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Acidic Magnetic Biocarbon-Enabled Upgrading of Biomass-Based Hexanedione into Pyrroles

Zhimei Li1, Kuan Tian2, Keping Wang2, Zhengyi Li2, Haoli Qin1,*, Hu Li2,*

1 School of Chemistry and Materials Science, Guizhou Normal University, Guiyang, 550001, China
2 National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, State-Local Joint Laboratory for Comprehensive Utilization of Biomass, Center for R&D of Fine Chemicals of Guizhou University, Guiyang, 550025, China

* Corresponding Authors: Haoli Qin. Email: email; Hu Li. Email: email

(This article belongs to the Special Issue: Biochar Based Materials for a Green Future)

Journal of Renewable Materials 2023, 11(11), 3847-3865. https://doi.org/10.32604/jrm.2023.030122

Abstract

Sustainable acquisition of bioactive compounds from biomass-based platform molecules is a green alternative for existing CO2-emitting fossil-fuel technologies. Herein, a core–shell magnetic biocarbon catalyst functionalized with sulfonic acid (Fe3O4@SiO2@chitosan-SO3H, MBC-SO3H) was prepared to be efficient for the synthesis of various N-substituted pyrroles (up to 99% yield) from bio-based hexanedione and amines under mild conditions. The abundance of Brønsted acid sites in the MBC-SO3H ensured smooth condensation of 2,5-hexanedione with a variety of amines to produce N-substituted pyrroles. The reaction was illustrated to follow the conventional PallKnorr coupling pathway, which includes three cascade reaction steps: amination, loop closure and dehydration. The prepared MBC-SO3H catalyst could effectively activate 2,5-hexanedione, thus weakening the dependence of the overall conversion process on the amine nucleophilicity. The influence of different factors (e.g., reaction temperature, time, amount of catalyst, molar ratio of substrates, and solvent type) on the reaction activity and selectivity were investigated comprehensively. Moreover, the MBC-SO3H possessed excellent thermochemical stability, reusability, and easy separation due to the presence of magnetic core-shell structures. Notably, there was no activity attenuation after 5 consecutive catalytic experiments. This work demonstrates a wide range of potential applications of developing functionalized core-shell magnetic materials to construct bioactive backbones from biomass-based platform molecules.

Graphical Abstract

Acidic Magnetic Biocarbon-Enabled Upgrading of Biomass-Based Hexanedione into Pyrroles

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APA Style
Li, Z., Tian, K., Wang, K., Li, Z., Qin, H. et al. (2023). Acidic magnetic biocarbon-enabled upgrading of biomass-based hexanedione into pyrroles. Journal of Renewable Materials, 11(11), 3847-3865. https://doi.org/10.32604/jrm.2023.030122
Vancouver Style
Li Z, Tian K, Wang K, Li Z, Qin H, Li H. Acidic magnetic biocarbon-enabled upgrading of biomass-based hexanedione into pyrroles. J Renew Mater. 2023;11(11):3847-3865 https://doi.org/10.32604/jrm.2023.030122
IEEE Style
Z. Li, K. Tian, K. Wang, Z. Li, H. Qin, and H. Li "Acidic Magnetic Biocarbon-Enabled Upgrading of Biomass-Based Hexanedione into Pyrroles," J. Renew. Mater., vol. 11, no. 11, pp. 3847-3865. 2023. https://doi.org/10.32604/jrm.2023.030122



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