Fabrication of surface passivated two-dimensional MFI zeolite for alkylation between toluene with methanol

doi:10.1007/s11705-024-2407-3

Front. Chem. Sci. Eng.

2024, Vol. 18

Issue (4) : 46 https://doi.org/10.1007/s11705-024-2407-3

Fabrication of surface passivated two-dimensional MFI zeolite for alkylation between toluene with methanol

Zhenyuan Zou¹, Shengzhi Gan¹, Ting Pu¹, Xingxing Zeng¹, Yi Huang², Baoyu Liu¹(

)

¹. School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China
². School of Engineering, Institute for Materials & Processes, the University of Edinburgh, Edinburgh EH9 3FB, United Kingdom

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Abstract

The fabrication of suitable MFI zeolites to effectively produce para-xylene through the alkylation between toluene and methanol is highly desired. Here, the two-dimensional pillared MFI zeolite was modified by silicalite-1, and its morphology and structure were systematically investigated by tuning the concentration of Si species during the secondary crystallization process. The MFI zeolites were characterized by X-ray diffraction, transmission electron microscopy, pyridine-infrared and N₂ adsorption-desorption isotherms. The characterization results showed that the external Brønsted acid sites of surface passivated P-MFI-x samples have been successfully shielded. Interestingly, the P-MFI-23 showed long lifetime and high selectivity of para-xylene (about 35%) based on the cooperation between opened interlamellar structure and passivated silicalite-1 layer. It was found that the accumulated hard coke in the interior of MFI zeolites not only blocked the channels of zeolites but also covered the acidic sites, resulting in the deactivation of catalyst. Furthermore, the highest selectivity of para-xylene (about 48%) can be achieved for P-MFI-30 under harsh reaction condition, which also exhibited excellent regeneration property in the alkylation reaction between toluene and methanol. The strategy described in present research may open a window for the design of other advanced materials.

Keywords alkylation MFI nanosheets catalysis

Corresponding Author(s): Baoyu Liu

Just Accepted Date: 12 January 2024 Issue Date: 15 March 2024

Cite this article:

Zhenyuan Zou,Shengzhi Gan,Ting Pu, et al. Fabrication of surface passivated two-dimensional MFI zeolite for alkylation between toluene with methanol[J]. Front. Chem. Sci. Eng., 2024, 18(4): 46.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-024-2407-3
https://academic.hep.com.cn/fcse/EN/Y2024/V18/I4/46

Scheme1 Schematic diagram of the preparation process for P-MFI-x.

Fig.1 Low-angle and high-angle XRD patterns of various zeolites.

Fig.2 TEM-HRTEM images of (a–c) P-MFI-23, (d–f) P-MFI-26 and (g–i) P-MFI-30, respectively.

Tab.1 Texture properties of various zeolites

Fig.3 (a) N₂ adsorption-desorption isotherms and (b) pore size distributions of BJH of various zeolites.

Scheme2 Process diagram of passivating P-MFI with silicalite-1.

Tab.2 Acidity of various zeolites

Fig.4 (a) FTIR spectra for pyridine and (b) 2,6-di-tert-butylpyridine adsorbed on various zeolites.

Fig.5 (a) Toluene conversion and (b) para-xylene selectivity of various zeolites.

Tab.3 Texture properties of fresh and spent zeolites

Tab.4 Acidity of various zeolites

Fig.6 TG profiles of spent zeolites.

Scheme3 Coke distribution on the (a) interior lamellar space and (b) exterior silicalite-1 channels for spent P-MFI-x.

Tab.5 Coke deposit of spent zeolites

Tab.6 Textural properties of fresh and regenerated zeolites

Fig.7 N₂ adsorption-desorption isotherms and BJH Pore size distributions of regenerated zeolites.

Fig.8 (a) Toluene conversion and (b) para-xylene selectivity of fresh and regenerated zeolites.

