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Modified Wacker TBHP oxidation of 1-dodecene

Paper ID Volume ID Publish Year Pages File Format Full-Text
43673 45982 2008 8 PDF Available
Title
Modified Wacker TBHP oxidation of 1-dodecene
Abstract

A higher 1-olefin (1-dodecene) was oxidized to 2-dodecanone and other ketones in a modified Wacker system featured by omitting the use of copper chloride and employing tert-butylhydroperoxide (TBHP) as oxidant. Acetonitrile was the solvent of choice due to its higher selectivity towards 2-dodecanone, the reaction occurring mostly in the interface. A maximum in conversion and selectivity was measured for a ratio [CH3CN]/[1-dodecene] = 10. The temperature abatement enhances the 2-dodecanone selectivity (61% at 40 °C) because of the lower extent of the competing isomerization reactions. An optimum in 2-dodecanone selectivity was found for a [TBHP]/[1-dodecene] ratio = 7. The use of H2O2 as oxidant led towards slower oxidation rates than TBHP. Other palladium salts (PdSO4 and Pd(CH3COO)2) and several R–CN solvents (propionitrile, benzonitrile, isobutyronitrile) yielded lower performances than palladium chloride and acetonitrile, respectively. On the contrary, β-cyclodextrin, a phase transfer catalyst, improved the selectivity towards 2-dodecanone.

Graphical abstractA higher 1-olefin (1-dodecene) was oxidized to 2-dodecanone and other ketones in a modified Wacker system featured by omitting the use of copper chloride and employing tert-butyl hydroperoxide (TBHP) as oxidant. Acetonitrile was the chosen solvent due to its higher selectivity towards 2-dodecanone. At 40 °C, ∼90% conversion with 61% selectivity towards 2-dodecanone was attained after 3 h of reaction.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Palladium chloride; Wacker oxidation; tert-Butylhydroperoxide; 2-Dodecanone; Acetonitrile
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 335, Issue 2, 8 February 2008, Pages 137–144
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