Citation: LIU Dong-mei, ZHAI Yu-chun, MA Jian, WANG Hai-yan. Study on thiophene alkylation performance of hierarchical ZSM-5 zeolites modified by different alikali[J]. Journal of Fuel Chemistry and Technology, ;2015, 43(4): 462-469. shu

Study on thiophene alkylation performance of hierarchical ZSM-5 zeolites modified by different alikali

1.
1. School of Materials and Metallurgy, Northeastern University, Shenyang 110004, China;

Corresponding author: ZHAI Yu-chun,
Received Date: 18 September 2014

Fund Project: 国家自然科学基金(21401093) (21401093)辽宁省自然科学基金(201202126)。 (201202126)

HZSM-5 zeolites were respectively treated by Na₂CO₃,TPAOH and mixed alkali solution of TPA⁺/CO₃^2-. The samples were characterized by FT-IR XRD, XRF, N₂ adsorption/desorption, SEM, NH₃-TPD and Py-FTIR techniques. It was found that the microporous and mesoporous hierarchical HZSM-5 (A) catalysts were formed after the treatment and their acidity were modulated. The largest surface area and the most mesoporous were found in the HZSM-5(TPA⁺/CO₃^2-) treated by the mixed alkali of TPA⁺/CO₃^2-s. The thiophene alkylation performance of HZSM-5 and HZSM-5(A) zeolites was investigated in a small-scale fixed bed reactor with model compounds as feedstock. The co-sequences displayed that HZSM-5 (TPA⁺/CO₃^2-) catalysts exhibited the higher conversion of thiophene and selectivity of 1-hexene because the zeolites had proper hierarchical pore diameter and more B-acid sites.
- Na₂CO₃,
- TPAOH,
- ZSM-5,
- hierarchical pore,
- thiophene alkylation
1. [1]
  [1] ZHANG Z K, LIU S L, ZHU X X, WANG Q X, XU L Y. Modification of Hβ zeolite by fluorine and its influence on olefin alkylation thiophenic sulfur in gasoline[J]. Fuel Process Technol, 2008, 89(1):103-110.
2. [2]
  [2] DUPUY B, LAFORGE S, BACHMANN C, MAGNOUX P, RICHARD F. Desulfurization of model FCC feedstocks by alkylation:Transformation of thiophenic compounds in presence of 2-methyl-1-pentene over acidic zeolites[J]. J Mol Catal A:Chem, 2012, 363-364:273-282.
3. [3]
  [3] ZHANG Z K, NIU X L, LIU S L, ZHU X X, YU H W, XU L Y. The performance of HMCM-22 zeolite catalyst on the olefin alkylation thiophenic sulfur in gasoline[J]. Catal Commun, 2008, 9(1):60-64.
4. [4]
  [4] 魏书梅, 徐亚荣, 徐新良, 王吉德. HY分子筛催化噻吩类硫化物的烷基化反应动力学[J]. 化学反应工程与工艺, 2012, 28(2):159-163. (WEI Shu-mei, XU Ya-rong, XU Xin-liang, WANG Ji-de. Kinetics of alkylation of thiophene over HY zeolite[J]. Chem React Eng Technol, 2012, 28(2):159-163.)
5. [5]
  [5] DUPUY B, LAFORGE S, MORAIS C, BACHMANN C, MAGNOUX P, RICHARD F. Alkylation of 3-methylthiophene by 2-methyl-1-pentene over HY, HBEA and HMCM-22 acidic zeolites[J]. Appl Catal A:Gen, 2012, 413-414(31):192-204.
6. [6]
  [6] PRADHAN V R, BURNETT P A, STACEY M D, HODGES M. Multistage process for removal of sulfur from components for blending of transportation fuels:US, 6733660[P]. 2004-05-11.
7. [7]
  [7] 赵岑, 刘冬梅, 魏民, 孙志岩, 王海彦. 多级孔ZSM-5分子筛的制备及催化噻吩烷基化性能研究[J]. 燃料化学学报, 2012, 40(5):583-588. (ZHAO Cen, LIU Dong-mei, Wei Min, SUN Zhi-yan, WANG Hai-yan. Preparation and thiophene alkylation performance of hierarchical ZSM-5 zeolites[J]. J Fuel Chem Technol, 2012, 40(5):583-588.)
8. [8]
  [8] LI Y N, LIU S L, ZHANG Z K, XIE S J, ZHU X X, XU L Y. Aromatization and isomerization of 1. Hexene over alkali-treated HZSM-5 zeolites:Improved Reaction Stability [J]. Appl Catal A:Gen, 2008, 338(4):100-113.
9. [9]
  [9] NAGABHATLA V, SANDEEP K S, JITENDRA K, PATA S, DEVAKI N. Catalytic performanceof nano crystalline HZSM-5 in ethanol to gasoline(ETG)reaction[J]. Fuel, 2012, 95(1):298-304.
