甲烷无氧直接制备芳烃研究进展
|
摘要
甲烷无氧直接制备芳烃和氢气是碳一化学与催化领域中一个极具挑战性的研究课题,具有碳原子利用率高、二氧化碳零排放、工艺流程短和绿色环保等优势,已经成为世界各国研究机构的重要研究方向。本研究基于作者课题组在甲烷无氧芳构化反应的研究工作,结合2013-2017年的相关文献,对目前甲烷无氧芳构化的研究现状进行综合评述。重点讨论甲烷无氧芳构化反应机理与积炭形成、催化剂改性及再生、膜反应器、非钼基催化剂体系等工作,并对甲烷无氧芳构化直接制备芳烃的未来前景进行了展望。
The direct,nonoxidative conversion of methane to aromatics and hydrogen is a challenging research topic in the field of C_1 chemistry due to the high carbon-atom utilization efficiency,zero CO_2 emissions and short process flow. In the present paper, the advance of methane dehydroaromatization( MDA) is reviewed based on the research works of our group and the pertinent literatures from 2013 to 2017. The reaction mechanism and coking formation for the MDA process,the catalyst modification and regeneration,the application of the membrane reactor,as well as the non-Mo-based catalyst system were considered, the future prospect was given for the MDA reaction.
The direct,nonoxidative conversion of methane to aromatics and hydrogen is a challenging research topic in the field of C_1 chemistry due to the high carbon-atom utilization efficiency,zero CO_2 emissions and short process flow. In the present paper, the advance of methane dehydroaromatization( MDA) is reviewed based on the research works of our group and the pertinent literatures from 2013 to 2017. The reaction mechanism and coking formation for the MDA process,the catalyst modification and regeneration,the application of the membrane reactor,as well as the non-Mo-based catalyst system were considered, the future prospect was given for the MDA reaction.
引文
[1]徐奕德,包信和,林励吾.甲烷直接催化脱氢转化为芳烃和氢新反应的研究[J].中国科学基金,2006,20(3):170-173.(XU Yi-de,BAO Xin-he,LIN Li-wu.Study on a new reaction:The direct conversion of methane to aromatics and hydrogen[J].Bull Natl Nat Sci Found Chin,2006,20(3):170-173.)
[2]WANG L S,TAO L X,XIE M S,XU G F,HUANG J S,XU Y D.Dehydrogenation and aromatization of methane under non-oxidizing conditions[J].Catal Lett,1993,21(1/2):35-41.
[3]ISMAGILOV Z R,MATUS E V,TSIKOZA L T.Direct conversion of methane on Mo/ZSM-5 catalysts to produce benzene and hydrogen:Achievements and perspectives[J].Energy Environ Sci,2008,1(5):526-541.
[4]SPIVEY J J,HUTCHINGS G.Catalytic aromatization of methane[J].Chem Soc Rev,2014,43(3):792-803.
[5]XU Y D,BAO X H,LIN L W.Direct conversion of methane under nonoxidative conditions[J].J Catal,2003,216(1/2):386-395.
[6]OLIVOS-SUAREZ A I,SZECSE NYI,HENSEN E J M,RUIZ-MARTINEZ J,PIDKO E A,GASCON J.Strategies for the direct catalytic valorization of methane using heterogeneous catalysis:Challenges and opportunities[J].ACS Catal,2016,6(5):2965-2981.
[7]SCHWACH P,PAN X L,BAO X H.Direct conversion of methane to value-added chemicals over heterogeneous catalysts:Challenges and prospects[J].Chem Rev,2017,177(13):8497-8520.
[8]MA S Q,GUO X G,ZHAO L X,SCOTT S,BAO X H.Recent progress in methane dehydroaromatization:From laboratory curiosities to promising technology[J].J Energy Chem,2013,22(1):1-20.
[9]MAJHI S,MOHANTY P,WANG H,PANT K K.Direct conversion of natural gas to higher hydrocarbons:A review[J].J Energy Chem,2013,22(4):543-554.
[10]魏飞,魏彤,黄河,骞伟中,汤效平.甲烷无氧芳构化研究进展及其工业应用前景[J].石油加工,2006,22(1):1-8.(WEI Fei,WEI Tong,HUANG He,QIAN Wei-zhong,TANG Xiao-ping.Development and industrial application analysis of methane dehydroaromatization[J].Acta Pet Sin(Pet Process Sect),2006,22(1):1-8.)
[11]SUN K,GINOSAR D,HE T,ZHANG Y,FAN M,CHEN R.Progress in nonoxidative dehydroaromatization of methane in the last 6 years[J].Ind Eng Chem Res,2018,57(6):1768-1789.
[12]姚本镇,陈瑾,刘殿华,房鼎业.甲烷无氧芳构化的热力学研究[J].化学世界,2007,10:594-597.(YAO Ben-zhen,CHEN Jin,LIU Dian-hua,FANG Ding-ye.Thermodynamic investigation on methane aromatization under nonoxidative condition[J].Chem World,2007,10:594-597.)
[13]王涛,刘志玲,张菊,张媛,张伟,卢永斌.甲烷无氧芳构化反应最新研究进展[J].天然气化工-C1化学与化工,2018,43(2):127-134.(WANG Tao,LIU Zhi-ling,ZHANG Ju,ZHANG Yuan,ZHANG Wei,LU Yong-bin.New advances in methane nonoxidative aromatization[J].Nat Gas Chem Ind,2018,43(2):127-134.)
[14]WANG D,LUNSFORD J,ROSYNEK M.Catalytic conversion of methane to benzene over Mo/ZSM-5[J].Top Catal,1996,3(3/4):289-297.
[15]GONALEZ I L,ORD R,ROVEZZI M,GLATZEL P,BOTCHWAY S W,WECKHUYSEN B M,BEALE A M.Molybdenum speciation and its impact on catalytic activity during methane dehydroaromatization in zeolite ZSM-5 as revealed by operando X-Ray methods[J].Angew Chem Int Ed,2016,55(17):5215-5219.
