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Issue 3, 2011
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Highly active and green aminopropyl-immobilized phosphotungstic acid on mesocellular silica foam for the O-heterocyclization of cycloocta-1,5-diene with aqueous H2O2

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Abstract

The heteropoly phosphotungstic acid, H3PW12O40 (HPW), was successfully immobilized on the surface of MCF, SBA-15 and MCM-41 by means of chemical bonding to aminosilane groups. The as-obtained materials were characterized by N2 sorption, TEM, XRD, FT-IR, 13C-, 29Si-, 31P-MAS NMR and XPS. Characterization results suggest that the surface area decreased after grafting amino groups to silica. The as-prepared HPW-NH2-MCF is highly efficient in the O-heterocyclization of cycloocta-1,5-diene (COD) to 2,6-dihydroxy-9-oxabicyclo[3.3.1] nonane (1) and 2-hydroxy-9-oxabicyclo [3.3.1] nonane-6-one (2) with a COD conversion of 100% and (1 + 2) selectivity up to 98%. It is worth mentioning that this material could be reused six times without any significant loss of activity and selectivity. The good stability can be attributed to the strong interaction between the amino groups on the surface of MCF and HPW anions.

Graphical abstract: Highly active and green aminopropyl-immobilized phosphotungstic acid on mesocellular silica foam for the O-heterocyclization of cycloocta-1,5-diene with aqueous H2O2

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Supplementary files

Article information


Submitted
15 Oct 2010
Accepted
06 Dec 2010
First published
03 Feb 2011

Green Chem., 2011,13, 702-708
Article type
Paper

Highly active and green aminopropyl-immobilized phosphotungstic acid on mesocellular silica foam for the O-heterocyclization of cycloocta-1,5-diene with aqueous H2O2

R. Gao, Q. Zhu, W. Dai and K. Fan, Green Chem., 2011, 13, 702
DOI: 10.1039/C0GC00691B

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