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One-pot synthesis of naturanol from α-pinene oxide on bifunctional heterogeneous catalysts: Part II. The reaction

Paper ID Volume ID Publish Year Pages File Format Full-Text
43581 45978 2007 9 PDF Available
Title
One-pot synthesis of naturanol from α-pinene oxide on bifunctional heterogeneous catalysts: Part II. The reaction
Abstract

Bifunctional Pt–Sn/SiO2 catalysts described in the Part I, prepared by co-impregnation varying the Pt and Sn loading and the Sn/Pt ratio, have been tested in the one-pot synthesis of α-campholenic alcohol (naturanol) from α-pinene oxide. The process involves the sequential isomerization of the substrate into α-campholenic aldehyde and the subsequent hydrogenation of this intermediate to naturanol. In this Part II, a kinetic investigation of the catalytic process is reported.First, the isomerization and hydrogenation steps were studied separately. Results obtained indicate that the role of tin in the Pt–Sn/SiO2 catalysts formulation is crucial, affecting strongly the activity and/or selectivity in both steps. In the isomerization step, the catalytic activity increases linearly with tin loading whereas the selectivity to campholenic aldehyde remains essentially unchanged. In the second step, high tin loadings increase the selectivity to naturanol but a careful control on the Sn/Pt ratio is necessary to obtain a satisfactory hydrogenation rate, because for Sn/Pt > 1 the catalytic activity falls out dramatically.The overall transformation of α-pinene oxide into naturanol was then investigated. It was found that the isomerization of α-pinene oxide to campholenic aldehyde is the step limiting the naturanol yield. Moreover, kinetic tests have shown that the ratio between the isomerization and hydrogenation rate is the other critical factor in order to synthesize naturanol in high yield. Optimizing the formulation of the Pt–Sn/SiO2 catalysts, a maximum naturanol yield of about 60% was obtained.

Graphical abstractBifunctional Pt–Sn/SiO2 catalysts have been tested in the one-pot synthesis of α-campholenic alcohol (naturanol, NAT) from α-pinene oxide. The process involve the sequential isomerization of the substrate into α-campholenic aldehyde and its subsequent hydrogenation to naturanol. Optimizing the formulation of the Pt–Sn/SiO2 catalyst, a maximum naturanol yield of about 60% was obtained. Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
α-Pinene oxide; Naturanol; Isomerization; Hydrogenation; One-pot synthesis; Pt–Sn catalysts
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One-pot synthesis of naturanol from α-pinene oxide on bifunctional heterogeneous catalysts: Part II. The reaction
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 325, Issue 1, 30 May 2007, Pages 25–33
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
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