Predication of Selective Ring-opening Hydrogenolysis for Furfuryl Alcohol to Produce Pentanediol over Dual-atom Catalysts

doi:10.1007/s40242-024-3243-1

Abstract

Abstract: Selective activation of C-O bond is of fundamental importance in the precise conversion of oxygenates into value-added compounds in an atom-economic and sustainable manner, and meanwhile, the structurally well-defined dual-atoms catalysts (DACs) have been scarcely investigated in this field. In this study, a series of transition metal DACs anchored on nitrogen-doped graphene (TM₂/NC, TM=Pt, Ir, Rh, Pd, Ru, Co, Ni and Cu) was constructed to make a comprehensive investigation of their selectivity in the hydrogenative transformation of furfuryl alcohol (FAL), an important biomass platform molecule, to 1,2-pentanediol (1,2-PeD) via selective cleavage of furanic C5-O bond, by density functional theory (DFT) calculations and microkinetic modeling. We found that Ir₂/NC demonstrated a high selectivity for the cleavage of furanic C5-O bond to produce 1,2-PeD, while the production of THFAL or 1,5-pentanediol (1,5-PeD) on other TM₂/NC catalysts are more favorable. Furthermore, we found that the selective C-O bond cleavage of FAL furan ring is affected by the orbital overlap between the d-orbitals of the anchored metal atoms and the p-orbitals of the adsorbed C atom in FAL, suggesting that the selectivity of the C-O bond cleavage is inextricably related with the electronic property of the anchored metals.

Key words: Furfuryl alcohol, Hydrogenation, Dual-atom catalyst, Density functional theory (DFT) calculation

WANG Tingting, WANG Jia, XI Yongjie, HU Bin, LI Fuwei. Predication of Selective Ring-opening Hydrogenolysis for Furfuryl Alcohol to Produce Pentanediol over Dual-atom Catalysts[J]. Chemical Research in Chinese Universities, 2024, 40(1): 55-63.

