Preparation of ZSM-5 containing vanadium and Brønsted acid sites with high promoting of styrene oxidation using 30% H2O2

doi:10.1016/j.cjche.2020.01.002

中国化学工程学报 ›› 2020, Vol. 28 ›› Issue (5): 1302-1310.DOI: 10.1016/j.cjche.2020.01.002

• Catalysis, Kinetics and Reaction Engineering • 上一篇下一篇

Preparation of ZSM-5 containing vanadium and Brønsted acid sites with high promoting of styrene oxidation using 30% H₂O₂

Xianfeng Liu^1,2, Fu Yang^1,3, Shuying Gao¹, Bo Shao¹, Shijian Zhou¹, Yan Kong¹

1 State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing 210009, China;
2 College of Environment Engineering, Nanjing Institute of Technology, Nanjing 211167, China;
3 School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, China

收稿日期:2019-03-08 修回日期:2019-10-19 出版日期:2020-05-28 发布日期:2020-07-29
通讯作者: Fu Yang, Yan Kong
基金资助:
This work was supported by the National Natural Science Foundation of China (Nos. 21476108, 21276125, 21776129, 21706121 and 21908085), Natural Science Foundation of Jiangsu Province (Nos. BK20170995 and BK20190961), General Program for University Natural Science Research of Jiangsu Province (No. 16KJB530003) and the Project of Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

Preparation of ZSM-5 containing vanadium and Brønsted acid sites with high promoting of styrene oxidation using 30% H₂O₂

Xianfeng Liu^1,2, Fu Yang^1,3, Shuying Gao¹, Bo Shao¹, Shijian Zhou¹, Yan Kong¹

1 State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Nanjing Tech University, Nanjing 210009, China;
2 College of Environment Engineering, Nanjing Institute of Technology, Nanjing 211167, China;
3 School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, China

Received:2019-03-08 Revised:2019-10-19 Online:2020-05-28 Published:2020-07-29
Contact: Fu Yang, Yan Kong
Supported by:
This work was supported by the National Natural Science Foundation of China (Nos. 21476108, 21276125, 21776129, 21706121 and 21908085), Natural Science Foundation of Jiangsu Province (Nos. BK20170995 and BK20190961), General Program for University Natural Science Research of Jiangsu Province (No. 16KJB530003) and the Project of Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).

摘要/Abstract

摘要： Design and synthesis of low cost and efficacious industrial catalyst for the oxidation of styrene has been an important research project. Herein, ZSM-5 zeolite containing tetrahedral vanadium (V) and Brønsted acid sites (V-H-ZSM-5) was prepared, and identified by characterizations such as XRD, SEM, UV-vis, NH₃-TPD, H₂-TPR N₂-adsorption/desorption and FTIR. V-H-ZSM-5 performed extremely enhanced catalytic activity for the oxidation of styrene with 30% H₂O₂ at 40℃. Moreover, in-situ FTIR spectrum was used to investigate the catalytic mechanism. The results demonstrate that Brønsted acid site could not only increase the adsorption concentration of styrene in the micropores of V-H-ZSM-5 via the π complex interaction between double bond of styrene and Brønsted acid sites, but also increase the oxidation potential of H₂O₂. The synergetic action of tetrahedral vanadium (V) and Brønsted acid enhanced the catalytic activity for the oxidation of styrene with 30% H₂O₂. Impressively, V-H-ZSM-5 performed high reusability within five runs at a low reaction temperature (40℃) for the first time.

