TBD-grafted activated carbon as an efficient solid base catalyst for continuous Knoevenagel reaction

• A novel chloromethylation method for activated carbon modification is applied. • TBD-grafted activated carbon is used for Knoevenagel reaction . • A continuous-flow processing based on micro-packed bed reactor is established. • The catalyst shows a higher TOF (147.7 h −1 ) than other in literature. The development of a highly efficient and stable metal-free solid base catalyst for the Knoevenagel reaction remains a significant challenge. In this study, activated carbon is selected as support material to develop a new base catalyst due to its excellent chemical stability. A novel surface chloromethylation method is applied to modify the activated carbon surface, followed by covalent grafting of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), resulting in a highly effective solid organic base catalyst. A continuous platform based on a micro-packed bed reactor has been optimized for the Knoevenagel reaction. The system achieves excellent space-time yields (19129.4 g P r o k g c a t - 1 h - 1 ) and demonstrates a broad substrate scope. The solid organic base catalyst exhibits a turnover frequency ( TOF ) exceeding 140 h - 1 , surpassing the performance of similar nitrogen-based catalysts reported in literature (7.6–68.0 h - 1 ). Moreover, the catalyst shows no signs of deactivation after more than 23 h of continuous operation with a turnover number ( TON ) exceeding 115, indicating comparable performance reported in literature (29.7–297.2). Catalyst deactivation is primarily attributed to the adsorption of raw materials and products onto the base sites, leading to a gradual loss of catalytic activity.

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Publication Details

Journal
Journal of Catalysis
Published
2025-04-22
DOI
https://doi.org/10.1016/j.jcat.2025.116156
Citations
2
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
Field-Weighted Citation Impact
1.87

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article

TBD-grafted activated carbon as an efficient solid base catalyst for continuous Knoevenagel reaction

Chenghao Zhang, Jisong Zhang, Wangyang Ma, Xueqing Ma et al.
2 citations
Journal of Catalysis
Multicomponent Synthesis of Heterocycles
1.87
article

TBD-grafted activated carbon as an efficient solid base catalyst for continuous Knoevenagel reaction

Chenghao Zhang, Jisong Zhang, Wangyang Ma, Xueqing Ma, Bingqi Xie, Yi Chen
article en
2 citations

Abstract

• A novel chloromethylation method for activated carbon modification is applied. • TBD-grafted activated carbon is used for Knoevenagel reaction . • A continuous-flow processing based on micro-packed bed reactor is established. • The catalyst shows a higher TOF (147.7 h −1 ) than other in literature. The development of a highly efficient and stable metal-free solid base catalyst for the Knoevenagel reaction remains a significant challenge. In this study, activated carbon is selected as support material to develop a new base catalyst due to its excellent chemical stability. A novel surface chloromethylation method is applied to modify the activated carbon surface, followed by covalent grafting of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), resulting in a highly effective solid organic base catalyst. A continuous platform based on a micro-packed bed reactor has been optimized for the Knoevenagel reaction. The system achieves excellent space-time yields (19129.4 g P r o k g c a t - 1 h - 1 ) and demonstrates a broad substrate scope. The solid organic base catalyst exhibits a turnover frequency ( TOF ) exceeding 140 h - 1 , surpassing the performance of similar nitrogen-based catalysts reported in literature (7.6–68.0 h - 1 ). Moreover, the catalyst shows no signs of deactivation after more than 23 h of continuous operation with a turnover number ( TON ) exceeding 115, indicating comparable performance reported in literature (29.7–297.2). Catalyst deactivation is primarily attributed to the adsorption of raw materials and products onto the base sites, leading to a gradual loss of catalytic activity.

Journal of CatalysisVol. 448
Hebei University of Science and Technology (CN), State Key Laboratory of Chemical Engineering (CN), Tsinghua University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 16%
Multicomponent Synthesis of Heterocycles
1.87
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