Epoxidation of Monomaleate with Hydrogen Peroxide Catalyzed by [π-C₅H₅N(CH₂)₁₅CH₃]₃PO₄(WO₃)₄

Abstract

In the study, epoxidation of dodecanol monomaleate, hexadecanol monomaleate, and octadecanol monomaleate were carried out using [π-C₅H₅N(CH₂)₁₅CH₃]₃PO₄(WO₃)₄ as phase-transfer catalyst with 30% hydrogen peroxide as oxidant. The experimental results showed that [π-C₅H₅N(CH₂)₁₅CH₃]₃PO₄(WO₃)₄ had excellent catalytic effect on translating C=C double-bond into an epoxy group and had a good yield rate. The synthesized epoxides of decanol monomaleate, hexadecanol monomaleate, and octadecanol monomaleate have enormous potential application in organic synthesis, and they could be readily transformed into various synthetically useful intermediates or final products in many fields of chemistry.

Keywords:

• Epoxidation
• monomaleate
• phase-transfer catalyst

ACKNOWLEDGMENT

Financial support from the Shandong Province Municipal Major Science and Technology Special Project (2006GG1108097-10) is gratefully acknowledged.

Notes

Note: Reaction condition: pH 5.0, 60 °C, reation time 2 h, and the amount of 2a–c was 1.0 mmol respectively.