Citation: | CHEN Qiang-qiang, GUO Yu, WU Hong-mei. Preparation of modified β zeolite with phosphorus for catalytic alkylation of C9 aromatics with propylene[J]. Journal of Fuel Chemistry and Technology, 2022, 50(1): 98-108. doi: 10.19906/j.cnki.JFCT.2021074 |
[1] |
卢暄. 从催化重整副产C9芳烃分离制取偏三甲苯、均三甲苯技术[J]. 化学工业,2010,28(12):30−33. doi: 10.3969/j.issn.1673-9647.2010.12.007
LU Xuan. Technological advance on comprehensive utilization of C9 heavy aromatics[J]. Chem Ind,2010,28(12):30−33. doi: 10.3969/j.issn.1673-9647.2010.12.007
|
[2] |
肖文, 周大军. 重整C9芳烃中提取高纯度均三甲苯的实验研究[J]. 石油学报(石油加工),2010,26(S1):93−97.
XIAO Wen, ZHOU Da-jun. Experimental study on manufacturing high purity mesitylene from C9 arene cut of reforming[J]. Acta Pet Sin (Pet Process Sect),2010,26(S1):93−97.
|
[3] |
刘杰, 刘岗. C9芳烃催化烷基化法生产高纯度均三甲苯过程与技术改造[J]. 化工技术与开发,2004,33(6):48−49+42. doi: 10.3969/j.issn.1671-9905.2004.06.015
LIU Jie, LIU Gang. Manufacture of high purity mesitylene from C9 aromatics mixture[J]. Technol Dev Chem Ind,2004,33(6):48−49+42. doi: 10.3969/j.issn.1671-9905.2004.06.015
|
[4] |
刘键, 刘恒源, 谭斌, 李平, 徐建鸿. 芳烃长链烷基化催化工艺研究进展[J]. 化工进展,2020,39(5):1744−1755.
LIU Jian, LIU Heng-yuan, TAN Bin, LI Ping, XU Jian-hong. Research progress in long chain catalytic alkylation of aromatic hydrocarbons[J]. Chem Ind Eng Prog (China),2020,39(5):1744−1755.
|
[5] |
郭文迪, 刘植昌, 黄崇品, 李强. 离子液体催化三甲苯烷基化反应提纯均三甲苯的研究[C]//第九届全国化学工艺学术年会论文集. 北京: 中国石化出版社, 2005: 1078–1083.
GUO Wen-di, LIU Zhi-chang, HUANG Chong-pin, LI Qiang. Separation 1,3,5-trimethylbenzene through alkylation catalyzed by ionic liquid[C]//Proceedings of the 9th National Chemical Technology Annual Conference. Beijing: China Petrochemical Press, 2005: 1078–1083.
|
[6] |
陈伴生, 周钰明, 张一卫. 用于烷基化C9芳烃分离制备均三甲苯的磷钨酸/高岭土催化剂的研究[J]. 石油炼制与化工,2006,37(4):28−31. doi: 10.3969/j.issn.1005-2399.2006.04.007
CHEN Ban-sheng, ZHOU Yu-ming, ZHANG Yi-wei. Study on kaolin supported phosphor-tungstic acid catalyst for mesitylene preparation by alkylation of C9 aromatics[J]. Pet Ref Chem Ind,2006,37(4):28−31. doi: 10.3969/j.issn.1005-2399.2006.04.007
|
[7] |
高滋, 何鸣元, 戴逸云. 沸石催化与分离技术[M]. 北京: 中国石化出版社, 1999: 295–306.
GAO Zi, HE Ming-yuan, DAI Yi-yun. Catalytic Separation of Zeolite[M]. Beijing: China Petrochemical Press, 1999: 295–306.
|
[8] |
王闻年, 袁德林, 李浩, 任申勇, 郭巧霞, 申宝剑. β沸石结构及其催化性能的调控[J]. 化工学报,2016,67(8):3429−3435.
WANG Wen-nian, YUAN De-lin, LI Hao, REN Shen-yong, GUO Qiao-xia, SHEN Bao-jian. Regulation of structure and catalytic performance of β-zeolite by post treatments[J]. CIESC J,2016,67(8):3429−3435.