关键词: Selective oxidation, Styrene, Brønsted acid, Bifunctional, Vanadium

Abstract: Design and synthesis of low cost and efficacious industrial catalyst for the oxidation of styrene has been an important research project. Herein, ZSM-5 zeolite containing tetrahedral vanadium (V) and Brønsted acid sites (V-H-ZSM-5) was prepared, and identified by characterizations such as XRD, SEM, UV-vis, NH₃-TPD, H₂-TPR N₂-adsorption/desorption and FTIR. V-H-ZSM-5 performed extremely enhanced catalytic activity for the oxidation of styrene with 30% H₂O₂ at 40℃. Moreover, in-situ FTIR spectrum was used to investigate the catalytic mechanism. The results demonstrate that Brønsted acid site could not only increase the adsorption concentration of styrene in the micropores of V-H-ZSM-5 via the π complex interaction between double bond of styrene and Brønsted acid sites, but also increase the oxidation potential of H₂O₂. The synergetic action of tetrahedral vanadium (V) and Brønsted acid enhanced the catalytic activity for the oxidation of styrene with 30% H₂O₂. Impressively, V-H-ZSM-5 performed high reusability within five runs at a low reaction temperature (40℃) for the first time.

Key words: Selective oxidation, Styrene, Brønsted acid, Bifunctional, Vanadium

Xianfeng Liu, Fu Yang, Shuying Gao, Bo Shao, Shijian Zhou, Yan Kong. Preparation of ZSM-5 containing vanadium and Brønsted acid sites with high promoting of styrene oxidation using 30% H₂O₂[J]. 中国化学工程学报, 2020, 28(5): 1302-1310.