[16]VOLLMER I,LINDEN B,OULD-CHIKH S,AGUILAR-TAPIA A,YARULINA I,ABOU-HAMAD E,SNEIDER Y,SUAREZ A,HAZEM ANN J,KAPTEIJN F,GASCON J.On the dynamic nature of M o sites for methane dehydroaromatization[J].Chem Sci,2018,9(21):4801-4807.
[17]YIN F,LI M R,WANG G C.Periodic density functional theory analysis of direct methane conversion into ethylene and aromatic hydrocarbons catalyzed by M o4C2/ZSM-5[J].Phys Chem Chem Phys,2017,19(33):22243-22255.
[18]MA D,SHU Y Y,CHENG M J,XU Y D,BAO X H.On the induction period of methane aromatization over Mo-based catalysts[J].J Catal,2000,194(1):105-114.
[19]WECKHUYSEN B M,ROSYNEK M P,LUNSFORD J H.Characterization of surface carbon formed during the conversion of methane to benzene over M o/H-ZSM-5 catalysts[J].Catal Lett,1998,52(1/2):31-36.
[20]KOSINOV N,COUMANS F J A G,USLAMIN E A,WIJPKEMA A S G,MEZARI B,HENSEN E J M.Methane dehydroaromatization by M o/HZSM-5:M ono-or bifunctional catalysis[J].ACS Catal,2017,7(1):520-529.
[21]KOSINOV N,WIJPKEMA A S G,USLAMIN E,ROHLING R,COUMANS F J A G,MEZARI B,PARASTAEV A,PORYVAEV A S,FEDIN M V,PIDKO E A,HENSEN E J M.Confined carbon mediates dehydroaromatization of methane over M o/ZSM-5[J].Angew Chem Int Ed,2018,57(4):1016-1020.
[22]MA D,WANG D Z,SU L L,SHU Y Y,XU Y D,BAO X H.Carbonaceous deposition on Mo/HMCM-22 catalysts for methane aromatization:A TP technique investigation[J].J Catal,2002,208(2):260-269.
[23]LIU H M,SU L L,WANG H X,SHEN W J,BAO X H,XU Y D.The chemical nature of carbonaceous deposits and their role in methane dehydroaromatization on M o/M CM-22 catalysts[J].Appl Catal A:Gen,2002,236:263-280.
[24]TEMPELMAN C H L,HENSEN E J M.On the deactivation of Mo/HZSM-5 in the methane dehydroaromatization reaction[J].Appl Catal B:Environ,2015,176-177:731-739.
[25]SONG Y,XU Y B,SUZUKI Y,NAKAGOME H,ZHANG Z G.A clue to exploration of the pathway of coke formation on Mo/HZSM-5catalyst in the non-oxidative methane dehydroaromatization at 1073 K[J].Appl Catal A:Gen,2014,482:387-396.
[26]SONG Y,XU Y B,SUZUKI Y,NAKAGOME H,MA X X,ZHANG Z G.The distribution of coke formed over a multilayer Mo/HZSM-5 fixed bed in H2co-fed methane aromatization at 1073 K:Exploration of the coking pathw ay[J].J Catal,2015,330:261-272.
[27]XU Y B,SONG Y,SUZUKI Y,ZHANG Z G.Effect of superficial velocity on the coking behavior of a nanozeolite-based Mo/HZSM-5catalyst in the non-oxidative CH4dehydroaromatization at 1073 K[J].Catal Sci Technol,2013,3(10):2769-2777.
[28]赵珂珂,黄鑫,贾丽涛,侯博,李德宝.W掺杂对Mo/HZSM-5催化甲烷无氧芳构化性能的影响[J].燃料化学学报,2017,45(11):1384-1391.(ZHAO Ke-ke,HUANG Xin,JIA Li-tao,HOU Bo,LI De-bao.Effect of W addition on the catalytic properties of Mo/HZSM-5 catalyst in methane non-oxidative dehydroaromatization[J].J Fuel Chem Technol,2017,45(11):1384-1391.)
[29]胥月兵,陆江银,王吉德,张战国.Mo基分子筛催化剂及甲烷无氧芳构化[J].化学进展,2011,23(1):90-106.(XU Yue-bing,LU Jiang-yin,WANG Ji-de,ZHANG Zhan-guo.Mo-based zeolite catalysts and oxygen-free methane aromatization[J].Prog Chem,2011,23(1):90-106.)
[30]马记源,陆江银,袁钊,王春晓.Co改性Mo/HZSM-5催化剂的甲烷无氧芳构化催化性能研究[J].石油炼制与化工,2013,44(11):29-34.(MA Ji-yuan,LU Jiang-yin,YUAN Zhao,WANG Chun-xiao.Methane dehydroaromatization over cobalt modified Mo/HZSM-5 catalysis in absence of oxidants[J].Pet Process Petrochem,2013,44(11):29-34.)
[31]FILA V,BERNAUER M,BERNAUER B,SOBALIK Z.Effect of addition of a second metal in Mo/ZSM-5 catalyst for methane aromatization reaction under elevated pressures[J].Catal Today,2015,256:269-275.
[32]马记源,张航飞,尹金莲,周蓉,陆江银.Ni改性Mo-Co/HZSM-5催化剂在甲烷无氧芳构化中的研究[J].天然气化工(C1化学与化工),2016,41(2):19-24.(MA Ji-yuan,ZHANG Hang-fei,YIN Jin-lian,ZHOU Rong,LU Jiang-yin.Methane dehydroaromatization over Ni modified Mo-Co/HZSM-5 catalysts[J].Nat Gas Chem Ind,2016,41(2):19-24.)
[33]TSHABALALA T E,COVILLE N J,ANDERSON J A,SCURREL M S.Dehydroaromaticzation of methane over Sn-Pt modified Mo/HZSM-5 zeolite catalysts:Effect of preparation method[J].Appl Catal A:Gen,2015,503:218-226.
