构筑开放锡位点实现酸性增强的二甲醚羰基化丝光沸石催化剂设计

Ying Li; Man Yu; Guodong Qi; Yunduo Liu; Jing Lv; Shouying Huang; Xinbin Ma

doi:10.1016/j.eng.2023.01.020

PDF(2361 KB)

工程（英文） ›› 2024, Vol. 35 ›› Issue (4) : 104-114. DOI: 10.1016/j.eng.2023.01.020

研究论文

Article

构筑开放锡位点实现酸性增强的二甲醚羰基化丝光沸石催化剂设计

Ying Li ^a^,^c ,
Man Yu ^a ,
Guodong Qi ^b ,
Yunduo Liu ^a ,
Jing Lv ^a ,
Shouying Huang ^a^,^* ,
Xinbin Ma ^a^,^*

作者信息 +

Designing a Mordenite Catalyst with Enhanced Acidity for Dimethyl Ether Carbonylation by Engineering Open Sn Sites

Ying Li ^a^,^c ,
Man Yu ^a ,
Guodong Qi ^b ,
Yunduo Liu ^a ,
Jing Lv ^a ,
Shouying Huang ^a^,^* ,
Xinbin Ma ^a^,^*

Author information +

History +

Abstract

Due to their tunable acidity, shape selectivity, and excellent stability, zeolites are of great importance as solid acid materials in industrial catalysis. Tuning the properties of the acid sites in zeolites allows for the rational design and fabrication of catalysts for target reactions. Dimethyl ether (DME) carbonylation, a critical chain-growth reaction for C1 resource utilization, is selectively catalyzed by the Brønsted acid sites within the eight-membered rings (8-MRs) of mordenite (MOR). It is anticipated that strengthening the Brønsted acidity—particularly in 8-MRs—will improve the catalytic performance of MOR. In this work, density functional theory (DFT) calculations are first employed and the results used to design a modified MOR with stannum (Sn) and to predict the corresponding changes in acidity. Guided by the theoretical studies, a series of Sn-modified MOR are synthesized via a defect-engineering and subsequent heteroatom-substitution strategy. After partial desilication, isolated tetrahedral Sn species in an open configuration are successfully synthesized for the first time, within which tetrahedrally coordinated Al sites are preserved. An acidic characterization is used to confirm that the acidity of the Brønsted acid sites is enhanced by the introduction of the Sn species; as a result, the sample exhibits excellent activity in DME carbonylation reaction. Kinetic and DFT studies reveal that this strengthened acidity facilitates the adsorption of DME and reduces the activation barriers of DME dissociation and acetyl formation, accounting for the improved activity. The work demonstrates mechanistic insights into the promoting effects of strong acidity on DME carbonylation and offers a promising strategy to precisely control the acidic strength of zeolites.

Keywords

Zeolite / Sn modification / Carbonylation / Brønsted acid catalysis / Acidic strength

引用本文

EndNote

Ris (Procite)

Bibtex

导出引用

Ying Li, Man Yu, Guodong Qi. . Engineering. 2024, 35(4): 104-114 https://doi.org/10.1016/j.eng.2023.01.020