参考文献

[1] X.L. Wang, G.D. Wu, F. Wang, H. Liu, T.F. Jin, Enhanced catalytic performances of Ag nanoparticles supported on layered double hydroxide for styrene epoxidation, Catal, Commun. 98(2017) 107-111.
[2] J. Sun, G.L. Yu, Q.S. Huo, Q.B. Kan, J.Q. Guan, Epoxidation of styrene over Fe(Cr)-MIL-101 metal-organic frameworks, RSC Adv. 4(2014) 38048-38054.
[3] J.Y. Liu, Z.H. Wang, P.M. Jian, R.Q. Jian, Highly selective oxidation of styrene to benzaldehyde over a tailor-made cobalt oxide encapsulated zeolite catalyst, J. Coll. Interface. Sci. 517(2018) 144-154.
[4] C. Mi, X.G. Meng, X.H. Liao, X. Peng, Selective oxidative cleavage of terminal olefins into aldehydes catalyzed by copper (II) complex, RSC Adv. 5(2015) 69487-69492.
[5] A. Stamatis, P. Doutsia, C. Vartzouma, K.C. Christoforidis, Y. Deligiannakis, M. Louloudi, Epoxidation of olefins with H₂O₂ catalyzed by new symmetrical acetylacetone-based Schiff bases/Mn(II) homogeneous systems:A catalytic and EPR study, J. Mol. Catal. A Chem. 297(1) (2009) 44-53.
[6] J. Haber, M. Kłosowski, J. Połtowicz, Co-oxidation of styrene and iso-butyraldehyde in the presence of polyaniline-supported metalloporphyrins, J. Mol. Catal. A Chem. 201(1-2) (2003) 167-178.
[7] D.H. Ge, J.Q. Wang, H.B. Geng, S.L. Lu, D.T. Wang, X.M. Li, X.L. Zhao, X.Q. Cao, H.W. Gu, Facile synthesis of copper-based metal oxide nanoparticles with exceptional catalytic activity for the selective oxidation of styrenes into benzaldehydes, ChemPlusChem. 80(3) (2015) 511-515.
[8] V. Pârvulescu1, C. Anastasescu1, B.L. Su, Vanadium incorporated mesoporous silicates as catalysts for oxidation of alcohols and aromatics, J. Mol. Catal. A Chem. 198(1-2) (2003) 249-261.
[9] S. Gómez, L.J. Garces, J. Villegas, R. Ghosh, O. Giraldo, S.L. Suib, Synthesis and characterization of TM-MCM-48(TM=Mn, V, Cr) and their catalytic activity in the oxidation of styrene, J. Catal. 233(1) (2005) 60-67.
[10] B. Singh, A.K. Sinha, Synthesis of hierarchical mesoporous vanadium silicate-1 zeolite catalysts for styrene epoxidation with organic hydroperoxide, J. Mater. Chem. A 2(2014) 1930-1939.
[11] J.Q. Xu, Q. Zhang, F. Guo, J.P. Hong, C. Wei, Effects of the crystallization time on the mesoporous structure, texture, morphology and styrene oxidation performances of V-MCM-41, J. Energy Chem. 25(6) (2016) 1058-1063.
[12] H.Q. Wang, W. Qian, J. Chen, Y. Wu, X.Y. Xu, J. Wang, Y. Kong, Spherical V-MCM-48:the synthesis, characterization and catalytic performance in styrene oxidation, RSC Adv. 4(2014) 50832-50839.
[13] M.R. Maurya, M. Kumar, S. Sikarwar, Polymer-anchored oxoperoxo complexes of vanadium(v), molybdenum(vi) and tungsten(vi) as catalyst for the oxidation of phenol and styrene using hydrogen peroxide as oxidant, React. Funct. Polym. 66(8) (2006) 808-818.
[14] Z.F. Li, L.L. Liu, J. Hu, H. Liu, S.J. Wu, Q.S. Huo, J.Q. Guan, Q.B. Kan, Epoxidation of styrene with molecular oxygen catalyzed by a novel oxovanadium(IV) catalyst containing two different kinds of ligands, Appl. Organometal. Chem. 26(2012) 252-257.
[15] A.D. Giuseppe, C.D. Nicola, R. Pettinari, I. Ferino, D. Meloni, M. Passacantando, M. Crucianelli, Selective catalytic oxidation of olefins by novel oxovanadium(IV) complexes having different donor ligands covalently anchored on SBA-15:A comparative study, Catal. Sci. Technol. 3(2013) 1972-1984.
