AlCl3 modified Pd/Al2O3 catalyst for enhanced anthraquinone hydrogenation

doi:10.1016/j.cjche.2023.06.021

摘要/Abstract

摘要： Anthraquinone hydrogenation to produce H₂O₂ is an economically interesting reaction with great industrial importance. Here, we report a series of Pd/xAl catalysts with different AlCl₃ contents by a conventional stepwise impregnation method. The optimal Pd/1.0Al catalyst exhibits a higher performance toward anthraquinone hydrogenation with 8.3 g·L^-1 hydrogenation efficiency, 99.5% selectivity and good stability, obviously superior to that of Pd/Al₂O₃ catalyst (5.2 g·L^-1 and 97.2%). Detailed characterization demonstrates that AlCl₃ can be grafted on the γ-Al₂O₃ support to obtain a modified support with abundant surface weak acid and Lewis acid, which can adsorb and activate anthraquinone. Meanwhile, its steric hindrance could isolate and disperse active metals to form more active sites. The synergies between metal sites and acid sites promotes the anthraquinone hydrogenation. Furthermore, the good stability after grafting AlCl₃ could attribute to the enhanced metal-support interaction inhibiting metal particles agglomeration and leaching.

关键词: AlCl₃, Pd-based catalyst, H₂O₂, Weak acid, Hydrogenation

Abstract: Anthraquinone hydrogenation to produce H₂O₂ is an economically interesting reaction with great industrial importance. Here, we report a series of Pd/xAl catalysts with different AlCl₃ contents by a conventional stepwise impregnation method. The optimal Pd/1.0Al catalyst exhibits a higher performance toward anthraquinone hydrogenation with 8.3 g·L^-1 hydrogenation efficiency, 99.5% selectivity and good stability, obviously superior to that of Pd/Al₂O₃ catalyst (5.2 g·L^-1 and 97.2%). Detailed characterization demonstrates that AlCl₃ can be grafted on the γ-Al₂O₃ support to obtain a modified support with abundant surface weak acid and Lewis acid, which can adsorb and activate anthraquinone. Meanwhile, its steric hindrance could isolate and disperse active metals to form more active sites. The synergies between metal sites and acid sites promotes the anthraquinone hydrogenation. Furthermore, the good stability after grafting AlCl₃ could attribute to the enhanced metal-support interaction inhibiting metal particles agglomeration and leaching.

Key words: AlCl₃, Pd-based catalyst, H₂O₂, Weak acid, Hydrogenation

Qinqin Yuan, Jingyue Liang, Wei Li, Jinli Zhang, Cuili Guo. AlCl₃ modified Pd/Al₂O₃ catalyst for enhanced anthraquinone hydrogenation[J]. 中国化学工程学报, 2023, 64(12): 271-280.

Qinqin Yuan, Jingyue Liang, Wei Li, Jinli Zhang, Cuili Guo. AlCl₃ modified Pd/Al₂O₃ catalyst for enhanced anthraquinone hydrogenation[J]. Chinese Journal of Chemical Engineering, 2023, 64(12): 271-280.