|
[9] |
BAI G, DOU H, QIU M, FAN X, FEI H, NIU L, MA Z. Friedel-Crafts hydroxyalkylation of anisole over oxalic acid modified Hβ zeolite[J]. Catal Lett,2010,138(3/4):187−192. doi: 10.1007/s10562-010-0387-z
|
[10] |
BELLUSSI G, PAZZUEONI G, PEREGO C, GIROTTI G, TERZONI G. Liquid phase alkylation of benzene with light olefins catalyzed by β-zeolites[J]. J Catal,1995,157:227−234. doi: 10.1006/jcat.1995.1283
|
[11] |
陈强强, 李杰. β沸石在C9芳烃烷基化提取均三甲苯中的催化性能[J]. 精细石油化工,2010,27(1):12−16. doi: 10.3969/j.issn.1003-9384.2010.01.004
CHEN Qiang-qiang, LI Jie. Catalytic performance of β zeolite on extraction of mesitylene from C9 aromatics alkylation[J]. Spec Petrochem,2010,27(1):12−16. doi: 10.3969/j.issn.1003-9384.2010.01.004
|
[12] |
杨平, 潘履让, 李赫咺. β沸石的酸性和苯-丙烯烷基化反应的研究[J]. 燃料化学学报,1990,18(1):16−23.
YANG Ping, PAN Lu-rang, LI He-xuan. Study of the acidity of β zeolite and the alkylation of benzene with propene[J]. J Fuel Chem Technol,1990,18(1):16−23.
|
[13] |
WANG H L, XIN W Y. Surface acidity of H-beta and its catalytic activity for alkylation of benzene with propylene[J]. Catal Lett,2001,76(3):225−229.
|
[14] |
RÖGER H P, MÖLLER K P, O'CONNOR C T. The transformation of 1,2,4-trimethylbenzene A probe reaction to monitor external surface modifications of HZSM-5?[J]. Microporous Mater,1997,8(3/4):151−157.
|
[15] |
谢在库, 陈庆龄, 张成芳, 刘红星, 陆贤. Hβ沸石上甲苯歧化和C9芳烃烷基转移反应[J]. 华东理工大学学报,2000,21(1):47−51.
XIE Zai-ku, CHEN Qing-ling, ZHANG Cheng-fang, LIU Hong-xing, LU Xian. Disproportionation of Toluene and Transalkylation of C9 Aromatics over Hβ Zeolite[J]. J East China Univ Sci Technol,2000,21(1):47−51.
|
[16] |
ČEJKA J, KOTRLA J, KREJČÍ A. Disproportionation of trimethyl benzenes over large pore zeolites: Catalytic and adsorption study[J]. Appl Catal A: Gen,2004,277(1):191−199.
|
[17] |
刘海燕, 施维, 任冬梅, 李平, 孙闻东. β沸石分子筛固体酸的制备及其在异丁烷和丁烯烷基化反应中的应用[J]. 分子科学学报,2005,21(3):29−35. doi: 10.3969/j.issn.1000-9035.2005.03.007
LIU Hai-yan, SHI Wei, REN Dong-mei, LI Ping, SUN Wen-dong. Hydrothermal synthesis of zeolite and its application in isobutane/butene alkylation[J]. J Mol Sci,2005,21(3):29−35. doi: 10.3969/j.issn.1000-9035.2005.03.007
|
[18] |
宋祥梅, 李英霞, 陈标华, 李成岳. 磷改性β分子筛的酸性及其苯与丙烯烷基化催化性能[J]. 石油化工高等学校学报,2004,17(4):34−37. doi: 10.3969/j.issn.1006-396X.2004.04.010
SONG Xiang-mei, LI Ying-xia, CHEN Biao-hua, LI Cheng-yue. Acidity and catalytic properties for benzene alkylation with propylene of β zeolite modified with phosphorus[J]. J Petrochem Univ,2004,17(4):34−37. doi: 10.3969/j.issn.1006-396X.2004.04.010
|
[19] |
晁会霞, 罗祥生, 张凤美. 高低温磷改性β分子筛及其烷基化反应性能研究[J]. 石油炼制与化工,2017,48(4):83−86. doi: 10.3969/j.issn.1005-2399.2017.04.018
CHAO Hui-xia, LUO Xiang-sheng, ZHANG Feng-mei. Alkylation of benzene with ethylene catalyzed by zeolite beta modified by phosphorus at normal and high temperature[J]. Pet Ref Chem Ind,2017,48(4):83−86. doi: 10.3969/j.issn.1005-2399.2017.04.018
|
[20] |
王园园, 宋华, 孙兴龙, 苑丹丹, 王雪芹. Hβ分子筛的磷改性及其催化甲苯和叔丁醇烷基化反应性能[J]. 东北石油大学学报,2020,44(4):85−90. doi: 10.3969/j.issn.2095-4107.2020.04.012
WANG Yuan-yuan, SONG Hua, SUN Xing-long, YUAN Dan-dan, WANG Xue-qin. Phosphprus modified Hβ zeolites and the catalytic perpormance for alkylation of toluene with tert-butyl alcohol[J]. J Northeast Pet Univ,2020,44(4):85−90. doi: 10.3969/j.issn.2095-4107.2020.04.012
|
[21] |
TREACY M M J, HIGGINS J B. Collection of Simulated XRD Powder Patterns for Zeolites[M]. 5nd ed. Oxford, UK: Elsevier Science, 2007: 82–83.
