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  • Adaptive organic nanoparticles of a teflon-coated iron (III) porphyrin catalytically activate dioxygen for cyclohexene oxidation.

Adaptive organic nanoparticles of a teflon-coated iron (III) porphyrin catalytically activate dioxygen for cyclohexene oxidation.

Macromolecular rapid communications (2012-04-21)
Amit Aggarwal, Sunaina Singh, Jacopo Samson, Charles Michael Drain
ABSTRACT

Self-organized organic nanoparticles (ONP) are adaptive to the environmental reaction conditions. ONP of fluorous alkyl iron(III) porphyrin catalytically oxidize cyclohexene to the allylic oxidation products. In contrast, the solvated metalloporphyrin yields both allylic oxidation and epoxidation products. The ONP system facilitates a greener reaction because about 89% reaction medium is water, molecular oxygen is used in place of synthetic oxidants, and the ambient reaction conditions used require less energy. The enhanced catalytic activity of these ONP is unexpected because the metalloporphyrins in the nanoaggregates are in the close proximity and the TON should diminish by self-oxidative degradation. The fluorous alkyl chain stabilizes the ONP toward self-oxidative degradation.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Cyclohexene, inhibitor-free, ReagentPlus®, 99%
Supelco
Cyclohexene, analytical standard, ≥99.5% (GC)
Sigma-Aldrich
Cyclohexene, contains 100 ppm BHT as inhibitor, ≥99.0%