Controllable synthesis of a large TS-1 catalyst for clean epoxidation of a C=C double bond under mild conditions

Abstract

Development of a titanium silicalite-1 (TS-1) catalyst with good crystallinity and a four-coordinate Ti framework is critical for efficient catalytic oxidation reaction under mild conditions. Herein, a size-controlled TS-1 zeolite (TS-1 0.1ACh (acetylcholine)) was synthesized via steam-assisted crystallization by introducing acetylcholine as a crystal growth modifier in the preparation process, and TS-1 0.1ACh was also employed in epoxidations of different substrates containing C=C double bonds. The crystalline sizes of the as-synthesized TS-1 0.1ACh catalysts were controlled with the acetylcholine content, and characterization results showed that the particle sizes of highly crystalline TS-1 0.1ACh zeolite reached 3.0 μm with a good Ti framework. Throughout the synthetic process, the growth rate of the crystals was accelerated by electrostatic interactions between the connected hydroxyl groups of the acetylcholine modifier and the negatively charged skeleton of the pre-zeolites. Furthermore, the TS-1 0.1ACh catalyst demonstrated maximum catalytic activity, good selectivity and high stability during epoxidation of allyl chloride. Importantly, the TS-1 0.1ACh catalyst was also highly versatile and effective with different unsaturated substrates. These findings may provide novel, easily separable and large TS-1 catalysts for efficient and clean industrial epoxidations of C=C double bonds.

Graphical abstract

Keywords

size-controlled TS-1 / crystal modifier / steam-assisted crystallization / epoxidation

References

[1] Li J, Meng X, Xiao F S. Zeolites for control of NO emissions: opportunities and challenges. Chem Catalysis, 2022, 2(2): 253–261

[2] Zhang Q, Yu J, Corma A. Applications of zeolites to C1 chemistry: recent advances, challenges, and opportunities. Advanced Materials, 2020, 32(44): e2002927

[3] Martínez C, Corma A. Inorganic molecular sieves: preparation, modification and industrial application in catalytic processes. Coordination Chemistry Reviews, 2011, 255(13–14): 1558–1580

[4] Li Y, Li L, Yu J. Applications of zeolites in sustainable chemistry. Chem, 2017, 3(6): 928–949

[5] Wang J, Jiang J, Ding J, Wang X, Sun Y, Ruan R, Ragauskas A J, Ok Y S, Tsang D C W. Promoting Diels-Alder reactions to produce bio-BTX: co-aromatization of textile waste and plastic waste over USY zeolite. Journal of Cleaner Production, 2021, 314: 127966

[6] Odedairo T, Al-Khattaf S. Comparative study of zeolite catalyzed alkylation of benzene with alcohols of different chain length: H-ZSM-5 versus mordenite. Catalysis Today, 2013, 204: 73–84

[7] Xie Y, Wang M, Wang X, Wang L, Ning P, Ma Y, Lu J, Cao R, Xue Y. Magnetic-field-assisted catalytic oxidation of arsine over Fe/HZSM-5 catalyst: synergistic effect of Fe species and activated surface oxygen. Journal of Cleaner Production, 2022, 337: 130549

[8] TaramassoMPeregoGNotariB. Preparation of porous crystalline synthetic materials comprised of silicon and titanium oxide. US Patent, 4410501, 1983

[9] Wu G, Lin Z, Li L, Zhang L, Hong Y, Wang W, Chen C, Jiang Y, Yan X. Experiments and kinetics of the epoxidation of allyl chloride with H₂O₂ over organic base treated TS-1 catalysts. Chemical Engineering Journal, 2017, 320: 1–10

[10] Khan I, Chu X, Liu Y, Khan S, Bai L, Jing L. Synthesis of Ni²⁺ cation modified TS-1 molecular sieve nanosheets as effective photocatalysts for alcohol oxidation and pollutant degradation. Chinese Journal of Catalysis, 2020, 41(10): 1589–1602

[11] Yao P, Wang Y, Zhang T, Wang S, Wu X. Effect of sodium ions in synthesis of titanium silicalite-1 on its catalytic performance for cyclohexanone ammoximation. Frontiers of Chemical Science and Engineering, 2014, 8(2): 149–155

