Abstract
Catalytic alkylation of benzene with ethanol has been considered as a sustainable alternative for producing ethylbenzene/diethylbenzene. This paper reports the promoted synthesis of hollow nano-sized (20–80 nm) ZSM-5 zeolite as excellent yet durable catalyst of benzene alkylation, which is achieved by adding N-methyl-2-pyrrolidone (NMP) and quaternary ammonium cationic hydroxyethyl cellulose (JR-400) in its synthesis gel during the synthesis. It is revealed by the ESI–MS and TEM characterization that the NMP promotes the dissolution–recrystallization of the ZSM-5 and a hollow structure is generated during the process. The JR-400 as special promoter further favors the formation of ordered nano-zeolite grain and suitable microstructure, confirmed by the molecular dynamic modeling and characterization. That action corporately contributed to the hollow nano-sized ZSM-5 zeolite that provided hierarchical porous structure and mild acid centers, as evidenced by the 129Xe and 1H NMR spectra. The obtained hollow zeolite ZSM-5 then exhibits enhanced catalytic activities and selectivity for benzene alkylation. Moreover, it also displays an extremely superior stability (deactivation rate constant, −0.06%/h) in the catalysis of benzene alkylation with ethanol. This behavior is attributed to its hierarchical porous structure (namely less diffusion resistance) and mild acid centers, which is beneficial to moderate the carbon deposition and then the catalyst deactivation. Those research results urge the JR-400-promoted synthesis as a facile strategy for the hollow nano-sized ZSM-5 with enhanced catalytic performance during the benzene alkylation with the ethanol.
Graphical abstract
Similar content being viewed by others
References
Guo S, Wu Y, Jin T et al (2020) Controllable alkylation of benzene with mixed olefins for producing C8–C15 aromatics in jet fuel. Fuel 275:117890–117897
Wang D, Wang C, Yang G, Du Y, Yang W (2019) First-principles kinetic study on benzene alkylation with ethanol vs. ethylene in H-ZSM-5. J Catal 374:1–11
Odedairo T, Al-Khattaf S (2010) Kinetic analysis of benzene ethylation over ZSM-5 based catalyst in a fluidized-bed reactor. Chem Eng J 157:204–215
Yang W, Wang Z, Sun H, Zhang B (2016) Advances in development and industrial applications of ethylbenzene processes. Chin J Catal 37:16–26
Ding C, Wang X, Guo X, Zhang S (2008) Characterization and catalytic alkylation of hydrothermally dealuminated nanoscale ZSM-5 zeolite catalyst. Catal Commun 9:487–493
Hodala J, Halgeri A, Shanbhag G (2014) Phosphate modified ZSM-5 for the shape-selective synthesis of para-diethylbenzene: role of crystal size and acidity. Appl Catal A-Gen 484:8–16
Ogunbadejo B, Aitani A, Čejka J, Kubů M, Al-Khattaf S (2016) The effect of alkylation route on ethyltoluene production over different structural types of zeolites. Chem Eng J 306:1071–1080
Lok CM, Van Doorn J, Aranda Almansa G (2019) Promoted ZSM-5 catalysts for the production of bio-aromatics, a review. Renew Sust Energ Rev 113:109248
Wang L, Lei H, Bu Q et al (2014) Aromatic hydrocarbons production from ex situ catalysis of pyrolysis vapor over Zinc modified ZSM-5 in a packed-bed catalysis coupled with microwave pyrolysis reactor. Fuel 129:78–85
Zheng C, Sun X, Li L, Guan N (2012) Scaling up of ethanol production from sugar molasses using yeast immobilized with alginate-based MCM-41 mesoporous zeolite composite carrier. Bioresource Technol 115:208–214