10. [10]
  [10] 何英萍, 刘民, 代成义. 四丙基氢氧化铵改性纳米HZSM-5分子筛及其在甲醇制汽油中的催化性能[J], 催化学报, 2013, 34(6):1148-1158. (HE Ying-ping, LIU Min, DAI Cheng-yi. HZSM-5 zeolites modified tetrapropylammonium hydroxide and the catalytic properties in methanol gasoline[J]. Chin J Catal, 2013, 34(6):1148-1158.)
11. [11]
  [11] 李莎, 李玉平, 狄春雨, 张鹏飞, 潘瑞丽, 窦涛. TPAOH/NaOH 混合碱体系对 ZSM-5 沸石的改性及其催化性能研究[J]. 燃料化学学报, 2012, 40(5):583-588. (LI Sha, LI Yu-ping, DI Chun-yu, ZHANG Peng-fei, PAN Rui-li, DOU Tao. Study on catalytic properties of ZSM-5 zeolites modified by TPAOH/NaOH mixed alkali system[J]. J Fuel Chem Technol, 2012, 40(5):583-588.)
12. [12]
  [12] 石冈, 林秀英, 范煜, 鲍晓军. ZSM-5分子筛的脱硅改性及加氢改质性能[J]. 燃料化学学报, 2013, 41(5):589-600. (SHI Gang, LIN Xiu-ying, FAN Yu, BAO Xiao-jun. Desilication modification of ZSM-5 zeolite and its catalytic properties in hydro-upgrading[J]. J Fuel Chem Technol, 2013, 41(5):589-600.)
13. [13]
  [13] 黄先亮. 二次晶化法修饰改性TS-1及催化环己酮氨氧化反应的研究[D]. 湘潭:湘潭大学, 2008. (HUANG Xian-liang. Study on secondary crystallization method modified TS-1and catalytic ammoxidation of cyclohexanone[D]. Xiangtan:Xiangtan University, 2008.)
14. [14]
  [14] OGURA M, SHINOMIYA S Y, TATNEO J, NARA Y, NOMURA M, KIKUCHI E, MATSUKATA M. Alkali-treatment technique-new method for modification of structure and acid-catalytic properties of ZSM-5 zeolites[J]. Appl Catal A:Gen, 2001, 219(1/2):33-43.
15. [15]
  [15] JELINEK J L, KOVATS E. True surface areas from nitrogen adsorption experiments[J]. Langmuir, 1994, 10(11):4225-4231.
16. [16]
  [16] MORTEN B, FINN J, MARTIN S H, UNNI O, KARL-PETTER L, STIAN S. Methanol to gasoline over zeolite H-ZSM-5:Improved catalystperformance by treatment with NaO[J]. Appl Catal A:Gen, 2008, 345(1):43-50.
17. [17]
  [17] 肖何, 高俊华, 胡津仙, 章斌, 刘平, 张侃. 酸碱改性HZSM-5分子筛上甲醇制取均四甲苯的研究[J]. 燃料化学学报, 2013, 41(1):102-109. (XIAO He, GAO Jun-hua, HU Jin-xian, ZHANG Bin, LIU Ping, ZHANG Kan. Research on four toluene prepared methanol properity of HZSM-5 zeolites modified acid[J]. J Fuel Chem Technol, 2013, 41(1):102-109.)
18. [18]
  [18] 梁战桥, 顾昊辉, 赵斌. 水热处理ZSM-5沸石对乙苯转化型二甲苯异构化催化剂性能的影响[J]. 石油化工, 2009, 38(9):940-944. (LIANG Zhan-qiao, GU Hao-hui, ZHAO Bin. Hydrothermal treatment of ZSM-5 zeolites influence on the conversion of ethlbenzen and xyene isomerization catalyst[J]. Petrochemical, 2009, 38(9):940-944.)
19. [19]
  [19] 聂宁, 沈健. USY分子筛催化噻吩烷基化性能的研究[J]. 石化技术与应用, 2013, 31(2):110-113. (NIE Ning, SHEN Jian. Research on thiophene alkylation performance of USY zeolite catalytic[J]. Petrochem Technol Appl, 2013, 31(2):110-113.)
20. [20]
  [20] BABICH I V, MOULIJN J A. Science and technology of novel processes for deep desulfurization of oil refinery streams:A review[J]. Fuel, 2003, 82(6):607-631.
21. [21]
  [21] 柯明, 汤奕婷, 曹文智, 彭洪湃, 周爱国. 二烯烃与噻吩烷基化反应研究[J]. 西安石油大学学报(自然科学版), 2008, 23(5):75-80. (KE Ming, TANG Yi-ting, CAO Wen-zhi, PENG Hong-pai, ZHOU Ai-guo. Study on alkylation reaction of diolefin with thiophene[J]. J Xi'an Shiyou Univ, 2008, 23(5):75-80.)
22. [22]
  [22] 郭晓野, 张泽凯, 刘盛林, 李玉宁, 戴洪义, 徐龙伢. 汽油在钾修饰MCM-22分子筛上的烷基化脱硫[J]. 工业催化, 2008, 16(6):31-34. (GUO Xiao-ye, ZHANG Ze-kai, LIU Sheng-lin, LI Yu-ning, DAI Hong-yi, XU Long-ya. Alyalation desulfurization of thiophene in gasoline over potassium modified MCM-22 zeolites[J]. Ind Catal, 2008, 16(6):31-34.)
1. [1]
  Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
2. [2]
