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Catalytic homogeneous oxyfunctionalization with hydrogen peroxide in the presence of a peroxotungstate

Paper ID Volume ID Publish Year Pages File Format Full-Text
43236 45959 2008 8 PDF Available
Title
Catalytic homogeneous oxyfunctionalization with hydrogen peroxide in the presence of a peroxotungstate
Abstract

The tetrahexylammonium (THA) salt of the peroxocomplex [W2O3(O2)4]2− was used as catalyst for the oxidation of cis-cyclooctene, geraniol and cyclooctane, with hydrogen peroxide, in acetonitrile. High catalytic activity for all substrates, with high efficiency of use of hydrogen peroxide, was found. Under the conditions used, the oxidation of cyclooctane gives rise to cyclooctanone, cyclooctanol and cyclooctyl hydroperoxide, with 90% and 97% of conversion after 6 and 12 h, respectively, reaching turnover numbers higher than 600. A possible mechanism for the oxidation of cyclooctane is proposed. The oxidation of cis-cyclooctene gives the corresponding epoxide with 100% conversion after 4 h, whereas geraniol yields mainly the 2,3-epoxide (94% selectivity) with 88% of conversion after 5 h of reaction. The crystal structure of (THA)2[W2O3(O2)4] is reported. The anion has two types of coordinated peroxide ligands, namely symmetrical and unsymmetrical bridging peroxo groups. This study indicates that the peroxocomplex [W2O3(O2)4]2− is catalytically active both in epoxidation reactions in acetonitrile and in the oxyfunctionalization of a cycloalkane.

Graphical abstractThe tetrahexylammonium (THA) salt of the peroxocomplex [W2O3(O2)4]2− was used, in acetonitrile, as catalyst for the oxidation with hydrogen peroxide of cis-cyclooctene, geraniol and cyclooctane. It was found that this peroxocomplex is catalytically active both in epoxidation reactions and in the oxyfunctionalization of a cycloalkane, with high efficiency of use of hydrogen peroxide. The crystal structure of (THA)2[W2O3(O2)4] was determined.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Oxidation; Hydrogen peroxide; Peroxocomplex; Tungsten; Crystal structure
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Catalytic homogeneous oxyfunctionalization with hydrogen peroxide in the presence of a peroxotungstate
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 351, Issue 2, 30 December 2008, Pages 166–173
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us