[12] Gordon C P, Engler H, Tragl A S, Plodinec M, Lunkenbein T, Berkessel A, Teles J H, Parvulescu A N, Coperet C. Efficient epoxidation over dinuclear sites in titanium silicalite-1. Nature, 2020, 586(7831): 708–713

[13] Wilde N, Pelz M, Gebhardt S G, Gläser R. Highly efficient nano-sized TS-1 with micro-/mesoporosity from desilication and recrystallization for the epoxidation of biodiesel with H₂O₂. Green Chemistry, 2015, 17(6): 3378–3389

[14] Wilde N, Přech J, Pelz M, Kubů M, Čejka J, Gläser R. Accessibility enhancement of TS-1-based catalysts for improving the epoxidation of plant oil-derived substrates. Catalysis Science & Technology, 2016, 6(19): 7280–7288

[15] Feng X, Lin D, Chen D, Yang C. Rationally constructed Ti sites of TS-1 for epoxidation reactions. Science Bulletin, 2021, 66(19): 1945–1949

[16] Yang Z, Zhang R, Liu R, Zhang S. Elucidating the zeolite particle size effect on butene/isobutane alkylation. Industrial & Engineering Chemistry Research, 2022, 61(2): 1032–1043

[17] Wu Q, Xu C, Zhu L, Meng X, Xiao F S. Recent strategies for synthesis of metallosilicate zeolites. Catalysis Today, 2022, 390-391: 2–11

[18] Lanzafame P, Papanikolaou G, Barbera K, Centi G, Perathoner S. Etherification of HMF to biodiesel additives: the role of NH⁴⁺ confinement in Beta zeolites. Journal of Energy Chemistry, 2019, 36: 114–121

[19] Ungula J, Swart H C. Controlling the morphology of ZnO NRs grown on GZO seed layer, by use of ethylenediamine and L-cysteine as crystal growth modifiers and complexing agents. Applied Surface Science, 2019, 487: 1198–1208

[20] Lu J, Li Q, Song W, Liu Z, Wang C. The influence of crystal modifiers on the crystallinity, particle morphology and brightness of precipitated calcite powders hydrothermally prepared from black marble waste. Powder Technology, 2020, 373: 535–542

[21] Ma W, Lutsko J F, Rimer J D, Vekilov P G. Antagonistic cooperativity between crystal growth modifiers. Nature, 2020, 577(7791): 497–501

[22] Jones F, Ogden M I. Controlling crystal growth with modifiers. CrystEngComm, 2010, 12(4): 1016–1023

[23] Li M, Shen X, Liu M, Lu J. Synthesis TS-1 nanozelites via L-lysine assisted route for hydroxylation of benzene. Molecular Catalysis, 2021, 513: 111779

[24] Song X, Yang X, Zhang T, Zhang H, Zhang Q, Hu D, Chang X, Li Y, Chen Z, Jia M, Zhang P, Yu J. Controlling the morphology and titanium coordination states of TS-1 zeolites by crystal growth modifier. Inorganic Chemistry, 2020, 59(18): 13201–13210

[25] Zhang J, Bai S, Chen Z, Wang Y, Dong L, Zheng H, Cai F, Hong M. Core-shell zeolite Y with ant-nest like hollow interior constructed by amino acids and enhanced catalytic activity. Journal of Materials Chemistry A: Materials for Energy and Sustainability, 2017, 5(39): 20757–20764

[26] Zhang Q, Mayoral A, Terasaki O, Zhang Q, Ma B, Zhao C, Yang G, Yu J. Amino acid-assisted construction of single-crystalline hierarchical nanozeolites via oriented-aggregation and intraparticle ripening. Journal of the American Chemical Society, 2019, 141(9): 3772–3776

[27] Yang C, Dong Z, Chu W, Wang Y, Zhao D, Chen F, Xin W, Zhu X, Liu S, Xu L. Understanding the roles of different acid sites in beta zeolites with different particle sizes catalyzed liquid-phase transalkylation of diethylbenzene with benzene. Catalysis Science & Technology, 2022, 12(2): 652–663

