Development of a new continuous process for the production of 3,5-dimethylpiperidine

doi:10.1016/j.cjche.2021.07.024

中国化学工程学报 ›› 2022, Vol. 41 ›› Issue (1): 374-383.DOI: 10.1016/j.cjche.2021.07.024

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

Development of a new continuous process for the production of 3,5-dimethylpiperidine

Tao Lin^1,2,3,4,5,6, Xiaoxun Ma^1,3,4,5,6

1 School of Chemical Engineering, Northwest University, Xi’an 710069, China;
2 Kaili Catalyst & New Materials Co., Ltd., Xi’an 710201, China;
3 Chemical Engineering Research Center of the Ministry of Education (MOE) for Advanced Use Technology of Shanbei Energy, Xi’an 710069, China;
4 Shaanxi Research Center of Engineering Technology for Clean Coal Conversion, Xi’an 710069, China;
5 Collaborative Innovation Center for Development of Energy and Chemical Industry in Northern Shaanxi, Xi’an 710069, China;
6 International Scientific and Technological Cooperation Base of the Ministry of Science and Technology (MOST) for Clean Utilization of Hydrocarbon Resources, Xi’an 710069, China

收稿日期:2021-03-18 修回日期:2021-06-24 出版日期:2022-01-28 发布日期:2022-02-25
通讯作者: Xiaoxun Ma,E-mail address:maxym@nwu.edu.cn
基金资助:
This word was supported by the National Natural Science Foundation of China (21536009), and the Science and Technology Plan Projects of Shaanxi Province (2017ZDCXL-GY-10-03).

Development of a new continuous process for the production of 3,5-dimethylpiperidine

Tao Lin^1,2,3,4,5,6, Xiaoxun Ma^1,3,4,5,6

1 School of Chemical Engineering, Northwest University, Xi’an 710069, China;
2 Kaili Catalyst & New Materials Co., Ltd., Xi’an 710201, China;
3 Chemical Engineering Research Center of the Ministry of Education (MOE) for Advanced Use Technology of Shanbei Energy, Xi’an 710069, China;
4 Shaanxi Research Center of Engineering Technology for Clean Coal Conversion, Xi’an 710069, China;
5 Collaborative Innovation Center for Development of Energy and Chemical Industry in Northern Shaanxi, Xi’an 710069, China;
6 International Scientific and Technological Cooperation Base of the Ministry of Science and Technology (MOST) for Clean Utilization of Hydrocarbon Resources, Xi’an 710069, China

Received:2021-03-18 Revised:2021-06-24 Online:2022-01-28 Published:2022-02-25
Contact: Xiaoxun Ma,E-mail address:maxym@nwu.edu.cn
Supported by:
This word was supported by the National Natural Science Foundation of China (21536009), and the Science and Technology Plan Projects of Shaanxi Province (2017ZDCXL-GY-10-03).

摘要/Abstract

摘要： This paper developed a new clean continuous process for the hydrogenation of 3,5-dimethylpyridine (DPY) to 3,5-dimethylpiperidine (DPI) without solvent. A series of Ru/C catalysts were prepared by impregnation method, which were characterized by the BET, ICP, CO chemisorptions, XRD, SEM, EDS, TEM and TG. The effect of active species, loading, catalyst support, reaction temperature and pressure on the catalytic performance was investigated. The influence of internal and external diffusion in the trickle-bed reactor (TBR) was basically eliminated by adjusting the particle size and dosage of the Ru/C catalyst. The reaction performance of the hydrogenation of DPY to DPI in the TBR and kettle reactor (KR) was compared, and the superiority of the TBR process was analyzed. The results show that this new continuous process developed in this study is an efficient way to realize the hydrogenation of DPY to DPI, and has a good industrial application prospect.

关键词: Trickle-bed reactor (TBR), Kettle reactor (KR), Hydrogenation, 3,5-Dimethylpyridine (DPY), 3,5-Dimethylpiperidine (DPI)

Abstract: This paper developed a new clean continuous process for the hydrogenation of 3,5-dimethylpyridine (DPY) to 3,5-dimethylpiperidine (DPI) without solvent. A series of Ru/C catalysts were prepared by impregnation method, which were characterized by the BET, ICP, CO chemisorptions, XRD, SEM, EDS, TEM and TG. The effect of active species, loading, catalyst support, reaction temperature and pressure on the catalytic performance was investigated. The influence of internal and external diffusion in the trickle-bed reactor (TBR) was basically eliminated by adjusting the particle size and dosage of the Ru/C catalyst. The reaction performance of the hydrogenation of DPY to DPI in the TBR and kettle reactor (KR) was compared, and the superiority of the TBR process was analyzed. The results show that this new continuous process developed in this study is an efficient way to realize the hydrogenation of DPY to DPI, and has a good industrial application prospect.

