Phosphotungstic acid encapsulated in USY zeolite as catalysts for the synthesis of cyclohexylbenzene

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Phosphotungstic acid encapsulated in USY zeolite as catalysts for the synthesis of cyclohexylbenzene Yufei Yang1 · Yue You1 · Junyan Wu1 · Junbo Feng1 · Yadong Zhang1,2 Received: 12 March 2019 / Accepted: 10 September 2020 © Iranian Chemical Society 2020

Abstract  In this work, a new type of catalyst, USY-HPW, was successfully prepared by encapsulating phosphotungstic acid (HPW) into ultra-stable Y zeolite (USY). The obtained catalyst USY-HPW was characterized by various techniques including ­N2 adsorption/desorption isotherms, XRD, SEM, TG-DSC, XPS, ­NH3-TPD, FT-IR, Py-IR. The catalytic properties of USYHPW were evaluated by using a model alkylation reaction of benzene with cyclohexene to form cyclohexylbenzene. The conversion rate of cyclohexene can reach as high as 99.99%. Compared with USY alone, USY-HPW displayed markedly improved selectivity and yield for the target product of cyclohexylbenzene, ca. 5.41% and 8.73%, respectively. Besides, reusability tests indicated the high durability USY-HPW as the yield of cyclohexylbenzene can still reach to 83.50% after eight runs. All these results demonstrate that USY-HPW catalyst has good performances and holds good potential in acid catalyzed organic chemistry. Graphical abstract

Keywords  Ultra-stable Y zeolite (USY) · Phosphotungstic acid · Benzene · Cyclohexene · Cyclohexylbenzene

Introduction

* Yadong Zhang [email protected] 1



School of Chemical Engineering and Energy, Zhengzhou University, Zhengzhou 450001, China



Jiyuan Research Institute, Zhengzhou University, Jiyuan 459000, China

2

Cyclohexylbenzene is an important chemical intermediate with a wide range of applications, for example, as electrolyte additive for overcharge protection of lithium ion battery [1, 2] and the raw material in the synthesis of TFT liquid crystal materials [3]. In addition, the oxidation decomposition of cyclohexylbenzene can afford important chemical substances, such as phenol and cyclohexanone [4], which are critical raw materials for the production of bisphenol A,

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phenolic resin, adipic acid [5], as well as ε-caprolactone [6], adipic acid [7] and caprolactam [8]. As a result, cyclohexylbenzene has attracted more and more attention researchers, and the synthesis of cyclohexylbenzene has become a research hotspot. Basically, synthesis cyclohexylbenzene is mainly divided into three broad categories, including the selective hydrogenation of biphenyl [9], the hydroalkylation of benzene [10–12] and the alkylation reaction of benzene and cyclohexene [13–16], which are summarized in Table 1. Among them, the hydroalkylation of benzene is the most simple and important method. But most of catalysts used in this method are precious metal compounds, and their catalytic conversion efficiencies still remain to be improved. The process of the selective hydrogenation of biphenyl is simple, but it is disappointing that the catalysts for this reaction are immature. In particular, the biphenyl i