References

[1] De S., Dutta S., Saha B., Catal. Sci. Technol., 2016, 6 (20), 7364
[2] Delidovich I., Hausoul P. J. C., Deng L., Pfützenreuter R., Rose M., Palkovits R., Chem. Rev., 2016, 116 (3), 1540
[3] Cai C. M., Zhang T., Kumar R., Wyman C. E., J. Chem. Technol. Biotechnol., 2014, 89 (1), 2
[4] Chen S., Wojcieszak R., Dumeignil F., Marceau E., Royer S., Chem. Rev., 2018, 118 (22), 11023
[5] Zhao Z., Yang C., Sun P., Gao G., Liu Q., Huang Z., Li F., ACS Catal., 2023, 13 (8), 5170
[6] Zhao Z., Gao G., Xi Y., Wang J., Sun P., Liu Q., Yan W., Cui Y., Jiang Z., Li F., Chem, 2022, 8 (4), 1034
[7] Zhang B., Zhu Y., Ding G., Zheng H., Li Y., Green Chem., 2012, 14 (12), 3402
[8] Wijaya H. W., Kojima T., Hara T., Ichikuni N., Shimazu S., ChemCatChem, 2017, 9 (14), 2869
[9] Zhao Z., Bababrik R., Xue W., Li Y., Briggs N. M., Nguyen D.-T., Nguyen U., Crossley S. P., Wang S., Wang B., Resasco D. E., Nat. Catal, 2019, 2 (5), 431
[10] Delaney H., Synthesis of the Fungicide Propiconazole a Systemic Foliar Fungicide, Technological University Dublin, Ireland, 2000
[11] Southby D. T., Szajewski R. P., Szajewski R., Southby D., Aqueous Inkjet Ink Useful for Printing Photo-Image on Both Photo-Glossy Receiver and Plain Paper Comprises Water, 1,2-Pentanediol, Humectant Distinct from 1,2-Pentanediol, and Dispersed Pigment Colorant, US2009169762-A1; WO2009085168-A1; EP2225335-A1; US8356892-B2; EP2225335-B1, 2009
[12] Liu H., Huang Z., Kang H., Xia C., Chen J., Chinese Journal of Catalysis, 2016, 37 (5), 700
[13] Mizugaki T., Yamakawa T., Nagatsu Y., Maeno Z., Mitsudome T., Jitsukawa K., Kaneda K., ACS Sustainable Chem. Eng., 2014, 2 (10), 2243
[14] Zhu Y., Zhao W., Zhang J., An Z., Ma X., Zhang Z., Jiang Y., Zheng L., Shu X., Song H., Xiang X., He J., ACS Catal., 2020, 10 (15), 8032
[15] Ma R., Wu X.-P., Tong T., Shao Z.-J., Wang Y., Liu X., Xia Q., Gong X.-Q., ACS Catal., 2017, 7 (1), 333
[16] Jenness G. R., Wan W., Chen J. G., Vlachos D. G., ACS Catal., 2016, 6 (10), 700
[17] Dai D., Feng C., Wang M., Du Q., Liu D., Pan Y., Liu Y., Catal. Sci. Technol., 2022, 12 (19), 5879
[18] Ying Y., Luo X., Qiao J., Huang H., Adv. Funct. Mater., 2021, 31 (3), 2007423
[19] Pan Y., Zhang C., Liu Z., Chen C., Li Y., Matter, 2020, 2 (1), 78
[20] Cao X., Zhao L., Wulan B., Tan D., Chen Q., Ma J., Zhang J., Angew. Chem. Int Ed., 2022, 61 (6), e202113918
[21] Li X., Zhong W., Cui P., Li J., Jiang J., J. Phys. Chem. Lett., 2016, 7 (9), 1750
[22] Chen Z. W., Yan J., Jiang Q., Small Methods., 2019, 3 (6), 1800291
[23] Di Liberto G., Cipriano L. A., Pacchioni G., J. Am. Chem. Soc., 2021, 143 (48), 20431
[24] Cui X., Tang C., Zhang Q., Advanced Energy Materials, 2018, 8 (22), 1800369
[25] Ren W., Tan X., Yang W., Jia C., Xu S., Wang K., Smith S. C., Zhao C., Angew. Chem. Int. Ed., 2019, 58 (21), 6972
[26] Zhao S., Yi H., Tang X., Gao F., Wang J., Huang Y., Yang Z., Adsorption, 2017, 23 (7/8), 1013
[27] Blöchl P. E., Phys. Rev. B, 1994, 50 (24), 17953
[28] Kresse G., Joubert D., Phys. Rev. B, 1999, 59 (3), 1758
[29] Perdew J. P., Burke K., Ernzerhof M., Phys. Rev. Lett., 1996, 77 (18), 3865
[30] Kresse G., Computational Materials Science, 1996, 6 (1), 15
[31] Kresse G., Furthmüller J., Phys. Rev. B, 1996, 54 (16), 11169
[32] Grimme S., Antony J., Ehrlich S., Krieg H., The Journal of Chemical Physics, 2010, 132 (15), 154104
[33] Henkelman G., The Journal of Chemical Physics, 2000, 113 (22), 9901
[34] Henkelman G., Jónsson H., The Journal of Chemical Physics, 1999, 111 (15), 7010
[35] Heyden A., Bell A. T., Keil F. J., The Journal of Chemical Physics, 2005, 123 (22), 224101
[36] Ribeiro R. F., Marenich A. V., Cramer C. J., Truhlar D. G., J. Phys. Chem. B, 2011, 115 (49), 14556
[37] Ulissi Z. W., Medford A. J., Bligaard T., Nørskov J. K., Nat. Commun., 2017, 8 (1), 14621
[38] Deringer V. L., Tchougréeff A. L., Dronskowski R., J. Phys. Chem. A, 2011, 115 (21), 5461
[39] Maintz S., Deringer V. L., Tchougréeff A. L., Dronskowski R., J. Comput. Chem., 2016, 37 (11), 1030
[40] Qian X., J. Phys. Chem. B, 2013, 117 (39), 11460
[41] Gilkey M. J., Mironenko A. V., Yang L., Vlachos D. G., Xu B., ChemSusChem, 2016, 9 (21), 3113
[42] Trinh Q. T., Chethana B. K., Mushrif S. H., J. Phys. Chem. C, 2015, 119 (30), 17137
[43] Banerjee A., Mushrif S. H., ChemCatChem, 2017, 9 (14), 2828