[34]TSHABALALA T E,COVILLE N J,SCURREL M S.Dehydroaromatization of methane over doped Pt/Mo/H-ZSM-5 zeolite catalysts:The promotional effect of tin[J].Appl Catal A:Gen,2014,485:238-244.
[35]ABDELSAYED V,SHEKHAWAT D,SMITH M W.Effect of Fe and Zn promoters on Mo/HZSM-5 catalyst for methane dehydroaromatization[J].Fuel,2015,139:401-410.
[36]CHENG X,YAN P,ZHANG X Z,YANG F,DAI C Y,LI D P,MA X X.Enhanced methane dehydroaromatization in the presence of CO2over Fe-and M g-modified M o/ZSM-5[J].M ol Catal,2017,437:114-120.
[37]DING W P,MEITZNER G D,IGLESIA E.The effects of silanation of external acid sites on the structure and catalytic behavior of Mo/HZSM 5[J].J Catal,2002,206(1):14-22.
[38]JIN Z H,SU L,QIN L,LIU Z C,WANG Y D,XIE Z K,WANG X Y.Methane dehydroaromatization by Mo-supported MFI-type zeolite w ith core-shell structure[J].Appl Catal A:Gen,2013,453:295-301.
[39]TEMPELMAN C H L,RODRIGUE V O D,ECK E R H,MAGUSIN P,HESEN E J M.Desilication and silylation of Mo/HZSM-5 for methane dehydroaromatization[J].M icroporous M esoporous M ater,2015,203:259-273.
[40]WU Y Q,LU Z,EMDADI L,OH S C,WANG J,LEI Y,CHEN H Y,TRAN D T,LEE I C,LIU D X.Tuning external surface of unitcell thick pillared M FI and M WW zeolites by atomic layer deposition and its consequences on acid-catalyzed reactions[J].J Catal,2016,337:177-187.
[41]CHU N B,WANG J Q,ZHANG Y,YANG J H,LU J M,YIN D H.Nestlike hollow hierarchical MCM-22 microspheres:Synthesis and exceptional catalytic properties[J].Chem M ater,2010,22(9):2757-2763.
[42]MARTINEZ A,PERIS E.Non-oxidative methane dehydroaromatization on Mo/HZSM-5 catalysts:Tuning the acidic and catalytic properties through partial exchange of zeolite protons w ith alkali and alkaline-earth cations[J].Appl Catal A:Gen,2016,515:32-44.
[43]TEMPELMAN C H L,PORTILLA M T,ARMERO M E M,MEZARI B,CALUWE N G R,MARTINEZ C,HENSEN E J M.One-pot synthesis of nano-crystalline M CM-22[J].M icroporous M esoporous M ater,2016,220:28-38.
[44]刘恒,阚秋斌.介孔材料为硅源合成多级孔Mo/H-IM-5催化剂及其在甲烷无氧芳构化反应中的应用[J].燃料化学学报,2016,44(11):1380-1387.(LIU Heng,KAN Qiu-bin.Synthesis of hierarchical Mo/H-IM-5 catalysts by using mesoporous material as the silica source and its application in methane non-oxidative aromatization[J].J Fuel Chem Technol,2016,44(11):1380-1387.)
[45]YANG J H,CHU J,WANG J Q,YIN D H,LU J M,ZHANG Y.Synthesis and catalytic performance of hierarchical MCM-22 zeolite aggregates w ith the assistance of carbon particles and fluoride ions[J].Chin J Catal,2014,35(1):49-57.
[46]HU J,WU S J,LIU H,DING H,LI Z F,GUAN J Q,KAN Q B.Effect of mesopore structure of TNU-9 on methane dehydroaromatization[J].RSC Adv,2014,4(51):26577-26584.
[47]ZHU P F,YANG G H,SUN J,FAN R G,ZHANG P P,YONEYAMA Y,TSUBAKI N.A hollow Mo/HZSM-5 zeolite capsule catalyst:Preparation and enhanced catalytic properties in methane dehydroaromatization[J].J M ater Chem A,2017,5(18):8599-8607.
[48]WU Y Q,EMDADI L,WANG Z P,FAN W,LIU D X.Textural and catalytic properties of Mo loaded hierarchical meso-/microporous lamellar M FI and M WW zeolites for direct methane conversion[J].Appl Catal A:Gen,2014,470:344-354.
[49]LIU H M,LI Y,SHEN W J,BAO X H,XU Y D.Methane dehydroaromatization over Mo/HZSM-5 catalysts in the absence of oxygen:Effects of silanation in HZSM-5 zeolite[J].Catal Today,2004,93/95:65-73.
[50]RAMIREZ J P,VERBOEKEND D,BONILLA A,ABELLO S.Hierarchical zeolite catalysts:Zeolite catalysts with tunable hierarchy factor by pore-grow th moderators[J].Adv Funct M ater,2009,19(24):3972-3979.
[51]WU Y Q,EMDADI L,OH S C,SAKBODIN M,LIU D X.Spatial distribution and catalytic performance of metal-acid sites in Mo/MFI catalysts w ith tunable meso-/microporous lamellar zeolite structures[J].J Catal,2015,323:100-111.
[52]WANG K,HUANG X,LI D B.Hollow ZSM-5 zeolite grass ball catalyst in methane dehydroaromatization:One-step synthesis and the exceptional catalytic performance[J].Appl Catal A:Gen,2018,556:10-19.
[53]KOSINOV N,COUMANS F J A G,LI G,USLAMIN E,MEZARI B,WIJPKEMA A S G,PIDKO E A,HENSEN E J M.Stable Mo/HZSM-5 methane dehydroaromatization catalysts optimized for high-temperature calcination-regeneration[J].J Catal,2017,346:125-133.