参考文献

原文顺序 | 文献年度倒序 | 文中引用次数倒序

[1]	L. Yang, C. Wang, L. Zhang, W. Dai, Y. Chu, J. Xu, et al. Stabilizing the framework of SAPO-34 zeolite toward long-term methanol-to-olefins conversion. Nat Commun, 12 (2021), pp. 4661-4671.
[2]	P. Del Campo, M.T. Navarro, S.K. Shaikh, M.D. Khokhar, F. Aljumah, C. Martinez, et al. Propene production by butene cracking. Descriptors for zeolite catalysts. ACS Catal, 10 (20) (2020), pp. 11878-11891.
[3]	S. Liu, Y. He, H. Zhang, Z. Chen, E. Lv, J. Ren, et al. Design and synthesis of Ga-doped ZSM-22 zeolites as highly selective and stable catalysts for n-dodecane isomerization. Catal Sci Technol, 9 (11) (2019), pp. 2812-2827.
[4]	Y. Liu, E. Barath, H. Shi, J. Hu, D.M. Camaioni, J.A. Lercher. Solvent-determined mechanistic pathways in zeolite-H-BEA-catalysed phenol alkylation. Nat Catal, 1 (2) (2018), pp. 141-147.
[5]	Y. Li, J. Yu. Emerging applications of zeolites in catalysis, separation and host-guest assembly. Nat Rev Mater, 6 (12) (2021), pp. 1156-1174.
[6]	A.J. Jones, E. Iglesia. The strength of bronsted acid sites in microporous aluminosilicates. ACS Catal, 5 (10) (2015), pp. 5741-5755.
[7]	A.A. Arvidsson, P.N. Plessow, F. Studt, A. Hellman. Influence of acidity on the methanol-to-DME reaction in zeotypes: a first principles-based microkinetic study. J Phys Chem C, 124 (27) (2020), pp. 14658-14663.
[8]	A.J. Jones, R.T. Carr, S.I. Zones, E. Iglesia. Acid strength and solvation in catalysis by MFI zeolites and effects of the identity, concentration and location of framework heteroatoms. J Catal, 312 (2014), pp. 58-68.
[9]	Z. Shi, M. Neurock, A. Bhan. Methanol-to-olefins catalysis on HSSZ-13 and HSAPO-34 and its relationship to acid strength. ACS Catal, 11 (3) (2021), pp. 1222-1232.
[10]	D. Yang, C. Sararuk, H. Wang, S.J. Zhang, Z.X. Li, C.S. Li. Effect of metal ion in bulk VPO in aldol condensation of formaldehyde and methyl acetate to methyl acrylate. Ind Eng Chem Res, 57 (1) (2018), pp. 93-100.
[11]	B.H. Wang, B.M. Ge, J. Zhu, L.N. Wang. Process optimization study on the carbonylation of methyl acetate. Chin J Chem Eng, 26 (9) (2018), pp. 1937-1942.
[12]	P. Dunås, L.C. Murfin, O.J. Nilsson, N. Jame, S.E. Lewis, N. Kann. Azulene functionalization by iron-mediated addition to a cyclohexadiene scaffold. J Org Chem, 85 (21) (2020), pp. 13453-13465.
[13]	C. Portilho Trentini, B.T.F. de Mello, V. Ferreira Cabral, C. da Silva. Crambe seed oil: extraction and reaction with dimethyl carbonate under pressurized conditions. J Supercrit Fluids, 159 (2020), Article 104780.
[14]	W. Zhou, J. Kang, K. Cheng, S. He, J. Shi, C. Zhou, et al. Direct conversion of syngas into methyl acetate, ethanol, and ethylene by relay catalysis via the intermediate dimethyl ether. Angew Chem Int Ed, 57 (37) (2018), pp. 12012-12016.
[15]	M. Boronat, C. Martínez-Sánchez, D. Law, A. Corma. Enzyme-like specificity in zeolites: a unique site position in mordenite for selective carbonylation of methanol and dimethyl ether with CO. J Am Chem Soc, 130 (48) (2008), pp. 16316-16323.
[16]	A. Bhan, A.D. Allian, G.J. Sunley, D.J. Law, E. Iglesia. Specificity of sites within eight-membered ring zeolite channels for carbonylation of methyls to acetyls. J Am Chem Soc, 129 (16) (2007), pp. 4919-4924.