Bhutto AW, Harijan K, Qureshi K, Bazmi AA, Bahadori A (2015) Perspectives for the production of ethanol from lignocellulosic feedstock – a case study. J Clean Prod 95:184–193
Choopun W, Jitkarnka S (2016) Catalytic activity and stability of HZSM-5 zeolite and hierarchical uniform mesoporous MSU-SZSM-5 material during bio-ethanol dehydration. J Clean Prod 135:368–378
Guan X, Li N, Wu G, Chen J, Zhang F, Guan N (2006) Para-selectivity of modified HZSM-5 zeolites by nitridation for ethylation of ethylbenzene with ethanol. J Mol Catal A-Chem 248:220–225
Osman M, Atanda L, Hossain MM, Al-Khattaf S (2013) Kinetics modeling of disproportionation and ethylation of ethylbenzene over HZSM-5: Effects of SiO2/Al2O3 ratio. Chem Eng J 222:498–511
Wang X, Zhao D, Chu W et al (2020) N-methyl-2-pyrrolidone-induced conversion of USY into hollow Beta zeolite and its application in the alkylation of benzene with isobutylene. Microporous Mesoporous Mater 294:109944–110955
Zhao D, Wang Y, Chu W et al (2019) Direct synthesis of hollow single-crystalline zeolite beta using a small organic lactam as a recyclable hollow-directing agent. J Mater Chem A 7:10795–10804
Zhao D, Chu W, Wang Y et al (2018) Organic promoter-driven fast synthesis of zeolite beta and its acceleration mechanism. J Mater Chem A 6:24614–24624
Liu L, Wang H, Wang R et al (2014) N-Methyl-2-pyrrolidone assisted synthesis of hierarchical ZSM-5 with house-of-cards-like structure. RSC Adv 4:21301–21305
Song Y, Sun Y, Zhang X, Zhou J, Zhang L (2008) Homogeneous quaternization of cellulose in NaOH/Urea aqueous solutions as gene carriers. Biomacromol 9:2259–2264
Pronk S, Páll S, Schulz R et al (2013) GROMACS 4.5: a high-throughput and highly parallel open source molecular simulation toolkit. Bioinformatics 29:845–854
Cygan R, Liang J, Kalinichev A (2004) Molecular models of hydroxide, oxyhydroxide, and clay phases and the gevelopment of a general force field. J Phys Chem B 108:1255–1266
Parrinello M, Rahman A (1981) Polymorphic transitions in single crystals: a new molecular dynamics method. J Appl Phys 52:7182–7190
Nosé S (2006) A molecular dynamics method for simulations in the canonical ensemble. Mol Phys 52:255–268
Hoover WG (1985) Canonical dynamics: equilibrium phase-space distributions. Phys Rev A 31:1695–1697
Essmann U, Perera L, Berkowitz ML, Darden T, Lee H, Pedersen LG (1995) A smooth particle mesh Ewald method. J Chem Phys 103:8577–8593
Fischer NM, van Maaren PJ, Ditz JC, Yildirim A, van der Spoel D (2015) Properties of organic liquids when simulated with long-range lennard-jones interactions. J Chem Theory Comput 11:2938–2944
Wang D, Sun H, Liu W, Shen Z, Yang W (2019) Hierarchical ZSM-5 zeolite with radial mesopores: preparation, formation mechanism and application for benzene alkylation. Front Chem Sci Eng 14:248–257
Zhang L, Fu W, Yu Q, Tang T, Zhao Y, Li Y (2017) Effect of citric acid addition on the morphology and activity of Ni2P supported on mesoporous zeolite ZSM-5 for the hydrogenation of 4,6-DMDBT and phenanthrene. J Catal 345:295–307
Rownaghi A, Rezaei F, Stante M, Hedlund J (2012) Selective dehydration of methanol to dimethyl ether on ZSM-5 nanocrystals. Appl Catal B-Environ 119–120:56–61
Li H, Wang Y, Meng F, Chen H, Sun C, Wang S (2016) Direct synthesis of high-silica nano ZSM-5 aggregates with controllable mesoporosity and enhanced catalytic properties. RSC Adv 6:99129–99138
Wang Y, Cao J, Ren X et al (2020) Synthesis of ZSM-5 using different silicon and aluminum sources nature for catalytic conversion of lignite pyrolysis volatiles to light aromatics. Fuel 268:117286–117293