[28] Chen C, Cai L, Li L, Bao L, Lin Z, Wu G. Heterogeneous and non-acid process for production of epoxidized soybean oil from soybean oil using hydrogen peroxide as clean oxidant over TS-1 catalysts. Microporous and Mesoporous Materials, 2019, 276: 89–97

[29] Ramírez Bocanegra N, Suarez Vázquez S I, Sandoval Rangel L, Garza Navarro M A, Rivera de la Rosa J, Lucio Ortiz C J, Flores-Escamilla G A, Santos López I A, Carrillo Pedraza E S, Bravo Sánchez M, De Haro Del Río D A. Catalytic conversion of GVL to biofuels using Cu and Pt catalysts over microwave-synthesized FAU zeolite. Catalysis Today, 2022, 392-393: 105–115

[30] Ueno K, Yamada S, Negishi H, Okuno T, Tawarayama H, Ishikawa S, Miyamoto M, Uemiya S, Oumi Y. Fabrication of pure-silica *BEA-type zeolite membranes on tubular silica supports coated with dilute synthesis gel via steam-assisted conversion. Separation and Purification Technology, 2020, 247: 116934

[31] Liu M, Chang Z, Wei H, Li B, Wang X, Wen Y. Low-cost synthesis of size-controlled TS-1 by using suspended seeds: from screening to scale-up. Applied Catalysis A: General, 2016, 525: 59–67

[32] Xu W, Zhang T, Bai R, Zhang P, Yu J. A one-step rapid synthesis of TS-1 zeolites with highly catalytically active mononuclear TiO₆ species. Journal of Materials Chemistry A: Materials for Energy and Sustainability, 2020, 8(19): 9677–9683

[33] Gao X, Zhang Y, Hong Y, Luo B, Yan X, Wu G. Efficient and clean epoxidation of methyl oleate to epoxidized methyl oleate catalyzed by external surface of TS-1 supported molybdenum catalysts. Microporous and Mesoporous Materials, 2022, 333: 111731

[34] Cai L, Chen C, Wang W, Gao X, Kuang X, Jiang Y, Li L, Wu G. Acid-free epoxidation of soybean oil with hydrogen peroxide to epoxidized soybean oil over titanium silicalite-1 zeolite supported cadmium catalysts. Journal of Industrial and Engineering Chemistry, 2020, 91: 191–200

[35] Li X, Yang X, Wang Q, Li S, Ye Y, Wang D, Zheng Z. Synthesis of Pt-based TS-1 catalysts for selective hydrogenation to produce C15–C18 alkanes from the FAME: effect of rare-earth metal additives. Journal of Cleaner Production, 2022, 350: 131520

[36] Xu J, Wang Y, Feng W, Lin Y, Wang S. Effect of triethylamine treatment of titanium silicalite-1 on propylene epoxidation. Frontiers of Chemical Science and Engineering, 2014, 8(4): 478–487

[37] Di Z, Chen H, Zhang R, Wang H, Jia J, Wei Y. Significant promotion of reducing treatment on Pd/TS-1 zeolite for formaldehyde catalytic purification at ambient temperature. Applied Catalysis B: Environmental, 2022, 304: 120843

[38] Chen Z, Zhang J, Yu B, Zheng G, Zhao J, Hong M. Amino acid mediated mesopore formation in LTA zeolites. Journal of Materials Chemistry A: Materials for Energy and Sustainability, 2016, 4(6): 2305–2313

[39] Thangaraj A, Eapen M J, Sivasanker S, Ratnasamy P. Studies on the synthesis of titanium silicalite, TS-1. Zeolites, 1992, 12(8): 943–950

[40] Wróblewska A, Tołpa J, Kłosin D, Miądlicki P, Koren Z C, Michalkiewicz B. The application of TS-1 materials with different titanium contents as catalysts for the autoxidation of α-pinene. Microporous and Mesoporous Materials, 2020, 305: 110384

[41] Yin H, Su F, Luo C, Zhu L, Zhong W, Mao L, You K, Yin D. Visible-light-mediated remote aliphatic C–H oxyfunctionalization over CuCl₂ decorated hollowed-TS-1 photocatalysts. Applied Catalysis B: Environmental, 2022, 302: 120851

