苯/甲醇烷基化反应研究进展
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摘要
针对我国苯的产能过大以及甲醇产能严重过剩的现状,综述了苯与甲醇烷基化制芳烃技术取得的进展。介绍了苯与甲醇烷基化反应催化剂种类、烷基化反应体系、烷基化主要面临的问题、烷基化研究进展,为苯与甲醇烷基化实现工业化提供依据。
Given China’s surplus capacities of benzene and methanol,this paper reviews the progress in the production of aromatics through the alkylation between benzene and methanol. The types of catalysts for alkylation of benzene with methanol,the alkylation reactive system,the main problems for alkylation and the research progress of alkylation are described in detail,which provides a basis for the industrialization of alkylation of benzene with methanol.
Given China’s surplus capacities of benzene and methanol,this paper reviews the progress in the production of aromatics through the alkylation between benzene and methanol. The types of catalysts for alkylation of benzene with methanol,the alkylation reactive system,the main problems for alkylation and the research progress of alkylation are described in detail,which provides a basis for the industrialization of alkylation of benzene with methanol.
引文
[1]Zhang Yingying,Li Yuefang,Lang Chen,et al.A new catalytic process for the synthesis of para-xylene through benzene methylation with CH3Br[J].Catal Commun,2014,54:6-10.
[2]Lu Ping,Fei Zhaoyang,Li Lei,et al.Effects of controlled SiO2deposition and phosphorus and nickel doping on surface acidity and diffusivity of medium and small sized HZSM-5 for para-selective alkylation of toluene by methanol[J].Appl Catal A-Gen,2013,453:302-309.
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[4]Hu Hualei,Lyu Jinghui,Wang Qingtao,et al.Alkylation of benzene with methanol over hierarchical porous ZSM-5:Synergy effects of hydrogen atmosphere and zinc modification[J].RSC Adv,2015,5:32679-32684.
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[9]Zhang Wanshuo,Zhang Shuang,Xin Wenjie,et al.Shaped binderless ZSM-11 zeolite catalyst prepared via a dry-gel conversion method:Characterization and application for alkylation of benzene with dimethyl ether[J].J Energy Chem,2017,26:380-389.
[10]Jiang Jian,Lu Guanzhong,Miao Changxi,et al.Catalytic performance of X molecular sieve modified by alkali metal ions for the side-chain alkylation of toluene with methanol[J].Micropor Mesopor Mater,2013,167:213-220.
[11]Yashima T,Yamazaki K,Ahmad H,et al,Alkylation on synthetic zeolites:Ⅱ.Selectivity p-xylene formation[J].J Catal,1970,17:151-156.
[12]Wang Yanan,Gao Yang,Xie Sujuan,et al.Adjustment of the Al siting in MCM-22 zeolite and its effect on alkylationperformance of ethylene with benzene[J].Catal Today,2018,316:71-77.
[13]Shi Yanchun,Xing Enhui,Xie Wenhua,et al.Shape selectivity of beta and MCM-49 zeolites in liquid-phase alkylation of benzene with ethylene[J].J Mol Catal A-Chem,2016,418/419:86-94.
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[16]Svelle Stian,Visur Melina,Olsbye Unni,et al.Mechanistic aspects of the zeolite catalyzed methylation of alkenes and aromatics with methanol:A review[J].Top Catal,2011,54(15):897-906.
[17]Venuto P B,Landis P S.Organic catalysis over crystalline aluminosilieates[M].New York and London:Petroleum Chemical Press,1968:2-17.
[18]赵博,刘民,谭伟,等.硅磷镁改性对纳米HZSM-5催化苯和甲醇烷基化反应的影响[J].石油学报:石油加工,2013,29(4):605-611.
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[20]Chen Huanhui,Li Xiaoci,Zhao Guoqing,et al.Free radical mechanism investigation of the side-chain alkylation of toluene with methanol on basic zeolites X[J].Chinese J Catal.,2015,36:1726-1732.
[21]Liu Hui,Wei Huijuan,Xin Wenjie,et al.Differences between Zn/HZSM-5 and Zn/HZSM-11 zeolite catalysts in alkylation of benzene with dimethyl ether[J].J Energy Chem,2014,23:617-624.
