p -Toluenesulfonic acid functionalized imidazole ionic liquids encapsulated into bismuth SBA-16 as high-efficiency catalysts for Friedel-Crafts acylation reaction

• Published in: Dalton transactions : an international journal of inorganic chemistry Vol. 50; no. 17; pp. 5871 - 5882
• Main Authors: Gao, Guofang, Zhao, Qian, Yang, Cheng, Jiang, Tingshun
• Format: Journal Article
• Language: English
• Published: England Royal Society of Chemistry 04.05.2021
• Subjects: Acylation; Anisole; Bismuth; Catalysts; Chemical synthesis; Conversion; Design of experiments; Friedel-Crafts reaction; Imidazole; Ionic liquids; Ions; Molecular structure; NMR; Nuclear magnetic resonance; Pore size
• ISSN: 1477-9226; 1477-9234
• DOI: 10.1039/d1dt00355k

Bismuth SBA-16 catalyst was synthesized by the hydrothermal method. Four kinds of p-toluenesulfonic acid functionalized imidazole ionic liquids were prepared by a two-step method and their molecular structures were characterized by 1H NMR and MS. The post-synthesis impregnation method was used to functionalize the Bi(10)-SBA-16 silicon mesoporous material with the ionic liquids and the obtained materials were characterized by FT-IR, XRD, BET, XPS, and TG. The results show that the volume and pore size of SBA-16 were changed by loading Bi and ionic liquids, while the three-dimensional cubic pore structure of SBA-16 was not destroyed. The composite catalyst was evaluated in Friedel-Crafts acylation of anisole with acetic anhydride. The effects of reaction temperature and the ratio of anisole and acylating agent on the acylation of anisole were investigated by experimental design. The results showed that 1.2ILc@Bi(10)-SBA-16 was used as the catalyst, the conversion of anisole was 85.41% and the yield of aromatic ketone was 69.19% under the conditions of a reaction temperature of 100 °C, a catalyst dosage of 0.5 g, a time period of 4 h and a molar ratio of 1 : 1.5. After 5 recycling runs, the reduction in the overall ratio of reactant conversion and product yield did not exceed 7.5%, indicating that 1.2ILc@Bi(10)-SBA-16 has good stability and reusability.