Limonene oxidation over Ti-MCM-41 and Ti-MWW catalysts with t-butyl hydroperoxide as the oxidant

Alicja Gawarecka,Agnieszka Wróblewska

doi:10.1007/s11144-018-1401-5

Alicja Gawarecka, Agnieszka Wróblewska

Open Access

https://doi.org/10.1007/s11144-018-1401-5

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Abstract

This paper presents the method of limonene epoxidation over Ti-MCM-41 and Ti-MWW catalysts in the presence of t-butyl hydroperoxide as an oxidant. Natural limonene used in the epoxidation process was obtained via steam distillation (97% purity). The purpose of the research was to obtain the highest yield of 1,2-epoxylimonene, but the performed studies showed that the process of limonene epoxidation is more complex because in addition to epoxidation products (1,2-epoxylimonene and its diol which were formed usually in small amount) also the following oxygenated derivatives of limonene are formed: carvone, carveol, and perillyl alcohol (products of allylic oxidation (hydroxylation) at positions 6 and 7 in limonene molecule). Therefore, ultimately, the most favorable conditions for the limonene oxidation process were selected at the highest conversion of limonene and at high values of perillyl alcohol and carveol or one of these two products. Perillyl alcohol and carveol have found numerous applications in medicine, among others, therefore this direction seems to be the most beneficial. This also work presents the short characteristization of the titanium silicate Ti-MCM-41 and Ti-MWW catalysts used in the research, taking into account their structure, properties and applications are presented.

Highlights

Crystalline aluminosilicates from the IA and IIA group are called zeolites
This paper presents the method of limonene epoxidation over Ti-MCM41 and Ti-MWW catalysts in the presence of t-butyl hydroperoxide as an oxidant
The purpose of the research was to obtain the highest yield of 1,2epoxylimonene, but the performed studies showed that the process of limonene epoxidation is more complex because in addition to epoxidation products (1,2epoxylimonene and its diol which were formed usually in small amount) the following oxygenated derivatives of limonene are formed: carvone, carveol, and perillyl alcohol (products of allylic oxidation at positions 6 and 7 in limonene molecule)

Summary

Introduction

Zeolites in aluminosilicate forms for a long time have been used as a solid–acid catalyst in petrochemical industry. An example is Faujasite, which is wildly used as a catalyst in catalytic cracking process. It replaced commonly used amorphous silica–alumina catalysts [1,2,3]. The Ti-MWW material is one of the latest titanium–silicate catalysts. It was prepared by the method of hydrothermal synthesis using hexamethyleneimine as the structure-directing agent (template). The catalytic properties of Ti-MWW catalyst were checked by Kim et al [5] in 1-hexene epoxidation, in the oxidative desulfurization (ODS) of model sulfur compounds, in the direct conversion of methanol and in allyl chloride (ALC) epoxidation.

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