[22]Li B,Chen H,Li S,et al.Distribution of Mo in Mo/ZSM-5 catalyst prepared by impregnation method[J].Chinese J Catal,2005,26:769-774.
[23]Tan Wei,Liu Min,Zhao Yan,et al.Para-selective methylation of toluene with methanol over nano-sized ZSM-5 catalysts:Synergistic effects of surface modifications with Si O2,P2O5and Mg O[J].Micropor Mesopor Mater,2014,196:18-30.
[24]Wang G R.Catalyst and catalysis[M].Dalian:Dalian University of Technology Press,2015:104-110.
[25]Nunan J,Cronin J,Cunningham J.Comparison of the surface reactivity and spectroscopy of alkaline-earth-metal oxides[J].J Catal,1984,87:77-85.
[26]Zheng S,Tanaka H,Jentys A,et al.Novel model explaining teluene diffusion in HZSM-5 after surface modification[J].J Phys Chem B,2004,108:1337-1343.
[27]Ji Xiangfei,Qin Zhangfeng,Dong Mei,et al.Friedel-Crafts acylation of anisole and toluene with acetic anhydride over nano-sized Beta zeolites[J].Catal Lett,2007,117:171-177.
[28]Bj?rgen M,Joensen F,Spangsberg M Holm,et al.Methanol to gasoline over zeolite H-ZSM-5:Improved catalyst performance by treatment with Na OH[J].Appl Catal:A,2008,345,43-50.
[29]Xu Weiyin,Stephen J Miller,Pradeep K Agrawal,et al.Positive effect of water on zeolite BEA catalyzed alkylation of phenol with propylene[J].Catal Lett,2014,144:434-438.
[30]Hu Hualei,Lyu Jinghui,Rui Jiayao,et al.The effect of Si/Al ratio on the catalytic performance of hierarchical porous ZSM-5 for catalyzing benzene alkylation with methanol[J].Catal Sci Technol,2016,6:2647-2652.
[2]Lu Ping,Fei Zhaoyang,Li Lei,et al.Effects of controlled SiO2deposition and phosphorus and nickel doping on surface acidity and diffusivity of medium and small sized HZSM-5 for para-selective alkylation of toluene by methanol[J].Appl Catal A-Gen,2013,453:302-309.
[3]Wen Zhenhao,Yang Daqiang,Yang Fan,et al.Methylation of toluene with methanol over HZSM-5:A periodic density functional theory investigation[J].Chinese J Catal,2016,37:1882-1890.
[4]Hu Hualei,Lyu Jinghui,Wang Qingtao,et al.Alkylation of benzene with methanol over hierarchical porous ZSM-5:Synergy effects of hydrogen atmosphere and zinc modification[J].RSC Adv,2015,5:32679-32684.
[5]Zhu Zhirong,Chen Qingling,Xie Zaiku,et al.The roles of acidity and structure of zeolite for catalyzing toluene alkylation with methanol to xylene[J].Micropor Mesopor Mat,2006,88:16-21.
[6]Vos A M,Rozanska X,Schoonheydt R A,et al,A theoretical study of the alkylation reaction of toluene with methanol catalyzed by acidic mordenite[J].J Am Chem Soc,2001,123:2799-2809.
[7]Wang Qingtao,Han Wenwen,Hu Hualei,et al.Influence of the post-treatment of HZSM-5 zeolite on catalytic performance for alkylation of benzene with methanol[J].Chinese J Chem Eng,2017,25:1777-1783.
[8]Sanjeev M Rao,Erisa Sara9i,Roger Glser,et al.Coppens Surface barriers as dominant mechanism to transport limitations in hierarchically structured catalysts-Application to the zeolite-catalyzed alkylation of benzene with ethylene[J].Chem Eng J,2017,329:45-55.
[9]Zhang Wanshuo,Zhang Shuang,Xin Wenjie,et al.Shaped binderless ZSM-11 zeolite catalyst prepared via a dry-gel conversion method:Characterization and application for alkylation of benzene with dimethyl ether[J].J Energy Chem,2017,26:380-389.
[10]Jiang Jian,Lu Guanzhong,Miao Changxi,et al.Catalytic performance of X molecular sieve modified by alkali metal ions for the side-chain alkylation of toluene with methanol[J].Micropor Mesopor Mater,2013,167:213-220.
