Quaternary ammonium functionalized polyacrylonitrile fiber supported phosphotungstic acid as efficient heterogeneous catalyst: Hydrophobic tuning of the catalytic microenvironment

磷钨酸 催化作用 化学 聚丙烯腈 胺气处理 有机化学 烷基化 废止 高分子化学 聚合物
作者
Jian Xiao,Lu Wang,Jiaoru Ran,Jingyan Zhao,Ning Ma,Minli Tao,Wenqin Zhang
出处
期刊:Journal of Cleaner Production [Elsevier]
卷期号:274: 122473-122473 被引量:32
标识
DOI:10.1016/j.jclepro.2020.122473
摘要

Thirteen novel amine or quaternary ammonium functionalized polyacrylonitrile fiber (PANF) supported phosphotungstic acid (PTA) catalysts were designed and prepared, and their catalytic activities were screened by choosing condensation/annulation tandem synthesis of 2,3-dihydroquinazolin-4(1H)-one compound via C–N bond formation between 2-aminobenzamide and p-chlorobenzaldehyde as a model reaction. By adjusting the functionality and hydrophobic/hydrophilic property of the amine/ammonium structure as well as the density of PTA sites, the fiber catalyst CAT-12 prepared from quaternary ammonium functionalized PANF containing benzyl group with high PTA loading achieved the best catalytic activity for most reactions in water. The CAT-12 can be easily separated from the reaction system and recycled for 7 times without significant loss of catalytic activity. Moreover, the reaction proceeded smoothly in gram scale and gave nearly quantitative yield using this efficient, eco-friendly and easily recyclable catalyst with great industrial potential which was also demonstrated in Friedel-Crafts alkylation of indoles with β-nitrostyrene. Vivid PTA immobilization processes and the corresponding "catch-catalyze" catalytic modes were further schematically described to address the effect of microenvironment-tuning on immobilization and catalysis, and accordingly the possible catalytic mechanisms of the two reactions were proposed.
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