Hydroesterification of 2-vinyl-6-methoxynaphthalene using palladium complexes containing chelating nitrogen ligands

TitleHydroesterification of 2-vinyl-6-methoxynaphthalene using palladium complexes containing chelating nitrogen ligands
Publication TypeJournal Article
Year of Publication2009
AuthorsAtla, SB, Kelkar, AA, Chaudhari, RV
JournalJournal of Molecular Catalysis A-Chemical
Date PublishedJUL
KeywordsCarbonylation, Hydroesterification, Naproxen, Palladium complex, Polymer of VMN, Promoters

Hydroesterification of 2-vinyl-6-methoxynaphthalene (VMN) to methyl ester of 6-methoxy naphthyl propionic acid (ester of naproxen) has been investigated using palladium complexes containing the chelating N(boolean AND)O and N(boolean AND)N ligands (pyridine-2-carboxylate, 2-acetylpyridine, 2-pyridine-carboxaldehyde, and bipyridine) as catalysts. Palladium complex containing 2-acetylpyridine as the ligand was found to be superior to other Pd-complexes. Both acid and halide promoters were necessary for high activity and selectivity. As an acid promoter, benzenesulfonic acid was found to be more effective compared to p-toluenesulfonic acid. Formation of ether 2-methoxy-6-(1-methoxyethyl)naphthalene and a polymer of VMN was observed in all the reactions. It was observed that active catalytic species generated during carbonylation reaction was responsible for the polymer formation. The effect of various parameters such as solvents, CO pressure, and alcohols on the catalytic activity as well as the selectivity was investigated. The turnover frequency using the complex Pd(acpy)(PPh(3))(OTs)(2) (acpy = 2-acetylpyridine) catalyst was found to be 42 h(-1), which is the highest for the hydroesterification of VMN. (C) 2009 Elsevier B.V. All rights reserved.

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Chemical Engineering & Process Development