Metathesis of cardanol over Ru catalysts supported on mesoporous molecular sieve SBA-15

摘要

The Hoveyda-Grubbs type Zhan catalysts (ZC) and Grubbs second generation catalyst (GII) were immobilized on SBA-15 mesoporous molecular sieve by non-covalent interactions and phosphine linkers, respectively. Both hybrid catalysts proved to be highly active and selective in cardanol metathesis and cardanol cross-metathesis with ethene and cis-1,4-diacetoxy-2-butene (DAB). GII/SBA-15 was less active than ZC/SBA-15, however, Ru leaching was significantly lower for GII/SBA-15 (0.5%) than for ZC/SBA-15 (2.5%). In ethenolysis of cardanol, 3-(non-8-enyl)phenol was isolated as a major product. In cross-metathesis with DAB 9-(3-hydroxyphenyl)non-2-enyl acetate and non-2-enyl acetate were formed with high selectivity. Easy catalyst-product separation and low Ru leaching provide the products (applicable as detergent precursors and fragrance and flavor agents) free from the catalyst residue.