[54]GAO J,ZHENG Y T,JEHNG J M,TANG Y D,WACHS I E,PODKOLZIN S G.Identification of molybdenum oxide nanostructures on zeolites for natural gas conversion[J].Science,2015,348(6235):686-690.
[55]PORTILLA M T,LLOPIS F J,MARTINEZ C.Non-oxidative dehydroaromatization of methane:An effective reaction-regeneration cyclic operation for catalyst life extension[J].Catal Sci Technol,2015,5(7):3806-3821.
[56]KOSINOV N,COUMANS F J A G,ULSAMIN E,KAPTEIJIN F,HENSEN E J M.Selective coke combustion by oxygen pulsing during M o/ZSM-5-Catalyzed methane dehydroaromatization[J].Angew Chem Int Ed,2016,55(48):15086-15090.
[57]SUN C Y,FANG G Z,GUO X G,HU Y L,MA S Q,YANG T H,HAN J,MA H,TAN D L,BAO X H.Methane dehydroaromatization w ith periodic CH4-H2sw itch:A promising process for aromatics and hydrogen[J].J Energy Chem,2015,24(3):257-263.
[58]XU Y B,LU J Y,SUZUKI Y,ZHANG Z G,MA H T,YAMAMOTO Y.Performance of a binder-free,spherical-shaped Mo/HZSM-5catalyst in the non-oxidative CH4dehydroaromatization in fixed-and fluidized-bed reactors under periodic CH4-H2sw itch operation[J].Chem Eng Process:Process Intensif,2013,72:90-102.
[59]PEREZ-URESTI S,ADRIAN-MENDIOLA J,El-HALWAGI M.Techno-Economic assessment of benzene production from shale gas[J].Processes,2017,5(33):1-10.
[60]XU Y,WANG J,SUZUKI Y,ZHANG Z.Improving effect of Fe additive on the catalytic stability of Mo/HZSM-5 in the methane dehydroaromatization[J].Catal Today,2012,185(1):41-46.
[61]XU Y,LU J,WANG J,SUZUKI Y,ZHANG Z.The catalytic stability of Mo/HZSM-5 in methane dehydroaromatization at severe and periodic CH4-H2sw itch operating conditions[J].Chem Eng J,2011,168(1):390-402.
[62]XU Y,WANG J,SUZUKI Y,ZHANG Z.Effect of transition metal additives on the catalytic stability of Mo/HZSM-5 in the methane dehydroaromatization under periodic CH4-H2sw itch operation at 1073 K[J].Appl Catal A:Gen,2011,409/410:181-193.
[63]XU Y B,SUZUKI Y,ZHANG Z G.Comparison of the activity stabilities of nanosized and microsized zeolites based Fe-Mo/HZSM-5catalysts in the non-oxidative CH4 dehydroaromatization under periodic CH4-H2sw itching operation at 1073 K[J].Appl Catal A:Gen,2013,452:105-116.
[64]XU Y B,SONG Y,SUZUKI Y,ZHANG Z G.Mechanism of Fe additive improving the activity stability of microzeolite-based Mo/HZSM-5 catalyst in non-oxidative methane dehydroaromatization at 1073 K under periodic CH4-H2sw itching modes[J].Catal Sci Technol,2014,4(10):3644-3656.
[65]SONG Y,ZHANG Q,XU Y B,ZHANG Y,MATSUOKA K,ZHANG Z G.Coke accumulation and deactivation behavior of microzeolitebased M o/HZSM-5 in the nonoxidative methane aromatization under cyclic CH4-H2feed sw itch mode[J].Appl Catal A:Gen,2017,530:12-20.
[66]NATESAKHAWAT S,MEANS N C,HOWARD B H,ABDELSAYED V,BALTRUS J P,CHENG Y,LEKSE J W,LINK D,M ORREALE B D.Improved benzene production from methane dehydroaromatization over M o/HZSM-5 catalysts via hydrogen-permselective palladium membrane reactors[J].Catal Sci Technol,2015,5(11):5023-5036.
[67]XUE J,CHEN Y,WEI Y Y,FELDHOFF A,WANG H H,CARO J.Gas to liquids:Natural gas conversion to aromatic fuels and chemicals in a hydrogen-permeable ceramic hollow fiber membrane reactor[J].ACS Catal,2016,6(4):2448-2451.
[68]CAO Z W,JIANG H Q,LUO H X,BAUMANN S,MEULENBERG W A,ASSMANN J,MLECZKO L,LIU Y,CARO J.Natural gas to fuels and chemicals:Improved methane aromatization in an oxygen-permeable membrane reactor[J].Angew Chem Int Ed,2013,52(51):13794-13797.
[69]MOREJUDO S H,ZANON R,ESCOLASTICO S,YUSTE I,MALEROD H,VESTRE P K,COORS W G,MARTINEZ A,NORBY T,SERRA J M,KJOLSETH C.Direct conversion of methane to aromatics in a catalytic co-ionic membrane reactor[J].Science,2016,353(6299):563-566.
[70]ABDELSAYED V,SMITH M W,SHEKHAWAT D.Investigation of the stability of Zn-based HZSM-5 catalysts for methane dehydroaromatization[J].Appl Catal A:Gen,2015,505:365-374.
[71]GIM M Y,HAN S J,KANG T H,SONG J H,KIM T H,KIM D H,LEE K Y,SONG I K.Benzene,toluene,and xylene production by direct dehydroaromatization of methane over WOy/HZSM-5 catalysts[J].J Nanosci Nanotechnol,2017,17(11):8226-8231.
[72]TSHABALALA T E,COVILLE N J,SCURELL M S.Methane dehydroaromatization over modified Mn/H-ZSM-5 zeolite catalysts:Effect of tungsten as a secondary metal[J].Catal Commun,2016,78:37-43.
[73]DUTTA K,LI L,GUPTA P,GUTIERREZ D P,KOPYSCINSKI J.Direct non-oxidative methane aromatization over gallium nitride catalyst in a continuous flow reactor[J].Catal Commun,2018,106:16-19.