Key words: Trickle-bed reactor (TBR), Kettle reactor (KR), Hydrogenation, 3,5-Dimethylpyridine (DPY), 3,5-Dimethylpiperidine (DPI)

Tao Lin, Xiaoxun Ma. Development of a new continuous process for the production of 3,5-dimethylpiperidine[J]. 中国化学工程学报, 2022, 41(1): 374-383.

Tao Lin, Xiaoxun Ma. Development of a new continuous process for the production of 3,5-dimethylpiperidine[J]. Chinese Journal of Chemical Engineering, 2022, 41(1): 374-383.

参考文献

[1] L.C. Creemer, H.A. Kirst, T.R. Shryock, J.B. Campbell, A.G. Webb, Synthesis, antimicrobial activity and in vivo fluorine NMR of a hexafluorinated derivative of tilmicosin, J. Antibiot. (Tokyo) 48(7) (1995) 671–675.
[2] K.R. Wan, T. Lin, J. Chen, L. Li, Y.K. Zeng, L.H. Zeng, Z.X. Zhang, The preparation method and application of the catalyst used for continuous preparation of 3,5-dimethyl piperidine, CN Pat., 201611126557.5(2016).
[3] R.C. Beier, L.C. Creemer, R.L. Ziprin, D.J. Nisbet, Production and characterization of monoclonal antibodies against the antibiotic tilmicosin, J. Agric. Food Chem. 53(25) (2005) 9679–9688.
[4] S.I. Zones, Y. Nakagawa, S.T. Evans, G.S. Lee, ZEOLITE SSZ-39, US Pat., 5958370A (1999).
[5] H. Xu, J. Zhang, Q.M. Wu, W. Chen, C. Lei, Q.Y. Zhu, S.C. Han, J.H. Fei, A.M. Zheng, L.F. Zhu, X.J. Meng, S. Maurer, D. Dai, A.N. Parvulescu, U. Müller, F.S. Xiao, Direct synthesis of aluminosilicate SSZ-39 zeolite using colloidal silica as a starting source, ACS Appl. Mater. Interfaces 11(26) (2019) 23112–23117.
[6] F.G. Sales, L.C.A. Maranhão, N.M.L. Filho, C.A.M. Abreu, Experimental evaluation and continuous catalytic process for fine aldehyde production from lignin, Chem. Eng. Sci. 62(18–20) (2007) 5386–5391.
[7] S. Machefer, L. Falk, F. de Panthou, Intensification principle of a new threephase catalytic slurry reactor. Part I: Performance characterisation, Chem. Eng. Process. Process Intensif. 70(2013) 277–288.
[8] C. Jiménez-González, P. Poechlauer, Q.B. Broxterman, B.S. Yang, D.A. Ende, J. Baird, C. Bertsch, R.E. Hannah, P. Dell’Orco, H. Noorman, S. Yee, R. Reintjens, A. Wells, V. Massonneau, J. Manley, Key green engineering research areas for sustainable manufacturing: A perspective from pharmaceutical and fine chemicals manufacturers, Org. Process Res. Dev. 15(4) (2011) 900–911.
[9] D. Heitmann, Continuous and intensified laboratory process development at clariant, Chem. Eng. Technol. 39(11) (2016) 1993–1995.
[10] S. Lomel, L. Falk, J.M. Commenge, J.L. Houzelot, K. Ramdani, The microreactor: A systematic and efficient tool for the transition from batch to continuous process?, Chem Eng. Res. Des. 84(5) (2006) 363–369.
[11] K. Plumb, Continuous processing in the pharmaceutical industry: Changing the mind set, Chem. Eng. Res. Des. 83(6) (2005) 730–738.
[12] J.G. Boelhouwer, H.W. Piepers, B.A.H. Drinkenburg, Advantages of forced nonsteady operated trickle-bed reactors, Chem. Eng. Technol. 25(6) (2002) 647.
[13] M.V. Rajashekharam, R. Jaganathan, R.V. Chaudhari, A trickle-bed reactor model for hydrogenation of 2, 4 dinitrotoluene: Experimental verification, Chem. Eng. Sci. 53(4) (1998) 787–805.
