Acetophenone Hydrogenation on Polymer–Palladium Catalysts. The Effect of Polymer Matrix

Drelinkiewicza, A.; Waksmundzka, Anna; Makowski, Wacław; Sobczak, Janusz W.; Król, A.; Ziȩba, A.

doi:10.1023/b:catl.0000020539.31128.d4

Cited by 84 publications

(52 citation statements)

References 34 publications

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“…Several authors report for this reaction that the rate of AP conversion depends on the properties of organic solvents used. [7][8][9][10][11] The group of Marchi et al investigated the selective hydrogenation of AP with a Ni/SiO2 catalyst in 10 organic solvents including protic polar, aprotic polar, and aprotic apolar ones. 12,13 They found that the rate of AP hydrogenation was even larger in cyclohexane than in aprotic polar solvents; the latter solvents were suggested to have strong interactions with the catalyst, as indicated by adsorption enthalpies, blocking its active sites.…”

Section: Introductionmentioning

confidence: 99%

Solvent effects in heterogeneous selective hydrogenation of acetophenone: differences between Rh/C and Rh/Al₂O₃ catalysts and the superiority of water as a functional solvent

et al. 2015

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Selective hydrogenation of acetophenone (AP) to 1-phenylethanol (PhE) was investigated over Rh/Al2O3 and Rh/C catalysts in 13 solvents including water and conventional organic solvents. Strong solvent effects on the overall rate of AP conversion were observed in different manners depending on the catalysts used. The conversion obtained is correlated with hydrogen-bond-donation (HBD) capability for Rh/C but with hydrogenbond-acceptance (HBA) capacity for Rh/Al2O3. The solvent effects should result from interactions between the carbonyl group of AP and the solvent molecules through hydrogen bonding for Rh/C and from those between the solvent molecules and the catalyst surface for Rh/Al2O3 having HBD hydroxyl groups on its surface. Water is the most effective functional solvent in the selective hydrogenation of AP for C and Al2O3-supported Rh catalysts due to its high HBD capability () and low HBA capability (), respectively. For the hydrogenation with Rh/Al2O3 in water, its large polarity/polarizability index (*) may contribute to the high selectivity to PhE.

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Section: Introductionmentioning

confidence: 99%

Solvent effects in heterogeneous selective hydrogenation of acetophenone: differences between Rh/C and Rh/Al₂O₃ catalysts and the superiority of water as a functional solvent

et al. 2015

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“…The hydrogenation of AP is usually performed on noble metal catalysts such as Ru [2,3], Pd [4,5], Pt [6,7], and so on. The hydrogenation of AP on Pt and Ru catalysts exhibits high selectivity for the hydrogenation of aromatic ring and poor selectivity for PHE [3,6].…”

Section: -Phenylethanol (Phe)mentioning

confidence: 99%

Highly Loaded and Dispersed Ni2P/Al2O3 Catalyst with High Selectivity for Hydrogenation of Acetophenone

Wang¹,

Wang²,

Chen³

et al. 2018

Catalysts

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Highly loaded and dispersed Ni 2 P/Al 2 O 3 catalyst was prepared by the phosphidation of Ni/Al 2 O 3 catalyst with Ni loading of 80 wt.% in liquid phase and compared with the Ni/Al 2 O 3 catalyst for the hydrogenation of acetophenone. X-ray diffraction (XRD), transmission electron microscopy (TEM) and X-ray photoelectron spectroscopy (XPS) etc. were used to characterize the textural and structural properties of the prepared catalysts. It was found that the Ni/Al 2 O 3 and Ni 2 P/Al 2 O 3 catalyst possessed high surface area, loading and dispersion. The Ni/Al 2 O 3 catalyst had higher apparent activity while the Ni 2 P/Al 2 O 3 catalyst had higher intrinsic activity for the hydrogenation of acetophenone (AP). Remarkably, the Ni 2 P/Al 2 O 3 catalyst exhibited high selectivity to 1-phenylethanol, due to repulsion of the phosphorous (P δ− ) for phenyl group and attraction of the nickel (Ni δ+ ) for oxygen atom of carbonyl group, leading to preferential hydrogenation of carbonyl group in acetophenone. The effect of the particle size of the catalyst on the chemical selectivity might be another reason for high selectivity on the Ni 2 P/Al 2 O 3 catalyst.

