Post-treatment of Ti-MWW zeolite with potassium fluoride for propylene epoxidation
Xintong Li, Xianchen Gong, Jilong Wang, Shengbo Jin, Hao Xu, Peng Wu
Post-treatment of Ti-MWW zeolite with potassium fluoride for propylene epoxidation
Epoxidation of propylene to propylene oxide (PO) with hydrogen peroxide (HPPO) is an environmentally friendly and cost-efficient process in which titanosilicates are used as catalysts. Ti-MWW is a potential industrial catalyst for this process, which involves the addition of HPPO to PO. The silanol groups generated during secondary crystallization unavoidably result in ring-opening of PO and inefficient decomposition of HPPO, which diminish the PO selectivity and the lifespan of Ti-MWW. To address this issue, we conducted post-treatment modifications of the structured Bf-Ti-MWW catalyst with potassium fluoride aqueous solutions. By quenching the silanol groups with potassium fluoride and implanting electron-withdrawing fluoride groups into the Ti-MWW framework, both the catalytic activity and HPPO utilization efficiency were increased. Moreover, the ring opening reaction of PO was prohibited. In a continuous fixed-bed liquid-phase propylene epoxidation reaction, the KF-treated structured Ti-MWW catalyst displayed an exceptionally long lifespan of 2700 h, with a PO yield of 590 g·kg−1·h−1.
titanosilicates / Ti-MWW / propylene epoxidation / structured catalyst / KF modification
[1] |
Xu H , Wu P . Two-dimensional zeolites in catalysis: current state-of-the-art and perspectives. Catalysis Reviews: Science and Engineering, 2021, 63(2): 234–301
CrossRef
Google scholar
|
[2] |
Smeets V , Gaigneaux E M , Debecker D P . Titanosilicate epoxidation catalysts: a review of challenges and opportunities. ChemCatChem, 2022, 14(1): e202101132
CrossRef
Google scholar
|
[3] |
WangRXiaCPengB. Fundamental understanding and catalytic applications of hollow MFI-type zeolites. Catalysis Today, 2022, 405–406: 111–124
|
[4] |
Li Y , Yi Y , Wang X , Gao B , Guo Y , Wu G , Feng Z , Guo H . Regeneration of a spent TS-1 zeolite catalyst for liquid-phase epoxidation of propylene and H2O2. Industrial & Engineering Chemistry Research, 2023, 62(31): 12152–12173
CrossRef
Google scholar
|
[5] |
Wang G , Li Y , Zhu Q , Li G , Zhang C , Guo H . Influence of impurities in a methanol solvent on the epoxidation of propylene with hydrogen peroxide over titanium silicalite-1. Catalysts, 2019, 10(1): 15
CrossRef
Google scholar
|
[6] |
Sulimov A V , Ovcharova A V , Ovcharov A , Flid V R , Leont’eva S V , Bruk L G , Pastukhova Z Y , Flid M R . Study of alkene epoxidation in the presence of extruded silicalite titanium. Russian Chemical Bulletin, 2016, 65(12): 2845–2849
CrossRef
Google scholar
|
[7] |
Song F , Liu Y , Wang L , Zhang H , He M , Wu P . Highly efficient epoxidation of propylene over a novel Ti-MWW catalyst. Studies in Surface Science and Catalysis, 2007, 170(07): 1236–1243
CrossRef
Google scholar
|
[8] |
Wu P , Tatsumi T , Komatsu T , Yashima T . A novel titanosilicate with MWW structure. I. Hydrothermal synthesis, elimination of extraframework titanium, and characterizations. Journal of Physical Chemistry B, 2001, 105(15): 2897–2905
CrossRef
Google scholar
|
[9] |
Yu Y , Fang N , Chen Z , Liu D , Liu Y , He M . Greening oxidation catalysis: water as a solvent for efficient alkene epoxidation over a titanosilicate/H2O2 system. ACS Sustainable Chemistry & Engineering, 2022, 10(35): 11641–11654
CrossRef
Google scholar
|
[10] |
Torres C , Pottis D S , Flaherty D W . Solvent mediated interactions on alkene epoxidations in Ti-MFI: effects of solvent identity and silanol density. ACS Catalysis, 2023, 13(13): 8925–8942
CrossRef
Google scholar
|
[11] |
Potts D S , Komar J K , Locht H , Flaherty D W . Understanding rates and regioselectivities for epoxide methanolysis within zeolites: mechanism and roles of covalent and non-covalent interactions. ACS Catalysis, 2023, 13(22): 14928–14944
CrossRef
Google scholar
|
[12] |
Tan J Z , Bregante D T , Torres C , Flaherty D W . Transition state stabilization depends on solvent identity, pore size, and hydrophilicity for epoxidations in zeolites. Journal of Catalysis, 2022, 405: 91–104
CrossRef
Google scholar
|
[13] |
Serrano D P , Sanz R , Pizarro P , Moreno I , Blázquez S . Preparation of extruded catalysts based on TS-1 zeolite for their application in propylene epoxidation. Catalysis Today, 2013, 143(1): 151–157
|
[14] |
Zhou J , Teng J , Ren L , Wang Y , Liu Z , Liu W , Yang W , Xie Z . Full-crystalline hierarchical monolithic ZSM-5 zeolites as superiorly active and long-lived practical catalysts in methanol-to-hydrocarbons reaction. Journal of Catalysis, 2016, 340: 166–176