  Shanyuan Bi , Jin Zhang , Dengchao Peng , Danhong Cheng , Jianping Zhang , Lupeng Han , Dengsong Zhang . Improved N₂ selectivity for low-temperature NO_x reduction over etched ZSM-5 supported MnCe oxide catalysts. Chinese Chemical Letters, 2025, 36(5): 110295-. doi: 10.1016/j.cclet.2024.110295
3. [3]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
4. [4]
  Xinyu You , Xin Zhang , Shican Jiang , Yiru Ye , Lin Gu , Hexun Zhou , Pandong Ma , Jamal Ftouni , Abhishek Dutta Chowdhury . Efficacy of Ca/ZSM-5 zeolites derived from precipitated calcium carbonate in the methanol-to-olefin process. Chinese Journal of Structural Chemistry, 2024, 43(4): 100265-100265. doi: 10.1016/j.cjsc.2024.100265
5. [5]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
6. [6]
  Chao Liu , Huan Yu , Jiaming Li , Xi Yu , Zhuangzhi Yu , Yuxi Song , Feng Zhang , Qinfang Zhang , Zhigang Zou . Facile synthesis of hierarchical Ti₃C₂/Bi₁₂O₁₇Br₂ Schottky heterojunction with photothermal effect for solar-driven antibiotics photodegradation. Acta Physico-Chimica Sinica, 2025, 41(7): 100075-. doi: 10.1016/j.actphy.2025.100075
7. [7]
  Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO₂ mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
8. [8]
  Cuiwu MO , Gangmin ZHANG , Chao WU , Zhipeng HUANG , Chi ZHANG . A(NH₂SO₃) (A=Li, Na): Two ultraviolet transparent sulfamates exhibiting second harmonic generation response. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1387-1396. doi: 10.11862/CJIC.20240045
9. [9]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
10. [10]
  Ruofan Yin , Zhaoxin Guo , Rui Liu , Xian-Sen Tao . Ultrafast synthesis of Na₃V₂(PO₄)₃ cathode for high performance sodium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109643-. doi: 10.1016/j.cclet.2024.109643
11. [11]
  Hui Li , Yanxing Qi , Jia Chen , Juanjuan Wang , Min Yang , Hongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO₂ and selectivity over N₂ and CH₄. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659
12. [12]
  Ping Lu , Baoyin Du , Ke Liu , Ze Luo , Abiduweili Sikandaier , Lipeng Diao , Jin Sun , Luhua Jiang , Yukun Zhu . Heterostructured In2O3/In2S3 hollow fibers enable efficient visible-light driven photocatalytic hydrogen production and 5-hydroxymethylfurfural oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100361-100361. doi: 10.1016/j.cjsc.2024.100361
13. [13]
  Mao-Fan Li , Ming‐Yu Guo , De-Xuan Liu , Xiao-Xian Chen , Wei-Jian Xu , Wei-Xiong Zhang . Multi-stimuli responsive behaviors in a new chiral hybrid nitroprusside salt (R-3-hydroxypyrrolidinium)₂[Fe(CN)₅(NO)]. Chinese Chemical Letters, 2024, 35(12): 109507-. doi: 10.1016/j.cclet.2024.109507
14. [14]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
15. [15]
  Linfang ZHANG , Wenzhu YIN , Gui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405
16. [16]
  Le Han , Zhou Yuan , Bohan Li , Yuchi Zhang , Lin Yang , Yan Xu . Highly-stable cesium lead halide perovskite CsPbBr₃/CsPb₂Br₅ heteronanocrystals in zeolitic imidazolate framework-8 for antibiotic photodegradation. Chinese Chemical Letters, 2025, 36(6): 110349-. doi: 10.1016/j.cclet.2024.110349
17. [17]
  Gregorio F. Ortiz . Some facets of the Mg/Na₃VCr_0.5Fe_0.5(PO₄)₃ battery. Chinese Chemical Letters, 2024, 35(10): 109391-. doi: 10.1016/j.cclet.2023.109391
18. [18]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
19. [19]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
20. [20]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(468)
HTML views(26)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142