[17]	H. Ham, H.S. Jung, H.S. Kim, J. Kim, S.J. Cho, W.B. Lee, et al. Gas-phase carbonylation of dimethyl ether on the stable seed-derived ferrierite. ACS Catal, 10 (9) (2020), pp. 5135-5146.
[18]	M. Lusardi, T.T. Chen, M. Kale, J.H. Kang, M. Neurock, M.E. Davis. Carbonylation of dimethyl ether to methyl acetate over SSZ-13. ACS Catal, 10 (1) (2020), pp. 842-851.
[19]	X. Feng, J. Yao, H. Li, Y. Fang, Y. Yoneyama, G. Yang, et al. A brand new zeolite catalyst for carbonylation reaction. Chem Commun, 55 (8) (2019), pp. 1048-1051.
[20]	Z. Xiong, E. Zhan, M. Li, W. Shen. DME carbonylation over a HSUZ-4 zeolite. Chem Commun, 56 (23) (2020), pp. 3401-4344.
[21]	H.B. Shen, Y. Li, S.Y. Huang, K. Cai, Z.Z. Cheng, J. Lv, et al. The carbonylation of dimethyl ether catalyzed by supported heteropoly acids: the role of Brønsted acid properties. Catal Today, 330 (2019), pp. 117-123.
[22]	K. Cai, Y. Li, H. Shen, Z. Cheng, S. Huang, Y. Wang, et al. A density functional theory study on the mechanism of dimethyl ether carbonylation over heteropolyacids catalyst. Front Chem Sci Eng, 15 (2) (2021), pp. 319-329.
[23]	K. Cai, S. Huang, Y. Li, Z. Cheng, J. Lv, X. Ma. Influence of acid strength on the reactivity of dimethyl ether carbonylation over H-MOR. ACS Sustain Chem Eng, 7 (2) (2019), pp. 2027-2034.
[24]	D. Verboekend, M. Milina, J. Perez-Ramirez. Hierarchical silicoaluminophosphates by postsynthetic modification: influence of topology, composition, and silicon distribution. Chem Mater, 26 (15) (2014), pp. 4552-4562.
[25]	V. Machado, J. Rocha, A.P. Carvalho, A. Martins. Modification of MCM-22 zeolite through sequential post-synthesis treatments. Implications on the acidic and catalytic behaviour. Appl Catal A, 445-446 (2012), pp. 329-338.
[26]	P. Gao, Q. Wang, J. Xu, G. Qi, C. Wang, X. Zhou, et al. Brønsted/Lewis acid synergy in methanol-to-aromatics conversion on Ga-modified ZSM-5 zeolites, as studied by solid-state NMR spectroscopy. ACS Catal, 8 (1) (2018), pp. 69-74.
[27]	Z. Yu, S. Li, Q. Wang, A. Zheng, X. Jun, L. Chen, et al. Brønsted/Lewis acid synergy in H-ZSM-5 and H-MOR zeolites studied by ¹H and ²⁷Al DQ-MAS solid-state NMR spectroscopy. J Phys Chem C, 115 (45) (2011), pp. 22320-22327.
[28]	S. Li, A. Zheng, Y. Su, H. Zhang, L. Chen, J. Yang, et al. Brønsted/Lewis acid synergy in dealuminated HY zeolite: a combined solid-state NMR and theoretical calculation study. J Am Chem Soc, 129 (36) (2007), pp. 11161-11171.
[29]	H.J. Cho, P. Dornath, W. Fan. Synthesis of hierarchical Sn-MFI as Lewis acid catalysts for isomerization of cellulosic sugars. ACS Catal, 4 (6) (2014), pp. 2029-2037.
[30]	B. Tang, W. Dai, G. Wu, N. Guan, L. Li, M. Hunger. Improved postsynthesis strategy to Sn-beta zeolites as Lewis acid catalysts for the ring-opening hydration of epoxides. ACS Catal, 4 (8) (2014), pp. 2801-2810.
[31]	Y. Injongkol, T. Maihom, P. Treesukul, J. Sirijaraensre, B. Boekfa, J. Limtrakul. Theoretical study on the reaction mechanism of hydrogenation of furfural to furfuryl alcohol on Lewis acidic BEA zeolites: effects of defect structure and tetravalent metals substitution. Phys Chem Chem Phys, 19 (35) (2017), pp. 24042-24048.
