Microporous Zeolites as Catalysts for the Preparation of Decyl Glucoside from Glucose with 1-Decanol by Direct Glucosidation

Kyong-Hwan Chung,Young-Kwon Park,Hyunwoong Park,Sang-Chul Jung,Ki-Joon Jeon

doi:10.3390/catal6120216

Kyong-Hwan Chung, Young-Kwon Park + Show 3 more

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https://doi.org/10.3390/catal6120216

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Abstract

The catalytic properties of microporous zeolite catalysts were evaluated in the synthesis of decyl glucoside from glucose with 1-decanol by direct glucosidation. The effects of the acidic properties and pore structure of the zeolite catalysts on the glucose conversions and decyl glucoside yields were investigated. The conversions of glucose on the H+ ion-exchanged FAU, MFI, and BEA zeolite catalysts were above 70%. The conversion increased with decreasing acid strength of the catalysts. The highest conversion and yield of decyl glucoside were exhibited on the H-FAU(3) zeolite catalyst. The catalytic activities were enhanced with increasing amounts of acid sites. The selectivity of decyl glucopyranoside increased with decreasing Si/Al values for the same zeolite catalysts. The pore structure of H-FAU zeolite would allow sufficient spatial restriction to produce decyl glucopyranoside through the isomerization of decyl glucofuranoside into decyl glucopyranoside in its extensive pore channels. The selectivities of the decyl glucoside isomers relied significantly on the restricted transition state to the primary products due to their pore topologies.

Highlights

Alkyl phenol ethoxylates and linear alkylbenzene sulfonates have been used as major surfactants.They degrade in the aerobic conditions found in sewage treatment plants and in the metabolite, nonylphenol, which has been found to be an endocrine disruptor [1]
The X-ray diffraction (XRD) patterns of the zeolites were in good agreement with those published in the literature [25]
The H-FAU(3) catalyst showed the highest decyl glucopyranoside (DGP) selectivity of the catalysts. This is attributed to its high pore volume and numerous weak acid sites, leading the production of DGP

Summary

Introduction

Alkyl phenol ethoxylates and linear alkylbenzene sulfonates have been used as major surfactants. They degrade in the aerobic conditions found in sewage treatment plants and in the metabolite, nonylphenol, which has been found to be an endocrine disruptor [1]. It has been established recently that nonylphenol has antiandrogenic activity, which means that it affects the appropriate functioning of the androgens that are necessary for the normal growth and reproductive organs of males [5]. Long-chain alkyl glucosides have excellent surfactant properties with biodegradability and low toxicity [6,7]. They have recently been considered as alternative surfactants to alkylphenols [8]

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