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Cyclization of (+)-citronellal to (−)-isopulegol catalyzed by H3PW12O40/SiO2

2004; Elsevier BV; Volume: 5; Issue: 8 Linguagem: Inglês

10.1016/j.catcom.2004.05.001

1873-3905

Kelly A. da Silva Rocha, Patrícia A. Robles-Dutenhefner, Edésia Martins Barros de Sousa, Elena F. Kozhevnikova, Ivan V. Kozhevnikov, Elena V. Gusevskaya,

Oxidative Organic Chemistry Reactions

Silica-supported heteropoly acid H3PW12O40 (PW) is a very efficient and environmentally benign solid acid catalyst for the liquid-phase cyclization of (+)-citronellal (1). The reaction has been performed in cyclohexane solutions at 15–40 °C yielding (−)−isopulegol (2) and (+)-neo-isopulegol (3) as main products in almost 100% total selectivity at 95–100% conversion, with an 80% selectivity to more valuable product 2. No PW leaching is observed during the reaction, and the catalysts can be recovered and reused several times without loss of activity. Sol–gel silica-included PW catalysts have been prepared and tested in the reaction; these showed no activity, however.