Production of linear alkylbenzene over Ce containing Beta zeolites

doi:10.1016/j.cjche.2023.11.007

Chinese Journal of Chemical Engineering ›› 2024, Vol. 67 ›› Issue (3): 220-227.DOI: 10.1016/j.cjche.2023.11.007

Previous Articles Next Articles

Production of linear alkylbenzene over Ce containing Beta zeolites

Shiqi Zhang^1,2, Shengzhi Gan^1,2, Baoyu Liu^1,2, Jinxiang Dong^1,2

1 School of Chemical Engineering and Light Industry, Guangdong Provincial Key Laboratory of Plant Resources Biorefinery, Guangzhou Key Laboratory of Clean Transportation Energy Chemistry, Guangdong University of Technology, Guangzhou 510006, China;
2 Jieyang Branch of Chemistry and Chemical Engineering Guangdong Laboratory (Rongjiang Laboratory), Jieyang 515200, China

Received:2023-06-22 Revised:2023-11-15 Online:2024-06-01 Published:2024-03-28
Contact: Baoyu Liu,E-mail address:baoyu.liu@gdut.edu.cn.
Supported by:
This work was supported by the National Natural Science Foundation of China (22278090, 21978055), Natural Science Foundation of Guangdong Province, China (2022A1515012088), the Science and Technology Planning Project of Guangdong Province, China (2022A0505030073, 2022A0505030013).

Production of linear alkylbenzene over Ce containing Beta zeolites

Shiqi Zhang^1,2, Shengzhi Gan^1,2, Baoyu Liu^1,2, Jinxiang Dong^1,2

1 School of Chemical Engineering and Light Industry, Guangdong Provincial Key Laboratory of Plant Resources Biorefinery, Guangzhou Key Laboratory of Clean Transportation Energy Chemistry, Guangdong University of Technology, Guangzhou 510006, China;
2 Jieyang Branch of Chemistry and Chemical Engineering Guangdong Laboratory (Rongjiang Laboratory), Jieyang 515200, China

通讯作者: Baoyu Liu,E-mail address:baoyu.liu@gdut.edu.cn.
基金资助:
This work was supported by the National Natural Science Foundation of China (22278090, 21978055), Natural Science Foundation of Guangdong Province, China (2022A1515012088), the Science and Technology Planning Project of Guangdong Province, China (2022A0505030073, 2022A0505030013).

Abstract

Abstract: Ce-encapsulated Beta zeolite was synthesized by a one-pot hydrothermal method with citric acid complexing Ce in the absence of Na species. Additional citric acid can effectively prevent the deposition of Ce species during the hydrothermal synthesis of zeolites, leading to uniform distribution of Ce cluster in the framework of Beta zeolites. Moreover, the sodium-free synthesis system resulted that the Brønsted acid sites were mainly located on the straight channels and external surface of Beta zeolites, improving the utilization of Brønsted acid sites. In addition, Ce encapsulated Beta zeolites showed enhanced activity and robust stability in the alkylation of benzene with 1-dodecene based on the synergistic effect between Ce species and Brønsted acid sites, which pave the way for its practical application in the production of alkylbenzene.

Key words: Beta zeolites, Catalysis, Alkylation, Long-chain olefins

摘要： Ce-encapsulated Beta zeolite was synthesized by a one-pot hydrothermal method with citric acid complexing Ce in the absence of Na species. Additional citric acid can effectively prevent the deposition of Ce species during the hydrothermal synthesis of zeolites, leading to uniform distribution of Ce cluster in the framework of Beta zeolites. Moreover, the sodium-free synthesis system resulted that the Brønsted acid sites were mainly located on the straight channels and external surface of Beta zeolites, improving the utilization of Brønsted acid sites. In addition, Ce encapsulated Beta zeolites showed enhanced activity and robust stability in the alkylation of benzene with 1-dodecene based on the synergistic effect between Ce species and Brønsted acid sites, which pave the way for its practical application in the production of alkylbenzene.

关键词: Beta zeolites, Catalysis, Alkylation, Long-chain olefins

Shiqi Zhang, Shengzhi Gan, Baoyu Liu, Jinxiang Dong. Production of linear alkylbenzene over Ce containing Beta zeolites[J]. Chinese Journal of Chemical Engineering, 2024, 67(3): 220-227.

