Regulating the oxidation state of Pd to enhance the selective hydrogenation for 5-hydroxymethylfurfural

doi:10.1016/j.cjche.2024.05.006

Abstract

Abstract: The highly selective hydrogenation of 5-hydroxymethylfurfural to 2,5-dihydroxymethylfuran is an important reaction in the field of biomass hydrogenation, because it is a bridge between biomass resources and chemical industry. Here, we precisely constructed carbon nitride supported Pd-based catalysts by a simple impregnation-reduction method. By changing the reduction temperature, catalysts with different oxidation state could be precisely constructed. Moreover, the important correlation between the ratio of Pd⁰/Pd²⁺ and catalytic activity is revealed during the selective hydrogenation of HMF. The Pd/g-C₃N₄-300 catalyst with a Pd⁰/Pd²⁺ ratio of 3/2 showed the highest catalytic activity, which could get 96.9% 5-hydroxymethylfurfural conversion and 90.3% 2,5-dihydroxymethylfuran selectivity. Further density functional theory calculation revealed that the synergistic effect between Pd⁰ and Pd²⁺ in Pd/g-C₃N₄-300 system could boost the adsorption of the substrate and the dissociation of hydrogen. In this work, we highlight the important correlation between metal oxidation state and catalytic activity, which provides valuable insights for the rational design of precious metal catalysts for hydrogenation reactions.

Key words: Pd/g-C₃N₄, Selective hydrogenation, 5-hydroxymethylfurfural, 2,5-dihydroxymethylfuran, Oxidation state

摘要： The highly selective hydrogenation of 5-hydroxymethylfurfural to 2,5-dihydroxymethylfuran is an important reaction in the field of biomass hydrogenation, because it is a bridge between biomass resources and chemical industry. Here, we precisely constructed carbon nitride supported Pd-based catalysts by a simple impregnation-reduction method. By changing the reduction temperature, catalysts with different oxidation state could be precisely constructed. Moreover, the important correlation between the ratio of Pd⁰/Pd²⁺ and catalytic activity is revealed during the selective hydrogenation of HMF. The Pd/g-C₃N₄-300 catalyst with a Pd⁰/Pd²⁺ ratio of 3/2 showed the highest catalytic activity, which could get 96.9% 5-hydroxymethylfurfural conversion and 90.3% 2,5-dihydroxymethylfuran selectivity. Further density functional theory calculation revealed that the synergistic effect between Pd⁰ and Pd²⁺ in Pd/g-C₃N₄-300 system could boost the adsorption of the substrate and the dissociation of hydrogen. In this work, we highlight the important correlation between metal oxidation state and catalytic activity, which provides valuable insights for the rational design of precious metal catalysts for hydrogenation reactions.

关键词: Pd/g-C₃N₄, Selective hydrogenation, 5-hydroxymethylfurfural, 2,5-dihydroxymethylfuran, Oxidation state

Xin Li, Yue Ma, Xuning Wang, Jianguo Wu, Dong Cao, Daojian Cheng. Regulating the oxidation state of Pd to enhance the selective hydrogenation for 5-hydroxymethylfurfural[J]. Chinese Journal of Chemical Engineering, 2024, 72(8): 60-68.

Xin Li, Yue Ma, Xuning Wang, Jianguo Wu, Dong Cao, Daojian Cheng. Regulating the oxidation state of Pd to enhance the selective hydrogenation for 5-hydroxymethylfurfural[J]. 中国化学工程学报, 2024, 72(8): 60-68.

