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磺化聚苯乙烯泡沫废料作为傅-克型反应的高效催化剂。

Sulfonated polystyrene foam waste as an efficient catalyst for Friedel-Crafts type reactions.

作者信息

Moazzen Behrang, Kamrouz Roya, Khorshidi Alireza

机构信息

Faculty of Chemistry, University of Guilan, P. O. Box: 41335-1914, Rasht, Iran.

出版信息

Sci Rep. 2025 Jan 2;15(1):250. doi: 10.1038/s41598-024-83968-2.

DOI:10.1038/s41598-024-83968-2
PMID:39747935
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11697390/
Abstract

The catalytic efficiency of sulfonated polystyrene foam waste (SPS) and sulfonated gamma alumina (SGA) in Friedel-Crafts type reactions was compared. All of the materials were studied using the state-of-the-art characterization techniques. SPS was found to carry a higher load of -SOH functional groups (1.62 mmol H per g) compared to SGA (1.23 mmol H per g), contributing to its slightly higher efficiency in the regioselective ring-opening of 2-(phenoxymethyl)oxirane with indole. Under mild and solvent-free conditions, SPS catalyzed the reaction of various indoles and oxiranes (9 examples) with acceptable yields (55-99%). The catalyst's efficiency was further validated in synthesizing various bis(indolyl)methanes (8 examples, 88-99% yield). Recyclability tests confirmed the stability of SPS over multiple cycles, maintaining significant catalytic activity. This study highlights the potential of SPS as a sustainable and efficient catalyst, offering a greener alternative to conventional methods and promoting the valorization of plastic waste in organic synthesis.

摘要

比较了磺化聚苯乙烯泡沫废料(SPS)和磺化γ-氧化铝(SGA)在傅克型反应中的催化效率。所有材料均采用最先进的表征技术进行研究。结果发现,与SGA(每克1.23毫摩尔氢)相比,SPS负载的-SOH官能团含量更高(每克1.62毫摩尔氢),这使得其在2-(苯氧基甲基)环氧乙烷与吲哚的区域选择性开环反应中效率略高。在温和且无溶剂的条件下,SPS催化了各种吲哚与环氧乙烷(9个实例)的反应,产率可接受(55-99%)。该催化剂在合成各种双(吲哚基)甲烷(8个实例,产率88-99%)中的效率得到进一步验证。可回收性测试证实了SPS在多个循环中的稳定性,保持了显著的催化活性。这项研究突出了SPS作为一种可持续且高效催化剂的潜力,为传统方法提供了更绿色的替代方案,并促进了有机合成中塑料废料的增值利用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bdd/11697390/7b8b84fcae58/41598_2024_83968_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bdd/11697390/49fdf1b4d39c/41598_2024_83968_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bdd/11697390/0b92c727a67e/41598_2024_83968_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bdd/11697390/a7e7c6c704e9/41598_2024_83968_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bdd/11697390/dfbabdd1d231/41598_2024_83968_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bdd/11697390/2e169313360a/41598_2024_83968_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bdd/11697390/7b8b84fcae58/41598_2024_83968_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bdd/11697390/49fdf1b4d39c/41598_2024_83968_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bdd/11697390/0b92c727a67e/41598_2024_83968_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bdd/11697390/a7e7c6c704e9/41598_2024_83968_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bdd/11697390/dfbabdd1d231/41598_2024_83968_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bdd/11697390/2e169313360a/41598_2024_83968_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8bdd/11697390/7b8b84fcae58/41598_2024_83968_Fig4_HTML.jpg

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