Stereoselective Aromatic Ring Hydrogenation over Supported Rhodium Catalysts in Supercritical Carbon Dioxide Solvent

M Shirai; N Hiyoshi; C V Rode

doi:10.1002/tcr.201800128

Stereoselective Aromatic Ring Hydrogenation over Supported Rhodium Catalysts in Supercritical Carbon Dioxide Solvent

Chem Rec. 2019 Sep;19(9):1926-1934. doi: 10.1002/tcr.201800128. Epub 2018 Dec 28.

Authors

M Shirai¹, N Hiyoshi², C V Rode³

Affiliations

¹ Faculty of Science and Technology, Iwate University, 4-3-5, Ueda, Morioka, Iwate, 020-8551, Japan.
² Research Institute for Chemical Process Technology, Advanced Institute of Science and Technology (AIST), 4-2-1, Nigatake, Miyagino, Sendai, 983-8551, Japan.
³ Chemical Engineering and Process Division, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune, 411008, India.

PMID: 30592372
DOI: 10.1002/tcr.201800128

Abstract

The combination of supported rhodium metal catalysts and supercritical carbon dioxide solvent was effective for the stereoselective ring hydrogenations of aromatic compounds at low temperature. Higher solubility of hydrogen in supercritical carbon dioxide provides higher concentration of hydrogen on the rhodium surface, but lower that of the intermediate on rhodium surface, which suppresses the flipping of surface intermediate, leading to higher catalyst activities and cis selectivities to the corresponding ring-hydrogenated products as compared with those in organic solvents.

Keywords: hydrogenation; rhodium catalyst; stereoselectivity; supercritical carbon dioxide.

Publication types

Review