References

[1] S. Chen, R. Wojcieszak, F. Dumeignil, E. Marceau, S. Royer, How catalysts and experimental conditions determine the selective hydroconversion of furfural and 5-hydroxymethylfurfural, Chem. Rev. 118 (22) (2018) 11023-11117.
[2] Hou Q, Qi X, Zhen M, Qian H, Nie Y, Bai C, Zhang S, Bai X, Ju M. Biorefinery roadmap based on catalytic production and upgrading 5-hydroxymethylfurfural. Green Chemistry 23 (1)(2021)119-231.
[3] Y.J. Zhang, J. Zhang, D.S. Su, 5-Hydroxymethylfurfural: Akey intermediate for efficient biomass conversion, J. Energy Chem. 24 (5) (2015) 548-551.
[4] C.W. Jiang, J.D. Zhu, B. Wang, L. Li, H. Zhong, One-pot synthesis of 5-hydroxymethylfurfural from glucose over zirconium doped mesoporous KIT-6, Chin. J. Chem. Eng. 26 (6) (2018) 1270-1277.
[5] H. Li, Y. Zhong, L.X. Wang, Q. Deng, J. Wang, Z.L. Zeng, X.X. Cao, S.G. Deng, Functionalized metal-organic frameworks with strong acidity and hydrophobicity as an efficient catalyst for the production of 5-hydroxymethylfurfural, Chin. J. Chem. Eng. 33 (2021) 167-174.
[6] Y.N. Wei, Y.L. Zhang, B. Li, W. Guan, C.H. Yan, X. Li, Y.S. Yan, Facile synthesis of metal-organic frameworks embedded in interconnected macroporous polymer as a dual acid-base bifunctional catalyst for efficient conversion of cellulose to 5-hydroxymethylfurfural, Chin. J. Chem. Eng. 44 (2022) 169-181.
[7] Y. Zhong, C.Y. Huang, L.J. Li, Q. Deng, J. Wang, Z.L. Zeng, S.G. Deng, Postsynthetic acid modification of amino-tagged metal-organic frameworks: Structure-functionrelationship for catalytic 5-hydroxymethylfurfural synthesis, Chin. J. Chem. Eng. 49 (2022) 245-252.
[8] M.J. Gilkey, B.J. Xu, Heterogeneous catalytic transfer hydrogenation as an effective pathway in biomass upgrading, ACS Catal. 6 (3) (2016) 1420-1436.
[9] L. Hu, L. Lin, Z. Wu, S.Y. Zhou, S.J. Liu, Recent advances in catalytic transformation of biomass-derived 5-hydroxymethylfurfural into the innovative fuels and chemicals, Renew. Sustain. Energy Rev. 74 (2017) 230-257.
[10] L. Hu, J.X. Xu, S.Y. Zhou, A.Y. He, X. Tang, L. Lin, J.M. Xu, Y.J. Zhao, Catalytic advances in the production and application of biomass-derived 2, 5-dihydroxymethylfuran, ACS Catal. 8 (4) (2018) 2959-2980.
[11] X. Tang, J.N. Wei, N. Ding, Y. Sun, X.H. Zeng, L. Hu, S.J. Liu, T.Z. Lei, L. Lin, Chemoselective hydrogenation of biomass derived 5-hydroxymethylfurfural to diols: Key intermediates for sustainable chemicals, materials and fuels, Renew. Sustain. Energy Rev. 77 (2017) 287-296.
[12] Chatterjee M, Ishizaka T, Kawanami H. Selective hydrogenation of 5-hydroxymethylfurfural to 2,5-bis-(hydroxymethyl)furan using Pt/MCM-41 in an aqueous medium: a simple approach. Green Chem. 16 (11) (2014) 4734-4739.
[13] Vikanova KV, Chernova MS, Redina EA, Kapustin GI, Tkachenko OP, Kustov LM. Heterogeneous additive-free highly selective synthesis of 2,5-bis(hydroxymethyl)furan over catalysts with ultra-low Pt content. J. Chem. Technol. Biotechnol. 96 (9) (2021) 2421-2425.
[14] J. Wang, J.R. Zhao, J.H. Fu, C.L. Miao, S.Y. Jia, P.F. Yan, J.H. Huang, Highly selective hydrogenation of 5-hydroxymethylfurfural to 2, 5-bis(hydroxymethyl)furan over metal-oxide supported Pt catalysts: The role of basic sites, Appl. Catal. A Gen. 643 (2022) 118762.
[15] Q. Zhu, Y. Zhuang, H.Q. Zhao, P. Zhan, C. Ren, C.S. Su, W.Q. Ren, J.W. Zhang, D. Cai, P.Y. Qin, 2, 5-Diformylfuran production by photocatalytic selective oxidation of 5-hydroxymethylfurfural in water using MoS₂/CdIn₂S₄ flower-like heterojunctions, Chin. J. Chem. Eng. 54 (2023) 180-191.
[16] A. Marotta, V. Ambrogi, P. Cerruti, A. Mija, Green approaches in the synthesis of furan-based diepoxy monomers, RSC Adv. 8 (29) (2018) 16330-16335.
[17] N. Yoshie, S. Yoshida, K. Matsuoka, Self-healing of biobased furan polymers: Recovery of high mechanical strength by mild heating, Polym. Degrad. Stab. 161 (2019) 13-18.