[14] J.K. Jeon, J.H. Yim, Y.K. Park, C9-aldehyde hydrogenation over nickel/kieselguhr catalysts in trickle bed reactor, Chem. Eng. J. 140(1–3) (2008) 555–561.
[15] A.J. Sederman, M.D. Mantle, C.P. Dunckley, Z.Y. Huang, L.F. Gladden, In situ MRI study of 1-octene isomerisation and hydrogenation within a trickle-bed reactor, Catal. Lett. 103(1) (2005) 1–8.
[16] J. Roininen, V. Alopaeus, S. Toppinen, J. Aittamaa, Modeling and simulation of an industrial trickle-bed reactor for benzene hydrogenation: Model validation against plant data, Ind. Eng. Chem. Res. 48(4) (2009) 1866–1872.
[17] D. Durante, T. Kilpiö, P. Suominen, V.S. Herrera, J. Wärnå, P. Canu, T. Salmi, Modeling and simulation of a small-scale trickle bed reactor for sugar hydrogenation, Comput. Chem. Eng. 66(2014) 22–35.
[18] T.A. Nijhuis, F.M. Dautzenberg, J.A. Moulijn, Modeling of monolithic and trickle-bed reactors for the hydrogenation of styrene, Chem. Eng. Sci. 58(7) (2003) 1113–1124.
[19] S. Machefer, L. Falk, F. de Panthou, Intensification principle of a new threephase catalytic slurry reactor. Part II: Eco-efficiency and techno-economic performances, Chem. Eng. Process. Process Intensif. 70(2013) 267–276.
[20] F.S. Mederos, J. Ancheyta, J.W. Chen, Review on criteria to ensure ideal behaviors in trickle-bed reactors, Appl. Catal. A: Gen. 355(1–2) (2009) 1–19.
[21] C.N. Satterfield, Trickle-bed reactors, AIChE J. 21(2) (1975) 209–228.
[22] T.W. Kim, J. Oh, Y.-W. Suh, Hydrogenation of 2-benzylpyridine over aluminasupported Ru catalysts: Use of Ru₃(CO)₁₂ as a Ru precursor, Appl. Catal. A: Gen. 547(2017) 183–190.
[23] C. Zhou, A Study on the Catalytic Hydrogenation of 3,5-Dimethylpyridine Master’s Thesis, Huazhong University of Science & Technology, Wuhan, 2008.
[24] F. Xue, The preparation of highly dispersed Ru catalyst and the study of the catalytic behavior on hydrogenation of N-heterocycles Master’s Thesis, Sichuan University, Chengdu, 2006.
[25] F. Xue, Q. Lin, C.F. Yang, X.J. Li, H. Chen, Hydrogenation of pyridine and its derivatives over supported nanometer noble metal catalysts, Chin. J. Catal. 27(2006) 921–926.
[26] N.Q. Budwine, N.L. Churissa, P.G. Walmart, Separation of cis-3,5-dimethylpiperidine from geometric isomers of cis-3,5-dimethylpiperidine, CN Pat., 200410031697.7(2004).
[27] Z.M. Du, C.Y. Zhou, W.F. Ji, J.S. Jiang, G.P. Yu, L.J. Ji, Preparation of cis-trans mixed isomer 3,5-dimethylpiperidine, CN Pat., 200610088375.3(2006).
[28] F. Gerald, L. Old, Filter-purifier cartyidge having separable elements, US Pat., 4138339(1979).
[29] T. Lin, J. Chen, B.L. Zhang, K.R. Wan, Y.K. Zeng, L.H. Zeng, W. Gao, Z.X. Zhang, A catalyst for hydrogenation of pyridine compounds and its application, CN Pat., 201711364538.0(2017).
[30] C. Moreno-Castilla, M.V. López-Ramón, F. Carrasco-Marín, Changes in surface chemistry of activated carbons by wet oxidation, Carbon 38(14) (2000) 1995–2001.
