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Int. J. Mol. Sci. 2010, 11(3), 912-926; doi:10.3390/ijms11030912

Oxidation of Isoeugenol by Salen Complexes with Bulky Substituents

Dipartimento di Scienze dell’Ambiente e del Territorio, Università degli Studi di Milano-Bicocca, Piazza della Scienza, 1, 20126, Milano, Italy
Author to whom correspondence should be addressed.
Received: 21 January 2010 / Revised: 9 February 2010 / Accepted: 28 February 2010 / Published: 4 March 2010
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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The catalytic properties of bulky water-soluble salen complexes in the oxidation of isoeugenol(2-methoxy-4-(1-propenyl) phenol) have been investigated in aqueous ethanol solutions in order to obtain a mixture of polymeric compounds through dehydrogenative polymerization. The average molecular weight of dehydrogenated polymers (DHPs) was monitored by GPC and correlated to reaction conditions such as time, concentration of substrate, concentration of catalyst, type of oxidation agent, etc. The DHP synthesized by adopting the best reaction conditions was characterized by different analytical techniques (GPC, 13C-NMR, 31P-NMR and LC-MS) to elucidate its structure. The lignin-like polymer resulting from isoeugenol radical coupling possesses valuable biological activity and finds applications in a variety of fields, such as packaging industry and cultural heritage conservation.
Keywords: salen; isoeugenol; dehydrogenative polymerization; GPC; NMR salen; isoeugenol; dehydrogenative polymerization; GPC; NMR

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Salanti, A.; Orlandi, M.; Tolppa, E.-L.; Zoia, L. Oxidation of Isoeugenol by Salen Complexes with Bulky Substituents. Int. J. Mol. Sci. 2010, 11, 912-926.

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