Shiqi Zhang, Shengzhi Gan, Baoyu Liu, Jinxiang Dong. Production of linear alkylbenzene over Ce containing Beta zeolites[J]. 中国化学工程学报, 2024, 67(3): 220-227.

References

[1] R.M. Li, S.Y. Xing, S.A. Zhang, M.H. Han, Effect of surface silicon modification of H-beta zeolites for alkylation of benzene with 1-dodecene, RSC Adv. 10(17)(2020)10006-10016.
[2] J.J. Wang, Y.Y. Chuang, H.Y. Hsu, T.C. Tsai, Toward industrial catalysis of zeolite for linear alkylbenzene synthesis:A mini review, Catal. Today 298(2017)109-116.
[3] A. Aitani, J.B. Wang, I. Wang, S. Al-Khattaf, T.C. Tsai, Environmental benign catalysis for linear alkylbenzene synthesis:A review, Catal. Surv. Asia 18(1)(2014)1-12.
[4] G. Zahedi, H. Yaqubi, M. Ba-Shammakh, Dynamic modeling and simulation of heavy paraffin dehydrogenation reactor for selective olefin production in linear alkyl benzene production plant, Appl. Catal. A 358(1)(2009)1-6.
[5] M.H. Han, Z. Cui, C. Xu, W. Chen, Y. Jin, Synthesis of linear alkylbenzene catalyzed by Hb-zeolite, Appl. Catal. A 238(1)(2003)99-107.
[6] T.C. Tsai, I. Wang, S.J. Li, J.Y. Liu, Development of a green LAB process:Alkylation of benzene with 1-dodecene over mordenite, Green Chem. 5(4)(2003)404-409.
[7] J.G. Ma, B.J. Boyd, C.J. Drummond, Positional isomers of linear sodium dodecyl benzene sulfonate:Solubility, self-assembly, and air/water interfacial activity, Langmuir 22(21)(2006)8646-8654.
[8] J.L.G. de Almeida, M. Dufaux, Y. Ben Taarit, C. Naccache, Linear alkylbenzene, J. Am. Oil Chem. Soc. 71(7)(1994)675-694.
[9] J.A. Kocal, B.V. Vora, T. Imai, Production of linear alkylbenzenes, Appl. Catal. A 221(1-2)(2001)295-301.
[10] S. Sivasanker, A. Thangaraj, Distribution of isomers in the alkylation of benzene with long-chain olefins over solid acid catalysts, J. Catal. 138(1)(1992)386-390.
[11] C. Perego, P. Ingallina, Recent advances in the industrial alkylation of aromatics:New catalysts and new processes, Catal. Today 73(1-2)(2002)3-22.
[12] C. DeCastro, E. Sauvage, M.H. Valkenberg, W.F. Holderich, Immobilised ionicliquids as lewis acid catalysts for the alkylation of aromatic compounds with dodecene, J. Catal. 196(1)(2000)86-94.
[13] G.P. Qi, F. Jiang, X.W. Sun, S.Q. Zhao, Alkylation mechanism of benzene with 1-dodecene catalyzed by Et₃NHCl-AlCl₃, Sci. China Chem. 53(5)(2010)1102-1107.
[14] H.L. Xin, Q. Wu, M.H. Han, D.Z. Wang, Y. Jin, Alkylation of benzene with 1-dodecene in ionic liquids[Rmim]⁺Al₂Cl₆X^-(R=butyl, octyl and dodecyl; X=chlorine, bromine and iodine), Appl. Catal. A 292(2005)354-361.
[15] H.O. Zhu, X.Q. Ren, J. Wang, A comparative study of the catalytic behavior of SBA-15 supported heteropoly acid H₃PW₁₂O₄₀ and H-Y catalysts in the alkylation of benzene with 1-dodecene, React. Kinet. Catal. Lett. 83(1)(2004)19-24.
[16] J.C. Zhang, B.H. Chen, C.Y. Li, Z.G. Zhu, L.Y. Wen, E.Z. Min, Kinetics of benzene alkylation with 1-dodecene over a supported tungstophosphoric acid catalyst, Appl. Catal. A 249(1)(2003)27-34.