[11]Yashima T,Yamazaki K,Ahmad H,et al,Alkylation on synthetic zeolites:Ⅱ.Selectivity p-xylene formation[J].J Catal,1970,17:151-156.
[12]Wang Yanan,Gao Yang,Xie Sujuan,et al.Adjustment of the Al siting in MCM-22 zeolite and its effect on alkylationperformance of ethylene with benzene[J].Catal Today,2018,316:71-77.
[13]Shi Yanchun,Xing Enhui,Xie Wenhua,et al.Shape selectivity of beta and MCM-49 zeolites in liquid-phase alkylation of benzene with ethylene[J].J Mol Catal A-Chem,2016,418/419:86-94.
[14]Raj K J A,Malar E J P,Vijayaraghavan V R.Shape-selective reactions with AEL and AFI type molecular sieves alkylation of benzene,toluene and ethylbenzene with ethanol,2-propanol,methanol and t-butanol[J].J Mol Catal A-Chem,2006,243:99-105.
[15]马沛生.有机化合物实验物性数据手册[M].北京:化学工业出版社,2006:460-537.
[16]Svelle Stian,Visur Melina,Olsbye Unni,et al.Mechanistic aspects of the zeolite catalyzed methylation of alkenes and aromatics with methanol:A review[J].Top Catal,2011,54(15):897-906.
[17]Venuto P B,Landis P S.Organic catalysis over crystalline aluminosilieates[M].New York and London:Petroleum Chemical Press,1968:2-17.
[18]赵博,刘民,谭伟,等.硅磷镁改性对纳米HZSM-5催化苯和甲醇烷基化反应的影响[J].石油学报:石油加工,2013,29(4):605-611.
[19]Anderson J R,Foger K,Mole T.Reactions on ZSM-5-type zeolite catalysts[J].J Catal,1979,58:114-130.
[20]Chen Huanhui,Li Xiaoci,Zhao Guoqing,et al.Free radical mechanism investigation of the side-chain alkylation of toluene with methanol on basic zeolites X[J].Chinese J Catal.,2015,36:1726-1732.
[21]Liu Hui,Wei Huijuan,Xin Wenjie,et al.Differences between Zn/HZSM-5 and Zn/HZSM-11 zeolite catalysts in alkylation of benzene with dimethyl ether[J].J Energy Chem,2014,23:617-624.
[22]Li B,Chen H,Li S,et al.Distribution of Mo in Mo/ZSM-5 catalyst prepared by impregnation method[J].Chinese J Catal,2005,26:769-774.
[23]Tan Wei,Liu Min,Zhao Yan,et al.Para-selective methylation of toluene with methanol over nano-sized ZSM-5 catalysts:Synergistic effects of surface modifications with Si O2,P2O5and Mg O[J].Micropor Mesopor Mater,2014,196:18-30.
[24]Wang G R.Catalyst and catalysis[M].Dalian:Dalian University of Technology Press,2015:104-110.
[25]Nunan J,Cronin J,Cunningham J.Comparison of the surface reactivity and spectroscopy of alkaline-earth-metal oxides[J].J Catal,1984,87:77-85.
[26]Zheng S,Tanaka H,Jentys A,et al.Novel model explaining teluene diffusion in HZSM-5 after surface modification[J].J Phys Chem B,2004,108:1337-1343.
[27]Ji Xiangfei,Qin Zhangfeng,Dong Mei,et al.Friedel-Crafts acylation of anisole and toluene with acetic anhydride over nano-sized Beta zeolites[J].Catal Lett,2007,117:171-177.
[28]Bj?rgen M,Joensen F,Spangsberg M Holm,et al.Methanol to gasoline over zeolite H-ZSM-5:Improved catalyst performance by treatment with Na OH[J].Appl Catal:A,2008,345,43-50.
[29]Xu Weiyin,Stephen J Miller,Pradeep K Agrawal,et al.Positive effect of water on zeolite BEA catalyzed alkylation of phenol with propylene[J].Catal Lett,2014,144:434-438.
[30]Hu Hualei,Lyu Jinghui,Rui Jiayao,et al.The effect of Si/Al ratio on the catalytic performance of hierarchical porous ZSM-5 for catalyzing benzene alkylation with methanol[J].Catal Sci Technol,2016,6:2647-2652.