|
[22] |
XIONG Y, CHEN W, ZENG A. Optimization for catalytic performances of Hβ zeolite in the acylation of 2-methylfuran by surface modification and solvents effect[J]. Res Chem Intermed,2017,43(3):1557−1574. doi: 10.1007/s11164-016-2715-4
|
[23] |
赵培侠, 刘靖, 张春勇. 铵盐改性对β分子筛的酸性及其催化二异丙苯异构化反应性能的影响[J]. 石油化工,2005,34(6):527−531. doi: 10.3321/j.issn:1000-8144.2005.06.005
ZHAO Pei-xia, LIU Jing, ZANG Chun-yong. Effects of ammonium salts modification on acidity of β molecular sieve and its catalytic performances in diisopropylbenzene isomerization[J]. Chin Petrochem Technol,2005,34(6):527−531. doi: 10.3321/j.issn:1000-8144.2005.06.005
|
[24] |
杨春, 须沁华. β沸石中铝的状态及归属[J]. 物理化学学报,1998,14(2):169−173. doi: 10.3866/PKU.WHXB19980214
YANG Chun, XU Qin-hua. States and assignment of aluminium in zeolite β[J]. Acta Phys-Chim Sin,1998,14(2):169−173. doi: 10.3866/PKU.WHXB19980214
|
[25] |
谢在库, 陈庆龄, 张成芳, 包佳青, 曹玉华, 杨一青. Hβ沸石表面酸性质的研究[J]. 催化学报,2000,21(1):47−51. doi: 10.3321/j.issn:0253-9837.2000.01.014
XIE Zai-ku, CHEN Qing-ling, ZHANG Cheng-fang, BAO Jia-qing, CAO Yu-hua, YANG Yi-qing. Study on the surface acid properties of Hβ zeolite[J]. Chin J Catal,2000,21(1):47−51. doi: 10.3321/j.issn:0253-9837.2000.01.014
|
[26] |
DING J, WANG M, PENG L, XUE N H, WANG Y M, HE M Y. Combined desilication and phosphorus modification for high-silica ZSM-5 zeolite with related study of hydrocarbon cracking performance[J]. Appl Catal A: Gen,2015,503:147−155. doi: 10.1016/j.apcata.2015.07.011
|
[27] |
宋守强, 李黎声, 李明罡, 张凤美, 舒兴田. H-SAPO-34分子筛磷改性机理及作用[J]. 石油学报(石油加工),2014,30(3):398−407.
SONG Shou-qiang, LI Li-sheng, LI Ming-gang, ZHANG Feng-mei, SHU Xing-tian. Effect and mechanism of phosphorus modification on H-SAPO-34 molecular sieves[J]. Acta Pet Sin (Pet Process Sect),2014,30(3):398−407.
|
[28] |
JANSSEN A H, KOSTER A J, DE JONG K P. Three-dimensional transmission electron microscopic observations of mesopores in dealuminated zeolite Y[J]. Angew Chem Int Ed,2001,40(6):1102−1104. doi: 10.1002/1521-3773(20010316)40:6<1102::AID-ANIE11020>3.0.CO;2-6
|
[29] |
王成强, 欧阳颖, 罗一斌. 脱除模板剂前后磷改性对β分子筛稳定性的影响[J]. 石油学报(石油加工),2018,34(6):1211−1216.
WANG Cheng-qiang, OUYANG Ying, LUO Yi-bin. Effects of phosphorus modification on the stability of β zeolite with and without template removal[J]. Acta Pet Sin (Pet Process Sect),2018,34(6):1211−1216.
|
[30] |
LIU J X, HE N, LIU C Y, WANG G R, XIN Q, GUO H C. Engineering the porosity and acidity of H-Beta zeolite by dealumination for the production of 2-ethylanthraquinone via 2-(4′-ethylbenzoyl)benzoic acid dehydration[J]. RSC Adv,2018,8(18):9731−9740. doi: 10.1039/C7RA13576A
|
[31] |
魏强, 周亚松, 黄梅梅, 张涛, 王燕. 磷改性Y型分子筛的合成与表征[J]. 石油学报(石油加工),2011,27(2):275−279.