[74]TAN P L.Active phase,catalytic activity,and induction period of Fe/zeolite material in nonoxidative aromatization of methane[J].J Catal,2016,338:21-29.
[75]LAI Y,VESER G.The nature of the selective species in Fe-HZSM-5 for non-oxidative methane dehydroaromatization[J].Catal Sci Technol,2016,6(14):5440-5452.
[76]GUO X G,FANG G Z,LI G,MA H,FAN H J,YU L,MA C,WU X,DENG D H,WEI M M,TAN D L,SI R,ZHANG S,LI J Q,SUN L T,TANG Z C,PAN X L,BAO X H.Direct,nonoxidative conversion of methane to ethylene,aromatics,and hydrogen[J].Science,2014,344(6184):616-619.
[77]SAKBODIN M,WU Y Q,OH S C,WACHSMAN E D,LIU D X.Hydrogen-permeable tubular membrane reactor:Promoting conversion and product selectivity for non-oxidative activation of methane over an FeSi O2catalyst[J].Angew Chem Int Ed,2016,55(52):16149-16152.
[2]WANG L S,TAO L X,XIE M S,XU G F,HUANG J S,XU Y D.Dehydrogenation and aromatization of methane under non-oxidizing conditions[J].Catal Lett,1993,21(1/2):35-41.
[3]ISMAGILOV Z R,MATUS E V,TSIKOZA L T.Direct conversion of methane on Mo/ZSM-5 catalysts to produce benzene and hydrogen:Achievements and perspectives[J].Energy Environ Sci,2008,1(5):526-541.
[4]SPIVEY J J,HUTCHINGS G.Catalytic aromatization of methane[J].Chem Soc Rev,2014,43(3):792-803.
[5]XU Y D,BAO X H,LIN L W.Direct conversion of methane under nonoxidative conditions[J].J Catal,2003,216(1/2):386-395.
[6]OLIVOS-SUAREZ A I,SZECSE NYI,HENSEN E J M,RUIZ-MARTINEZ J,PIDKO E A,GASCON J.Strategies for the direct catalytic valorization of methane using heterogeneous catalysis:Challenges and opportunities[J].ACS Catal,2016,6(5):2965-2981.
[7]SCHWACH P,PAN X L,BAO X H.Direct conversion of methane to value-added chemicals over heterogeneous catalysts:Challenges and prospects[J].Chem Rev,2017,177(13):8497-8520.
[8]MA S Q,GUO X G,ZHAO L X,SCOTT S,BAO X H.Recent progress in methane dehydroaromatization:From laboratory curiosities to promising technology[J].J Energy Chem,2013,22(1):1-20.
[9]MAJHI S,MOHANTY P,WANG H,PANT K K.Direct conversion of natural gas to higher hydrocarbons:A review[J].J Energy Chem,2013,22(4):543-554.
[10]魏飞,魏彤,黄河,骞伟中,汤效平.甲烷无氧芳构化研究进展及其工业应用前景[J].石油加工,2006,22(1):1-8.(WEI Fei,WEI Tong,HUANG He,QIAN Wei-zhong,TANG Xiao-ping.Development and industrial application analysis of methane dehydroaromatization[J].Acta Pet Sin(Pet Process Sect),2006,22(1):1-8.)
[11]SUN K,GINOSAR D,HE T,ZHANG Y,FAN M,CHEN R.Progress in nonoxidative dehydroaromatization of methane in the last 6 years[J].Ind Eng Chem Res,2018,57(6):1768-1789.
[12]姚本镇,陈瑾,刘殿华,房鼎业.甲烷无氧芳构化的热力学研究[J].化学世界,2007,10:594-597.(YAO Ben-zhen,CHEN Jin,LIU Dian-hua,FANG Ding-ye.Thermodynamic investigation on methane aromatization under nonoxidative condition[J].Chem World,2007,10:594-597.)
[13]王涛,刘志玲,张菊,张媛,张伟,卢永斌.甲烷无氧芳构化反应最新研究进展[J].天然气化工-C1化学与化工,2018,43(2):127-134.(WANG Tao,LIU Zhi-ling,ZHANG Ju,ZHANG Yuan,ZHANG Wei,LU Yong-bin.New advances in methane nonoxidative aromatization[J].Nat Gas Chem Ind,2018,43(2):127-134.)
[14]WANG D,LUNSFORD J,ROSYNEK M.Catalytic conversion of methane to benzene over Mo/ZSM-5[J].Top Catal,1996,3(3/4):289-297.
[15]GONALEZ I L,ORD R,ROVEZZI M,GLATZEL P,BOTCHWAY S W,WECKHUYSEN B M,BEALE A M.Molybdenum speciation and its impact on catalytic activity during methane dehydroaromatization in zeolite ZSM-5 as revealed by operando X-Ray methods[J].Angew Chem Int Ed,2016,55(17):5215-5219.
[16]VOLLMER I,LINDEN B,OULD-CHIKH S,AGUILAR-TAPIA A,YARULINA I,ABOU-HAMAD E,SNEIDER Y,SUAREZ A,HAZEM ANN J,KAPTEIJN F,GASCON J.On the dynamic nature of M o sites for methane dehydroaromatization[J].Chem Sci,2018,9(21):4801-4807.
[17]YIN F,LI M R,WANG G C.Periodic density functional theory analysis of direct methane conversion into ethylene and aromatic hydrocarbons catalyzed by M o4C2/ZSM-5[J].Phys Chem Chem Phys,2017,19(33):22243-22255.
[18]MA D,SHU Y Y,CHENG M J,XU Y D,BAO X H.On the induction period of methane aromatization over Mo-based catalysts[J].J Catal,2000,194(1):105-114.
[19]WECKHUYSEN B M,ROSYNEK M P,LUNSFORD J H.Characterization of surface carbon formed during the conversion of methane to benzene over M o/H-ZSM-5 catalysts[J].Catal Lett,1998,52(1/2):31-36.