参考文献

[1] R. Hage, A. Lienke, Applications of transition-metal catalysts to textile and wood-pulp bleaching, Angew. Chem. Int. Ed. 45 (2) (2006) 206–222.
[2] Electrocatalytic H₂O₂ generation for disinfection.
[3] R.P. Guan, X.Z. Yuan, Z.B. Wu, L.B. Jiang, Y.F. Li, G.M. Zeng, Principle and application of hydrogen peroxide based advanced oxidation processes in activated sludge treatment: A review, Chem. Eng. J. 339 (2018) 519–530.
[4] M.M. Heravi, N. Ghalavand, E. Hashemi, Hydrogen peroxide as a green oxidant for the selective catalytic oxidation of benzylic and heterocyclic alcohols in different media: An overview, Chemistry 2 (1) (2020) 101–178.
[5] X.J. Shi, S. Back, T.M. Gill, S. Siahrostami, X.L. Zheng, Electrochemical synthesis of H₂O₂ by two-electron water oxidation reaction, Chem 7 (1) (2021) 38–63.
[6] L.B. Belykh, N.I. Skripov, T.P. Sterenchuk, V.V. Akimov, V.L. Tauson, T.A. Savanovich, F.K. Schmidt, Role of phosphorus in the formation of selective palladium catalysts for hydrogenation of alkylanthraquinones, Appl. Catal. A 589 (2020) 117293.
[7] J.P. Zhou, J.W. Chen, Z.C. Yang, P. Liu, J.L. Luo, C. Du, H. Li, W.L. Liu, W.Q. Cai, Pd nanoparticles anchored and stabilized on N-doped boehmite@C with enhanced catalytic performance in 2-ethyl-9, 10 anthraquinone hydrogenation, Colloids Surf. A 647 (2022) 128977.
[8] J.Y. Liang, F.Y. Wang, W. Li, J.L. Zhang, C.L. Guo, Highly dispersed and stabilized Pd species on H₂ pre-treated Al₂O₃ for anthraquinone hydrogenation and H₂O₂ production, Mol. Catal. 524 (2022) 112264.
[9] L. Wang, Y.E. Zhang, Q.Q. Ma, Z.Y. Pan, B.N. Zong, Hydrogenation of alkyl-anthraquinone over hydrophobically functionalized Pd/SBA-15 catalysts, RSC Adv. 9 (59) (2019) 34581–34588.
[10] Q.L. Chen, Development of an anthraquinone process for the production of hydrogen peroxide in a trickle bed reactor—from bench scale to industrial scale, Chem. Eng. Process. 47 (5) (2008) 787–792.
[11] R. Kosydar, A. Drelinkiewicz, J.P. Ganhy, Degradation reactions in anthraquinone process of hydrogen peroxide synthesis, Catal. Lett. 139 (3) (2010) 105–113.
[12] H.X. Bai, X.C. Fang, C. Peng, Synthesis of tailored egg-shell Pd@Al₂O₃ catalyst for catalytic hydrogenation of 2-alkylanthraquinone, ACS Sustainable Chem. Eng. 7 (8) (2019) 7700–7707.
[13] E.X. Yuan, X.W. Ren, L. Wang, W.T. Zhao, A comparison of the catalytic hydrogenation of 2-amylanthraquinone and 2-ethylanthraquinone over a Pd/Al₂O₃ catalyst, Front. Chem. Sci. Eng. 11 (2) (2017) 177–184.
[14] W.Y. Liang, J.F. Dong, M.Q. Yao, J.S. Fu, H.L. Chen, X.M. Zhang, Pd-Al/AC catalysts for direct synthesis of H₂O₂ with high productivity, ChemistrySelect 5 (42) (2020) 12910–12914.
[15] Y.Y. Guo, C.N. Dai, Z.G. Lei, Hydrogenation of 2-ethylanthraquinone with bimetallic monolithic catalysts: An experimental and DFT study, Chin. J. Catal. 39 (6) (2018) 1070–1080.
[16] Y.Y. Guo, Y.C. Dong, Z.G. Lei, Z.X. Liu, J.Q. Zhu, High-performance Pd-N (N = Ga or Ag) bimetallic monolithic catalyst for the hydrogenation of 2-ethylanthraquinone: Experimental and DFT studies, Mol. Catal. 509 (2021) 111604.
[17] E.X. Yuan, C. Wu, X. Hou, M.B. Dou, G.Z. Liu, G.Z. Li, L. Wang, Synergistic effects of second metals on performance of (Co, Ag, Cu)-doped Pd/Al₂O₃ catalysts for 2-ethyl-anthraquinone hydrogenation, J. Catal. 347 (2017) 79–88.
[18] C.L. Miao, T.L. Hui, Y.N. Liu, J.T. Feng, D.Q. Li, Pd/MgAl-LDH nanocatalyst with vacancy-rich sandwich structure: Insight into interfacial effect for selective hydrogenation, J. Catal. 370 (2019) 107–117.
