环己烷催化裂化反应化学研究进展
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摘要
详述了近年来国内外研究者在环己烷催化裂化转化途径及反应机理的探索中获得的研究成果,分析了不同催化剂和工艺条件对环己烷的转化规律的影响,对环己烷的转化途径进行总结,讨论了裂化、异构化、氢转移、脱氢和烷基化等环己烷在催化裂化中主要发生的几种反应的化学机理;列举了几种先进的表征手段和常见的研究方法,在现有研究的基础上对该领域未来的发展提出了展望。
Achievements of domestic and foreign researches on cyclohexane conversion and reaction mechanism of cyclohexane catalytic cracking are reviewed. The paper analyzes the effects of different catalysts and different process conditions on conversion rules of cyclohexane concludes the conversion approaches of cyclohexane,and discusses the mechanism of several reactions mainly occurring in catalytic cracking of cyclohexane,such as cracking,isomerization,hydrogen transfer,dehydrogenation and alkylation;Several characterization methods and research methods are exemplified. Based on the existing research,development prospect of the field is proposed.
Achievements of domestic and foreign researches on cyclohexane conversion and reaction mechanism of cyclohexane catalytic cracking are reviewed. The paper analyzes the effects of different catalysts and different process conditions on conversion rules of cyclohexane concludes the conversion approaches of cyclohexane,and discusses the mechanism of several reactions mainly occurring in catalytic cracking of cyclohexane,such as cracking,isomerization,hydrogen transfer,dehydrogenation and alkylation;Several characterization methods and research methods are exemplified. Based on the existing research,development prospect of the field is proposed.
引文
[1]许友好.催化裂化化学与工艺[M].北京:科学出版社,2013:491-522.
[2]陈俊武,许友好.催化裂化工艺与工程[M].北京:中国石化出版社,2015:564-576.
[3]祝馨怡,刘泽龙,田松柏,等.重馏分油烃类碳数分布的气相色谱-场电离飞行时间质谱测定[J].石油学报:石油加工,2012,28(3):426-431.
[4]Corma A,González-Alfaro V,Orchillés A V.Decalin and tetralin as probe molecules for cracking and hydrotreating the light cycle oil[J].J Catal,2001,200(1):34-44.
[5]Pujro R,Falco M,Sedran U.Production of aromatic compounds in the heavy naphtha and light cycle oil ranges:Catalytic cracking of aromatics and C10 naphthenic-aromatics[J].J Chem Technol Biotechnol,2016,91(2):336-345.
[6]Raichle A,Traa Y,Fuder F.Haag-dessau catalysts for ring opening of cycloalkanes.[J].Angew Chem,Int Ed,2001,40(7):1243-1246.
[7]赵景慧,韩静.环已烷在ZSM-5和Y型沸石催化剂上的裂化反应[J].石油炼制与化工,1992(3):24-28.
[8]Primo A,Garcia H.Zeolites as catalysts in oil refining[J].Chem Soc Rev,2014,43(22):7548-7561.
[9]袁帅,龙军,周涵,等.芳烃、环烷烃分子在MFI和FAU分子筛中扩散行为的分子模拟[J].石油学报:石油加工,2011,27(4):508-515.
[10]Abbot J.ChemInform abstract:Active sites and intermediates for isomerization and cracking of cyclohexane on HY[J].ChemInform,1990,123(2):383-395.
[11]Corma A,Agudo A L.Isomerization,dehydrogenation and cracking of methylcyclohexane over HNaY zeolites[J].React Kinet Catal Lett,1981,16(2/3):253-257.
[12]Izan S M,Triwahyono S,Jalil A A,et al.Additional Lewis acid sites of protonated fibrous silica@BEA zeolite(HSi@BEA)improving the generation of protonic acid sites in the isomerization of C6 alkane and cycloalkanes[J].Appl Catal,A,2018,570:228-237.
[13]Lin Longfei,Qiu Caifeng,Zhuo Zuoxi,et al.Acid strength controlled reaction pathways for the catalytic cracking of 1-butene to propene over ZSM-5[J].J Catal,2014,309:136-145.
