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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

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Title: 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
Authors: Yoshida, Hiroshi Browse this author
Onodera, Yuichi Browse this author
Fujita, Shin-ichiro Browse this author
Kawamori, Hiroki Browse this author
Arai, Masahiko Browse this author →KAKEN DB
Keywords: hydrogenation
acetophenone
solvent effects
water
Issue Date: 1-Mar-2015
Publisher: ROYAL SOC CHEMISTRY
Journal Title: Green Chemistry
Volume: 17
Issue: 3
Start Page: 1877
End Page: 1883
Publisher DOI: 10.1039/c4gc02211d
Abstract: 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 hydrogen-bond-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 (a) and low HBA capability (beta), respectively. For the hydrogenation with Rh/Al2O3 in water, its large polarity/polarizability index (pi*) may contribute to the high selectivity to PhE.
Type: article (author version)
URI: http://hdl.handle.net/2115/60514
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 荒井 正彦

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