[16] J.Y. Xie, W.X. Zhuang, N. Yan, Y.H. Du, S.B. Xi, W. Zhang, J.J. Tang, Y. Zhou, J. Wang, Directly synthesized V-containing BEA zeolite:Acid-oxidation bifunctional catalyst enhancing c-alkylation selectivity in liquid-phase methylation of phenol, Chem. Eng. J. 328(2017) 1031-1042.
[17] R.M. Leithall, V.N. Shetti, S. Maurelli, M. Chiesa, E. Gianotti, R. Raja, Toward understanding the catalytic synergy in the design of bimetallic molecular sieves for selective aerobic oxidations, J. Am. Chem. Soc. 135(8) (2013) 2915-2918.
[18] F. Yang, J.J. Tang, R. Ou, Z.J. Guo, S.Y. Gao, Y.Z. Wang, X.Y. Wang, L. Chen, A.H. Yuan, Fully catalytic upgrading synthesis of 5-ethoxymethylfurfural from biomass-derived 5-hydroxymethylfurfural over recyclable layered-niobium-molybdate solid acid, Appl. Catal. B Environ. 256(2019) 117786.
[19] D. Verboekend, N. Nuttens, R. Locus, J. Van Aelst, P. Verolme, J.C. Groen, J. PérezRamírez, B.F. Sels, Synthesis, characterisation, and catalytic evaluation of hierarchical faujasite zeolites:milestones, challenges, and future directions, Chem. Soc. Rev. 45(2016) 3331-3352.
[20] B. Guo, L.F. Zhu, X.K. Hu, Q. Zhang, D.M. Tong, G.Y. Lia, C.W. Hu, Nature of vanadium species on vanadium silicalite-1 zeolite and their stability in hydroxylation reaction of benzene to phenol, Catal. Sci. Technol. 1(2011) 1060-1067.
[21] X.F. Liu, S.L. Zhong, F. Yang, H. Su, W. Lin, J.C. Chen, L.M. Peng, S.J. Zhou, Y. Kong, Template-free synthesis of high-content vanadium-doped ZSM-5 with enhanced catalytic performance, Chemistry Select. 2(35) (2017) 11513-11520.
[22] A. Bhan, Y.V. Joshi, W.N. Delgass, K.T. Thomson, DFT investigation of alkoxide formation from olefins in H-ZSM-5, J. Phys. Chem. B 107(2003) 10476-10487.
[23] Y. Jung, Y.J. Shin, Y.D. Pyo, C.P. Cho, J. Jang, G. Kim, NO_x and N₂O emissions over a urea-SCR system containing both V₂O₅-WO₃/TiO₂ and Cu-zeolite catalysts in a diesel engine, Chem. Eng. J. 326(2017) 853-862.
[24] A. Bellmann, H. Atia, U. Bentrup, A. Brückner, Mechanism of the selective reduction of NO_x by methane over Co-ZSM-5, Appl. Catal. B Environ. 230(2018) 184-193.
[25] B.H. Chen, Z.S. Chao, H. He, C. Huang, Y.J. Liu, W.J. Yi, X.L. Wei, J.F. An, Towards a full understanding of the nature of Ni(II) species and hydroxyl groups over highly siliceous HZSM-5 zeolite supported nickel catalysts prepared by a deposition-precipitation method, Dalton Trans. 45(2016) 2720-2739.
[26] R. Baran, Y. Millot, T. Onfroy, F. Averseng, J.M. Krafft, S. Dzwigaj, Influence of the preparation procedure on the nature and environment of vanadium in VSiBEA zeolite:XRD, DR UV-vis, NMR, EPR and TPR studies, Micro. Meso. Mater. 161(2012) 179-186.
[27] S. Dzwigaj, E. Ivanova, R. Kefirov, K. Hadjiivanov, F. Averseng, J.M. Krafft, M. Che, Remarkable effect of the preparation method on the state of vanadium in BEA zeolite:Lattice and extra-lattice V species, Catal. Today 142(2009) 185-191.
[28] R. Baran, T. Onfroy, T. Grzybek, S. Dzwigaj, Influence of the nature and environment of vanadium in VSiBEA zeolite on selective catalytic reduction of NO with ammonia, Appl. Catal. B Environ. 136-137(2013) 186-192.