[32]	Y. Li, S. Huang, Z. Cheng, K. Cai, L. Li, E. Milan, et al. Promoting the activity of Ce-incorporated MOR in dimethyl ether carbonylation through tailoring the distribution of bronsted acids. Appl Catal B, 256 (2019), Article 117777.
[33]	J.S. Bates, B.C. Bukowski, J.W. Harris, J. Greeley, R. Gounder. Distinct catalytic reactivity of Sn substituted in framework locations and at defect grain boundaries in Sn-zeolites. ACS Catal, 9 (7) (2019), pp. 6146-6168.
[34]	J.W. Harris, M.J. Cordon, J.R. Di Iorio, J.C. Vega-Vila, F.H. Ribeiro, R. Gounder. Titration and quantification of open and closed Lewis acid sites in Sn-beta zeolites that catalyze glucose isomerization. J Catal, 335 (2016), pp. 141-154.
[35]	L. Qi, Y. Zhang, M.A. Conrad, C.K. Russell, J. Miller, A.T. Bell. Ethanol conversion to butadiene over isolated zinc and yttrium sites grafted onto dealuminated beta zeolite. J Am Chem Soc, 142 (34) (2020), pp. 14674-14687.
[36]	M.M. Antunes, S. Lima, P. Neves, A.L. Magalhaes, E. Fazio, A. Fernandes, et al. One-pot conversion of furfural to useful bio-products in the presence of a Sn, Al-containing zeolite beta catalyst prepared via post-synthesis routes. J Catal, 329 (2015), pp. 522-537.
[37]	V. Petranovskii, V. Gurin, R. Machorro. Spectroscopic observation and ab initio simulation of copper clusters in zeolites. Catal Today, 107-108 (2005), pp. 892-900.
[38]	J. Dijkmans, M. Dusselier, D. Gabriels, K. Houthoofd, P.C.M.M. Magusin, S. Huang, et al. Cooperative catalysis for multistep biomass conversion with Sn/Al beta zeolite. ACS Catal, 5 (2) (2015), pp. 928-940.
[39]	C. Paris, M. Moliner, A. Corma. Metal-containing zeolites as efficient catalysts for the transformation of highly valuable chiral biomass-derived products. Green Chem, 15 (8) (2013), pp. 2101-2109.
[40]	W. Dai, C. Wang, B. Tang, G. Wu, N. Guan, Z. Xie, et al. Lewis acid catalysis confined in zeolite cages as a strategy for sustainable heterogeneous hydration of epoxides. ACS Catal, 6 (5) (2016), pp. 2955-2964.
[41]	E. Yuan, W. Dai, G. Wu, N. Guan, M. Hunger, L. Li. Facile synthesis of Sn-containing MFI zeolites as versatile solid acid catalysts. Microporous Mesoporous Mater, 270 (2018), pp. 265-273.
[42]	J.M. Campelo, D. Luna, R. Luque, J.M. Marinas, A.A. Romero, J.J. Calvino, et al. Synthesis of acidic Al-MCM-48: influence of the Si/Al ratio, degree of the surfactant hydroxyl exchange, and post-treatment in NH₄F solution. J Catal, 230 (2) (2005), pp. 327-338.
[43]	X. Yang, Y. Liu, X. Li, J. Ren, L. Zhou, T. Lu, et al. Synthesis of Sn-containing nanosized beta zeolite as efficient catalyst for transformation of glucose to methyl lactate. ACS Sustain Chem Eng, 6 (7) (2018), pp. 8256-8265.
[44]	R. Anquetil, J. Saussey, J.C. Lavalley. Confinement effect on the interaction of hydroxy groups contained in the side pockets of H-mordenite with nitriles; a FT-IR study. Phys Chem Chem Phys, 1 (4) (1999), pp. 555-560.
[45]	W. Daniell, N.Y. Topsoe, H. Knozinger. An FTIR study of the surface acidity of USY zeolites: comparison of CO, CD₃CN, and C₅H₅N probe molecules. Langmuir, 17 (20) (2001), pp. 6233-6239.
