A Highly Efficient Ni/Al2O3-LaOx Catalyst for the Reductive Amination of Furfural to Furfurylamine: the Promoting Effect of La

doi:10.1007/s40242-023-3216-9

Abstract

Abstract: The reductive amination of furfural to furfurylamine is an important and still challenging topic in the field of biomass conversion. In this work, we prepared a series of Ni/Al₂O₃-LaO_x catalysts by co-precipitation method, the role of La played in promoting the catalytic performances of reductive amination furfural was discussed based on the changes in the electronic state of Ni species, acidity, and Ni particle size. The catalytic activity and the selectivity of furfurylamine are highly dependent on the surface properties and the structure of the catalyst. The addition of La promoted the amount of strong acidic sites and the H₂dissociation and spillover on the surface, thus inducing the improvement of the catalytic activity and furfurylamine selectivity. The Ni/Al₂O₃-0.5LaO_xcatalyst with suitable acid sites gave a high yield of furfurylamine (94.9%) under mild reaction conditions. Moreover, the catalyst could be recycled five times without significant loss in activity. The Ni/Al₂O₃-LaO_x catalyst is of great promise in the production of amines via reductive amination reaction.

Key words: Reductive amination, Furfural, Nickel catalyst, Furfurylamine, Lanthanum

YANG Yinze, ZHANG Liyan, ZHOU Leilei, CHENG Haiyang, ZHAO Fengyu. A Highly Efficient Ni/Al₂O₃-LaO_x Catalyst for the Reductive Amination of Furfural to Furfurylamine: the Promoting Effect of La[J]. Chemical Research in Chinese Universities, 2024, 40(1): 36-46.