[14]Lin L F,Zhang H F,Zhang D W.Acid strength controlled reaction pathways for the catalytic cracking of 1-pentene to propene over ZSM-5[J].ACS Catal,2015,5(7):4048-4059.
[15]Konno H,Tago T,Nakasaka Y,et al.Effectiveness of nano-scale ZSM-5 zeolite and its deactivation mechanism on catalytic cracking of representative hydrocarbons of naphtha[J].Microporous Mesoporous Mater,2013,175(13):25-33.
[16]Konno H,Ohnaka R,Jun-ichi N,et al.Kinetics of the catalytic cracking of naphtha over ZSM-5 zeolite:Effect of reduced crystal size on the reaction of naphthenes[J].Catal Sci Technol,2014,4(12),4265-4273.
[17]张瑞驰,李再婷.高温水热处理对HZSM-5催化剂择形裂化性能及氢转移性能的影响[J].石油炼制与化工,1992(9):12-17.
[18]Slagtern?se,Dahl I M,Jens K J,et al.Cracking of cyclohexane by high Si HZSM-5[J].Appl Catal,A,2010,375(2):213-221.
[19]唐津莲,许友好,汪燮卿.八氢菲在分子筛催化剂上的环烷环开环反应[J].石油学报:石油加工,2012,28(6):900-906.
[20]Ipatieff V N,Komarewsky V I.The action of aluminum chloride on benzene and cyclohexane[J].J Am Chem Soc,1934,56(9):1926-1928.
[21]Corma A,Planelles J,Sánchez-Marín J,et al.The role of different types of acid site in the cracking of alkanes on zeolite catalysts[J].J Catal,1985,93(1):30-37.
[22]Whitmore F C.Mechanism of the polymerization of olefins by acid catalysts[J].Ind Eng Chem,1934,26(1):94-95.
[23]Whitmore F C.Alkylation and related processes of modern petroleum practice[J].Chem Eng New Arch,1948(10):668-674.
[24]Olah G A.Stable carbocations.CXVⅢ.General concept and structure of carbocations based on differentiation of trivalent(classical)carbenium ions from three-center bound penta-of tetracoordinated(nonclassical)carbonium ions.Role of carbocations in electrophi[J].J Am Chem Soc,1972,94(3):808-820.
[25]Puente G D L,Sedran U.Conversion of methylcyclopentane on rare earth exchanged Y zeolite FCC catalysts[J].Appl Catal,A,1996,144(1):147-158.
[26]Rochettes B M D,Marcilly C,Gueguen C,et al.Kinetic study of hydrogen transfer of olefins under catalytic cracking conditions[J].Appl Catal,1990,58(1):35-52.
[27]Puente Gabriela de la,Sedran Ulises.Evaluation of hydrogen transfer in FCC catalysts.A new approach for cyclohexene as a test reactant[J].Chem Eng Sci,2000,55(4):759-765.
[28]白风宇,代振宇,魏晓丽,等.改善直馏石脑油催化裂解过程中环烷烃裂解选择性的研究[J].石油炼制与化工,2018,49(9):32-36.
[29]Qin Yucai,Mo Zuosheng,Yu Wenguang,et al.Adsorption behaviors of thiophene,benzene,and cyclohexene on FAUzeolites:Comparison of CeY obtained by liquid-,and solid-state ion exchange[J].Appl Surf Sci,2014,292:5-15.
[30]Ye L,Teixeira I,Lo B T W,et al.Spatial differentiation of Br?nsted acid sites by probe molecule in zeolite USY using synchrotron X-ray powder diffraction[J].Chem Commun,2017,53:9725-9728.
[31]Vogt E T C,Weckhuysen B M.Fluid catalytic cracking:Recent developments on the grand old lady of zeolite catalysis[J].Chem Soc Rev,2015,44(20):7342-7370.
[32]Haensel V,Ipatieff V N.Cracking cyclohexane thermal and catalytic decomposition at high pressures[J].Ind Eng Chem,1943,35(6):632-638.
[33]Potapenko O V,Doronin V P,Sorokina T P,et al.Astudy of intermolecular hydrogen transfer from naphthenes to 1-hexene over zeolite catalysts[J].Appl Catal,A,2016,516(25):153-159.