CrossRef
Google scholar
|
[15] |
Li Z , Jiang X , Xiong G , Nie B , Liu C , He N , Liu J . Towards the preparation of binderless ZSM-5 zeolite catalysts: the crucial role of silanol nests. Catalysis Science & Technology, 2020, 10(23): 7829–7841
CrossRef
Google scholar
|
[16] |
Xu H , Tian W , Xu L , Jin X , Xue T , Chen L , He M , Wu P . Crossed intergrowth triggered TS-2 microsphere: formation mechanism, modification and catalytic performance. Chinese Journal of Catalysis, 2020, 41(7): 1109–1117
CrossRef
Google scholar
|
[17] |
Yin J , Jin X , Xu H , Guan Y , Peng R , Chen L , Jiang J , Wu P . Structured binder-free MWW-type titanosilicate with Si-rich shell for selective and durable propylene epoxidation. Chinese Journal of Catalysis, 2021, 42(9): 1561–1575
CrossRef
Google scholar
|
[18] |
Lu X , Xu H , Yan J , Zhou W J , Liebens A , Wu P . One-pot synthesis of ethylene glycol by oxidative hydration of ethylene with hydrogen peroxide over titanosilicate catalysts. Journal of Catalysis, 2018, 358: 89–99
CrossRef
Google scholar
|
[19] |
Wu L , Zhao S , Lin L , Fang X , Liu Y , He M . In-depth understanding of acid catalysis of solvolysis of propene oxide over titanosilicates and titanosilicate/H2O2 systems. Journal of Catalysis, 2016, 337: 248–259
CrossRef
Google scholar
|
[20] |
Sever R R , Root T W . DFT study of solvent coordination effects on titanium-based epoxidation catalysts. Part Ⅰ: formation of the titanium hydroperoxo intermediate. Journal of Physical Chemistry B, 2003, 107(17): 4090–4099
CrossRef
Google scholar
|
[21] |
Sever R R , Root T W . DFT study of solvent coordination effects on titanium-based epoxidation catalysts. Part two: reactivity of titanium hydroperoxo complexes in ethyleneepoxidation. Journal of Physical Chemistry B, 2003, 107(17): 4090–4099
CrossRef
Google scholar
|
[22] |
Gordon C P , Engler H , Tragl A S , Plodinec M , Lunkenbein T , Berkessel A , Teles J H , Parvulescu A N , Copéret C . Efficient epoxidation over dinuclear sites in titanium silicalite-1. Nature, 2020, 586(7831): 708–713
CrossRef
Google scholar
|
[23] |
Wang Y , Yang H , Zuo Y , Tian D , Hou G , Su Y , Feng Z , Guo X , Li C . New penta- and hexa-coordinated titanium sites in titanium silicalite-1 catalyst for propylene epoxidation. Applied Catalysis B: Environmental, 2023, 325: 122396
CrossRef
Google scholar
|
[24] |
Bregante D T , Chan M C , Tan J Z , Ayla E Z , Nicholas C P , Shukla D , Flaherty D W . The shape of water in zeolites and its impact on epoxidation catalysis. Nature Catalysis, 2021, 4(9): 797–808
CrossRef
Google scholar
|
[25] |
Clerici M G , Ingallina P . Epoxidation of lower olefins with hydrogen peroxide and titanium silicalite. Journal of Catalysis, 1993, 140(1): 71–83
CrossRef
Google scholar
|
[26] |
Yang Y , Ding J , Wang B , Wu J , Zhao C , Gao G , Wu P . Influences of fluorine implantation on catalytic performance and porosity of MOR-type titanosilicate. Journal of Catalysis, 2014, 320: 160–169
CrossRef
Google scholar
|
[27] |
Lu X , Wu H , Jiang J , He M , Wu P . Selective synthesis of propylene oxide through liquid-phase epoxidation of propylene with H2O2 over formed Ti-MWW catalyst. Journal of Catalysis, 2016, 342: 173–183
|
[28] |
Goa Y , Wu P , Tatsumi T . Influence of fluorine on the catalytic performance of Ti-Beta zeolite. Journal of Physical Chemistry B, 2004, 108(14): 4242–4244
CrossRef
Google scholar
|
[29] |
Fang X , Wang Q , Zheng A , Liu Y , Wang Y , Deng X , Wu H , Deng F , He M , Wu P . Fluorine-planted titanosilicate with enhanced catalytic activity in alkene epoxidation with hydrogen peroxide. Catalysis Science & Technology, 2012, 2(12): 2433
CrossRef
Google scholar
|
[30] |
Fang X , Wang Q , Zheng A . Post-synthesis, characterization and catalytic properties of fluorine-planted MWW-type titanosilicate. Physical Chemistry Chemical Physics, 2013, 2013,15(14): 4930–4938
|
[31] |
Fang X , Sun L , Lin L , Wu L , Liu Y . Enhanced catalytic oxidation performance of F-Ti-MWW through the synergistic effect of anion and cation. Catalysis Communications, 2017, 96: 54–57
CrossRef
Google scholar
|
[32] |
Kuwahara Y , Nishizawa K , Nakajima T , Kamegawa T , Mori K , Yamashita H . Enhanced catalytic activity on titanosilicate molecular sieves controlled by cation-π interactions. Journal of the American Chemical Society, 2011, 133(32): 12462–12465
CrossRef
Google scholar
|
[33] |
Lamberti C , Bordiga S , Arduino D , Zecchina A , Geobaldo F , Spanó G , Genoni F , Petrini G , Carati A , Villain F .