[18] F. Chacon-Huete, C. Messina, F. Chen, L. Cuccia, X. Ottenwaelder, P. Forgione, Solvent-free mechanochemical oxidation and reduction of biomass-derived 5-hydroxymethyl furfural, Green Chem. 20 (23) (2018) 5261-5265.
[19] G. Gao, Z.C. Jiang, C.W. Hu, Selective hydrogenation of the carbonyls in furfural and 5-hydroxymethylfurfural catalyzed by PtNi alloy supported on SBA-15 in aqueous solution under mild conditions, Front. Chem. 9 (2021) 759512.
[20] M. Chatterjee, T. Ishizaka, H. Kawanami, Hydrogenation of 5-hydroxymethylfurfural in supercritical carbon dioxide-water: a tunable approach to dimethylfuran selectivity, Green Chem. 16 (3) (2014) 1543.
[21] Nakagawa Y, Takada K, Tamura M, Tomishige K. Total Hydrogenation of Furfural and 5-Hydroxymethylfurfural over Supported Pd-Ir Alloy Catalyst. ACS Catal. 4 (8) (2014) 2718-2726.
[22] S. Nishimura, N. Ikeda, K. Ebitani, Selective hydrogenation of biomass-derived 5-hydroxymethylfurfural (HMF) to 2, 5-dimethylfuran (DMF) under atmospheric hydrogen pressure over carbon supported PdAu bimetallic catalyst, Catal. Today 232 (2014) 89-98.
[23] Pisal DS, Yadav GD. Production of biofuel 2,5-dimethylfuran using highly efficient single-step selective hydrogenation of 5-hydroxymethylfurfural over novel Pd-Co/Al-Zr mixed oxide catalyst. Fuel. 290 (2021) 119947.
[24] A.D. Talpade, M.S. Tiwari, G.D. Yadav, Selective hydrogenation of bio-based 5-hydroxymethyl furfural to 2, 5-dimethylfuran over magnetically separable Fe-Pd/C bimetallic nanocatalyst, Mol. Catal. 465 (2019) 1-15.
[25] T. Thananatthanachon, T.B. Rauchfuss, Efficient production of the liquid fuel 2, 5-dimethylfuran from fructose using formic acid as a reagent, Angew. Chem. Int. Ed Engl. 49 (37) (2010) 6616-6618.
[26] J.Z. Chen, R.L. Liu, Y.Y. Guo, L.M. Chen, H. Gao, Selective hydrogenation of biomass-based 5-hydroxymethylfurfural over catalyst of palladium immobilized on amine-functionalized metal-organic frameworks, ACS Catal. 5 (2) (2015) 722-733.
[27] Sarkar C, Koley P, Shown I, Lee J, Liao Y-F, An K, Tardio J, Nakka L, Chen K-H, Mondal J. Integration of Interfacial and Alloy Effects to Modulate Catalytic Performance of Metal-Organic-Framework-Derived Cu-Pd Nanocrystals toward Hydrogenolysis of 5-Hydroxymethylfurfural. ACS Sustain Chem Eng. 7 (12) (2019) 10349-10362.
[28] F. liu, M. Audemar, K. De Oliveira Vigier, J.M. Clacens, F. De Campo, F. Jerome, Combination of Pd/C and Amberlyst-15 in a single reactor for the acid/hydrogenating catalytic conversion of carbohydrates to 5-hydroxy-2, 5-hexanedione, Green Chem. 16 (9) (2014) 4110-4114.
[29] J. Baumgard, M.M. Pohl, U. Kragl, N. Steinfeldt, Preparation of tailor-made supported catalysts using asymmetric flow field flow fractionation and their application in hydrogenation, Nanotechnol. Rev. 3 (1) (2014) 87-98.
[30] Luijkx G C. A., Huck N P. M, van Rantwijk F, Maat L, van Bekkum H. Ether Formation in the Hydrogenolysis of Hydroxymethylfurfural over Palladium Catalysts in Alcoholic Solution. Heterocycles. 77 (2009) 1037-1044.
[31] S.C. Lee, H.O. Lintang, L. Yuliati, Photocatalytic removal of phenol under visible light irradiation on zinc phthalocyanine/mesoporous carbon nitride nanocomposites, J. Exp. Nanosci. 9 (1) (2014) 78-86.
[32] N.V. Long, T. Hayakawa, T. Matsubara, N.D. Chien, M. Ohtaki, M. Nogami, Controlled synthesis and properties of palladium nanoparticles, J. Exp. Nanosci. 7 (4) (2012) 426-439.
[33] Y. Mizukoshi, K. Sato, J. Kugai, T.A. Yamamoto, T.J. Konno, N. Masahashi, Catalytic activities of sonochemically prepared Au-core/Pd-shell-structured bimetallic nanoparticles immobilised on TiO₂ and its dependence on Pd-shell thickness, J. Exp. Nanosci. 10 (3) (2015) 235-247.
[34] O. El-Sharnouby, H.K. Boparai, J. Herrera, D.M. O’Carroll, Aqueous-phase catalytic hydrodechlorination of 1, 2-dichloroethane over palladium nanoparticles (nPd) with residual borohydride from nPd synthesis, Chem. Eng. J. 342 (2018) 281-292.