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“…The effect has usually a complex nature and may be related to reactant-solvent, product-solvent and/or catalyst-solvent interactions [34,36]. Often, the solvent effect is rationalized by correlating the reaction rates and product distribution with solvent polarity or dielectric constant [13,19]. For instance, the activity of Pd/AlPO 4 in hydrogenation of ACT in various alcohols decreases when increasing the alcohol dielectric constant [18].…”

Section: Recovery and Reusementioning

confidence: 99%

“…An exception is Pt/TiO 2 catalyst which exhibit high and selective ability for C=O activation due to the presence of active centers formed as the result of strong metal support interactions [14][15][16]. Palladium supported catalysts, besides being highly reactive toward C=O hydrogenation to C-OH, they catalyze the hydrogenolysis of C-OH to give ethylbenzene as a final product [13,[17][18][19][20]. Ruthenium supported catalysts are also tested in hydrogenation of ACT because of their high ability to hydrogenate carbonyl group in the vicinity of conjugated and isolated double bonds [11,12,21,22].…”

Section: Introductionmentioning

confidence: 99%

Hydrogenation of Acetophenone in the Presence of Ru Catalysts Supported on Amine Groups Functionalized Polymer

et al. 2010

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Liquid phase hydrogenation of acetophenone (ACT) is studied over ruthenium catalysts (1-4 wt% Ru) supported on gel-type methacrylate-styrene resin (FCN) functionalized with C=O, -NH, and -NH 2 groups. Microscopic studies (SEM, STEM) show that the nature of Ru particles depends on the level of Ru doping. At low Ru content (1-2 wt%) ruthenium nano-clusters are formed, while at 4 wt% Ru, metal crystallites of few nanometers in size are observed. Catalytic reactions are performed at mild conditions (atmospheric pressure of hydrogen, 40°C) in biphasic isooctane-water (IO/H 2 O) solvent system, and, for comparison, in a single component solvent (isooctane or ethanol). The use of biphasic IO/H 2 O solvent system results in a dramatic improvement of selectivity. The hydrogenation of C=O in acetophenone dominates over the hydrogenation of aromatic ring, yielding 1-phenylethanol with ca. 80% selectivity. Ru/FCN catalysts exhibit higher selectivity than the reference Ru/Al 2 O 3 . This is tentatively assigned to the steric effects induced by the polymer network on migrating reactant molecules. Advantageous influence of biphasic IO/H 2 O solvent system has been attributed to the solvation of phenyl ring of acetophenone by non-polar isooctane, which facilitates the interaction with the catalyst surface via carbonyl group and leads to the preferential reduction to 1-phnenylethanol.

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Acetophenone Hydrogenation on Polymer–Palladium Catalysts. The Effect of Polymer Matrix

Cited by 84 publications

References 34 publications

Solvent effects in heterogeneous selective hydrogenation of acetophenone: differences between Rh/C and Rh/Al₂O₃ catalysts and the superiority of water as a functional solvent

Solvent effects in heterogeneous selective hydrogenation of acetophenone: differences between Rh/C and Rh/Al₂O₃ catalysts and the superiority of water as a functional solvent

Highly Loaded and Dispersed Ni2P/Al2O3 Catalyst with High Selectivity for Hydrogenation of Acetophenone

Hydrogenation of Acetophenone in the Presence of Ru Catalysts Supported on Amine Groups Functionalized Polymer

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Acetophenone Hydrogenation on Polymer–Palladium Catalysts. The Effect of Polymer Matrix

Cited by 84 publications

References 34 publications

Solvent effects in heterogeneous selective hydrogenation of acetophenone: differences between Rh/C and Rh/Al2O3 catalysts and the superiority of water as a functional solvent

Solvent effects in heterogeneous selective hydrogenation of acetophenone: differences between Rh/C and Rh/Al2O3 catalysts and the superiority of water as a functional solvent

Highly Loaded and Dispersed Ni2P/Al2O3 Catalyst with High Selectivity for Hydrogenation of Acetophenone

Hydrogenation of Acetophenone in the Presence of Ru Catalysts Supported on Amine Groups Functionalized Polymer

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Solvent effects in heterogeneous selective hydrogenation of acetophenone: differences between Rh/C and Rh/Al₂O₃ catalysts and the superiority of water as a functional solvent

Solvent effects in heterogeneous selective hydrogenation of acetophenone: differences between Rh/C and Rh/Al₂O₃ catalysts and the superiority of water as a functional solvent