[42] Zhang Z, Cao G P, Cai Q, Lu H, Ji S, Fang R, Gao P, Feng M. Steam-assisted in situ prepared TS-1 with hierarchical pores and tunable acid sites grown on carbon nanotubes decorated nickel foam. Industrial & Engineering Chemistry Research, 2020, 59(7): 2761–2772

[43] Song Z, Yuan J, Cai Z, Lin D, Feng X, Sheng N, Liu Y, Chen X, Jin X, Chen D, Yang C. Engineering three-layer core−shell S-1/TS-1@dendritic-SiO₂ supported Au catalysts towards improved performance for propene epoxidation with H₂ and O₂. Green Energy & Environment, 2020, 5(4): 473–483

[44] Wei Y, Li G, Lü Q, Cheng C, Guo H. Green and efficient epoxidation of methyl oleate over hierarchical TS-1. Chinese Journal of Catalysis, 2018, 39(5): 964–972

[45] Sun Y, Li G, Gong Y, Sun Z, Yao H, Zhou X. Ag and TiO₂ nanoparticles co-modified defective zeolite TS-1 for improved photocatalytic CO₂ reduction. Journal of Hazardous Materials, 2021, 403: 124019

[46] Sun W, Song H, Xi Z, Ma J, Wang B, Liu X, Hao C, Chen K. Synthesis and enhanced electrorheological properties of TS-1/titanium oxide core/shell nanocomposite. Industrial & Engineering Chemistry Research, 2020, 59(3): 1168–1182

[47] Kazarina O V, Agieienko V N, Nagrimanov R N, Atlaskina M E, Petukhov A N, Moskvichev A A, Nyuchev A V, Barykin A V, Vorotyntsev I V. A rational synthetic approach for producing quaternary ammonium halides and physical properties of the room temperature ionic liquids obtained by this way. Journal of Molecular Liquids, 2021, 344: 117925

[48] Zhang Q, Chen G, Wang Y, Chen M, Guo G, Shi J, Luo J, Yu J. High-quality single-crystalline MFI-type nanozeolites: a facile synthetic strategy and MTP catalytic studies. Chemistry of Materials, 2018, 30(8): 2750–2758

[49] Guo D, Lai J, Cheng F, Zhao W, Chen H, Li H, Liu X, Yin D, Yu N. Titanium silicalite-1 supported bimetallic catalysts for selective hydrogenolysis of 5-hydroxymethylfurfural to biofuel 2,5-dimethylfuran. Chemical Engineering Journal Advances, 2021, 5: 100081

[50] Zhuang J, Ma D, Yan Z, Liu X, Han X, Bao X, Zhang Y, Guo X, Wang X. Effect of acidity in TS-1 zeolites on product distribution of the styrene oxidation reaction. Applied Catalysis A: General, 2004, 258(1): 1–6

[51] Wei Y, Li G, Wang C, Guo H. Integrated fast-mass transfer and high Ti-sites utilization into hybrid amphiphilic TS@PMO catalyst towards efficient solvent-free methyl oleate epoxidation. Journal of Colloid and Interface Science, 2021, 586: 233–242

[52] Nakagawa Y, Kamata K, Kotani M, Yamaguchi K, Mizuno N. Polyoxovanadometalate-catalyzed selective epoxidation of alkenes with hydrogen peroxide. Angewandte Chemie International Edition, 2005, 44(32): 5136–5141

[53] Bhattacharya S, Kumari N. Metallomicelles as potent catalysts for the ester hydrolysis reactions in water. Coordination Chemistry Reviews, 2009, 253(17-18): 2133–2149

Acknowledgements

This work was supported by the financial support from the National Natural Science Foundation of China (Grant Nos. 21802055 and 32160537), Jiangxi Provincial Natural Science Foundation (Grant No. 20202BABL205013) and Jiangxi Provincial Department of Education Foundation (Grant No. GJJ190179).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://dx.doi.org/10.1007/s11705-022-2280-x and is accessible for authorized users.

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