[31] T. Lin, K.R. Wan, J. Chen, Z.X. Zhang, Y.K. Zeng, L.H. Zeng, W. Gao, An online device used for evaluating the fixed bed catalyst performance, CN Pat., 201520609359.9(2015).
[32] G. Peng, M. Steib, F. Gramm, C. Ludwig, F. Vogel, Synthesis factors affecting the catalytic performance and stability of Ru/C catalysts for supercritical water gasification, Catal. Sci. Technol. 4(9) (2014) 3329–3339.
[33] R.M. Mironenko, O.B. Belskaya, T.I. Gulyaeva, A.I. Nizovskii, A.V. Kalinkin, V.I. Bukhtiyarov, A.V. Lavrenov, V.A. Likholobov, Effect of the nature of carbon support on the formation of active sites in Pd/C and Ru/C catalysts for hydrogenation of furfural, Catal. Today 249(2015) 145–152.
[34] I. Rossetti, L. Forni, Effect of Ru loading and of Ru precursor in Ru/C catalysts for ammonia synthesis, Appl. Catal. A: Gen. 282(1–2) (2005) 315–320.
[35] V.A. Sifontes Herrera, D.E. Rivero Mendoza, A.-R. Leino, J.-P. Mikkola, A. Zolotukhin, K. Eränen, T. Salmi, Sugar hydrogenation in continuous reactors: From catalyst particles towards structured catalysts, Chem. Eng. Process.-Process. Intensif. 109(2016) 1–10.
[36] A. Müller, G. Hilpmann, S. Haase, R. Lange, Continuous hydrogenation of L-arabinose and D-galactose in a mini packed-bed reactor, Chem. Eng. Technol. 40(11) (2017) 2113–2122.
[37] C.N. Satterfield, A.A. Pelossof, T.K. Sherwood, Mass transfer limitations in a trickle-bed reactor, AIChE J. 15(2) (1969) 226–234.
[38] J. Nie, H. Liu, Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2, 5-diformylfuran on manganese oxide catalysts, J. Catal. 316(2014) 57–66.
[39] T. Fovanna, S. Campisi, A. Villa, A. Kambolis, G. Peng, D. Rentsch, O. Kröcher, M. Nachtegaal, D. Ferri, Ruthenium on phosphorous-modified alumina as an effective and stable catalyst for catalytic transfer hydrogenation of furfural, RSC Adv. 10(19) (2020) 11507–11516.
[40] F. Su, L. Lv, F.Y. Lee, T. Liu, A.I. Cooper, X.S. Zhao, Thermally reduced ruthenium nanoparticles as a highly active heterogeneous catalyst for hydrogenation of monoaromatics, J. Am. Chem. Soc. 129(46) (2007) 14213–14223.
[41] P. Veerakumar, N. Dhenadhayalan, K.C. Lin, S.B. Liu, Highly stable ruthenium nanoparticles on 3D mesoporous carbon: An excellent opportunity for reduction reactions, J. Mater. Chem. A 3(46) (2015) 23448–23457.
[42] L. Wu, J. Song, B. Zhou, T. Wu, T. Jiang, B. Han, Preparation of Ru/graphene using glucose as carbon source and hydrogenation of levulinic acid to cvalerolactone, Chem. Asian J. 11(19) (2016) 2792–2796.
[43] María.L. Bosko, N. Ferreira, A. Catena, M. Sergio Moreno, J.F. Múnera, L. Cornaglia, Catalytic behavior of Ru nanoparticles supported on carbon fibers for the ethanol steam reforming reaction, Catal. Commun. 114(2018) 19–23.
[44] A. Bjelić, M. Grilc, M. Huš, B. Likozar, Hydrogenation and hydrodeoxygenation of aromatic lignin monomers over Cu/C, Ni/C, Pd/C, Pt/C, Rh/C and Ru/C catalysts: Mechanisms, reaction micro-kinetic modelling and quantitative structure-activity relationships, Chem. Eng. J. 359(2019) 305–320.