[35] M. Hronec, K. Fulajtarova, I. Vavra, T. Sotak, E. Dobrocka, M. Micusik, Carbon supported Pd-Cu catalysts for highly selective rearrangement of furfural to cyclopentanone, Appl. Catal. B Environ. 181 (2016) 210-219.
[36] Kim SC, Shim WG. Properties and performance of Pd based catalysts for catalytic oxidation of volatile organic compounds. Appl Catal B. 92 (2009) 429-436.
[37] K.L. Liu, R.X. Qin, L.Y. Zhou, P.X. Liu, Q.H. Zhang, W.T. Jing, P.P. Ruan, L. Gu, G. Fu, N.F. Zheng, Cu 2 O-supported atomically dispersed Pd catalysts for semihydrogenation of terminal alkynes: critical role of oxide supports, CCS Chem. 1 (2) (2019) 207-214.
[38] Senftle TP, van Duin ACT, Janik MJ. Role of Site Stability in Methane Activation on PdxCe_1-xO_δ Surfaces. ACS Catal. 5 (10) (2015) 6187-6199.
[39] F. Wang, C.G. Xia, S.P. de Visser, Y. Wang, How does the oxidation state of palladium surfaces affect the reactivity and selectivity of direct synthesis of hydrogen peroxide from hydrogen and oxygen gases? A density functional study, J. Am. Chem. Soc. 141 (2) (2019) 901-910.
[40] D. Cao, J.Y. Wang, H.X. Xu, D.J. Cheng, Construction of dual-site atomically dispersed electrocatalysts with Ru-C₅ single atoms and Ru-O₄ nanoclusters for accelerated alkali hydrogen evolution, Small 17 (31) (2021) e2101163.
[41] Z.P. Chen, S. Pronkin, T.P. Fellinger, K. Kailasam, G. Vile, D. Albani, F. Krumeich, R. Leary, J. Barnard, J.M. Thomas, J. Perez-Ramirez, M. Antonietti, D. Dontsova, Merging single-atom-dispersed silver and carbon nitride to a joint electronic system via copolymerization with silver tricyanomethanide, ACS Nano 10 (3) (2016) 3166-3175.
[42] Y. Wang, J. Yao, H.R. Li, D.S. Su, M. Antonietti, Highly selective hydrogenation of phenol and derivatives over a Pd@carbon nitride catalyst in aqueous media, J. Am. Chem. Soc. 133 (8) (2011) 2362-2365.
[43] F.L. Hu, L.P. Leng, M.Y. Zhang, W.X. Chen, Y.L. Yu, J. Wang, J.H. Horton, Z.J. Li, Direct synthesis of atomically dispersed palladium atoms supported on graphitic carbon nitride for efficient selective hydrogenation reactions, ACS Appl. Mater. Interfaces 12 (48) (2020) 54146-54154.
[44] X.H. Huang, Y.J. Xia, Y.J. Cao, X.S. Zheng, H.B. Pan, J.F. Zhu, C. Ma, H.W. Wang, J.J. Li, R. You, S.Q. Wei, W.X. Huang, J.L. Lu, Enhancing both selectivity and coking-resistance of a single-atom Pd1/C₃N₄ catalyst for acetylene hydrogenation, Nano Res. 10 (4) (2017) 1302-1312.
[45] X. Long, W.Q. Chen, C. Lei, Q.Q. Xie, F.Z. Zhang, B.B. Huang, Ultrafine Pd nanoparticles@g-C₃N₄ for highly efficient dehalogenation of chlorinated environmental pollutant: Structure, efficacy and mechanisms, Sci. Total Environ. 775 (2021) 145178.
[46] Y. Nan, Z.R. Deng, Z.Y. Xi, D.F. Wu, Controlled synthesis of α-Al₂O₃ supported Ag particles with tuning catalytic performance, J. Exp. Nanosci. 17 (1) (2022) 1-13.
[47] J.Z. Chen, F. Lu, J.J. Zhang, W.Q. Yu, F. Wang, J. Gao, J. Xu, Immobilized Ru clusters in nanosized mesoporous zirconium silica for the aqueous hydrogenation of furan derivatives at room temperature, ChemCatChem 5 (10) (2013) 2822-2826.
[48] J. Ohyama, A. Esaki, Y. Yamamoto, S. Arai, A. Satsuma, Selective hydrogenation of 2-hydroxymethyl-5-furfural to 2, 5-bis(hydroxymethyl)furan over gold sub-nano clusters, RSC Adv. 3 (4) (2013) 1033-1036.
[49] M. Tamura, K. Tokonami, Y. Nakagawa, K. Tomishige, Rapid synthesis of unsaturated alcohols under mild conditions by highly selective hydrogenation, Chem. Commun. 49 (63) (2013) 7034-7036.
[50] Wang XL, Fang WQ, Liu W, Jia Y, Jing D, Wang Y, Yang L-Y, Gong X-Q, Yao Y-F, Yang HG, Yao X. Broensted base site engineering of graphitic carbon nitride for enhanced photocatalytic activity. J Mater Chem A. 5 (36) (2017):19227-19236.