[17] J.C. Zhang, Z.G. Zhu, C.Y. Li, L.Y. Wen, E.Z. Min, Characterization and kinetic investigation of tungstophosphoric supported on SiO₂ for alkylation of benzene with 1-dodecene to synthesize linear alkylbenzene, J. Mol. Catal. 198(1-2)(2003)359-367.
[18] M.A. Harmer, Q. Sun, Solid acid catalysis using ion-exchange resins, Appl. Catal. A 221(1-2)(2001)45-62.
[19] J.H. Clark, G.L. Monks, D.J. Nightingale, P.M. Price, J.F. White, A new solid acidbased route to linear alkylbenzenes, J. Catal. 193(2)(2000)348-350.
[20] F. Zarkesh, F. Farzaneh, A.M. Ghandi, Metal ions exchanged montmorillonite as catalyst for alkylation of benzene with 1-dodecene, React. Kinet. Catal. Lett. 89(2)(2006)247-252.
[21] B.Y. Liu, Z.T. Liao, Y. Wu, C.H. Ding, F.S. Butt, Y. Huang, J.X. Dong, Efficient production of linear alkylbenzene by liquid alkylation between benzene and 1-dodecene over MWW zeolites, Mol. Catal. 531(2022)112642.
[22] X.D. Yuan, J.N. Park, J. Wang, C.W. Lee, S.E. Park, Alkylation of benzene with 1-dodecene over usy zeolite catalyst:Effect of pretreatment and reaction conditions, Korean J. Chem. Eng. 19(4)(2002)607-610.
[23] W. Aslam, M.A.B. Siddiqui, B. Rabindran Jermy, A. Aitani, J. Cejka, S. Al-Khattaf, Selective synthesis of linear alkylbenzene by alkylation of benzene with 1-dodecene over desilicated zeolites, Catal. Today 227(2014)187-197.
[24] S.Y. Xing, T.F. Wang, M.H. Han, Effect of different frameworks on the zeolite catalyzed alkylation of benzene with 1-dodecene, Mol. Catal. 531(2022)112644.
[25] J.S. Lin, J.J. Wang, J. Wang, I. Wang, R.J. Balasamy, A. Aitani, S. Al-Khattaf, T.C. Tsai, Catalysis of alkaline-modified mordenite for benzene alkylation of diolefin-containing dodecene for linear alkylbenzene synthesis, J. Catal. 300(2013)81-90.
[26] M. Horn acek, P. Hudec, A. Smieskova, T. Jakubík, Alkylation of benzene with 1-alkenes over beta zeolite in liquid phase, React. Kinet. Mech. Catal. 99(2)(2010)431-437.
[27] M. Horna cek, P. Hudec, A. Nociar, A. Smieskov a, T. Jakubík, Activity and regenerability of dealuminated zeolite Y in liquid phase alkylation of benzene with 1-alkene, Chem. Pap. 64(4)(2010)469-474.
[28] Y. Cao, Alkylation of benzene with dodecene. The activity and selectivity of zeolite type catalysts as a function of the porous structure, Appl. Catal. A 184(2)(1999)231-238.
[29] B. Thomas, S. Sugunan, Alkylation of benzene with 1-octene over rare earth exchanged HFAU-Y zeolites, React. Kinet. Catal. Lett. 85(1)(2005)29-36.
[30] Z.K. Zhao, W.H. Qiao, G.R. Wang, Z.S. Li, L. Cheng, Alkylation of a-methylnaphthalene with long-chain olefins catalyzed by rare earth lanthanum modified HY zeolite, J. Mol. Catal. 250(1-2)(2006)50-56.
[31] N. Wang, Q.M. Sun, R.S. Bai, X. Li, G.Q. Guo, J.H. Yu, In situ confinement of ultrasmall Pd clusters within nanosized silicalite-1 zeolite for highly efficient catalysis of hydrogen generation, J. Am. Chem. Soc. 138(24)(2016)7484-7487.
