Oxidation of olefins using atmospheric oxygen atoms initiated by tert-butylhydroperoxide or hydrogen peroxide with silver nanoparticles deposited on MCM-41 as catalysts

• Published in: Green chemistry : an international journal and green chemistry resource : GC Vol. 18; no. 11; pp. 3354 - 3359
• Main Authors: Chen, Zhichao, Luck, Rudy L
• Format: Journal Article
• Language: English
• Published: 2016
• Subjects: Catalysis; Catalysts; Formations; Olefins; Oxidation; Oxygen atoms; Radicals; Silver
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/c5gc03110a

Silver nanosized particles were grown on the surface and in the channels of mesoporous silica (MCM-41) by stirring a mixture of AgNO sub(3) and polyvinylpyrrolidone (PVP) in ethylene glycol in a 1 : 20 weight ratio with MCM-41 for 1 h. The heterogeneous product was analysed by BET surface area and X-ray powder diffraction measurements, as well as TEM images which indicated that 5 to 20 nm sized Ag particles were on the surface of MCM-41. The dried material, suspended in a mixture of 1,2-dichloroethane and acetonitrile and in the presence of tBuOOH held at 80 degree C for 24 h, was capable of the oxidation of the olefins (Z)-cyclooctene, cyclohexene, styrene and indene resulting in a variety of oxidized products. Comparable oxidation was also accomplished in a green solvent mixture consisting of 3% NaCl dissolved in H sub(2)O and tBuOH (1 : 1 by volume). The catalyst was active for five sequential cycles. After the first cycle, H sub(2)O sub(2) instead of tBuOOH could be used as the radical initiator as the Ag nanoparticles were passivated by the formation of AgCl on the surface. This research illustrates a method of oxygen activation allowing for the transfer of an oxygen atom from the atmosphere onto an olefin, presumably viathe formation of a peroxide radical.