Zhang L, Liu S, Xie S, Xu L (2012) Organic template-free synthesis of ZSM-5/ZSM-11 co-crystalline zeolite. Microporous Mesoporous Mater 147:117–126
Li H, Wang Y, Meng F et al (2017) Controllable fabrication of single-crystalline, ultrafine and high-silica hierarchical ZSM-5 aggregates via solid-like state conversion. RSC Adv 7:25605–25620
Liu X, Wang T, Wang C et al (2020) A chemical approach for ultrafast synthesis of SAPO-n molecular sieves. Chem Eng J 381:122759–122757
Springuel-Huet M, Nosov A, Fraissard J (1996) 129Xe NMR study of the bed resistance to molecular transport in assemblages of zeolite crystallites. J Phys Chem 100:7200–7203
Liu Y, Zhang W, Liu Z et al (2008) Direct observation of the mesopores in ZSM-5 zeolites with hierarchical porous structures by laser-hyperpolarized 129Xe NMR. J Phys Chem C 112:5375–15381
He T, Liu X, Xu S et al (2016) Role of 12-Ring channels of mordenite in DME carbonylation investigated by solid-state NMR. J Phys Chem C 120:22526–22531
Zhao Z, Li X, Li S et al (2019) Structural investigation of interlayer-expanded zeolite by hyperpolarized 129Xe and 1H NMR spectroscopy. Microporous Mesoporous Mater 288:109555–109560
Lim IH, Schrader W, Schüth F (2013) The formation of zeolites from solution – analysis by mass spectrometry. Microporous Mesoporous Mater 166:20–36
Bourgeat-Lami E, Di Renzo F, Fajula F, Mutin PH, Des Courieres T (1992) Mechanism of the thermal decomposition of tetraethylammonium in zeolite beta. J Phy Chem 96:3807–3811
Castro M, Haouas M, Lim I et al (2016) Zeolite Beta formation from clear sols: silicate speciation, oarticle formation and crystallization monitored by complementary analysis methods. Chem-Eur J 22:15307–15319
Liu X, Song H, Sun W et al (2020) Strong nano size effect of titanium silicalite (TS-1) zeolites for electrorheological fluid. Chem Eng J 384:123267–123281
Castro M, Haouas M, Taulelle F et al (2014) Multidiagnostic analysis of silicate speciation in clear solutions/sols for zeolite synthesis. Microporous Mesoporous Mater 189:158–162
Liu X, Xie B, Zhang B, Ma L (2018) Preparation of hierarchical TS-1 zeolite membrane via a dissolution–recrystallization process. J Mater Sci 53:1851–1861 https://doi.org/10.1007/s10853-017-1641-1
Gao X, Zhou Y, Gu J, Li L, Li Y (2019) Facile synthesis of hierarchical manganese-containing TS-1 and its application on the oxidation of cyclohexanone with molecular oxygen. Microporous Mesoporous Mater 275:263–269
Liu X, Ge P, Zhang Y et al (2018) Highly oriented thin membrane fabrication with hierarchically porous zeolite seed. Cryst Growth Des 18:4544–4554
Liu X, Zhang Y, Wang Z et al (2018) A catalytic hydrocracking approach for zeolite detemplation at mild condition. Chem Eng J 346:600–605
Zhang L, Zhang H, Chen Z, Liu S, Ren J (2019) Effect of framework Al siting on catalytic performance in methanol to aromatics over ZSM-5 zeolites. J Fuel Chem Technol 47:1468–1475
Gackowski M, Podobiński J, Hunger M (2019) Evidence for a strong polarization of n-hexane in zeolite H-ZSM-5 by FT-IR and solid-state NMR spectroscopy. Microporous Mesoporous Mater 273:67–72
Heeribout L, Dorémieux-Morin C, Nogier JP, Vincent R, Fraissard J (1998) Study of high-silica H-ZSM-5 acidity by 1H NMR techniques using water as base. Microporous Mesoporous Mater 24:101–112
Saxena SK, Viswanadham N (2016) Hierarchically nano porous nano crystalline ZSM-5 for improved alkylation of benzene with bio-ethanol. Appl Mater Today 5:25–32