[32] Q.M. Sun, N. Wang, Q.M. Bing, R. Si, J.Y. Liu, R.S. Bai, P. Zhang, M.J. Jia, J.H. Yu, Subnanometric hybrid Pd-M (OH)2, M=Ni, Co, clusters in zeolites as highly efficient nanocatalysts for hydrogen generation, Chem 3(3)(2017)477-493.
[33] H. Wang, L.A. Wang, F.S. Xiao, Metal@zeolite hybrid materials for catalysis, ACS Cent. Sci. 6(10)(2020)1685-1697.
[34] W.L. Han, Z.C. Tang, P. Zhang, G.X. Lu, Study of one step synthesis of rare earth zeolite (ln-ZSM-5) and application for low temperature CO catalytic oxidation, Catal. Surv. Asia 17(3)(2013)147-155.
[35] E. Beche, P. Charvin, D. Perarnau, S. Abanades, G. Flamant, Ce 3d XPS inves-^tigation of cerium oxides and mixed cerium oxide (CexTiyOz), Surf. Interface Anal. 40(2008)264-267, 2008.
[36] Z.J. Wu, S. Goel, M. Choi, E. Iglesia, Hydrothermal synthesis of LTAencapsulated metal clusters and consequences for catalyst stability, reactivity, and selectivity, J. Catal. 311(2014)458-468.
[37] W.M. Hao, W.M. Zhang, Z.B. Guo, J.H. Ma, R.F. Li, Mesoporous beta zeolite catalysts for benzylation of naphthalene:Effect of pore structure and acidity, Catalysts 8(11)(2018)504.
[38] J. Fahy, D.L. Trimm, D.J. Cookson, Four component catalysis for the hydroalkylation of benzene to cyclohexyl benzene, Appl. Catal. A 211(2)(2001)259-268.
[39] S. Inagaki, K. Kamino, E. Kikuchi, M. Matsukata, Shape selectivity of MWWtype aluminosilicate zeolites in the alkylation of toluene with methanol, Appl. Catal. A 318(2007)22-27.
[40] J. Pérez-Ramírez, J.C. Groen, A. Brückner, M.S. Kumar, U. Bentrup, M.N. Deb-bagh, L.A. Villaescusa, Evolution of isomorphously substituted iron zeolites during activation:Comparison of Fe-beta and Fe-ZSM-5, J. Catal. 232(2)(2005)318-334.
[41] R.A. García-Muñoz, D.P. Serrano, G. Vicente, M. Linares, D. Vitvarova, J.~Cejka, Remarkable catalytic properties of hierarchical zeolite-Beta in epoxide rearrangement reactions, Catal. Today 243(2015)141-152.
[42] X.F. Zhang, R.J. Wang, X.X. Yang, Effect of alkaline treatment on pore structure and acidity of HZSM-5 in the synthesis of ethyl mercaptan, Catal. Commun. 60(2015)32-36.
[43] K. Góra-Marek, K. Tarach, M. Choi, 2, 6-di-tert-butylpyridine sorption approach to quantify the external acidity in hierarchical zeolites, J. Phys. Chem. C 118(23)(2014)12266-12274.
[44] J.J. Huang, B.Y. Liu, Z.T. Liao, H.Y. Chen, K. Yan, Fabrication of Cu-encapsulated hierarchical MEL zeolites for alkylation of mesitylene with benzyl alcohol, Ind. Eng. Chem. Res. 58(36)(2019)16636-16644.
[45] V. Pashkova, P. Klein, J. Dedecek, V. Tokarov a, B. Wichterlov a, Incorporation of Al at ZSM-5 hydrothermal synthesis. Tuning of Al pairs in the framework, Microporous Mesoporous Mater. 202(2015)138-146.
