Abstract
A series of novel graphitic carbon nitride g-C3N4-HMCM-22 composite catalysts were successfully prepared. Their structure and acid properties were well characterized by thermogravimetric analysis (TGA), X-ray diffraction (XRD), N2 adsorption–desorption, Fourier transform infrared spectroscopy (TFIR), X-ray photoelectron spectroscopy (XPS), Scanning Electron Microscopy (SEM), and Py-FTIR. The prepared g-C3N4-HMCM-22 composite catalysts were then used for m-xylene (MX) isomerization. The effect of introduction of g-C3N4 on catalytic performance was studied. Compared with parent HMCM-22 catalyst, g-C3N4-HMCM-22 composite catalysts exhibited an improved p-xylene (PX) selectivity in MX isomerization. Moreover, G1H1 composite catalyst showed the highest PX selectivity than other as-prepared composite samples. Correlating the catalyst performance with its physical and chemical properties uncovers that increasing amounts of Lewis acid sites and effectively inhibiting the external Brönsted acid sites of HMCM-22 would be the key to improving the selectivity of PX.
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References
Amin R, Chang XQ, Liu BS (2017) Synergistic effect of CeO2 in CH4/CO2 dry reforming reaction over stable xCeO2yNi/MCM-22 catalysts. Ind Eng Chem Res 56:7445–7453. https://doi.org/10.1021/acs.iecr.7b01375
Araujo AS, Domingos TB, Souza MJB, Silva AOS (2001) m-xylene isomerization in SAPO-11/HZSM-5 mixed catalyst. React Kinet Catal Lett 73:283–290. https://doi.org/10.1023/A:1014155106147
Ayrault P, Datka J, Laforge S, Martin D, Guisnet M (2004) Characterization of the internal and external acidity of HMCM-22 zeolites. J Phys Chem B 108:13755–13763. https://doi.org/10.1021/jp048242z
Bailleul S, Yarulina I, Hoffman AEJ, Dokania A, Abou-Hamad E, Chowdhury AD, Pieters G, Hajek J, Wispelaere KD, Waroquier M, Gascon J, Speybroeck VV (2019) A supramolecular view on the cooperative role of Brönsted and Lewis acid sites in zeolites for methanol conversion. J Am Chem Soc 141:14823–14842. https://doi.org/10.1021/jacs.9b07484
Chaida-Chenni FZ, Belhadj F, Casas MSG, Márquez-Álvarez C, Hamacha R, Bengueddach A, Pérez-Pariente J (2018) Synthesis of mesoporous-zeolite materials using Beta zeolite nanoparticles as precursors and their catalytic performance in m-xylene isomerization and disproportionation. Appl Catal A-Gen 568:148–156. https://doi.org/10.1016/j.apcata.2018.10.005
Chu NB, Wang JQ, Zhang Y, Yang JH, Lu JM, Yin DH (2010) Nestlike hollow hierarchical MCM-22 microspheres: synthesis and exceptional catalytic properties. Chem Mater 22:2757–2763. https://doi.org/10.1021/cm903645p
Dusselier M, Davis ME (2018) Small-pore zeolites: synthesis and catalysis. Chem Rev 118:5265–5329. https://doi.org/10.1021/acs.chemrev.7b00738
Ghasemian N, Falamaki C, Kalbasi M (2014) Clinoptilolite zeolite as a potential catalyst for propane-SCR-NOx: performance investigation and kinetic analysis. Chem Eng J 236:464–470. https://doi.org/10.1016/j.cej.2013.10.061
Glotov AP, Artemova MI, Demikhova NR, Smirnova EM, Ivanov EV, Gushchin PA, Egazar’yants SV, Vinokurov VA (2019) A study of platinum catalysts based on ordered Al–MCM-41 aluminosilicate and natural halloysite nanotubes in xylene isomerization. Petrol Chem 59, 1226-1234 https://doi.org/10.1134/S0965544119110033
Groenewolt M, Antonietti M (2005) Synthesis of g-C3N4 Nanoparticles in Mesoporous Silica Host Matrices. Adv Mater 17:1789–1792. https://doi.org/10.1002/adma.200401756
Hao H, Chang Y, Yu W, Lou LL, Liu S (2017) Hierarchical porous MCM-68 zeolites: Synthesis, characterization and catalytic performance in m-xylene isomerization. Micropor Mesopor Mat 263:135–141. https://doi.org/10.1016/j.micromeso.2017.12.009
He P, Li Y, Cai K, Xiong X, Lv J, Wang Y, Huang SY, Ma XB (2020) Nano-assembled mordenite zeolite with tunable morphology for carbonylation of dimethyl Ether. ACS Appl Nano Mater 3:6460–6468. https://doi.org/10.1021/acsanm.0c00929
