Kinetics of hydroxylation of phenol with SiC foam supported TS-1 structured catalyst

Abstract

In light of the challenges associated with catalyst separation and recovery, as well as the low production efficiency resulting from intermittent operation for titanium silicalite-1 (TS-1) catalyzed phenol hydroxylation to dihydroxybenzene in the slurry bed, researchers keep on exploring the use of a continuous fixed bed to replace the slurry bed process in recent years. This study focuses on preparing a TS-1 coated structured catalyst on SiC foam, which exhibits significant process intensification in performance. We investigated the kinetics of this structured catalyst and compared it with those of extruded TS-1 catalyst; the dynamic equations of the two catalysts were obtained. It was observed that both catalysts followed E-R adsorption mechanism model, with an effective internal diffusion factor ratio between structured and extruded TS-1 of approximately 7.71. It was confirmed that the foamed SiC-based structured TS-1 catalyst exhibited significant improvements in phenol hydroxylation in fixed-bed reactor due to its well-developed pore structure, good thermal conductivity, excellent internal mass transfer performance, and short reactant diffusion distance, leading to higher utilization efficiency of active components. This finding also provides a foundation for designing and developing phenol hydroxylation processes in fixed-bed using structured catalysts through computational fluid dynamics calculations.

Graphical abstract

Keywords

titanium silicalite-1 / phenol hydroxylation / SiC foam / structured catalyst / coating

References

[1] Bukowska B , Michalowicz J , Marczak A . The effect of catechol on human peripheral blood mononuclear cells (in vitro study). Environmental Toxicology and Pharmacology, 2015, 39(1): 187–193

[2] Iniesta J , Michaud P A , Panizza M , Cerisola G , Aldaz A , Comninellis C . Electrochemical oxidation of phenol at boron-doped diamond electrode. Electrochimica Acta, 2001, 46(23): 3573–3578

[3] Gupta K C , Sutar A K . Polymer supported catalysts for oxidation of phenol and cyclohexene using hydrogen peroxide as oxidant. Journal of Molecular Catalysis A Chemical, 2008, 280(1-2): 173–185

[4] Shi H N , Wang Y Q , Wu G Q , Feng W P , Lin Y , Zhang T , Jin X , Wang S H , Wu X X , Yao P X . Deactivation and regeneration of TS-1/SiO₂ catalyst for epoxidation of propylene with hydrogen peroxide in a fixed-bed reactor. Frontiers of Chemical Science and Engineering, 2013, 7(2): 202–209

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

[6] Yao P X , Wang Y Q , Zhang T , Wang S H , Wu X 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

[7] Liu B Y , Mu Q W , Huang J J , Tan W , Xiao J . Fabrication of titanosilicate pillared MFI zeolites with tailored catalytic activity. Frontiers of Chemical Science and Engineering, 2020, 14(5): 772–782

[8] Vega G , Quintanilla A , Belmonte M , Casas J A . Kinetic study of phenol hydroxylation by H₂O₂ in 3D Fe/SiC honeycomb monolithic reactors: enabling the sustainable production of dihydroxybenzenes. Chemical Engineering Journal, 2022, 428: 9–17

[9] Dehghanpour S B , Razavi M , Parvizian F . Synthesis of ultra-fine TS-1 catalyst with high titanium content and its performance in phenol hydroxylation. New Journal of Chemistry, 2023, 47(42): 19439–19446

[10] Li H , Zhai Y , Zhang X B , Lv G J , Shen Y , Wang X Q , Jiang T , Wu Y Z . Iron-containing TS-1 zeolites with controllable mesopores by desilication and their application in phenol hydroxylation. Industrial & Engineering Chemistry Research, 2020, 59(22): 10289–10297

[11] Yang Z Y , Guan Y N , Xu L , Zhou Y T , Fan X L , Jiao Y L . Tetrapropylammonium hydroxide treatment of aged dry gel to make hierarchical TS-1 zeolites for catalysis. Crystal Growth & Design, 2023, 23(3): 1775–1785

[12] Zong L , Liu Y , Xin F . In situ synthesis of titanium silicalite-1 on monolithic cordierite support. Journal of Inorganic Materials, 2007, 22: 1227–1232

[13] Liu X H , Yang C Y , Wang Y Q , Guo Y L , Guo Y , Lu G Z . Effect of the diatomite pretreatment on the catalytic performance of TS-1/diatomite for toluene hydroxylation by H₂O₂ in fixed-bed reactor. Chemical Engineering Journal, 2014, 243: 192–196

