Abstract
Development of highly active heterogeneous catalysts is an effective strategy for modern organic synthesis chemistry. In this work, acidic mesoporous zeolite ZSM-5 (HZSM-5-M), acidic-free mesoporous zeolite TS-1 (TS-1-M), and basic ETS-10 zeolite supported metal Cu catalysts were prepared to investigate their catalytic performances in the hydroxysulfurization of styrenes with diaryl disulfides. The effect of pore size and acidities of the supports, as well as the Cu species electronic properties of the catalysts on reaction activity were investigated. The results show that Cu+ and Cu2+ binded on HZSM-5-M show the highest activity and product selectivity for the desired β-hydroxysulfides compounds.
Highlights
Introduction βHydroxysulfides are important intermediates for synthesis of various valuable biological active compounds, pharmaceuticals, and natural products, such as renin and leukotrienes [1,2,3]
Traditional methods for the preparation of β-hydroxysulfides involve the ring opening of epoxides with sulfenyl that comes from thiols in the homogenous metal-catalyzed reaction systems [4,5,6]
Various functional organic ligands were added into reaction mixtures for modification of the metals’ electronic property to improve the reaction activity [7,8]; irradiation or peroxides were used in the reaction systems for the generation of sulfenyl radicals, improving the product selectivity [3,9,10]
Summary
Water glass is a sodium silicate (Na2O·4SiO2, SiO2 24.6 wt. %, Na2O 6.8 wt. %) solution, which was purchased from Zhejiang Tongxiang Water Glass Factory (Tongxiang, China). %) solution, which was purchased from Zhejiang Tongxiang Water Glass Factory (Tongxiang, China). The other chemicals, aluminum sulfate (Al2(SO4)3·18H2O, 99%) and tetrapropylammonium hydroxide (TPAOH, 25%), were purchased from Sinopharm Chemical Reagent Co., Ltd. 40 mL acidic aluminum sulfate solution (0.05 mol/L) was added dropwise in to the mixture and stirred for 2 h. The composition of this gel was Al2O3/45SiO2/12Na2O/0.28RCC/ 0.2TPAOH/2049H2O. After this gel hydrothermal treatment at 170 ◦C for 48 h in Teflon-coated stainless-steel autoclave, the sample was collected by filtrating, washing with water, drying at 100 ◦C for 12 h, and calcination at 550 ◦C for 5 h in air. ZSM-5-M and ZSM-5 samples were ion-exchanged with NH4NO3 (1 M) solution for 4 h at 80 ◦C, and was collected by filtration, drying at 100 ◦C for 12 h, and calcination in air at 500 ◦C for 4 h for transformation to H-form samples (HZSM-5-M and HZSM-5)
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