Abstract
The rational design of efficient heterogeneous catalysts for Friedel-Crafts acylation reactions is highly desirable for meeting the need for the industrial production of various aromatic ketone compounds and biomass-derived chemicals. Herein, we reported that graphitic carbon wrapped FeCo bimetallic nanoparticles confined in nitrogen-doped carbon nanotubes, which were prepared by pyrolysis of FeCo-based Prussian blue analogue and melamine via a two-stage programmed heating procedure, exhibited excellent catalytic activity and recyclability for the acylation of aromatic compounds with acyl chlorides. The oxidized bimetallic species embedded in the external graphitic carbon shell should be the main active sites for the acylation reaction. The graphitic carbon shell and the carbon nanotube could provide effective protection on the active metal species against leaching through multiple interactions, leading to the formation of a highly active and durable heterogeneous catalyst for the acylation reaction.
Similar content being viewed by others
References
Sartori G., Maggi R., Chemical Reviews, 2011, 111, PR181.
Chalotra N., Sultan S., Shah B. A., Asian J. Org. Chem., 2020, 9, 863.
Alalq I., Nguyen-Phu H., Crossley S., J. Catal., 2023, 426, 222.
Bejblová M., Procházková D., Cejka J., ChemSusChem, 2009, 2, 486.
Gao G. F., Zhao Q., Yang C., Jiang T. S., Dalton Trans., 2021, 50, 5871.
Hu W. H., Liu M. N., Luo Q. X., Zhang J. B., Chen H. Y., Xu L., Sun M., Ma X. X., Hao Q. Q., Chem. Eng. J., 2023, 466, 11.
Tiwari M. S., Yadav G. D., Chem. Eng. J., 2015, 266, 64.
Lu H. Y., Xie J., Wu X. J., Ma Q. L., Cheng J. N., Li Z. L., Hu D. C., Appl. Catal. A: Gen., 2022, 648, 7.
Deka R. C., Deka A., Deka P., Saikia S., Baruah J., Sarma P. J., J. Nanosci. Nanotechnol., 2020, 20, 5153.
Ammar M., Jiang S., Ji S. F., J. Solid State Chem., 2016, 233, 303.
Schiaroli N., Allegri A., Eberle M., Billi S., Guerrini A., Albonetti S., Vaccari A., Tabanelli T., Lucarelli C., ChemSusChem, 2023, 16, 11.
Ly I., Layan E., Picheau E., Chanut N., Nallet F., Bentaleb A., Dourges M. A., Pellenq R. J., Hillard E. A., ACS Appl. Mater. Interfaces, 2022, 14, 13305.
Mu M. M., Chen L. G., Liu Y. L., Fang W. W., Li Y., A. RSC Adv., 2014, 4, 36951.
Li S., Jin C. H., Feng N. D., Deng F., Xiao L. P., Fan J., Catal. Commun., 2019, 123, 54.
Reddy K. R., Venkanna D., Kantam M. L., Bhargava S. K., Srinivasu P., Ind. Eng. Chem. Res., 2015, 54, 7005.
Fang Z., He W., Tu T., Lv N. N., Qiu C. H., Li X., Zhu N., Wan L., Guo K., Chem. Eng. J., 2018, 331, 443.
Chen Y. Q., Yang Y., Zhou Z., Luo W., Liu J. H., Wang F., New J. Chem., 2020, 44, 10492.
Vardon A., Layan E., Louërat F., Nallet F., Bentaleb A., Dourges M. A., Toupance T., Laurichesse E., Sanchez C., Parizel N., Sidhoum C., Baaziz W., Ersen O., Pigot T., Backov R., Chem. Mat., 2023, 35, 6502.
Zhang H., Song X. J., Zhao C., Hu D. W., Zhang W. X., Jia M. J., ACS Appl. Nano Mater., 2020, 3, 6664.
Zhang H., Song X. J., Sun H., Lei Z. Y., Bao S. X., Zhao C., Hu D. A. W., Zhang W. X., Liu J. Y., Jia M. J., Catal. Sci. Technol., 2021, 11, 7943.
Zhao C., Zhang H., Lei Z. Y., Miao S. S., Sun H. L., Sun Y. T., Zhang W. X., Jia M. J., Catal. Today, 2022, 402, 220.
Yang Y., Lun Z. Y., Xia G. L., Zheng F. C., He M. N., Chen Q. W., Energy Environ. Sci., 2015, 8, 3563.
Su J. W., Yang Y., Xia G. L., Chen J. T., Jiang P., Chen Q. W., Nat. Commun., 2017, 8, 10.
Yang L. J., Feng S. Z., Xu G. C., Wei B., Zhang L., ACS Sustain. Chem. Eng., 2019, 7, 5462.
Chen S. M., Ma L. T., Wu S. L., Wang S. Y., Li Z. B., Emmanuel A. A., Huqe M. R., Zhi C. Y., Zapien J. A., Adv. Funct. Mater., 2020, 30, 9.
