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Hafnium-Doped Mesoporous Silica as Efficient Lewis Acidic Catalyst for Friedel–Crafts Alkylation Reactions

The development of an efficient solid catalyst for Friedel–Crafts (FC) reactions is of great importance to organic synthetic chemistry. Herein, we reported the hafnium-doped mesoporous silica catalyst Hf/SBA-15 and its first use for Friedel–Crafts alkylation reactions. Catalysts with different Si/Hf...

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Autores principales: Huang, Yao-Bing, Luo, Yu-Jia, Wang, Fei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6723505/
https://www.ncbi.nlm.nih.gov/pubmed/31387334
http://dx.doi.org/10.3390/nano9081128
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author Huang, Yao-Bing
Luo, Yu-Jia
Wang, Fei
author_facet Huang, Yao-Bing
Luo, Yu-Jia
Wang, Fei
author_sort Huang, Yao-Bing
collection PubMed
description The development of an efficient solid catalyst for Friedel–Crafts (FC) reactions is of great importance to organic synthetic chemistry. Herein, we reported the hafnium-doped mesoporous silica catalyst Hf/SBA-15 and its first use for Friedel–Crafts alkylation reactions. Catalysts with different Si/Hf ratios were prepared and characterized, among which Hf/SBA-15(20) (Si/Hf = 20:1) was the most active catalyst, offering up to 99.1% benzylated product under mild reaction conditions. The influences of reaction conditions on the product were systematically investigated and compared. Pyridine-IR characterization of the catalyst showed that Lewis acid formed the primary active sites for the Friedel–Crafts alkylation reaction. X-ray photoelectron spectroscopy (XPS) characterization revealed that the electron shift from the Hf center to the silica framework resulted in a more active Lewis metal center for FC reactions. Moreover, the catalyst was successfully applied to the alkylation reaction with different alcohols and aromatic compounds. Finally, the Hf/SBA-15(20) catalyst also showed good recyclability in the recycling runs, demonstrating its high potential of being used for large scale FC reactions in the industry.
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spelling pubmed-67235052019-09-10 Hafnium-Doped Mesoporous Silica as Efficient Lewis Acidic Catalyst for Friedel–Crafts Alkylation Reactions Huang, Yao-Bing Luo, Yu-Jia Wang, Fei Nanomaterials (Basel) Article The development of an efficient solid catalyst for Friedel–Crafts (FC) reactions is of great importance to organic synthetic chemistry. Herein, we reported the hafnium-doped mesoporous silica catalyst Hf/SBA-15 and its first use for Friedel–Crafts alkylation reactions. Catalysts with different Si/Hf ratios were prepared and characterized, among which Hf/SBA-15(20) (Si/Hf = 20:1) was the most active catalyst, offering up to 99.1% benzylated product under mild reaction conditions. The influences of reaction conditions on the product were systematically investigated and compared. Pyridine-IR characterization of the catalyst showed that Lewis acid formed the primary active sites for the Friedel–Crafts alkylation reaction. X-ray photoelectron spectroscopy (XPS) characterization revealed that the electron shift from the Hf center to the silica framework resulted in a more active Lewis metal center for FC reactions. Moreover, the catalyst was successfully applied to the alkylation reaction with different alcohols and aromatic compounds. Finally, the Hf/SBA-15(20) catalyst also showed good recyclability in the recycling runs, demonstrating its high potential of being used for large scale FC reactions in the industry. MDPI 2019-08-05 /pmc/articles/PMC6723505/ /pubmed/31387334 http://dx.doi.org/10.3390/nano9081128 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Huang, Yao-Bing
Luo, Yu-Jia
Wang, Fei
Hafnium-Doped Mesoporous Silica as Efficient Lewis Acidic Catalyst for Friedel–Crafts Alkylation Reactions
title Hafnium-Doped Mesoporous Silica as Efficient Lewis Acidic Catalyst for Friedel–Crafts Alkylation Reactions
title_full Hafnium-Doped Mesoporous Silica as Efficient Lewis Acidic Catalyst for Friedel–Crafts Alkylation Reactions
title_fullStr Hafnium-Doped Mesoporous Silica as Efficient Lewis Acidic Catalyst for Friedel–Crafts Alkylation Reactions
title_full_unstemmed Hafnium-Doped Mesoporous Silica as Efficient Lewis Acidic Catalyst for Friedel–Crafts Alkylation Reactions
title_short Hafnium-Doped Mesoporous Silica as Efficient Lewis Acidic Catalyst for Friedel–Crafts Alkylation Reactions
title_sort hafnium-doped mesoporous silica as efficient lewis acidic catalyst for friedel–crafts alkylation reactions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6723505/
https://www.ncbi.nlm.nih.gov/pubmed/31387334
http://dx.doi.org/10.3390/nano9081128
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AT wangfei hafniumdopedmesoporoussilicaasefficientlewisacidiccatalystforfriedelcraftsalkylationreactions