1	H Han , A F Zhang , L M Ren , X W Nie , M Liu , Y Liu , C Shi , H Yang , C S Song , X W Guo . Coke-resistant (Pt + Ni)/ZSM-5 catalyst for shape-selective alkylation of toluene with methanol to para-xylene. Chemical Engineering Science, 2022, 252: 117529 https://doi.org/10.1016/j.ces.2022.117529
2	R A F Tomás , J C M Bordado , J F P Gomes . p-xylene oxidation to terephthalic acid: a literature review oriented toward process optimization and development. Chemical Reviews, 2013, 113(10): 7421–7469 https://doi.org/10.1021/cr300298j
3	H Han , H Yang , A F Zhang , L M Ren , X W Nie , C Q Chen , M Liu , C A Shi , C S Song , X W Guo . Design of highly stable metal/ZSM-5 catalysts for the shape-selective alkylation of toluene with methanol to para-xylene. Inorganic Chemistry Frontiers, 2022, 9(13): 3348–3358 https://doi.org/10.1039/D2QI00686C
4	M T Ashraf , R Chebbi , N A Darwish . Process of p-xylene production by highly selective methylation of toluene. Industrial & Engineering Chemistry Research, 2013, 52(38): 13730–13737 https://doi.org/10.1021/ie401156x
5	W Vermeiren , J P Gilson . Impact of zeolites on the petroleum and petrochemical industry. Topics in Catalysis, 2009, 52(9): 1131–1161 https://doi.org/10.1007/s11244-009-9271-8
6	A M Niziolek , O Onel , C A Floudas . Production of benzene, toluene, and xylenes from natural gas via methanol: process synthesis and global optimization. AIChE Journal. American Institute of Chemical Engineers, 2016, 62(5): 1531–1556 https://doi.org/10.1002/aic.15144
7	T Li , T Shoinkhorova , J Gascon , J Ruiz-Martínez . Aromatics production via methanol-mediated transformation routes. ACS Catalysis, 2021, 11(13): 7780–7819 https://doi.org/10.1021/acscatal.1c01422
8	S Ilias , A Bhan . The mechanism of aromatic dealkylation in methanol-to-hydrocarbons conversion on H-ZSM-5: What are the aromatic precursors to light olefins?. Journal of Catalysis, 2014, 311: 6–16 https://doi.org/10.1016/j.jcat.2013.11.003
9	J Čejka , B Wichterlová . Acid-catalyzed synthesis of mono- and dialkyl benzenes over zeolites: active sites, zeolite topology, and reaction mechanisms. Catalysis Reviews. Science and Engineering, 2002, 44(3): 375–421 https://doi.org/10.1081/CR-120005741
10	B Xue , J Chen , N Liu , J Guo , J Xu , C F Xu , Q M Shen , Y X Li . Role of complex equilibrium in the shape-selective performances of MgO/MCM-22 catalysts prepared by complexing impregnation. Catalysis Communications, 2014, 56: 174–178 https://doi.org/10.1016/j.catcom.2014.07.019
11	C Lee , S Lee , W Kim , R Ryoo . High utilization of methanol in toluene methylation using MFI zeolite nanosponge catalyst. Catalysis Today, 2018, 303: 143–149 https://doi.org/10.1016/j.cattod.2017.09.056
12	Y R Wang , M Liu , A F Zhang , Y Zuo , F S Ding , Y Chang , C S Song , X W Guo . Methanol usage in toluene methylation over Pt modified ZSM-5 catalyst: effects of total pressure and carrier gas. Industrial & Engineering Chemistry Research, 2017, 56(16): 4709–4717 https://doi.org/10.1021/acs.iecr.7b00318
13	J H Li , H Xiang , M Liu , Q L Wang , Z R Zhu , Z H Hu . The deactivation mechanism of two typical shape-selective HZSM-5 catalysts for alkylation of toluene with methanol. Catalysis Science & Technology, 2014, 4(8): 2639–2649 https://doi.org/10.1039/c4cy00095a
14	C Jo , K Cho , J Kim , R Ryoo . MFI zeolite nanosponges possessing uniform mesopores generated by bulk crystal seeding in the hierarchical surfactant-directed synthesis. Chemical Communications, 2014, 50(32): 4175–4177 https://doi.org/10.1039/C4CC01070A
15	J L Sotelo , M A Uguina , J L Valverde , D P Serrano . Deactivation of toluene alkylation with methanol over magnesium-modified ZSM-5 Shape selectivity changes induced by coke formation. Applied Catalysis A, General, 1994, 114(2): 273–285 https://doi.org/10.1016/0926-860X(94)80179-7
16	P Dong , Z Y Li , D L Wang , X R Wang , Y Q Guo , G X Li , D Q Zhang . Alkylation of benzene by methanol: thermodynamics analysis for designing and designing for enhancing the selectivity of toluene and para-xylene. Catalysis Letters, 2019, 149(1): 248–258 https://doi.org/10.1007/s10562-018-2590-2
17	S Ren , C Tian , Y H Yue , W Zou , W M Hua , Z Gao . Selective alkylation of benzene with methanol to toluene and xylene over sheet-like ZSM-5 with controllable b-oriented length. Catalysis Letters, 2023, 4: 352–361 https://doi.org/10.1007/s10562-023-04352-9