[46]	R. Otomo, R. Kosugi, Y. Kamiya, T. Tatsumi, T. Yokoi. Modification of Sn-beta zeolite: characterization of acidic/basic properties and catalytic performance in Baeyer-Villiger oxidation. Catal Sci Technol, 6 (8) (2016), pp. 2787-2795.
[47]	G. Qi, Q. Wang, J. Xu, Q. Wu, C. Wang, X. Zhao, et al. Direct observation of tin sites and their reversible interconversion in zeolites by solid-state NMR spectroscopy. Commun Chem, 1 (1) (2018), p. 22.
[48]	A.V. Yakimov, Y.G. Kolyagin, S. Tolborg, P.N.R. Vennestrøm, I.I. Ivanova. ¹¹⁹Sn MAS NMR study of the interaction of probe molecules with Sn-BEA: the origin of penta- and hexacoordinated tin formation. J Phys Chem C, 120 (49) (2016), pp. 28083-28092.
[49]	M. Wang, S. Huang, J. Lu, Z. Cheng, Y. Li, S. Wang, et al. Modifying the acidity of H-MOR and its catalytic carbonylation of dimethyl ether. Chin J Catal, 37 (9) (2016), pp. 1530-1537.
[50]	C.A. Emeis. Determination of integrated molar extinction coefficients for infrared absorption bands of pyridine adsorbed on solid acid catalysts. J Catal, 141 (2) (1993), pp. 347-354.
[51]	J. Xu, A. Zheng, X. Wang, G. Qi, J. Su, J. Du, et al. Room temperature activation of methane over Zn modified H-ZSM-5 zeolites: insight from solid-state NMR and theoretical calculations. Chem Sci, 3 (10) (2012), pp. 2932-2940.
[52]	D.H. Barich, J.B. Nicholas, T. Xu, J.F. Haw. Theoretical and experimental study of the ¹³C chemical shift tensors of acetone complexed with Brønsted and Lewis acids. J Am Chem Soc, 120 (47) (1998), pp. 12342-12350.
[53]	S. Li, S.J. Huang, W. Shen, H. Zhang, H. Fang, A. Zheng, et al. Probing the spatial proximities among acid sites in dealuminated H-Y zeolite by solid-state NMR spectroscopy. J Phys Chem C, 112 (37) (2008), pp. 14486-14494.
[54]	L.K. Ono, C.B. Roldan. Size effects on the desorption of O₂ from Au₂O₃/Au⁰ nanoparticles supported on SiO₂: a TPD study. J Phys Chem C, 112 (47) (2008), pp. 18543-18550.
[55]	K. Cao, D. Fan, L. Li, B. Fan, L. Wang, D. Zhu, et al. Insights into the pyridine-modified MOR zeolite catalysts for DME carbonylation. ACS Catal, 10 (5) (2020), pp. 3372-3380.
[56]	P. Cheung, A. Bhan, G.J. Sunley, D.J. Law, E. Iglesia. Site requirements and elementary steps in dimethyl ether carbonylation catalyzed by acidic zeolites. J Catal, 245 (1) (2007), pp. 110-123.
[57]	B.J. Li, J. Xu, B. Han, X.M. Wang, G.D. Qi, Z.F. Zhang, et al. Insight into dimethyl ether carbonylation reaction over mordenite zeolite from in-situ solid-state NMR spectroscopy. J Phys Chem C, 117 (11) (2013), pp. 5840-5847.
[58]	D.B. Rasmussen, J.M. Christensen, B. Temel, F. Studt, P.G. Moses, J. Rossmeisl, et al. Ketene as a reaction intermediate in the carbonylation of dimethyl ether to methyl acetate over mordenite. Angew Chem Int Ed, 54 (25) (2015), pp. 7261-7264.
[59]	H. Zhou, W.L. Zhu, L. Shi, H.C. Liu, S.P. Liu, Y.M. Ni, et al. In situ DRIFT study of dimethyl ether carbonylation to methyl acetate on H-mordenite. J Mol Catal Chem, 417 (2016), pp. 1-9.
[60]	Y. Li, S.Y. Huang, Z.Z. Cheng, S.P. Wang, Q.F. Ge, X.B. Ma. Synergy between Cu and Brønsted acid sites in carbonylation of dimethyl ether over Cu/H-MOR. J Catal, 365 (2018), pp. 440-449.