[20]KOSINOV N,COUMANS F J A G,USLAMIN E A,WIJPKEMA A S G,MEZARI B,HENSEN E J M.Methane dehydroaromatization by M o/HZSM-5:M ono-or bifunctional catalysis[J].ACS Catal,2017,7(1):520-529.
[21]KOSINOV N,WIJPKEMA A S G,USLAMIN E,ROHLING R,COUMANS F J A G,MEZARI B,PARASTAEV A,PORYVAEV A S,FEDIN M V,PIDKO E A,HENSEN E J M.Confined carbon mediates dehydroaromatization of methane over M o/ZSM-5[J].Angew Chem Int Ed,2018,57(4):1016-1020.
[22]MA D,WANG D Z,SU L L,SHU Y Y,XU Y D,BAO X H.Carbonaceous deposition on Mo/HMCM-22 catalysts for methane aromatization:A TP technique investigation[J].J Catal,2002,208(2):260-269.
[23]LIU H M,SU L L,WANG H X,SHEN W J,BAO X H,XU Y D.The chemical nature of carbonaceous deposits and their role in methane dehydroaromatization on M o/M CM-22 catalysts[J].Appl Catal A:Gen,2002,236:263-280.
[24]TEMPELMAN C H L,HENSEN E J M.On the deactivation of Mo/HZSM-5 in the methane dehydroaromatization reaction[J].Appl Catal B:Environ,2015,176-177:731-739.
[25]SONG Y,XU Y B,SUZUKI Y,NAKAGOME H,ZHANG Z G.A clue to exploration of the pathway of coke formation on Mo/HZSM-5catalyst in the non-oxidative methane dehydroaromatization at 1073 K[J].Appl Catal A:Gen,2014,482:387-396.
[26]SONG Y,XU Y B,SUZUKI Y,NAKAGOME H,MA X X,ZHANG Z G.The distribution of coke formed over a multilayer Mo/HZSM-5 fixed bed in H2co-fed methane aromatization at 1073 K:Exploration of the coking pathw ay[J].J Catal,2015,330:261-272.
[27]XU Y B,SONG Y,SUZUKI Y,ZHANG Z G.Effect of superficial velocity on the coking behavior of a nanozeolite-based Mo/HZSM-5catalyst in the non-oxidative CH4dehydroaromatization at 1073 K[J].Catal Sci Technol,2013,3(10):2769-2777.
[28]赵珂珂,黄鑫,贾丽涛,侯博,李德宝.W掺杂对Mo/HZSM-5催化甲烷无氧芳构化性能的影响[J].燃料化学学报,2017,45(11):1384-1391.(ZHAO Ke-ke,HUANG Xin,JIA Li-tao,HOU Bo,LI De-bao.Effect of W addition on the catalytic properties of Mo/HZSM-5 catalyst in methane non-oxidative dehydroaromatization[J].J Fuel Chem Technol,2017,45(11):1384-1391.)
[29]胥月兵,陆江银,王吉德,张战国.Mo基分子筛催化剂及甲烷无氧芳构化[J].化学进展,2011,23(1):90-106.(XU Yue-bing,LU Jiang-yin,WANG Ji-de,ZHANG Zhan-guo.Mo-based zeolite catalysts and oxygen-free methane aromatization[J].Prog Chem,2011,23(1):90-106.)
[30]马记源,陆江银,袁钊,王春晓.Co改性Mo/HZSM-5催化剂的甲烷无氧芳构化催化性能研究[J].石油炼制与化工,2013,44(11):29-34.(MA Ji-yuan,LU Jiang-yin,YUAN Zhao,WANG Chun-xiao.Methane dehydroaromatization over cobalt modified Mo/HZSM-5 catalysis in absence of oxidants[J].Pet Process Petrochem,2013,44(11):29-34.)
[31]FILA V,BERNAUER M,BERNAUER B,SOBALIK Z.Effect of addition of a second metal in Mo/ZSM-5 catalyst for methane aromatization reaction under elevated pressures[J].Catal Today,2015,256:269-275.
[32]马记源,张航飞,尹金莲,周蓉,陆江银.Ni改性Mo-Co/HZSM-5催化剂在甲烷无氧芳构化中的研究[J].天然气化工(C1化学与化工),2016,41(2):19-24.(MA Ji-yuan,ZHANG Hang-fei,YIN Jin-lian,ZHOU Rong,LU Jiang-yin.Methane dehydroaromatization over Ni modified Mo-Co/HZSM-5 catalysts[J].Nat Gas Chem Ind,2016,41(2):19-24.)
[33]TSHABALALA T E,COVILLE N J,ANDERSON J A,SCURREL M S.Dehydroaromaticzation of methane over Sn-Pt modified Mo/HZSM-5 zeolite catalysts:Effect of preparation method[J].Appl Catal A:Gen,2015,503:218-226.
[34]TSHABALALA T E,COVILLE N J,SCURREL M S.Dehydroaromatization of methane over doped Pt/Mo/H-ZSM-5 zeolite catalysts:The promotional effect of tin[J].Appl Catal A:Gen,2014,485:238-244.
[35]ABDELSAYED V,SHEKHAWAT D,SMITH M W.Effect of Fe and Zn promoters on Mo/HZSM-5 catalyst for methane dehydroaromatization[J].Fuel,2015,139:401-410.
[36]CHENG X,YAN P,ZHANG X Z,YANG F,DAI C Y,LI D P,MA X X.Enhanced methane dehydroaromatization in the presence of CO2over Fe-and M g-modified M o/ZSM-5[J].M ol Catal,2017,437:114-120.
[37]DING W P,MEITZNER G D,IGLESIA E.The effects of silanation of external acid sites on the structure and catalytic behavior of Mo/HZSM 5[J].J Catal,2002,206(1):14-22.