[46] J. Dedecek, V. Balgova, V. Pashkova, P. Klein, B. Wichterlov a, Synthesis of ZSM-5 zeolites with defined distribution of Al atoms in the framework and multinuclear MAS NMR analysis of the control of Al distribution, Chem. Mater. 24(16)(2012)3231-3239.
[47] Y.Y. Ji, C.Y. Wang, Y.C. Zou, J.W. Song, J.Y. Wang, F. Li, F.S. Xiao, Design and synthesis of microporous and micro/mesoporous silica materials with excellent adsorption properties via self-assembly of silica species with tetraethyl ammonium in acidic aqueous media, J. Phys. Chem. C 112(49)(2008)19367-19371.
[48] M. Hunger, Brønsted acid sites in zeolites characterized by multinuclear solidstate NMR spectroscopy, Catal. Rev. 39(4)(1997)345-393.
[49] R.R. Pinto, P. Borges, M.A.N.D.A. Lemos, F. Lemos, J.C. Vedrine, E.G. Der-ouane, F.R. Ribeiro, Correlating NH₃-TPD and ¹H MAS NMR measurements of zeolite acidity:Proposal of an acidity scale, Appl. Catal. A 284(1-2)(2005)39-46.
[50] Z.M. Yan, D. Ma, J.Q. Zhuang, X.C. Liu, X.M. Liu, X.W. Han, X.H. Bao, F.X. Chang, L. Xu, Z.M. Liu, On the acid-dealumination of USY zeolite:A solid state NMR investigation, J. Mol. Catal. 194(1-2)(2003)153-167.
[51] M. Müller, G. Harvey, R. Prins, Comparison of the dealumination of zeolites beta, mordenite, ZSM-5 and ferrierite by thermal treatment, leaching with oxalic acid and treatment with SiCl₄ by ¹H, ²⁹Si and ²⁷Al MAS NMR, Microporous Mesoporous Mater. 34(2)(2000)135-147.
[52] E.G. Derouane, J.C. Vedrine, R.R. Pinto, P.M. Borges, L. Costa, M.A.N.D.A. Lemos, F. Lemos, F.R. Ribeiro, The acidity of zeolites:Concepts, measurements and relation to catalysis:A review on experimental and theoretical methods for the study of zeolite acidity, Catal. Rev. 55(4)(2013)454-515.
[53] I. Fechete, A. Simon-Masseron, E. Dumitriu, D. Lutic, P. Caullet, H. Kessler, The role of acidity of CeHeEMTetype zeolite for catalyzing toluene alkylation with methanol to xylenes, Rev. Roum. Chim. 53(2008)55-61.
[54] L.H. Duan, Z.L. Sun, D.S. Liu, Z.H. Dai, X.Q. Li, L.J. Song, Adsorption and diffusion of thiophene, benzene, n-octane, and 1-octene on FAU zeolites, Stud. Surf. Sci. Catal. 170(2007)910-917.
[55] L.H. Duan, X.H. Gao, X.H. Meng, H.T. Zhang, Q.A. Wang, Y.C. Qin, X.T. Zhang, L.J. Song, Adsorption, co-adsorption, and reactions of sulfur compounds, aromatics, olefins over Ce-exchanged Y zeolite, J. Phys. Chem. C 116(49)(2012)25748-25756.
[56] H.G. Wang, L.J. Song, H. Jiang, J. Xu, L.L. Jin, X.T. Zhang, Z.L. Sun, Effects of olefin on adsorptive desulfurization of gasoline over Ce (IV) Y zeolites, Fuel Process. Technol. 90(6)(2009)835-838.
[57] I. Craciun, M.F. Reyniers, G.B. Marin, Liquid-phase alkylation of benzene with octenes over Y zeolites:Kinetic modeling including acidity descriptors, J. Catal. 294(2012)136-150.
[58] V.R. Choudhary, S.K. Jana, Benzylation of benzene and substituted benzenes by benzyl chloride over InCl₃, GaCl₃, FeCl₃ and ZnCl₂ supported on clays and SiMCM-41, J. Mol. Catal. 180(1-2)(2002)267-276.