18	F Xiong , C Ji , S Z Gan , P Liang , Y Huang , J Shang , B Y Liu , J X Dong . Tuning the mesoscopically structured ZSM-5 nanosheets for the alkylation between toluene and methanol. AIChE Journal. American Institute of Chemical Engineers, 2023, 69(6): e18054 https://doi.org/10.1002/aic.18054
19	C F Wang , Q Zhang , Y F Zhu , D K Zhang , J Y Chen , F K Chiang . p-Xylene selectivity enhancement in methanol toluene alkylation by separation of catalysis function and shape-selective function. Molecular Catalysis, 2017, 433: 242–249 https://doi.org/10.1016/j.mcat.2016.12.007
20	J Prech , P Pizarro , D P Serrano , J Cejka . From 3D to 2D zeolite catalytic materials. Chemical Society Reviews, 2018, 47(22): 8263–8306 https://doi.org/10.1039/C8CS00370J
21	X L Shao , S Q Wang , Y H Zhou , X Zhang , H Z Tian , Z Wang , Z Y Yuan , H T Wang . Synthesis of multilamellar ZSM-5 nanosheets with tailored b-axis thickness. Microporous and Mesoporous Materials, 2022, 345: 112252 https://doi.org/10.1016/j.micromeso.2022.112252
22	X H Meng , C H Lin , Y H Zhang , H B Qin , S Cao , L H Duan . Mass transfer behavior of benzene in hierarchically structured ZSM-5. Frontiers in Chemistry, 2019, 7: 502 https://doi.org/10.3389/fchem.2019.00502
23	M Choi , K Na , J Kim , Y Sakamoto , O Terasaki , R Ryoo . Stable single-unit-cell nanosheets of zeolite MFI as active and long-lived catalysts. Nature, 2009, 461(7261): 246–249 https://doi.org/10.1038/nature08288
24	K Na , M Choi , W Park , Y Sakamoto , O Terasaki , R Ryoo . Pillared MFI zeolite nanosheets of a single-unit-cell thickness. Journal of the American Chemical Society, 2010, 132(12): 4169–4177 https://doi.org/10.1021/ja908382n
25	X F Shen , W T Mao , Y H Ma , D D Xu , P Wu , O Terasaki , L Han , S N Che . A hierarchical MFI zeolite with a two-dimensional square mesostructure. Angewandte Chemie International Edition, 2018, 57(3): 724–728 https://doi.org/10.1002/anie.201710748
26	B Y Liu , C Wattanaprayoon , S C Oh , L Emdadi , D X Liu . Synthesis of organic pillared MFI zeolite as bifunctional acid-base catalyst. Chemistry of Materials, 2015, 27(5): 1479–1487 https://doi.org/10.1021/cm5033833
27	D D Xu , Y H Ma , Z F Jing , L Han , B Singh , J Feng , X F Shen , F L Cao , P Oleynikov , H Sun . et al.. π–π interaction of aromatic groups in amphiphilic molecules directing for single-crystalline mesostructured zeolite nanosheets. Nature Communications, 2014, 5(1): 4262 https://doi.org/10.1038/ncomms5262
28	J Hao , D G Cheng , F Q Chen , X L Zhan . n-heptane catalytic cracking on ZSM-5 zeolite nanosheets: effect of nanosheet thickness. Microporous and Mesoporous Materials, 2021, 310: 110647 https://doi.org/10.1016/j.micromeso.2020.110647
29	L Wei , K C Song , W Wu , S Holdren , G H Zhu , E Shulman , W J Shang , H Y Chen , M R Zachariah , D X Liu . Vapor-phase strategy to pillaring of two-dimensional zeolite. Journal of the American Chemical Society, 2019, 141(22): 8712–8716 https://doi.org/10.1021/jacs.9b03479
30	W Park , D Yu , K Na , K E Jelfs , B Slater , Y Sakamoto , R Ryoo . Hierarchically structure-directing effect of multi-ammonium surfactants for the generation of MFI zeolite nanosheets. Chemistry of Materials, 2011, 23(23): 5131–5137 https://doi.org/10.1021/cm201709q
31	X F Shen , W T Mao , Y H Ma , H G Peng , D D Xu , P Wu , L Han , S A Che . Mesoporous MFI zeolite with a 2D square structure directed by surfactants with an azobenzene tail group. Chemistry, 2018, 24(34): 8615–8623 https://doi.org/10.1002/chem.201800307
32	K S W Sing . Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity (Recommendations 1984). Pure and Applied Chemistry, 1985, 57(4): 603–619 https://doi.org/10.1351/pac198557040603
33	P Morales-Pacheco , F Alvarez , L Bucio , J M Domínguez . Synthesis and structural properties of zeolitic nanocrystals II: FAU-type zeolites. Journal of Physical Chemistry C, 2009, 113(6): 2247–2255 https://doi.org/10.1021/jp8070713
34	Y Q Huang , F Xiong , Z Y Zou , Y Huang , Z X Zhao , B Y Liu , J X Dong . Fabrication of β-zeolite nanocrystal aggregates for the alkylation of benzene and cyclohexene. Industrial & Engineering Chemistry Research, 2023, 62(1): 190–198 https://doi.org/10.1021/acs.iecr.2c03417
35	Y Q Huang , M N Wang , Y Huang , J Shang , B Y Liu . Mesoporous beta zeolites with controlled distribution of bronsted acid sites for alkylation of benzene with cyclohexene. Results in Engineering, 2023, 19: 101377 https://doi.org/10.1016/j.rineng.2023.101377

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