[19] W.Q. Li, F.M. Wang, X.B. Zhang, M.S. Sun, J.Q. Hu, Y. Zhai, H.H. Lv, G.J. Lv, Highly dispersed Pd nanoparticles supported on γ-Al₂O₃ modified by minimal 3-aminopropyltriethoxysilane as effective catalysts for 2-ethyl-anthraquinone hydrogenation, Appl. Catal. A 619 (2021) 118124.
[20] F.Y. Wang, Y.M. Jia, J.Y. Liang, Y. Han, J.L. Zhang, X.Y. Li, W. Li, Intensifying strategy of ionic liquids for Pd-based catalysts in anthraquinone hydrogenation, Catal. Sci. Technol. 12 (6) (2022) 1766–1776.
[21] J.T. Feng, H.Y. Wang, D.G. Evans, X. Duan, D.Q. Li, Catalytic hydrogenation of ethylanthraquinone over highly dispersed eggshell Pd/SiO₂-Al₂O₃ spherical catalysts, Appl. Catal. A 382 (2) (2010) 240–245.
[22] A. Li, Y.H. Wang, J. Ren, J.L. Zhang, W. Li, C.L. Guo, Enhanced catalytic activity and stability over P-modified alumina supported Pd for anthraquinone hydrogenation, Appl. Catal. A 593 (2020) 117422.
[23] Y.L. Li, X. Meng, R.W. Luo, H.N. Zhou, S.Y. Lu, S.N. Yu, P. Bai, X.H. Guo, J.F. Lyu, Aluminum/Tin-doped UiO-66 as Lewis acid catalysts for enhanced glucose isomerization to fructose, Appl. Catal. A 632 (2022) 118501.
[24] M.J. Luo, Q.F. Wang, G.Z. Li, X.W. Zhang, L. Wang, T. Jiang, Enhancing tetralin hydrogenation activity and sulphur-tolerance of Pt/MCM-41 catalyst with Al(NO₃)₃, AlCl₃ and Al(CH₃)₃, Catal. Sci. Technol. 4 (7) (2014) 2081–2090.
[25] R.J. Deng, K.Y. You, L. Yi, F.F. Zhao, J.A. Jian, Z.P. Chen, P.L. Liu, Q.H. Ai, H.A. Luo, Solvent-free, low-temperature, highly efficient catalytic nitration of toluene with NO₂ promoted by molecular oxygen over immobilized AlCl₃–SiO₂, Ind. Eng. Chem. Res. 57 (39) (2018) 12993–13000.
[26] J.B. Wen, K.Y. You, F.F. Zhao, J. Jian, P.L. Liu, Q.H. Ai, H.A. Luo, AlCl₃ immobilized on silicic acid as efficient Lewis acid catalyst for highly selective preparation of dicyclohexylamine from the vapor phase hydroamination of cyclohexene with cyclohexylamine, Catal. Commun. 145 (2020) 106112.
[27] X.N. Xiong, I.K.M. Yu, D.C.W. Tsang, L. Chen, Z.S. Su, C.W. Hu, G. Luo, S.C. Zhang, Y.S. Ok, J.H. Clark, Study of glucose isomerisation to fructose over three heterogeneous carbon-based aluminium-impregnated catalysts, J. Clean. Prod. 268 (2020) 122378.
[28] I.K.M. Yu, X.N. Xiong, D.C.W. Tsang, L. Wang, A.J. Hunt, H. Song, J. Shang, Y.S. Ok, C.S. Poon, Aluminium-biochar composites as sustainable heterogeneous catalysts for glucose isomerisation in a biorefinery, Green Chem. 21 (6) (2019) 1267–1281.
[29] Y. Han, Z.Y. He, Y.C. Guan, W. Li, J.L. Zhang, Catalytic performance of PdAu/Al₂O₃ catalyst with special structural and electronic properties in the 2-ethylanthraquinone hydrogenation reaction, Acta Phys. Chim. Sin. 31 (4) (2015) 729–737.
[30] Y.H. Wang, M. Peng, C.L. Ye, C.N. Gan, J.L. Zhang, C.L. Guo, Enhanced catalytic performance of Pd-Ga bimetallic catalysts for 2-ethylanthraquinone hydrogenation, Appl. Organomet. Chem. 33 (8) (2019). DOI:10.1002/aoc.5076.
[31] J.L. Zhang, K.G. Gao, S.L. Wang, W. Li, Y. Han, Performance of bimetallic PdRu catalysts supported on gamma alumina for 2-ethylanthraquinone hydrogenation, RSC Adv. 7 (11) (2017) 6447–6456.
[32] P. Bai, W. Xing, Z.X. Zhang, Z.F. Yan, Facile synthesis of thermally stable mesoporous crystalline alumina by using a novel cation-anion double hydrolysis method, Mater. Lett. 59 (24–25) (2005) 3128–3131.