CrossRef
Google scholar
|
[34] |
Xu L , Huang D D , Li C G , Ji X , Jin S , Feng Z , Xia F , Li X , Fan F , Li C .
CrossRef
Google scholar
|
[35] |
Lu X , Zhou W J , Guan Y , Liebens A , Wu P . Enhancing ethylene epoxidation of a MWW-type titanosilicate/H2O2 catalytic system by fluorine implanting. Catalysis Science & Technology, 2017, 7(12): 2624–2631
CrossRef
Google scholar
|
[36] |
Bregante D T , Johnson A M , Patel A Y , Ayla E Z , Cordon M J , Bukowski B C , Greeley J , Gounder R , Flaherty D W . Cooperative effects between hydrophilic pores and solvents: catalytic consequences of hydrogen bonding on alkene epoxidation in zeolites. Journal of the American Chemical Society, 2019, 141(18): 7302–7319
CrossRef
Google scholar
|
[37] |
Bregante D T , Flaherty D W . Impact of specific interactions among reactive surface intermediates and confined water on epoxidation catalysis and adsorption in lewis acid zeolites. ACS Catalysis, 2019, 9(12): 10951–10962
CrossRef
Google scholar
|
[38] |
Zhang K , Lively R P , Noel J D , Dose M E , Mccool B A , Chance R R , Koros W J . Adsorption of water and ethanol in MFI-type zeolites. Langmuir, 2012, 28(23): 8664–8673
CrossRef
Google scholar
|
[39] |
Özgür Yazaydın A , Thompson R W . Molecular simulation of water adsorption in silicalite: effect of silanol groups and different cations. Microporous and Mesoporous Materials, 2009, 123(1–3): 169–176
CrossRef
Google scholar
|
[40] |
Trzpit M , Soulard M , Patarin J , Desbiens N , Cailliez F , Boutin A , Demachy I , Fuchs A H . The effect of local defects on water adsorption in silicalite-1 zeolite: a joint experimental and molecular simulation study. Langmuir, 2007, 23(20): 10131–10139
CrossRef
Google scholar
|
[41] |
JinXPengRTongWYinJXuHWuP. Investigation of the active centers and structural modifications for TS-1 in catalyzing the Beckmann rearrangement. Catalysis Today, 2022, 405–406(1): 193–202
|
[42] |
Xu L , Ding J , Yang Y , Wu P . Distinctions of hydroxylamine formation and decomposition in cyclohexanone ammoximation over microporous titanosilicates. Journal of Catalysis, 2014, 309: 1–10
CrossRef
Google scholar
|
[43] |
Xu H , Guan Y , Lu X , Yin J , Li X , Zhou D , Wu P . Relation of selective oxidation catalytic performance to microenvironment of Ti(IV) active site based on isotopic labeling. ACS Catalysis, 2020, 10(8): 4813–4819
CrossRef
Google scholar
|
[44] |
Na K , Jo C , Kim J , Ahn W S , Ryoo R . MFI titanosilicate nanosheets with single-unit-cell thickness as an oxidation catalyst using peroxides. ACS Catalysis, 2011, 1(8): 901–907
CrossRef
Google scholar
|
[45] |
Wang Y , Liu Y , Li X , Wu H , He M , Wu P . Intermolecular condensation of ethylenediamine to 1,4-diazabicyclo[2,2,2]octane over TS-1 catalysts. Journal of Catalysis, 2009, 266(2): 258–267
CrossRef
Google scholar
|
/
〈 | 〉 |