References

[1] Luo N., Montini T., Zhang J., Fornasiero P., Fonda E., Hou T., Nie W., Lu J., Liu J., Heggen M., Lin L., Ma C., Wang M., Fan F., Jin S., Wang F., Nat. Energy, 2019, 4, 575
[2] Climent M. J., Corma A., Iborra S., Green Chem., 2014, 16, 516
[3] Bozell J. J., Petersen G. R., Green Chem., 2010, 12, 539
[4] Li H., Yang S., Saravanamurugan S., Riisager A., ACS Catal., 2017, 7, 3010
[5] Zhuang X., Liu J., Zhong S., Ma L., Green Chem., 2022, 24, 271
[6] van Putten R. J., van der Waal J. C., de Jong E., Rasrendra C. B., Heeres H. J., de Vries J. G., Chem. Rev., 2013, 113, 1499
[7] Carnevali D., Guévremont O., Rigamonti M. G., Stucchi M., Cavani F., Patience G. S., ACS Sustain. Chem. Eng., 2018, 6, 5580
[8] Irrgang T., Kempe R., Chem. Rev., 2020, 120, 9583
[9] Dunbabin A., Subrizi F., Ward J. M., Sheppard T. D., Hailes H. C., Green Chem., 2017, 19, 397
[10] Chatterjee M., Ishizaka T., Kawanami H., Green Chem., 2016, 18, 487
[11] Wang Y., Yang X., Zheng H., Li X., Zhu Y., Li Y., Mol. Catal., 2019, 463, 130
[12] Mariscal R., Maireles-Torres P., Ojeda M., Sádaba I., López Granados M., Energy Environ. Sci., 2016, 9, 1144
[13] Xie C., Song J., Hua M., Hu Y., Huang X., Wu H., Yang G., Han B., ACS Catal., 2020, 10, 7763
[14] Liang G., Wang A., Li L., Xu G., Yan N., Zhang T., Angew. Chem. Int. Ed., 2017, 56, 3050
[15] Komanoya T., Kinemura T., Kita Y., Kamata K., Hara M., J. Am. Chem. Soc., 2017, 139, 11493
[16] Dong C., Wang H., Du H., Peng J., Cai Y., Guo S., Zhang J., Samart C., Ding M., Mol. Catal., 2020, 482, 110755
[17] Zhou K., Chen B., Zhou X., Kang S., Xu Y., Wei J., ChemCatChem, 2019, 11, 5562
[18] Sheng M., Fujita S., Yamaguchi S., Yamasaki J., Nakajima K., Yamazoe S., Mizugaki T., Mitsudome T., JACS Au, 2021, 1, 501
[19] Pan Z., Zhang Q., Wang W., Wang L., Wang G.-H., ACS Sustain. Chem. Eng., 2022, 10, 3777
[20] Gokhale T. A., Raut A. B., Bhanage B. M., Mol. Catal., 2021, 510, 111667
[21] Yuan H., Li J. P., Su F., Yan Z., Kusema B. T., Streiff S., Huang Y., Pera-Titus M., Shi F., ACS Omega, 2019, 4, 2510
[22] Dong C., Wu Y., Wang H., Peng J., Li Y., Samart C., Ding M., ACS Sustain. Chem. Eng., 2021, 9, 7318
[23] Bhunia M. K., Chandra D., Abe H., Niwa Y., Hara M., ACS Appl. Mater. Interfaces, 2022, 14, 4144
[24] Xue Z., Wu S., Fu Y., Luo L., Li M., Li Z., Shao M., Zheng L., Xu M., Duan H., J. Energy Chem., 2023, 76, 239
[25] Fischer A., Maciejewski M., Burgi T., Mallat T., Baiker A., J. Catal., 1999, 183, 373
[26] Guo W., Wang Z.-Q., Xiang S., Jing Y., Liu X., Guo Y., Gong X.-Q., Wang Y., Chin. J. Catal., 2023, 47, 181
[27] Yogita, Rao K. T. V., Kumar P. M., Lingaiah N., Sustain. Energ. Fuels, 2022, 6, 4692
[28] Liu J., Zhu Y., Wang C., Singh T., Wang N., Liu Q., Cui Z., Ma L., Green Chem., 2020, 22, 7387
[29] Manzoli M., Gaudino E. C., Cravotto G., Tabasso S., Baig R. B. N., Colacino E., Varma R. S., ACS Sustain. Chem. Eng., 2019, 7, 5963
[30] Luo D., He Y., Yu X., Wang F., Zhao J., Zheng W., Jiao H., Yang Y., Li Y., Wen X., J. Catal., 2021, 395, 293
[31] Hahn G., Kunnas P., de Jonge N., Kempe R., Nat. Catal., 2018, 2, 71
[32] Wang H., Zhang Y., Luo D., Wang H., He Y., Wang F., Wen X., Mol. Catal., 2023, 536, 112914
[33] Zhang J., Yang J., Li X., Mu B., Liu H., Xia C., Wang A., Huang Z., Green Synth. Catal., 2023, DOI: 10.1016/j.gresc.2023.02.003
[34] Song W., Wan Y., Li Y., Luo X., Fang W., Zheng Q., Ma P., Zhang J., Lai W., Catal. Sci. Technol., 2022, 12, 7208
[35] Yang Y., Zhou L., Wang X., Zhang L., Cheng H., Zhao F., Nano Res., 2023, 16, 3719
[36] Ma Y., Su Z., Tang N., Chen S., Wang W., Yuan J., Cao Z., He H., Cong Y., Chem. Phys. Lett., 2021, 775, 138604
[37] Cui Y., Zhang H., Xu H., Li W., Appl. Catal. A: Gen., 2007, 331, 60
[38] Mazumder J., de Lasa H., Appl. Catal. B: Environ., 2014, 160/161, 67
[39] Sanchezsanchez M., Navarro R., Fierro J., Catal. Today, 2007, 129, 336
[40] Martı́nez R., Romero E., Guimon C., Bilbao R., Appl. Catal. A: Gen., 2004, 274, 139
[41] Al-Mubaddel F. S., Kumar R., Sofiu M. L., Frusteri F., Ibrahim A. A., Srivastava V. K., Kasim S. O., Fakeeha A. H., Abasaeed A. E., Osman A. I., Al-Fatesh A. S., Int. J. Hydrogen Energy, 2021, 46, 14225
[42] Song J. H., Yoo S., Yoo J., Park S., Gim M. Y., Kim T. H., Song I. K., Mol. Catal., 2017, 434, 123
[43] Boudjeloud M., Boulahouache A., Rabia C., Salhi N., Int. J. Hydrogen Energ., 2019, 44, 9906
[44] Brussino P., Bortolozzi J. P., Dalla Costa B., Banús E. D., Ulla M. A., Appl. Catal. A: Gen., 2019, 575, 1
[45] Keghouche N., Chettibi S., Latrèche F., Bettahar M. M., Belloni J., Marignier J. L., Radiat. Phys. Chem., 2005, 74, 185
[46] Sepehri S., Rezaei M., Garbarino G., Busca G., Int. J. Hydrogen Energy, 2016, 41, 8855
[47] Xu L., Mi W., Su Q., J. Nat. Gas Chem., 2011, 20, 287
[48] Melchor-Hernández C., Gómez-Cortés A., Díaz G., Fuel, 2013, 107, 828
[49] Qin H., Guo C., Wu Y., Zhang J., Korean J. Chem. Eng., 2014, 31, 1168
[50] Hossain M. M., Lopez D., Herrera J., de Lasa H. I., Catal. Today, 2009, 143, 179
[51] Mahata N., Cunha A. F., Órfão J. J. M., Figueiredo J. L., Appl. Catal. A: Gen., 2008, 351, 204
[52] Lin W., Cheng H., He L., Yu Y., Zhao F., J. Catal., 2013, 303, 110
[53] Damyanova S., Daza L., Fierro J. L. G., J. Catal., 1996, 159, 150
[54] Quindimil A., De-La-Torre U., Pereda-Ayo B., González-Marcos J. A., González-Velasco J. R., Appl. Catal. B: Environ., 2018, 238, 393
[55] Chen C., Wu D., Liu P., Xia H., Zhou M., Hou X., Jiang J., React. Chem. Eng., 2021, 6, 559
[56] Krupka J., Dluhoš L., Mrózek L., Chem. Eng. Technol., 2017, 40, 870
[57] Liu Y., Zhao J., He Y., Feng J., Wu T., Li D., J. Catal., 2017, 348, 135
[58] Bailón-García E., Carrasco-Marín F., Pérez-Cadenas A. F., Maldonado-Hódar F. J., Catal. Commun., 2016, 82, 36

A Highly Efficient Ni/Al₂O₃-LaO_x Catalyst for the Reductive Amination of Furfural to Furfurylamine: the Promoting Effect of La

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