[14] Liu G Q , Kuang J G , Wu J , Luo H A . Synthesis and characterization of extruded titanium silicate-1 and its catalysis performance in cyclohexanone ammoximation. Chemical Reaction Engineering and Technology, 2010, 26: 42–46

[15] Vega G , Quintanilla A , Menendez N , Belmonte M , Casas J A . 3D honeycomb monoliths with interconnected channels for the sustainable production of dihydroxybenzenes: towards the intensification of selective oxidation processes. Chemical Engineering and Processing-Process Intensification, 2021, 165: 13–25

[16] Jiao Y L , Yang X D , Jiang C H , Tian C , Yang Z M , Zhang J S . Hierarchical ZSM-5/SiC nano-whisker/SiC foam composites: preparation and application in MTP reactions. Journal of Catalysis, 2015, 332: 70–76

[17] Ding Q Y , Shen H Y , Kou Z L , Li H , Fan X L , Ou X X , Jiao Y L , Gao X . Heteropoly acid supported on hierarchical Y zeolite decorated SiC foam as the structured catalytic packing for reactive distillation synthesis of ethyl lactate. Chemical Engineering Journal, 2023, 476: 146493

[18] Guan Y N , Zhou Y T , Jiang C H , Xu X X , Yang Z M , Zhang J S , Fan X L , Jiao Y L . Catalytic combustion of volatile organic compounds (VOCs) over structured Co₃O₄ nano-flowers on silicalite-1/SiC foam catalysts. Microporous and Mesoporous Materials, 2021, 323: 12–23

[19] Yang X D , Jiang C H , Yang Z M , Zhang J S . Hydrochlorination of acetylene using SiC foam supported structured C/Au catalysts. Journal of Materials Science and Technology, 2014, 30(5): 434–440

[20] Liu H , Lu G Z , Guo Y L , Guo Y , Wang J S . Chemical kinetics of hydroxylation of phenol catalyzed by TS-1/diatomite in fixed-bed reactor. Chemical Engineering Journal, 2006, 116(3): 179–186

[21] Sulimov A V , Danov S M , Ovcharova A V , Ovcharov A A , Flid V R . Kinetics of allyl chloride epoxidation with hydrogen peroxide catalyzed by extruded titanium silicalite. Kinetics and Catalysis, 2014, 55(6): 712–721

[22] Klaewkla R , Kulprathipanja S , Rangsunvigit P , Rirksomboon T , Rathbun W , Nemeth L . Kinetic modelling of phenol hydroxylation using titanium and tin silicalite-1s: effect of tin incorporation. Chemical Engineering Journal, 2007, 129(1-3): 21–30

[23] Mears D E . Tests for transport limitations in experimental catalytic reactors. Industrial & Engineering Chemistry Process Design and Development, 1971, 10(4): 541–547

[24] Wen M , Ding J , Wang C Z , Li Y K , Zhao G F , Liu Y , Lu Y . High-performance SS-fiber@HZSM-5 core shell catalyst for methanol-to-propylene: a kinetic and modeling study. Microporous and Mesoporous Materials, 2016, 221: 187–196

[25] Liu M , Guo X W , Wang X S . Highly effective phenol hydroxylation over Ti-ZSM-5 catalyst prepared using B-ZSM-5 as precursor. Chinese Journal of Catalysis, 2004, 25: 169–170

[26] Zhang H J , Yao M K , Xie W , Liu Y M , Wu P . Synthesis of TS-1 using inorganic SiO₂-TiO₂ precursor and its catalytic performance for hydroxylation of phenol. Chinese Journal of Catalysis, 2007, 28: 895–899

[27] Tuel A , Moussa-Khouzami S , Taarit Y B , Naccache C . Hydroxylation of phenol over TS-1: surface and solvent effects. Journal of Molecular Catalysis, 1991, 68(1): 45–52

[28] Wu G Q , Lin Z G , Li L , Zhang L , Hong Y P , Wang W J , Chen C , Jiang Y , Yan X Z . 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

[29] Liu H , Lu G Z , Guo Y L , Guo Y , Wang J S . Catalytic performance of titanium silicalite-1 for hydroxylation of phenol in fixed-bed reactor. Chinese Journal of Catalysis, 2004, 25: 49–54

Competing interests

The authors declare that they have no competing interests.

Acknowledgements

This project has received funding from the National Key Research and Development Program (Grant No. 2023YFB3810600), the National Natural Science Foundation of China (Grant No. 2237081611), the European Union’s Horizon 2020 Research and Innovation Program (Grant No. 872102) and the Natural Science Foundation of Liaoning Province (Grant No. 2022-MS-002).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11705-024-2481-6 and is accessible for authorized users.

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