[38]JIN Z H,SU L,QIN L,LIU Z C,WANG Y D,XIE Z K,WANG X Y.Methane dehydroaromatization by Mo-supported MFI-type zeolite w ith core-shell structure[J].Appl Catal A:Gen,2013,453:295-301.
[39]TEMPELMAN C H L,RODRIGUE V O D,ECK E R H,MAGUSIN P,HESEN E J M.Desilication and silylation of Mo/HZSM-5 for methane dehydroaromatization[J].M icroporous M esoporous M ater,2015,203:259-273.
[40]WU Y Q,LU Z,EMDADI L,OH S C,WANG J,LEI Y,CHEN H Y,TRAN D T,LEE I C,LIU D X.Tuning external surface of unitcell thick pillared M FI and M WW zeolites by atomic layer deposition and its consequences on acid-catalyzed reactions[J].J Catal,2016,337:177-187.
[41]CHU N B,WANG J Q,ZHANG Y,YANG J H,LU J M,YIN D H.Nestlike hollow hierarchical MCM-22 microspheres:Synthesis and exceptional catalytic properties[J].Chem M ater,2010,22(9):2757-2763.
[42]MARTINEZ A,PERIS E.Non-oxidative methane dehydroaromatization on Mo/HZSM-5 catalysts:Tuning the acidic and catalytic properties through partial exchange of zeolite protons w ith alkali and alkaline-earth cations[J].Appl Catal A:Gen,2016,515:32-44.
[43]TEMPELMAN C H L,PORTILLA M T,ARMERO M E M,MEZARI B,CALUWE N G R,MARTINEZ C,HENSEN E J M.One-pot synthesis of nano-crystalline M CM-22[J].M icroporous M esoporous M ater,2016,220:28-38.
[44]刘恒,阚秋斌.介孔材料为硅源合成多级孔Mo/H-IM-5催化剂及其在甲烷无氧芳构化反应中的应用[J].燃料化学学报,2016,44(11):1380-1387.(LIU Heng,KAN Qiu-bin.Synthesis of hierarchical Mo/H-IM-5 catalysts by using mesoporous material as the silica source and its application in methane non-oxidative aromatization[J].J Fuel Chem Technol,2016,44(11):1380-1387.)
[45]YANG J H,CHU J,WANG J Q,YIN D H,LU J M,ZHANG Y.Synthesis and catalytic performance of hierarchical MCM-22 zeolite aggregates w ith the assistance of carbon particles and fluoride ions[J].Chin J Catal,2014,35(1):49-57.
[46]HU J,WU S J,LIU H,DING H,LI Z F,GUAN J Q,KAN Q B.Effect of mesopore structure of TNU-9 on methane dehydroaromatization[J].RSC Adv,2014,4(51):26577-26584.
[47]ZHU P F,YANG G H,SUN J,FAN R G,ZHANG P P,YONEYAMA Y,TSUBAKI N.A hollow Mo/HZSM-5 zeolite capsule catalyst:Preparation and enhanced catalytic properties in methane dehydroaromatization[J].J M ater Chem A,2017,5(18):8599-8607.
[48]WU Y Q,EMDADI L,WANG Z P,FAN W,LIU D X.Textural and catalytic properties of Mo loaded hierarchical meso-/microporous lamellar M FI and M WW zeolites for direct methane conversion[J].Appl Catal A:Gen,2014,470:344-354.
[49]LIU H M,LI Y,SHEN W J,BAO X H,XU Y D.Methane dehydroaromatization over Mo/HZSM-5 catalysts in the absence of oxygen:Effects of silanation in HZSM-5 zeolite[J].Catal Today,2004,93/95:65-73.
[50]RAMIREZ J P,VERBOEKEND D,BONILLA A,ABELLO S.Hierarchical zeolite catalysts:Zeolite catalysts with tunable hierarchy factor by pore-grow th moderators[J].Adv Funct M ater,2009,19(24):3972-3979.
[51]WU Y Q,EMDADI L,OH S C,SAKBODIN M,LIU D X.Spatial distribution and catalytic performance of metal-acid sites in Mo/MFI catalysts w ith tunable meso-/microporous lamellar zeolite structures[J].J Catal,2015,323:100-111.
[52]WANG K,HUANG X,LI D B.Hollow ZSM-5 zeolite grass ball catalyst in methane dehydroaromatization:One-step synthesis and the exceptional catalytic performance[J].Appl Catal A:Gen,2018,556:10-19.
[53]KOSINOV N,COUMANS F J A G,LI G,USLAMIN E,MEZARI B,WIJPKEMA A S G,PIDKO E A,HENSEN E J M.Stable Mo/HZSM-5 methane dehydroaromatization catalysts optimized for high-temperature calcination-regeneration[J].J Catal,2017,346:125-133.
[54]GAO J,ZHENG Y T,JEHNG J M,TANG Y D,WACHS I E,PODKOLZIN S G.Identification of molybdenum oxide nanostructures on zeolites for natural gas conversion[J].Science,2015,348(6235):686-690.
[55]PORTILLA M T,LLOPIS F J,MARTINEZ C.Non-oxidative dehydroaromatization of methane:An effective reaction-regeneration cyclic operation for catalyst life extension[J].Catal Sci Technol,2015,5(7):3806-3821.
[56]KOSINOV N,COUMANS F J A G,ULSAMIN E,KAPTEIJIN F,HENSEN E J M.Selective coke combustion by oxygen pulsing during M o/ZSM-5-Catalyzed methane dehydroaromatization[J].Angew Chem Int Ed,2016,55(48):15086-15090.
[57]SUN C Y,FANG G Z,GUO X G,HU Y L,MA S Q,YANG T H,HAN J,MA H,TAN D L,BAO X H.Methane dehydroaromatization w ith periodic CH4-H2sw itch:A promising process for aromatics and hydrogen[J].J Energy Chem,2015,24(3):257-263.
