 2) demethoxylation to form 4-alkylphenol. Although subsequent phenol to cyclohexanol conversion is fast, the rate is limited for the removal of the methoxy group from 2-methoxycyclohexanol. Overall, this last reaction is the rate-limiting step and requires a sufficient temperature (>250 °C) to overcome the energy barrier. Substrate reactivity (with respect to the type of alkyl chain) and details of the catalyst properties (nickel loading and nickel particle size) on the reaction rates are reported in detail for the Ni/CeO2 catalyst. The best Ni/CeO2 catalyst reaches 4-alkylcyclohexanol yields over 80 %, is even able to convert real softwood-derived guaiacol mixtures and can be reused in subsequent experiments. A proof of principle of the projected cascade conversion of lignocellulose feedstock entirely into caprolactone is demonstrated by using Cu/ZrO2 for the dehydrogenation step to produce the resultant cyclohexanones (≈80 %) and tin-containing beta zeolite to form 4-alkyl-ε-caprolactones in high yields, according to a Baeyer-Villiger-type oxidation with H2 O2 .

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Section: Resultssupporting

confidence: 93%

Selective Nickel‐Catalyzed Conversion of Model and Lignin‐Derived Phenolic Compounds to Cyclohexanone‐Based Polymer Building Blocks

et al. 2015

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“…This was due to the strong adsorption of the basic double bonds of unsaturated FAME molecules on the strong acidic sites of Al 2 O 3 support that retards their desorption and prevents the access of the other reactant molecules onto the surface of Pd particles. The adsorption of basic double bonds on the acidic support was also observed by Hu et al [7]. They found that toluene, an electron-enriched aromatic compound, strongly adsorbs onto the Al 2 O 3 support.…”

Section: Dear Sirsupporting

confidence: 64%

Effect of Support Acidic Properties on Sulfur Tolerance of Pd Catalysts for Partial Hydrogenation of Rapeseed Oil‐Derived FAME

Numwong

Luengnaruemitchai

Chollacoop

et al. 2012

J Americ Oil Chem Soc

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“…The XPS Al 2s peaks of the Raney Ni/PA and Ni/Al 2 O 3 catalysts were located at 74.03 and 73.93 eV, respectively, which were almost the same within the experimental error and indicated no charge-transfer (base-acid neutralization) interaction between basic PA6 and acidic Al 2 O 3 in the Raney Ni. It is well accepted that the adsorption ability of a catalyst support to reactants and products can largely affect the catalytic reactivity [37,38]. Since the N atoms in PA6 can form hydrogen bonds with the -OH groups in n -butanol and the interval between every two neighboring N atoms in PA6 molecule chain is only about 0.86 nm, the PA6 support possesses strong adsorption ability toward n -butanol.…”

Section: Application Of Polymer-supported Raney Catalysts In Cleanmentioning

confidence: 99%

Polymer-Supported Raney Nickel Catalysts for Sustainable Reduction Reactions

Jiang

Zhang

et al. 2016

Molecules

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Abstract:Green is the future of chemistry. Catalysts with high selectivity are the key to green chemistry. Polymer-supported Raney catalysts have been found to have outstanding performance in the clean preparation of some chemicals. For example, a polyamide 6-supported Raney nickel catalyst provided a 100.0% conversion of n-butyraldehyde without producing any detectable n-butyl ether, the main byproduct in industry, and eliminated the two main byproducts (isopropyl ether and methyl-iso-butylcarbinol) in the hydrogenation of acetone to isopropanol. Meanwhile, a model for how the polymer support brought about the elimination of byproducts is proposed and confirmed. In this account the preparation and applications of polymer-supported Raney catalysts along with the corresponding models will be reviewed.

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The effect of surface acidic and basic properties on the hydrogenation of aromatic rings over the supported nickel catalysts

Cited by 77 publications

References 89 publications

Selective Nickel‐Catalyzed Conversion of Model and Lignin‐Derived Phenolic Compounds to Cyclohexanone‐Based Polymer Building Blocks

Selective Nickel‐Catalyzed Conversion of Model and Lignin‐Derived Phenolic Compounds to Cyclohexanone‐Based Polymer Building Blocks

Effect of Support Acidic Properties on Sulfur Tolerance of Pd Catalysts for Partial Hydrogenation of Rapeseed Oil‐Derived FAME

Polymer-Supported Raney Nickel Catalysts for Sustainable Reduction Reactions

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