Production of linear alkylbenzene over Ce containing Beta zeolites

Production of linear alkylbenzene over Ce containing Beta zeolites

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Siyue Wang, Jinhong Li, Qingxin Xu, Shengjie Song, Yu'ni Jiang, Lidong Chen, Xin Shi, Weiguo Cheng. Synthesis of spherical nano-ZSM-5 zeolite with intergranular mesoporous for alkylation of ethylbenzene with ethanol to produce m-diethylbenzene [J]. Chinese Journal of Chemical Engineering, 2024, 67(3): 298-309.
[2]	Yi-Fei Liang, Jin-Rong Lu, Shang-Kun Tian, Wen-Quan Cui, Li Liu. Pt nanoclusters modified porous g-C₃N₄ nanosheets to significantly enhance hydrogen production by photocatalytic water reforming of methanol [J]. Chinese Journal of Chemical Engineering, 2024, 66(2): 40-50.
[3]	Rui Yu, Zhensheng Shen, Yanan Liu, Chengxiang Shi, Juncong Qu, Lun Pan, Zhenfeng Huang, Xiangwen Zhang, Ji-Jun Zou. Tandem hydroalkylation and deoxygenation of lignin-derived phenolics to synthesize high-density fuels [J]. Chinese Journal of Chemical Engineering, 2024, 66(2): 104-109.
[4]	Zhihao Guo, Jiuxuan Zhang, Lanlan Chen, Chaoqun Fan, Hong Jiang, Rizhi Chen. Hollow ZIF-67-derived Co@N-doped carbon nanotubes boosting the hydrogenation of phenolic compounds to alcohols [J]. Chinese Journal of Chemical Engineering, 2024, 66(2): 157-166.
[5]	Yinghui Liu, Shaoduo Liu, Xiaosheng Wang, Hongjing Wang, Ranjia Li, Changchun Yu, Chunming Xu, Yuxiang Liu, Zhengqiu Xie, Yongqiang Wang, Pan Tang. Synthesis of mordenite by solvent-free method and its application in the dimethyl ether carbonylation reaction [J]. Chinese Journal of Chemical Engineering, 2024, 66(2): 216-223.
[6]	Guixian Li, Tao Tian, Hanxu Li, Jinlian Li, Tingna Shao, Qi Zhang, Peng Dong. Anti-carbon deposition performance of twinned HZSM-5 encapsulated Ru in the toluene alkylation with methanol [J]. Chinese Journal of Chemical Engineering, 2023, 61(9): 1-8.
[7]	Ting Li, Hongxia Guo, Xiao Wang, Huan Wang, Li Liu, Wenquan Cui, Xiaoran Sun, Yinghua Liang. Loading CuO on the surface of MgO with low-coordination basic O^2- sites for effective enhanced CO₂ capture and photothermal synergistic catalytic reduction of CO₂ to ethanol [J]. Chinese Journal of Chemical Engineering, 2023, 61(9): 58-67.
[8]	Baoyu Liu, Feng Xiong, Jianwen Zhang, Manna Wang, Yi Huang, Yanxiong Fang, Jinxiang Dong. Enhanced ortho-selective t–butylation of phenol over sulfonic acid functionalized mesopore MTW zeolites [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 1-7.
[9]	Fei Li, Xuemei Wang, Pengze Zhang, Qinqin Wang, Mingyuan Zhu, Bin Dai. Nitrogen and phosphorus co-doped activated carbon induces high density Cu⁺ active center for acetylene hydrochlorination [J]. Chinese Journal of Chemical Engineering, 2023, 59(7): 193-199.
[10]	Tingjun Fu, Ran Wang, Kun Ren, Liangliang Zhang, Zhong Li. Intensified shape selectivity and alkylation reaction for the two-step conversion of methanol aromatization to p-xylene [J]. Chinese Journal of Chemical Engineering, 2023, 59(7): 240-250.
[11]	Haodi Tan, Minjiao Yang, Yingquan Chen, Xu Chen, Francesco Fantozzi, Pietro Bartocci, Roman Tschentscher, Federica Barontini, Haiping Yang, Hanping Chen. Preparation of aromatic hydrocarbons from catalytic pyrolysis of digestate [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 1-9.
[12]	Chenyang Zhao, Yinhan Cheng, Guangfei Qu, Yongheng Yuan, Fenghui Wu, Ye Liu, Shan Liu, Junyan Li, Ping Ning. High-performance liquid-phase catalytic purification of phosphine in tail gas using Pd(II)/Cu(II) composite [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 98-108.
[13]	Shiyong Xing, Yan Cui, Tiefeng Wang, Jinwei He, Minghan Han. Elucidating the effect of oxides on the zeolite catalyzed alkylation of benzene with 1-dodecene [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 126-135.
[14]	Juan Du, Aibing Chen, Senlin Hou, Xueqing Gao. Self-deposition for mesoporous carbon nanosheet with supercapacitor application [J]. Chinese Journal of Chemical Engineering, 2023, 55(3): 34-40.
[15]	Mengting Liu, Xuexue Dong, Zengjing Guo, Aihua Yuan, Shuying Gao, Fu Yang. Enabling tandem oxidation of benzene to benzenediol over integrated neighboring V-Cu oxides in mesoporous silica [J]. Chinese Journal of Chemical Engineering, 2023, 55(3): 236-245.