Jeong H, Kim Y, Lee Y, Kang M (2009) Control of acidity on the external surface of zeolite Y for m-xylene isomerization using a mechanochemical neutralization method. Korean J Chem Eng 26:371–376. https://doi.org/10.1007/s11814-009-0062-5
Leonowicz ME, Lawton JA, Lawton SL, Rubin MK (1994) A molecular-sieve with two independent multidimensional channel systems. Science 264:1910–1913. https://doi.org/10.1126/science.264.5167.1910
Li Y, Yu JH (2014) New stories of zeolite structures: their descriptions, determinations, predictions, and evaluations. Chem Rev 114:7268–7316. https://doi.org/10.1021/cr500010r
Liu S, Yang S, He J, Miao D, Yin C (2021) Efficient synthesis of chain-like ZSM-5 zeolite for the m-xylene isomerization reaction. Inorg Chem Commun 128:108564–108567. https://doi.org/10.1016/j.inoche.2021.108564
Ma XT, Zhou D, Chu X, Li D, Wang J, Song WC, Xia QH (2017) Highly selective isomerization of biomass β-pinene over hierarchically acidic MCM-22 catalyst. Micropor Mesopor Mat 237:180–188. https://doi.org/10.1016/j.micromeso.2016.09.040
Miao DY, Ding Y, Yu T, Li J, Pan XL, Bao XH (2020) Selective synthesis of benzene, toluene, and xylenes from syngas. ACS Catal 10:7389–7397. https://doi.org/10.1021/acscatal.9b05200
Min HK, Cha SH, Hong SB (2012) Mechanistic insights into the zeolite-catalyzed isomerization and disproportionation of m-xylene. ACS Catal 2:971–981. https://doi.org/10.1021/cs300127w
Qi L, Zhang YF, Conrad MA, Russell CK, Miller J, Bell AT (2020) Ethanol conversion to butadiene over isolated zinc and yttrium sites grafted onto dealuminated Beta Zeolite. J Am Chem Soc 142:14674–14687. https://doi.org/10.1021/jacs.0c06906
Rahbari ZV, Khosravan M, Kharat AN (2017) Effect of synthesis parameters on the crystallinity of EU-1 zeolite for the m-xylene isomerization reaction. Russ J Appl Chem 90:818–825. https://doi.org/10.1134/S107042721705024X
Shamzhy M, Opanasenko M, Concepción P, Martínez A (2019) New trends in tailoring active sites in zeolite-based catalysts. Chem Soc Rev 48:1095–1149. https://doi.org/10.1039/c8cs00887f
Shang YC, Yang PP, Jia MJ, Zhang WX, Wu TH (2008) Modification of MCM-22 zeolites with silylation agents: Acid properties and catalytic performance for the skeletal isomerization of n-butene. Catal Commun 9:907–912. https://doi.org/10.1016/j.catcom.2007.09.028
Shi Q, Goncalves JC, Ferreira AFP, Plaza MG, Rodrigues AE (2018) Xylene isomerization over beta zeolites in liquid phase. Ind Eng Chem Res 57:5568–5579. https://doi.org/10.1021/acs.iecr.8b00585
Talapaneni SN, Anandan S, Mane GP, Anand C, Dhawale DS, Varghese S, Mano A, Moricd T, Vinu A (2012) Facile synthesis and basic catalytic application of 3D mesoporous carbon nitride with a controllable bimodal distribution. J Mater Chem 22:9831–9840. https://doi.org/10.1039/c2jm30229b
Tsai TC, Wang I, Huang CK, Liu SD (2007) Study on the ethylbenzene and xylene conversion over modified ZSM-5. Appl Catal A 321:125–134. https://doi.org/10.1016/j.apcata.2007.01.041
Wang X, Dai WL, Wu GJ, Li LD, Guan NJ, Hunger M (2012) Phosphorus modified HMCM-22: characterization and catalytic application in methanol-to-hydrocarbons conversion. Micropor Mesopor Mat 151:99–106. https://doi.org/10.1016/j.micromeso.2011.11.008
Wang S, Wei ZH, Chen YY, Qin ZF, Ma H, Dong M, Fan WB, Wang JG (2015) Methanol to olefins over HMCM-22 zeolite: theoretical study on the catalytic roles of various pores. ACS Catal 5:1131–1144. https://doi.org/10.1021/cs501232r
Wang Y, Yokoi T, Namba S, Kondo JN, Tatsumi T (2015) Catalytic cracking of n-hexane for producing propylene on MCM-22 zeolites. Appl Catal A 504:192–202. https://doi.org/10.1016/j.apcata.2014.12.018
Wang HF, Fang LP, Yang YF, Zhang L, Wang YJ (2016) H5PMo10V2O40 immobilized on functionalized chloromethylated polystyrene by electrostatic interactions: A highly efficient and recyclable heterogeneous catalyst for hydroxylation of benzene. Catal Sci Technol 6:8005–8015. https://doi.org/10.1039/C6CY01270A
Wang YN, Gao Y, Xie SJ, Liu SL, Chen FC, Xin WJ, Zhu XX, Li XJ, Jiang N, Xu LY (2018) Adjustment of the Al siting in MCM-22 zeolite and its effect on alkylation performance of ethylene with benzene. Catal Today 316:71–77. https://doi.org/10.1016/j.cattod.2018.02.040