[45] C.L. Xu, M. Ming, Q. Wang, C. Yang, G.Y. Fan, Y. Wang, D.J. Gao, J. Bi, Y. Zhang, Facile synthesis of effective Ru nanoparticles on carbon by adsorption-low temperature pyrolysis strategy for hydrogen evolution, J. Mater. Chem. A 6(29) (2018) 14380–14386.
[46] M.G. Hosseini, P. Zardari, Electrocatalysis of oxygen reduction on multi-walled carbon nanotube supported Ru-based catalysts in alkaline media, Int. J. Hydrog. Energy 41(21) (2016) 8803–8818.
[47] A. Jafari, N. Saadatjou, S. Sahebdelfar, Influence of chemical treatments of activated carbon support on the performance and deactivation behavior of promoted Ru catalyst in ammonia synthesis, Int. J. Hydrog. Energy 40(9) (2015) 3659–3671.
[48] H. Zhao, S. Chen, M. Guo, D. Zhou, Z. Shen, W. Wang, B. Feng, B. Jiang, Catalytic Dehydrochlorination of 1,2-Dichloroethane into Vinyl Chloride over NitrogenDoped Activated Carbon, ACS Omega 4(1) (2019) 2081–2089.
[49] Z. Wei, X. Li, J. Deng, J. Wang, H. Li, Y. Wang, Improved catalytic activity and stability for hydrogenation of levulinic acid by Ru/N-doped hierarchically porous carbon, Mol. Catal. 448(2018) 100–107.
[50] M. Balaraju, V. Rekha, B.L.A.P. Devi, R.B.N. Prasad, P.S.S. Prasad, N. Lingaiah, Surface and structural properties of titania-supported Ru catalysts for hydrogenolysis of glycerol, Appl. Catal. A: Gen. 384(1–2) (2010) 107–114.
[51] H. Kobayashi, H. Matsuhashi, T. Komanoya, K. Hara, A. Fukuoka, Transfer hydrogenation of cellulose to sugar alcohols over supported ruthenium catalysts, Chem. Commun. (Camb.) 47(8) (2011) 2366–2368.
[52] Y. Wang, Z.M. Rong, Y. Wang, J.P. Qu, Ruthenium nanoparticles loaded on functionalized graphene for liquid-phase hydrogenation of fine chemicals: Comparison with carbon nanotube, J. Catal. 333(2016) 8–16.
[53] J. Li, H.Y. Zhang, M. Cai, L.F. Li, Y.Q. Li, R. Zhao, J.L. Zhang, Enhanced catalytic performance of activated carbon-supported ru-based catalysts for acetylene hydrochlorination by azole ligands, Appl. Catal. A-Gen. 592(2020) 117431.
[54] X. Liu, G. Lan, P. Su, L. Qian, T. Ramirez Reina, L. Wang, Y. Li, J. Liu, Highly stable Ru nanoparticles incorporated in mesoporous carbon catalysts for production of c-valerolactone, Catal. Today 351(2020) 75–82.
[55] B.C. Man, H.Y. Zhang, J.L. Zhang, X. Li, N. Xu, H. Dai, M.Y. Zhu, B. Dai, Oxidation modification of Ru-based catalyst for acetylene hydrochlorination, RSC Adv. 7(38) (2017) 23742–23750.
[56] S.S. Guo, K.Y. Liew, J.L. Li, Catalytic activity of ruthenium nanoparticles supported on carbon nanotubes for hydrogenation of soybean oil, J. Am. Oil Chem. Soc. 86(12) (2009) 1141–1147.
[57] B. Lin, Y. Guo, C. Cao, J. Ni, J. Lin, L. Jiang, Carbon support surface effects in the catalytic performance of Ba-promoted Ru catalyst for ammonia synthesis, Catal. Today 316(2018) 230–236.
[58] Y. Wang, J. Wang, G. Han, C. Du, Y. Sun, L. Du, M. An, G. Yin, Y. Gao, Y. Song, Superior catalytic performance and CO tolerance of Ru@Pt/C-TiO₂ electrocatalyst toward methanol oxidation reaction, Appl. Surf. Sci. 473(2019) 943–950.