WEI Qiang, ZHOU Ya-song, HUANG Mei-mei, ZHANG Tao, WANG Yan. Synthesis and characterization of phosphorous modified Y zeolite[J]. Acta Pet Sin (Pet Process Sect),2011,27(2):275−279.
|
[32] |
李曼尼, 吴瑞凤, 张景林. 磷改性斜发沸石的组成和结构表征[J]. 石油化工,2002,31(8):656−661. doi: 10.3321/j.issn:1000-8144.2002.08.015
LI Man-ni, WU Rui-feng, ZHANG Jing-lin. Composition and structure characterization of phosphorus–modified clinoptilolite[J]. Chin Petrochem Technol,2002,31(8):656−661. doi: 10.3321/j.issn:1000-8144.2002.08.015
|
[33] |
邓德斌, 马丽景, 刘秀英, 李宣文. β沸石骨架铝化改性的红外光谱[J]. 物理化学学报,2000,16(2):162−165. doi: 10.3866/PKU.WHXB20000212
DENG De-bin, MA Li-jing, LIU Xiu-ying, Li Xuan-wen. Study of the Realumination of H zeolite framework by infrared spectroscopy[J]. Acta Phys Chim Sin,2000,16(2):162−165. doi: 10.3866/PKU.WHXB20000212
|
[34] |
张建业, 李宣文, 刘兴云. β沸石骨架稳定性与表面酸性的红外光谱研究[J]. 物理化学学报,1999,15(12):37−42.
ZHANG Jian-ye, LI Xuan-wen, LIU Xingyun. Study on the framework stability and surface acidity of Hβ zeolite by infrared spectroscopy[J]. Acta Phys Chim Sin,1999,15(12):37−42.
|
[35] |
惠宇, 刘金玲, 秦玉才, 孙兆林, 宋丽娟. 柠檬酸改性Hβ分子筛酸性中心的调变与解析[J]. 石油化工高等学校学报,2020,33(3):14−20. doi: 10.3969/j.issn.1006-396X.2020.03.003
HUI Yu, LIU Jin-ling, QIN Yu-cai, SUN Zhao-lin, SONG Li-juan. Discrimination and regulation of the acidic sites of Hβ zeolite with citric acid treatment[J]. J Petrochem Univ,2020,33(3):14−20. doi: 10.3969/j.issn.1006-396X.2020.03.003
|
[36] |
MITRAN G, CHEN S J, Dolge K L, HUANG W Y, SEO D K. Ketonic decarboxylation and esterification of propionic acid over beta zeolites[J]. Microporous Mesoporous Mater,2021,310.
|
[37] |
SING K S W, EVERETT D H, HAUL R A W, MOSCOU L, PIEROTTI R A, ROUQUEROL J, SIEMIENIEWSKA T. Reporting physisorption data for gas/solid systems with special reference to determination of surface area and porosity[J]. Pure Appl Chem,1985,57(4):603−619. doi: 10.1351/pac198557040603
|
[38] |
YANG L J, SONG Z Y, YU Y M, L J, XIA D H. Bimetallic bifunctional Pt-NiP/Hβ as a novel and highly efcient catalyst for n-hexane isomerization[J]. Catal Surv from Asia,2020,24(2):104−114. doi: 10.1007/s10563-020-09295-4
|
[39] |
孔德存, 施力, 王昕, 孟璇, 刘乃旺. 氟化铵改性USY分子筛及催化脱烯烃反应的研究[J]. 石油炼制与化工,2020,51(6):6−12. doi: 10.3969/j.issn.1005-2399.2020.06.002
KONG De-cun, SHI Li, WANG Xin, MENG Xuan, LIU Nai-wang. Study of USY molecular sieve modified by ammonium fluoride and its catalytic deolefin performance[J]. Pet Ref Chem Ind,2020,51(6):6−12. doi: 10.3969/j.issn.1005-2399.2020.06.002
|
[40] |
苏炜, 韩娜, 陈政利, 沈健, 王雷, 刘姝, 杨丽娜. Hβ分子筛改性及其催化苯和氯化苄反应性能[J]. 石油学报(石油加工),2020,36(1):38−44.
SU Wei, HAN Na, CHEN Zheng-li, SHEN Jian, WANG Lei, LIU Shu, YANG Li-na. Modification of Hβ molecular sieve and its catalytic performance in benzylation[J]. Acta Pet Sin (Pet Process Sect),2020,36(1):38−44.
|
[41] |
陈尚斌, 朱炎铭, 王红岩, 刘洪林, 魏伟, 方俊华. 川南龙马溪组页岩气储层纳米孔隙结构特征及其成藏意义[J]. 煤炭学报,2012,37(3):438−444.