Yang C, Xie S, Liu H et al (2018) IM-5 zeolite treated with mixed solution of NaOH and TPABr: Characterization and application for alkylation of benzene with ethanol. Catal Lett 148:2030–2041
Xin W, Yang C, Liu S, Xu L (2018) Gas alkylation of ethanol with benzene over ZSM-11 zeolite catalysts synthesized via different preparation methods. Acta Perolei Sinica 34:1233–1239
Saenluang K, Imyen T, Wannapakdee W et al (2020) Hierarchical nanospherical ZSM-5 nanosheets with uniform Al distribution for alkylation of benzene with ethanol. ACS Appl Nano Mater 3:3252–3263
Hodala J, Bhat Y, Halgeri A, Shanbhag G (2015) Shape-selective synthesis of para-diethylbenzene over pore-engineered ZSM-5: a kinetic study. Chem Eng Sci 138:396–402
Nie X, Liu X, Song C, Guo X (2009) Theoretical study on alkylation of benzene with ethanol and ethylene over H-ZSM-5. Chin J Catal 30:453–458
Yaripour F, Shariatinia Z, Sahebdelfar S, Irandoukht A (2015) Effect of boron incorporation on the structure, products selectivities and lifetime of H-ZSM-5 nanocatalyst designed for application in methanol-to-olefins (MTO) reaction. Microporous Mesoporous Mater 203:41–53
Jin Y, Zhang L, Liu J et al (2017) Mesopore modification of beta zeolites by sequential alkali and acid treatments: Composition-dependent T-atoms removal behavior back donating to hierarchical structure and catalytic activity in benzene alkylation. Microporous Mesoporous Mater 248:7–17
Lu P, Fei Z, Li L et al (2013) Effects of controlled SiO2 deposition and phosphorus and nickel doping on surface acidity and diffusivity of medium and small sized HZSM-5 for para-selective alkylation of toluene by methanol. Appl Catal A-Gen 453:302–309
Zhang H, Hu Z, Huang L et al (2015) Dehydration of glycerol to acrolein over hierarchical ZSM-5 zeolites: effects of mesoporosity and acidity. ACS Catal 5:2548–2558
Liu F, Wang X, Xu F et al (2017) Fabrication and characterization of composites comprising (CHA)SAPO-34 with (MFI)ZSM-5 topologies and their catalytic performances on MTO reaction. Microporous Mesoporous Mater 252:197–206
Yan T, Yang L, Dai W et al (2018) On the deactivation mechanism of zeolite catalyst in ethanol to butadiene conversion. J Catal 367:7–15
Todorova T, Shestakova P, Petrova T, Popova M, Lazarova H, Kalvachev Y (2020) Fluoride etching of AlZSM-5 and GaZSM-5 zeolites. J Mater Sci 55:13799–13814 https://doi.org/10.1007/s10853-020-05030-6
Kalvachev Y, Jaber M, Mavrodinova V, Dimitrov L, Nihtianova D, Valtchev V (2013) Seeds-induced fluoride media synthesis of nanosized zeolite beta crystals. Microporous Mesoporous Mater 177:127–134
Acknowledgements
This work was supported by the Yangfan Project of Guangdong Province, China [grant number, 2015YT02C089], the Taishan Scholar Foundation of Shandong Province (tsqn201812074) and the Natural Science Foundation of Shandong Province (ZR2020MB113).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare that they have no conflict of interest.
Additional information
Handling Editor: Stephen Eichhorn.
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary information
Rights and permissions
About this article
Cite this article
Nie, P., Liu, X., Zhang, P. et al. Quaternary ammonium cellulose promoted synthesis of hollow nano-sized ZSM-5 zeolite as stable catalyst for benzene alkylation with ethanol. J Mater Sci 56, 8461–8478 (2021). https://doi.org/10.1007/s10853-021-05856-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10853-021-05856-8