[29] H.L. Janardhan, G.V. Shanbhag, A.B. Halgeri, Shape-selective catalysis by phosphate modified zsm-5:Generation of new acid sites with pore narrowing, Appl. Catal. A Gen. 471(2014) 12-18.
[30] A.A. Ismail, R.M. Mohamed, I.A. Ibrahim, G. Kini, B. Koopman, Synthesis, optimization and characterization of zeolite A and its ion-exchange properties, Colloids, Surf. A. Physicochemical. Eng. Asp. 366(2010) 80-87.
[31] X.H. Yang, F. Wang, R.P. Wei, S. Li, Y.F. Wu, P.X. Shen, H.Z. Wang, L.J. Gao, G.M. Xiao, Synergy effect between hierarchical structured and Sn-modified H[Sn, Al]ZSM-5 zeolites on the catalysts for glycerol aromatization, Micro. Meso. Mater. 257(2018) 154-161.
[32] M. Nemanashi, R. Meijboom, Dendrimer derived titania-supported Au nanoparticles as potential catalysts in styrene oxidation, Catal. Lett. 143(4) (2013) 324-332.
[33] C. Liu, J. Huang, D. Sun, Y. Zhou, X. Jing, M. Du, H. Wang, Q. Li, Anatase type extraframework titanium in TS-1:A vital factor influencing the catalytic activity toward styrene epoxidation, Appl. Catal. A Gen. 459(2013) 1-7.
[34] A.J. Medford, A. Vojvodic, J.S. Hummelshøj, J. Voss, F. Abild-Pedersen, F. Studt, T. Bligaard, A. Nilsson, J.K. Nørskov, From the Sabatier principle to a predictive theory of transition-metal heterogeneous catalysis, J. Catal. 328(2015) 36-42.
[35] S. Schallmoser, G.L. Haller, M. Sanchez-Sanchez, J.A. Lercher, Role of spatial constraints of Brønsted acid sites for adsorption and surface reactions of linear pentenes, J. Am. Chem. Soc. 139(25) (2017) 8646-8652.
[36] H. Ishikawa, E.Yoda, J.N. Kondo, F. Wakabayashi, K. Domen, Stable dimerized alkoxy species of 2-methylpropene on mordenite zeolite studied by FT-IR. J. Phys. Chem. B 103(27) (1999), 5681-5686.
[37] C. M. Nguyen, B. A. D. Moor, M.F. Reyniers, G, B. Marin, Physisorption and chemisorption of linear alkenes in zeolites:A combined QM-Pot (MP2//B3LYP:GULP)-statistical thermodynamics study, J. Phys. Chem. C. 115(48) (2011) 23831-23847.
[38] M.H. Wang, D.J. Xu, Y.Q. Zhou, S.J. Zhang, General chemistry, Higher Education Press, Fifth ED, p167-p169, Beijing, 2011.
[39] S. Quinebèche, C. Navarro, Y. Gnanou, M. Fontanille, In situ mid-IR and UV-visible spectroscopies applied to the determination of kinetic parameters in the anionic copolymerization of styrene and isoprene, Polym. 50(2009) 1351-1357.
[40] H. Shima, T. Tatsumi, J.N. Kondo, Direct FT-IR observation of oxidation of 1-hexene and cyclohexene with H₂O₂ over TS-1, Micro, Meso. Mater. 135(2010) 13-20.
[41] F. Rajabi, N. Karimi, M.R. Saidi, A. Primo, R.S. Varma, R. Luque, Unprecedented selective oxidation of styrene derivatives using a supported iron oxide nanocatalyst in aqueous medium, Adv. Synth. Catal. 354(9) (2012) 1707-1711.
[42] F. Yang, B. Shao, X.F. Liu, S.Y. Gao, X. Hu, M. Xu, Y. Wang, S.J. Zhou, Y. Kong, Nanosheet-like Ni-based metasilicate towards the regulated catalytic activity in styrene oxidation via introducing heteroatom metal, Appl. Surf. Sci. 471(2019) 822-834.
[43] F. Yang, Y. Ding, S.J. Zhou, B.B. Wang, Y. Kong, Oriented surface decoration of (CoMn) bimetal oxides on nanospherical porous silica and synergetic effect in biomass-derived 5-hydroxymethylfurfural oxidation, Mol. Catal. 435(2017) 144-155.