Wang Z., Fang Y., Yang Y., Qiu B., Li H. P., Chem. Eng. J., 2023, 454, 15.
Goda E. S., Lee S., Sohail M., Yoon K. R., J. Energy Chem., 2020, 50, 206.
Niu H. J., Chen Y. P., Sun R. M., Wang A. J., Mei L. P., Zhang L., Feng J. J., J. Power Sources, 2020, 480, 11.
Chen D., Li G. F., Chen X., Li C. J., Zhang Y. C., Hu J., Yu J. H., Yu L. Y., Dong L. F., J. Alloy. Compd., 2022, 910, 10.
Wang Z., Ang J. M., Zhang B. W., Zhang Y. F., Ma X. Y. D., Yan T., Liu J., Che B. Y., Huang Y. Z., Lu X. H., Appl. Catal. B: Environ., 2019, 254, 26.
Xie D. Y., Yu D. S., Hao Y. A., Han S. L., Li G. H., Wu X. L., Hu F., Li L. L., Chen H. Y., Liao Y. F., Peng S. J., Small, 2021, 17, 11.
Xu X. Q., Xie J. H., Liu B., Wang R. Y., Liu M. Y., Zhang J., Liu J., Cai Z., Zou J. L., Appl. Catal. B: Environ., 2022, 316, 12.
Feng Y., Han H., Kim K. M., Dutta S., Song T., J. Catal., 2019, 369, 168.
Hu L., Zhang R. R., Wei L. Z., Zhang F. P., Chen Q. W., Nanoscale, 2015, 7, 450.
Uemura T., Kitagawa S., J. Am. Chem. Soc., 2003, 125, 7814.
Ge Y. C., Dong P., Craig S. R., Ajayan P. M., Ye M. X., Shen J. F., Adv. Energy Mater., 2018, 8, 9.
Zhu Z. G., Xu Q. Q., Ni Z. T., Luo K. F., Liu Y. Y., Yuan D. S., Chem. Eng., 2021, 9, 13491.
Yang W. X., Liu X. J., Yue X. Y., Jia J. B., Guo S. J., J. Am. Chem. Soc., 2015, 137, 1436.
Wu S. K., Shen X. P., Zhu G. X., Zhou E., Ji Z. Y., Ma L. B., Xu K. Q., Yang J., Yuan A. H., Carbon, 2017, 116, 68.
Gong Y., Pan J., Zhang L. L., Wang X., Song S. Y., Zhang H.Y., Chem. Res. Chinese Universities, 2022, 38, 1287.
Ferrari A. C., Basko D. M., Nat. Nanotechnol., 2013, 8, 235.
Zheng F. C., Yang Y., Chen Q. W., Nat. Commun., 2014, 5, 10.
Zhang Z. Q., Wang H. B., Li Y. X., Xie M. G., Li C. G., Lu H. Y., Peng Y., Shi Z., Chem. Res. Chinese Universities, 2022, 38, 750.
Sun F. Z., Wang G., Ding Y. Q., Wang C., Yuan B. B., Lin Y. Q., Adv. Energy Mater., 2018, 8, 11.
Wei K. L., Wang X., Jiao X. L., Li C., Chen D. R., Appl. Surf. Sci., 2021, 550, 10.
Song C. S., Wu S. K., Shen X. P., Miao X. L., Ji Z. Y., Yuan A. H., Xu K. Q., Liu M. M., Xie X. L., Kong L. R., Zhu G. X., Shah S. A., J. Colloid Interface Sci., 2018, 524, 93.
Wang J., Wei Z. Z., Gong Y. T., Wang S. P., Su D. F., Han C. L., Li H. R., Wang Y., Chem. Commun., 2015, 51, 12859.
Wang S. G., Qin J. W., Meng T., Cao M. H., Nano Energy, 2017, 39, 626.
Chen L., Zuo S. Y., Guan Z. Y., Xu H. M., Xia D. S., Li D. Y., Res. Chem. Intermed., 2021, 47, 795.
Long J. Y., Yan Z. S., Gong Y., Lin J. H., Appl. Surf. Sci., 2018, 448, 50.
Iglesias D., Melchionna M., Catalysts, 2019, 9, 128.
Acknowledgements
This work was supported by the National Natural Science Foundation of China (No. 22172058).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflicts of interest.
Electronic Supplementary Information
40242_2024_4020_MOESM1_ESM.pdf
Supporting Information: Prussian blue analogue derived N-doped graphitic carbon wrapped iron-cobalt nanoparticles as recyclable heterogeneous catalysts for Friedel-Crafts acylation
Rights and permissions
About this article
Cite this article
Lei, Z., Sun, H., Dong, Z. et al. Prussian Blue Analogue Derived N-Doped Graphitic Carbon Wrapped Iron-Cobalt Nanoparticles as Recyclable Heterogeneous Catalysts for Friedel-Crafts Acylation. Chem. Res. Chin. Univ. (2024). https://doi.org/10.1007/s40242-024-4020-x
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s40242-024-4020-x