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Supported rhodium nanoparticles obtained by Metal Vapour Synthesis as catalysts in the preparation of valuable organic compounds

Paper ID Volume ID Publish Year Pages File Format Full-Text
43283 45961 2008 9 PDF Available
Title
Supported rhodium nanoparticles obtained by Metal Vapour Synthesis as catalysts in the preparation of valuable organic compounds
Abstract

Rhodium nanoparticles, derived from mesitylene-solvated rhodium atoms, deposited on γ-Al2O3, are excellent catalysts for the selective hydrogenation of the double bond in α,β-unsaturated carbonyl compounds. The low metal loading Rh on γ-Al2O3 catalyst, containing trioctylamine, TOA, as stabilizing agent of the metal nanoparticles, Rh(TOA)/γ-Al2O3, 0.1 wt.% Rh, showed the highest catalytic activity. Using this catalyst 4-(6,-methoxy-2,-naphthyl)-3-buten-2-one was reduced to the anti-inflammatory drug 4-(6,-methoxy-2,-naphthyl)-butan-2-one, Nabumetone™, with complete selectivity and under mild reaction conditions (room temperature, atmospheric pressure of hydrogen). Similarly, 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene was hydrogenated with high selectivity (85%) to 2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, precursor of antitumor anthracyclinic compounds, which was obtained chemically pure by crystallization. No leaching of rhodium was observed. The catalyst was completely recovered and, if reused, it works without loss of activity. 1H NMR DOSY analysis of the Rh(TOA)/mesitylene solution evidenced the presence of nanoparticles with a diameter of about 1.1 nm.

Graphical abstractThe low metal loading Rh on γ-Al2O3 catalyst, containing trioctylamine, TOA, derived from mesitylene-solvated rhodium atoms, Rh(TOA)/γ-Al2O3, 0.1 wt.% Rh, showed a high catalytic activity and selectivity in the hydrogenation of 4-(6-methoxy-2-naphthyl)-3-buten-2-one and of 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene to 4-(6-methoxy-2-naphthyl)-butan-2-one, Nabumetone™, and to 2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, an anti-inflammatory drug, precursor of antitumor anthracyclinic compounds, respectively, at room temperature and atmospheric pressure of hydrogen. No leaching of rhodium was observed. The catalyst was completely recovered and, if reused, it works without loss of activity. 1H NMR DOSY analysis of the Rh(TOA)/mesitylene solution evidenced the presence of nanoparticles with a diameter of about 1.1 nm.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Supported rhodium nanoparticles; Metal Vapour Synthesis; Selective hydrogenation; α,β-Unsaturated ketones; 1H NMR DOSY analysis
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Supported rhodium nanoparticles obtained by Metal Vapour Synthesis as catalysts in the preparation of valuable organic compounds
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 339, Issue 1, 15 April 2008, Pages 84–92
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us