[34]Kubo K,Takahashi T,Iida H,et al.Reactivities of C6-8hydrocarbons and effect of coexistence of another hydrocarbon in cracking on H-ZSM-5 catalyst at high temperatures[J].Appl Catal,A,2014,482(12):370-376.
[35]Shimada I,Takizawa K,Fukunaga H,et al.Catalytic cracking of polycyclic aromatic hydrocarbons with hydrogen transfer reaction[J].Fuel,2015,161:207-214.
[36]唐津莲,许友好,汪燮卿.全氢菲在分子筛催化剂上的环烷环开环反应[J].石油学报:石油加工,2012,40(6):721-726.
[37]Pujro R,Falco M,Sedran U.Catalytic cracking of heavy aromatics and polycyclic aromatic hydrocarbons over fluidized catalytic cracking catalysts[J].Energy Fuels,2015,29(3):1543-1549.
[2]陈俊武,许友好.催化裂化工艺与工程[M].北京:中国石化出版社,2015:564-576.
[3]祝馨怡,刘泽龙,田松柏,等.重馏分油烃类碳数分布的气相色谱-场电离飞行时间质谱测定[J].石油学报:石油加工,2012,28(3):426-431.
[4]Corma A,González-Alfaro V,Orchillés A V.Decalin and tetralin as probe molecules for cracking and hydrotreating the light cycle oil[J].J Catal,2001,200(1):34-44.
[5]Pujro R,Falco M,Sedran U.Production of aromatic compounds in the heavy naphtha and light cycle oil ranges:Catalytic cracking of aromatics and C10 naphthenic-aromatics[J].J Chem Technol Biotechnol,2016,91(2):336-345.
[6]Raichle A,Traa Y,Fuder F.Haag-dessau catalysts for ring opening of cycloalkanes.[J].Angew Chem,Int Ed,2001,40(7):1243-1246.
[7]赵景慧,韩静.环已烷在ZSM-5和Y型沸石催化剂上的裂化反应[J].石油炼制与化工,1992(3):24-28.
[8]Primo A,Garcia H.Zeolites as catalysts in oil refining[J].Chem Soc Rev,2014,43(22):7548-7561.
[9]袁帅,龙军,周涵,等.芳烃、环烷烃分子在MFI和FAU分子筛中扩散行为的分子模拟[J].石油学报:石油加工,2011,27(4):508-515.
[10]Abbot J.ChemInform abstract:Active sites and intermediates for isomerization and cracking of cyclohexane on HY[J].ChemInform,1990,123(2):383-395.
[11]Corma A,Agudo A L.Isomerization,dehydrogenation and cracking of methylcyclohexane over HNaY zeolites[J].React Kinet Catal Lett,1981,16(2/3):253-257.
[12]Izan S M,Triwahyono S,Jalil A A,et al.Additional Lewis acid sites of protonated fibrous silica@BEA zeolite(HSi@BEA)improving the generation of protonic acid sites in the isomerization of C6 alkane and cycloalkanes[J].Appl Catal,A,2018,570:228-237.
[13]Lin Longfei,Qiu Caifeng,Zhuo Zuoxi,et al.Acid strength controlled reaction pathways for the catalytic cracking of 1-butene to propene over ZSM-5[J].J Catal,2014,309:136-145.
[14]Lin L F,Zhang H F,Zhang D W.Acid strength controlled reaction pathways for the catalytic cracking of 1-pentene to propene over ZSM-5[J].ACS Catal,2015,5(7):4048-4059.
[15]Konno H,Tago T,Nakasaka Y,et al.Effectiveness of nano-scale ZSM-5 zeolite and its deactivation mechanism on catalytic cracking of representative hydrocarbons of naphtha[J].Microporous Mesoporous Mater,2013,175(13):25-33.
[16]Konno H,Ohnaka R,Jun-ichi N,et al.Kinetics of the catalytic cracking of naphtha over ZSM-5 zeolite:Effect of reduced crystal size on the reaction of naphthenes[J].Catal Sci Technol,2014,4(12),4265-4273.
[17]张瑞驰,李再婷.高温水热处理对HZSM-5催化剂择形裂化性能及氢转移性能的影响[J].石油炼制与化工,1992(9):12-17.