Preparation of ZSM-5 containing vanadium and Brønsted acid sites with high promoting of styrene oxidation using 30% H₂O₂

Preparation of ZSM-5 containing vanadium and Brønsted acid sites with high promoting of styrene oxidation using 30% H₂O₂

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	Xinxin Li, Hongwei Shao, Shichao Zhang, Yong Li, Jingjing Gu, Qiang Huang, Jin Ran. Two dimensional MoS₂ finding its way towards constructing high-performance alkaline recovery membranes[J]. 中国化学工程学报, 2023, 60(8): 155-164.
[2]	Qiongna Xiao, Yuyan Jiang, Weiqiang Yuan, Jingjing Chen, Haohong Li, Huidong Zheng. Styrene epoxidation catalyzed by polyoxometalate/quaternary ammonium phase transfer catalysts: The effect of cation size and catalyst deactivation mechanism[J]. 中国化学工程学报, 2023, 55(3): 192-201.
[3]	Qian Zhu, Yan Zhuang, Hongqing Zhao, Peng Zhan, Cong Ren, Changsheng Su, Wenqiang Ren, Jiawen Zhang, Di Cai, Peiyong Qin. 2,5-Diformylfuran production by photocatalytic selective oxidation of 5-hydroxymethylfurfural in water using MoS₂/CdIn₂S₄ flower-like heterojunctions[J]. 中国化学工程学报, 2023, 54(2): 180-191.
[4]	Qing Lin, Guoquan Zhang, Kun Wang, Dongmei Luo, Siyang Tang, Hairong Yue. Two-stage cyclic ammonium sulfate roasting and leaching of extracting vanadium and titanium from vanadium slag[J]. 中国化学工程学报, 2022, 47(7): 39-47.
[5]	Xiao Zhao, Xuan Shi, Zhongshun Chen, Long Xu, Chengyi Dai, Yazhou Zhang, Xinwen Guo, Dongyuan Yang, Xiaoxun Ma. Efficient conversion of benzene and syngas to toluene and xylene over ZnO-ZrO₂&H-ZSM-5 bifunctional catalysts[J]. 中国化学工程学报, 2022, 45(5): 203-210.
[6]	Yanan Wei, Yunlei Zhang, Bing Li, Wen Guan, Changhao Yan, Xin Li, Yongsheng Yan. Facile synthesis of metal-organic frameworks embedded in interconnected macroporous polymer as a dual acid-base bifunctional catalyst for efficient conversion of cellulose to 5-hydroxymethylfurfural[J]. 中国化学工程学报, 2022, 44(4): 169-181.
[7]	Jun Chen, Liandong Li, Liu Yang, Chang Chen, Shitao Wang, Yan Huang, Dapeng Cao. A dual metal-organic framework strategy for synthesis of FeCo@NC bifunctional oxygen catalysts for clean energy application[J]. 中国化学工程学报, 2022, 43(3): 161-168.
[8]	Muhammad Faizan, Yingwei Li, Ruirui Zhang, Xingsheng Wang, Piao Song, Ruixia Liu. Progress of vanadium phosphorous oxide catalyst for n-butane selective oxidation[J]. 中国化学工程学报, 2022, 43(3): 297-315.
[9]	Yinbin Wang, Senjun Yao, Wei Wang, Chenglong Qiu, Jing Zhang, Shengwei Deng, Hong Dong, Chuan Wu, Jianguo Wang. Pyrolysis of vulcanized styrene-butadiene rubber via ReaxFF molecular dynamics simulation[J]. 中国化学工程学报, 2021, 29(3): 94-102.
[10]	Rongrui Deng, Hao Xiao, Zhaoming Xie, Zuohua Liu, Qiang Yu, Geng Chen, Changyuan Tao. A novel method for extracting vanadium by low temperature sodium roasting from converter vanadium slag[J]. 中国化学工程学报, 2020, 28(8): 2208-2213.
[11]	Bowen Jiang, Lei Hu, Xiaoming Yan, Jiahui Sun, Li Gao, Yan Dai, Xuehua Ruan, Gaohong He. A new long-side-chain sulfonated poly(2,6-dimethyl-1,4-phenylene oxide) (PPO)/polybenzimidazole (PBI) amphoteric membrane for vanadium redox flow battery[J]. 中国化学工程学报, 2020, 28(7): 1918-1924.
[12]	Yahui Wang, Kaimin Feng, Liming Ding, Lihua Wang, Xutong Han. Influence of solvent on ion conductivity of polybenzimidazole proton exchange membranes for vanadium redox flow batteries[J]. 中国化学工程学报, 2020, 28(6): 1701-1708.
[13]	Jing Zhao, Yifu Zhang, Lei Xu, Fuping Tian, Tao Hu, Changgong Meng. Weak base favoring the synthesis of highly ordered V-MCM-41 with well-dispersed vanadium and the catalytic performances on selective oxidation of benzyl alcohol[J]. 中国化学工程学报, 2020, 28(5): 1424-1435.
[14]	Weimin Zhong, Shuming Liu, Feng Wan, Zhi Li. Equipment selection knowledge base system for industrial styrene process[J]. Chinese Journal of Chemical Engineering, 2018, 26(8): 1707-1712.
[15]	Pan Sun, Kun Huang, Xiaoqin Wang, Na Sui, Jieyuan Lin, Wenjuan Cao, Huizhou Liu. Three-liquid-phase extraction and separation of V(V) and Cr(VI) from acidic leach solutions of high-chromium vanadium-titanium magnetite[J]. Chinese Journal of Chemical Engineering, 2018, 26(7): 1451-1457.