[58]XU Y B,LU J Y,SUZUKI Y,ZHANG Z G,MA H T,YAMAMOTO Y.Performance of a binder-free,spherical-shaped Mo/HZSM-5catalyst in the non-oxidative CH4dehydroaromatization in fixed-and fluidized-bed reactors under periodic CH4-H2sw itch operation[J].Chem Eng Process:Process Intensif,2013,72:90-102.
[59]PEREZ-URESTI S,ADRIAN-MENDIOLA J,El-HALWAGI M.Techno-Economic assessment of benzene production from shale gas[J].Processes,2017,5(33):1-10.
[60]XU Y,WANG J,SUZUKI Y,ZHANG Z.Improving effect of Fe additive on the catalytic stability of Mo/HZSM-5 in the methane dehydroaromatization[J].Catal Today,2012,185(1):41-46.
[61]XU Y,LU J,WANG J,SUZUKI Y,ZHANG Z.The catalytic stability of Mo/HZSM-5 in methane dehydroaromatization at severe and periodic CH4-H2sw itch operating conditions[J].Chem Eng J,2011,168(1):390-402.
[62]XU Y,WANG J,SUZUKI Y,ZHANG Z.Effect of transition metal additives on the catalytic stability of Mo/HZSM-5 in the methane dehydroaromatization under periodic CH4-H2sw itch operation at 1073 K[J].Appl Catal A:Gen,2011,409/410:181-193.
[63]XU Y B,SUZUKI Y,ZHANG Z G.Comparison of the activity stabilities of nanosized and microsized zeolites based Fe-Mo/HZSM-5catalysts in the non-oxidative CH4 dehydroaromatization under periodic CH4-H2sw itching operation at 1073 K[J].Appl Catal A:Gen,2013,452:105-116.
[64]XU Y B,SONG Y,SUZUKI Y,ZHANG Z G.Mechanism of Fe additive improving the activity stability of microzeolite-based Mo/HZSM-5 catalyst in non-oxidative methane dehydroaromatization at 1073 K under periodic CH4-H2sw itching modes[J].Catal Sci Technol,2014,4(10):3644-3656.
[65]SONG Y,ZHANG Q,XU Y B,ZHANG Y,MATSUOKA K,ZHANG Z G.Coke accumulation and deactivation behavior of microzeolitebased M o/HZSM-5 in the nonoxidative methane aromatization under cyclic CH4-H2feed sw itch mode[J].Appl Catal A:Gen,2017,530:12-20.
[66]NATESAKHAWAT S,MEANS N C,HOWARD B H,ABDELSAYED V,BALTRUS J P,CHENG Y,LEKSE J W,LINK D,M ORREALE B D.Improved benzene production from methane dehydroaromatization over M o/HZSM-5 catalysts via hydrogen-permselective palladium membrane reactors[J].Catal Sci Technol,2015,5(11):5023-5036.
[67]XUE J,CHEN Y,WEI Y Y,FELDHOFF A,WANG H H,CARO J.Gas to liquids:Natural gas conversion to aromatic fuels and chemicals in a hydrogen-permeable ceramic hollow fiber membrane reactor[J].ACS Catal,2016,6(4):2448-2451.
[68]CAO Z W,JIANG H Q,LUO H X,BAUMANN S,MEULENBERG W A,ASSMANN J,MLECZKO L,LIU Y,CARO J.Natural gas to fuels and chemicals:Improved methane aromatization in an oxygen-permeable membrane reactor[J].Angew Chem Int Ed,2013,52(51):13794-13797.
[69]MOREJUDO S H,ZANON R,ESCOLASTICO S,YUSTE I,MALEROD H,VESTRE P K,COORS W G,MARTINEZ A,NORBY T,SERRA J M,KJOLSETH C.Direct conversion of methane to aromatics in a catalytic co-ionic membrane reactor[J].Science,2016,353(6299):563-566.
[70]ABDELSAYED V,SMITH M W,SHEKHAWAT D.Investigation of the stability of Zn-based HZSM-5 catalysts for methane dehydroaromatization[J].Appl Catal A:Gen,2015,505:365-374.
[71]GIM M Y,HAN S J,KANG T H,SONG J H,KIM T H,KIM D H,LEE K Y,SONG I K.Benzene,toluene,and xylene production by direct dehydroaromatization of methane over WOy/HZSM-5 catalysts[J].J Nanosci Nanotechnol,2017,17(11):8226-8231.
[72]TSHABALALA T E,COVILLE N J,SCURELL M S.Methane dehydroaromatization over modified Mn/H-ZSM-5 zeolite catalysts:Effect of tungsten as a secondary metal[J].Catal Commun,2016,78:37-43.
[73]DUTTA K,LI L,GUPTA P,GUTIERREZ D P,KOPYSCINSKI J.Direct non-oxidative methane aromatization over gallium nitride catalyst in a continuous flow reactor[J].Catal Commun,2018,106:16-19.
[74]TAN P L.Active phase,catalytic activity,and induction period of Fe/zeolite material in nonoxidative aromatization of methane[J].J Catal,2016,338:21-29.
[75]LAI Y,VESER G.The nature of the selective species in Fe-HZSM-5 for non-oxidative methane dehydroaromatization[J].Catal Sci Technol,2016,6(14):5440-5452.
[76]GUO X G,FANG G Z,LI G,MA H,FAN H J,YU L,MA C,WU X,DENG D H,WEI M M,TAN D L,SI R,ZHANG S,LI J Q,SUN L T,TANG Z C,PAN X L,BAO X H.Direct,nonoxidative conversion of methane to ethylene,aromatics,and hydrogen[J].Science,2014,344(6184):616-619.
[77]SAKBODIN M,WU Y Q,OH S C,WACHSMAN E D,LIU D X.Hydrogen-permeable tubular membrane reactor:Promoting conversion and product selectivity for non-oxidative activation of methane over an FeSi O2catalyst[J].Angew Chem Int Ed,2016,55(52):16149-16152.