[18]Slagtern?se,Dahl I M,Jens K J,et al.Cracking of cyclohexane by high Si HZSM-5[J].Appl Catal,A,2010,375(2):213-221.
[19]唐津莲,许友好,汪燮卿.八氢菲在分子筛催化剂上的环烷环开环反应[J].石油学报:石油加工,2012,28(6):900-906.
[20]Ipatieff V N,Komarewsky V I.The action of aluminum chloride on benzene and cyclohexane[J].J Am Chem Soc,1934,56(9):1926-1928.
[21]Corma A,Planelles J,Sánchez-Marín J,et al.The role of different types of acid site in the cracking of alkanes on zeolite catalysts[J].J Catal,1985,93(1):30-37.
[22]Whitmore F C.Mechanism of the polymerization of olefins by acid catalysts[J].Ind Eng Chem,1934,26(1):94-95.
[23]Whitmore F C.Alkylation and related processes of modern petroleum practice[J].Chem Eng New Arch,1948(10):668-674.
[24]Olah G A.Stable carbocations.CXVⅢ.General concept and structure of carbocations based on differentiation of trivalent(classical)carbenium ions from three-center bound penta-of tetracoordinated(nonclassical)carbonium ions.Role of carbocations in electrophi[J].J Am Chem Soc,1972,94(3):808-820.
[25]Puente G D L,Sedran U.Conversion of methylcyclopentane on rare earth exchanged Y zeolite FCC catalysts[J].Appl Catal,A,1996,144(1):147-158.
[26]Rochettes B M D,Marcilly C,Gueguen C,et al.Kinetic study of hydrogen transfer of olefins under catalytic cracking conditions[J].Appl Catal,1990,58(1):35-52.
[27]Puente Gabriela de la,Sedran Ulises.Evaluation of hydrogen transfer in FCC catalysts.A new approach for cyclohexene as a test reactant[J].Chem Eng Sci,2000,55(4):759-765.
[28]白风宇,代振宇,魏晓丽,等.改善直馏石脑油催化裂解过程中环烷烃裂解选择性的研究[J].石油炼制与化工,2018,49(9):32-36.
[29]Qin Yucai,Mo Zuosheng,Yu Wenguang,et al.Adsorption behaviors of thiophene,benzene,and cyclohexene on FAUzeolites:Comparison of CeY obtained by liquid-,and solid-state ion exchange[J].Appl Surf Sci,2014,292:5-15.
[30]Ye L,Teixeira I,Lo B T W,et al.Spatial differentiation of Br?nsted acid sites by probe molecule in zeolite USY using synchrotron X-ray powder diffraction[J].Chem Commun,2017,53:9725-9728.
[31]Vogt E T C,Weckhuysen B M.Fluid catalytic cracking:Recent developments on the grand old lady of zeolite catalysis[J].Chem Soc Rev,2015,44(20):7342-7370.
[32]Haensel V,Ipatieff V N.Cracking cyclohexane thermal and catalytic decomposition at high pressures[J].Ind Eng Chem,1943,35(6):632-638.
[33]Potapenko O V,Doronin V P,Sorokina T P,et al.Astudy of intermolecular hydrogen transfer from naphthenes to 1-hexene over zeolite catalysts[J].Appl Catal,A,2016,516(25):153-159.
[34]Kubo K,Takahashi T,Iida H,et al.Reactivities of C6-8hydrocarbons and effect of coexistence of another hydrocarbon in cracking on H-ZSM-5 catalyst at high temperatures[J].Appl Catal,A,2014,482(12):370-376.
[35]Shimada I,Takizawa K,Fukunaga H,et al.Catalytic cracking of polycyclic aromatic hydrocarbons with hydrogen transfer reaction[J].Fuel,2015,161:207-214.
[36]唐津莲,许友好,汪燮卿.全氢菲在分子筛催化剂上的环烷环开环反应[J].石油学报:石油加工,2012,40(6):721-726.
[37]Pujro R,Falco M,Sedran U.Catalytic cracking of heavy aromatics and polycyclic aromatic hydrocarbons over fluidized catalytic cracking catalysts[J].Energy Fuels,2015,29(3):1543-1549.