Development of a new continuous process for the production of 3,5-dimethylpiperidine

Development of a new continuous process for the production of 3,5-dimethylpiperidine

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]	Peipei Ai, Huiqing Jin, Jie Li, Xiaodong Wang, Wei Huang. Ultra-stable Cu-based catalyst for dimethyl oxalate hydrogenation to ethylene glycol[J]. 中国化学工程学报, 2023, 60(8): 186-193.
[2]	Qunfeng Zhang, Bingcheng Li, Yuan Zhou, Deshuo Zhang, Chunshan Lu, Feng Feng, Jinghui Lv, Qingtao Wang, Xiaonian Li. Regulation of the selective hydrogenation performance of sulfur-doped carbon-supported palladium on chloronitrobenzene[J]. 中国化学工程学报, 2023, 58(6): 69-75.
[3]	Bin Gao, Junwen Chen, Qi Zuo, Hongyan Wang, Wenlin Li. The critical role of Zr in controlling the activity of Pd/Beta on the hydrogenation of phenol to cyclohexanone[J]. 中国化学工程学报, 2023, 57(5): 79-87.
[4]	Qi Yang, Weikang Dai, Maoshuai Li, Jie Wei, Yi Feng, Cheng Yang, Wanxin Yang, Ying Zheng, Jie Ding, Mei-Yan Wang, Xinbin Ma. Enhanced selective hydrogenation of glycolaldehyde to ethylene glycol over Cu⁰-Cu⁺ sites[J]. 中国化学工程学报, 2023, 57(5): 141-150.
[5]	Peipei Ai, Li Zhang, Jinchi Niu, Huiqing Jin, Wei Huang. Boron-doped lamellar porous carbon supported copper catalyst for dimethyl oxalate hydrogenation[J]. 中国化学工程学报, 2023, 55(3): 222-229.
[6]	Xianglin Liu, Minjie Xu, Chenxi Cao, Zixu Yang, Jing Xu. Effects of zinc on χ-Fe₅C₂ for carbon dioxide hydrogenation to olefins: Insights from experimental and density function theory calculations[J]. 中国化学工程学报, 2023, 54(2): 206-214.
[7]	Lu Lv, Min Zhao, Yanan Liu, Yufei He, Dianqing Li. Fabrication of hydrophobic Pd/Al₂O₃-phosphoric acid via P-O-Al bond for liquid hydrogenation reaction[J]. 中国化学工程学报, 2023, 53(1): 232-242.
[8]	Junru Liu, Rui Hu, Xinlei Liu, Qunfeng Zhang, Guanghua Ye, Zhijun Sui, Xinggui Zhou. Modeling of propane dehydrogenation combined with chemical looping combustion of hydrogen in a fixed bed reactor[J]. 中国化学工程学报, 2022, 47(7): 165-173.
[9]	Qunhong Liu, Jiangtao Yang, Hongwei Zhang, Hongming Sun, Shuzheng Wu, Bingqing Ge, Rong Wang, Pei Yuan. Tuning the properties of Ni-based catalyst via La incorporation for efficient hydrogenation of petroleum resin[J]. 中国化学工程学报, 2022, 45(5): 41-50.
[10]	Ning Liu, Xingping Liu, Fumin Wang, Feng Xin, Mingshuai Sun, Yi Zhai, Xubin Zhang. CFD simulation study of the effect of baffles on the fluidized bed for hydrogenation of silicon tetrachloride[J]. 中国化学工程学报, 2022, 45(5): 219-228.
[11]	Chunhua Zhang, Zhengyan Qu, Hong Jiang, Rizhi Chen, Weihong Xing. Nb₂O₅ promoted Pd/AC catalyst for selective phenol hydrogenation to cyclohexanone[J]. 中国化学工程学报, 2022, 44(4): 87-93.
[12]	Bo Wu, Xing Yu, Min Huang, Liangshu Zhong, Yuhan Sun. Rh single atoms embedded in CeO₂ nanostructure boost CO₂ hydrogenation to HCOOH[J]. 中国化学工程学报, 2022, 43(3): 62-69.
[13]	Youwei Yang, Jingyu Zhang, Yueqi Gao, Busha Assaba Fayisa, Antai Li, Shouying Huang, Jing Lv, Yue Wang, Xinbin Ma. Highly dispersed nickel boosts catalysis by Cu/SiO₂ in the hydrogenation of CO₂-derived ethylene carbonate to methanol and ethylene glycol[J]. 中国化学工程学报, 2022, 43(3): 77-85.
[14]	Di Gao, Yibo Zhi, Liyuan Cao, Liang Zhao, Jinsen Gao, Chunming Xu, Mingzhi Ma, Pengfei Hao. Influence of zinc state on the catalyst properties of Zn/HZSM-5 zeolite in 1-hexene aromatization and cyclohexane dehydrogenation[J]. 中国化学工程学报, 2022, 43(3): 124-134.
[15]	Bofeng Zhang, Mingxia Song, Hongwang Liu, Guozhu Li, Sibao Liu, Li Wang, Xiangwen Zhang, Guozhu Liu. Role of Ni species in ZnO supported on Silicalite-1 for efficient propane dehydrogenation[J]. 中国化学工程学报, 2022, 43(3): 240-247.