Weston SC, Peterson BK, Gatt JE, Lonergan WW, Vroman HB, Afeworki M, Kennedy GJ, Dorset DL, Shannon MD, Strohmaier KG (2019) KMM-17, a new three-dimensional zeolite with unique 11-ring channels and superior catalytic isomerization performance. J Am Chem Soc 141:15910–15920. https://doi.org/10.1021/jacs.9b07102
Wu P, Komatsu T, Yashima T (1998) Selective formation of p-xylene with disproportionation of toluene over MCM-22 catalysts. Micropor Mesopor Mat 22:343–356. https://doi.org/10.1016/S1387-1811(98)00114-0
Wu YJ, Ren XQ, Lu YD, Wang J (2008) Crystallization and morphology of zeolite MCM-22 influenced by various conditions in the static hydrothermal synthesis. Micropor Mesopor Mat 112:138–146. https://doi.org/10.1016/j.micromeso.2007.09.022
Wu X, Hu C, Zhao GQ, Yuan Y, Zhu ZR (2016) Catalytic performance of modified HMCM-22 catalysts in xylene isomerization. Chin J Chem 34:1291–1296. https://doi.org/10.1002/cjoc.201600416
Xu H, Yan J, She XJ, Xu L, Xia JX, Xu YG, Song YH, Huang LY, Li HM (2014) Graphene-analogue carbon nitride: novel exfoliation synthesis and its application in photocatalysis and photoelectrochemical selective detection of trace amount of Cu2+. Nanoscale 6:1406–1415. https://doi.org/10.1039/c3nr04759h
Xu YG, Xie M, Huang SQ, Xu H, Ji HY, Xia JX, Li YP, Li HM (2015) High yield synthesis of nano-size g-C3N4 derivatives by a dissolve-regrowth method with enhanced photocatalytic ability. RSC Adv 5:26281–26290. https://doi.org/10.1039/c5ra01206f
Xue B, Li YX, Deng LJ (2009) Selective synthesis of p-xylene by alkylation of toluene with dimethyl carbonate over MgO-modified MCM-22. Catal Commun 10:1609–1614. https://doi.org/10.1016/j.catcom.2009.04.028
Xue B, Su J, Huang Q, Xu J, Li Y (2014) Preparation of MgO/MCM-22 catalysts by a novel two-step impregnation and their shape-selective performance in the synthesis of p-xylene. Catal Commun 45:49–53. https://doi.org/10.1016/j.catcom.2013.10.033
Yaripour F, Shariatinia Z, Sahebdelfar S, Irandoukht A (2015) Conventional hydrothermal synthesis of nanostructured H-ZSM-5 catalysts using various templates for light olefins production from methanol. J Nat Gas Sci Eng 22:260–269. https://doi.org/10.1016/j.jngse.2014.12.001
Yeong YF, Abdullah AZ, Ahmad AL, Bhatia S (2010) Synthesis, characterization and reactive separation activity of acid-functionalized silicalite-1 catalytic membrane in m-xylene isomerization. J Membr Sci 360:109–122. https://doi.org/10.1016/j.memsci.2010.05.009
Zhang WF, Liang JH, Liu YQ, SunS F, Ren XQ, Jiang M (2013) Knoevenagel condensation reaction over acid-base bifunctional MgO/HMCM-22 catalysts. Chin J Catal 34:559–566. https://doi.org/10.1016/S1872-2067(11)60493-2
Zhao P, Wang J, Chen G, Zhou Y, Huang J (2013) Phase-transfer hydroxylation of benzene with H2O2 catalyzed by a nitrile-functionalized pyridinium phosphovanadomolybdate. Catal Sci Technol 3:1394–1404. https://doi.org/10.1039/c3cy20796j
Zhou J, Liu Z, Li L, Wang Y, Gao H, Yang W, Xie Z, Tang Y (2013) Hierarchical mesoporous ZSM-5 zeolite with increased external surface acid sites and high catalytic performance in o-xylene isomerization. Chin J Catal 34:1429–1433. https://doi.org/10.1016/S1872-2067(12)60602-0
Funding
This work was supported by National Natural Science Foundation of China (21878027), Advanced Catalysis and Green Manufacturing Collaborative Innovation Center (ACGM2020-08), Natural Science Foundation of the Jiangsu Higher Education Institutions (18KJA150001 and 19KJA430003), and Foundation of State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering (2017-K28).
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Liu, Z., Zhang, Z., Xie, D. et al. Preparation of graphitic carbon nitride g-C3N4-HMCM-22 composite catalysts and enhanced para-selectivity in m-xylene isomerization. Chem. Pap. 76, 1875–1884 (2022). https://doi.org/10.1007/s11696-021-01982-4
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DOI: https://doi.org/10.1007/s11696-021-01982-4