CHEN Shang-bin, ZHU Yan-ming, WANG Hong-yan, LIU Hong-lin, WEI Wei, FANG Jun-hua. Structure characteristics and accumulation significance of nanopores in Longmaxi shale gas reservoir in the southern Sichuan Basin[J]. J China Coal Soc,2012,37(3):438−444.
|
[42] |
赵尹, 王海彦, 魏民, 马骏. 磷改性β沸石催化剂上催化裂化轻汽油的醚化[J]. 燃料化学学报,2004,32(2):225−229. doi: 10.3969/j.issn.0253-2409.2004.02.020
ZHAO Yin, WANG Hai-yan, WEI Min, MA Jun. Etherification of FCC light gasoline over P-loaded zeolite β catalyst[J]. J Fuel Chem Technol,2004,32(2):225−229. doi: 10.3969/j.issn.0253-2409.2004.02.020
|
[43] |
沈志虹, 潘惠芳, 徐春生, 赵业文, 邹晓风. 磷对烃类催化裂化催化剂表面酸性及抗碳性能的影响[J]. 石油大学学报(自然科学版),1994,18(2):86−89.
SHEN Zhi-hong, PAN Hui-fang, XU Chun-sheng, ZHAO Ye-wen, ZOU Xiao-feng. Effect of phosphate on the acidity and coking of hydrocarbon catalyst[J]. J China Univ Pet: Nat Sci,1994,18(2):86−89.
|
[44] |
WEI Z H, XIA T F, LIU M H, CAO Q S, XU Y R, ZHU K K, ZHU X D. Alkaline modification of ZSM-5 catalysts for methanol aromatization: The effect of the alkaline concentration[J]. Front Chem Sci Eng,2015,9(4):450−460. doi: 10.1007/s11705-015-1542-2
|
[45] |
EMEIS C A. Determination of integrated molar extinction coefficients for infrared absorption bands of pyridine adsorbed on solid acid catalysts[J]. J Catal,1993,141:347−354. doi: 10.1006/jcat.1993.1145
|
[46] |
程晓晶, 王祥生. C9芳烃在不同结构分子筛催化剂上的反应[J]. 石油化工,2013,42(1):24−29. doi: 10.3969/j.issn.1000-8144.2013.01.005
CHENG Xiao-jing, WANG Xiang-sheng. Reactions of C9 aromatics over zeolite catalysts with different structures[J]. Chin Petrochem Technol,2013,42(1):24−29. doi: 10.3969/j.issn.1000-8144.2013.01.005
|
[47] |
刘红星, 谢在库, 张成芳, 陈庆龄. 甲苯歧化与三甲苯烷基转移反应体系的化学平衡[J]. 石油化工,2003,32(1):28−32. doi: 10.3321/j.issn:1000-8144.2003.01.008
LIU Hong-xing, XIE Zai-ku, ZHANG Cheng-fang, CHEN Qing-ling. Chemical equilibrium of toluene disproportionation and trimethylbenzene transalkylatio[J]. Chin Petrochem Technol,2003,32(1):28−32. doi: 10.3321/j.issn:1000-8144.2003.01.008
|
[48] |
肖欢, 张维民, 马静红, 李瑞丰. 1,3,5-三甲苯在沸石催化剂上的催化转化[J]. 石油学报(石油加工),2019,35(2):369−375.
XIAO Huan, ZHANG Wei-min, MA Jing-hong, LI Rui-feng. 1,3,5-trimethylbenzene transformation over zeolite catalyst[J]. Acta Pet Sin (Pet Process Sect),2019,35(2):369−375.
|
[49] |
李萌萌, 董秀芹, 张敏华. P改性ZSM-5分子筛的结构及酸性变化[J]. 计算机与应用化学,2012,29(2):245−248. doi: 10.3969/j.issn.1001-4160.2012.02.028
LI Meng-meng, DONG Xiu-qin, ZHANG Min-hua. DFT study on the structural and acidity of P-ZSM-5[J]. Comput Appl Chem,2012,29(2):245−248. doi: 10.3969/j.issn.1001-4160.2012.02.028
|
[50] |
田玲, 李建伟, 李英霞, 陈标华. 磷改性MCM-22分子筛上苯与1-十二烯烷基化合成十二烷基苯[J]. 催化学报,2008,29(9):889−894. doi: 10.3321/j.issn:0253-9837.2008.09.012
TIAN Ling, LI Jian-wei, LI Ying-xia, CHEN Biao-hua. Synthesis of dodecylbenzene with benzene and 1-dodecene over MCM-22 zeolite modified with phosphorus[J]. Chin J Catal,2008,29(9):889−894. doi: 10.3321/j.issn:0253-9837.2008.09.012
|