[33] C.L. Lu, J.G. Lv, L. Xu, X.F. Guo, W.H. Hou, Y. Hu, H. Huang, Crystalline nanotubes of γ-AlOOH and γ-Al₂O₃: Hydrothermal synthesis, formation mechanism and catalytic performance, Nanotechnology 20 (21) (2009) 215604.
[34] P.P. Wu, L. Song, Y. Wang, X.H. Liu, Z.K. He, P. Bai, Z.F. Yan, High-performance benzyl alcohol oxidation catalyst: Au-Pd alloy with ZrO₂ as promoter, Appl. Surf. Sci. 537 (2021) 148059.
[35] Y.Q. Wu, L. Tan, T. Zhang, H.J. Xie, G.H. Yang, N. Tsubaki, J.G. Chen, Effect of preparation method on ZrO₂-based catalysts performance for isobutanol synthesis from syngas, Catalysts 9 (9) (2019) 752.
[36] J. Huang, Y.J. Jiang, N. van Vegten, M. Hunger, A. Baiker, Tuning the support acidity of flame-made Pd/SiO₂-Al₂O₃ catalysts for chemoselective hydrogenation, J. Catal. 281 (2) (2011) 352–360.
[37] L.K. Ouyang, G.J. Da, P.F. Tian, T.Y. Chen, G.D. Liang, J. Xu, Y.F. Han, Insight into active sites of Pd-Au/TiO₂ catalysts in hydrogen peroxide synthesis directly from H₂ and O₂, J. Catal. 311 (2014) 129–136.
[38] T. Yang, J. Lin, X.H. Chen, Y. Zheng, An attempt to tailor methane oxidation behaviors over Pd/Al₂O₃ systems through the concerted fashion of Zn and alkaline-metal promoters, J. Alloys Compd. 904 (2022) 164065.
[39] G. Spezzati, Y.Q. Su, J.P. Hofmann, A.D. Benavidez, A.T. DeLaRiva, J. McCabe, A.K. Datye, E.J.M. Hensen, Atomically dispersed Pd-O species on CeO₂(111) as highly active sites for low-temperature CO oxidation, ACS Catal. 7 (10) (2017) 6887–6891.
[40] K. Li, T.T. Lyu, J.Y. He, B.W.L. Jang, Selective hydrogenation of acetylene over Pd/CeO₂, Front. Chem. Sci. Eng. 14 (6) (2020) 929–936.
[41] D.X. Han, Z.G. Zhang, Z.B. Bao, H.B. Xing, Q.L. Ren, Pd-Ni nanoparticles supported on titanium oxide as effective catalysts for Suzuki-Miyaura coupling reactions, Front. Chem. Sci. Eng. 12 (1) (2018) 24–31.
[42] R.R. Hong, Y.F. He, J.T. Feng, D.Q. Li, Fabrication of supported Pd–Ir/Al₂O₃ bimetallic catalysts for 2-ethylanthraquinone hydrogenation, AIChE J. 63 (9) (2017) 3955–3965.
[43] E.X. Yuan, C. Wu, G.Z. Liu, L. Wang, One-pot synthesis of Pd nanoparticles on ordered mesoporous Al₂O₃ for catalytic hydrogenation of 2-ethyl-anthraquinone, Appl. Catal. A 525 (2016) 119–127.
[44] D.F. Yin, Q.H. Xin, S.T. Yu, L. Jiang, L. Li, C.X. Xie, Q. Wu, H.L. Yu, Y.X. Liu, Y.E. Liu, S.W. Liu, Selective hydrogenation of phenol to cyclohexanone over a highly stable core-shell catalyst with Pd-lewis acid sites, J. Phys. Chem. C 125 (49) (2021) 27241–27251.
[45] G.Z. Jia, C.M. Guo, W. Wang, X.F. Bai, X.M. Wei, X.F. Su, T. Li, L.F. Xiao, W. Wu, The synergic effects of highly selective bimetallic Pt-Pd/SAPO-41 catalysts for the n-hexadecane hydroisomerization, Front. Chem. Sci. Eng. 15 (5) (2021) 1111–1124.
[46] O.M. Busch, W. Brijoux, S. Thomson, F. Schüth, Spatially resolving infrared spectroscopy for parallelized characterization of acid sites of catalysts via pyridine sorption: Possibilities and limitations, J. Catal. 222 (1) (2004) 174–179.
[47] X.C. Cao, J.P. Zhao, F. Long, X.L. Zhang, J.M. Xu, J.C. Jiang, Al-modified Pd@mSiO₂ core-shell catalysts for the selective hydrodeoxygenation of fatty acid esters: Influence of catalyst structure and Al atoms incorporation, Appl. Catal. B 305 (2022) 121068.

AlCl₃ modified Pd/Al₂O₃ catalyst for enhanced anthraquinone hydrogenation

AlCl₃ modified Pd/Al₂O₃ catalyst for enhanced anthraquinone hydrogenation

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