酸碱复合改性丝光沸石催化4-异丙基联苯异丙基化

doi:10.11949/j.issn.0438-1157.20150849

化工学报 ›› 2015, Vol. 66 ›› Issue (9): 3470-3475.DOI: 10.11949/j.issn.0438-1157.20150849

• 催化、动力学与反应器 • 上一篇下一篇

酸碱复合改性丝光沸石催化4-异丙基联苯异丙基化

刘民¹, 沈忠明¹, 郭新闻¹, 宋春山^1,2

1 大连理工大学化工学院, 精细化工国家重点实验室, 宾州-大连联合能源研究中心, 辽宁大连 116024;
2 宾州州立大学能源研究所, 能源与矿物工程系, 美国宾夕法尼亚 16802

收稿日期:2015-06-08 修回日期:2015-06-15 出版日期:2015-09-05 发布日期:2015-09-05
通讯作者: 郭新闻

Isopropylation of 4-isopropybiphenyl to 4,4'-diisopropylbiphenyl over alkalis and acid modified mordenite zeolites

LIU Min¹, SHEN Zhongming¹, GUO Xinwen¹, SONG Chunshan^1,2

1 PSU-DUT Joint Center for Energy Research, State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, China;
2 EMS Energy Institute, Department of Energy & Mineral Engineering, Pennyslvania State University, Pennyslvania 16802, United States

Received:2015-06-08 Revised:2015-06-15 Online:2015-09-05 Published:2015-09-05

摘要/Abstract

摘要：

采用酸碱复合改性的方法,制备了同时具有微孔和介孔孔道的丝光沸石,用于固定床4-异丙基联苯的异丙基化反应。通过X射线衍射(XRD)、透射电子显微镜(TEM)、NH₃程序升温脱附(NH₃-TPD)、N₂物理吸附脱附等方法对改性丝光沸石进行表征。结果表明,碱改性处理调变了丝光沸石的孔道结构和酸性质,同时保持了其MOR拓扑结构,提高了4-异丙基联苯的转化率和反应的稳定性。碱处理后再进行酸处理,可以有效清除碱处理过程中产生的非骨架铝物种和样品外表面的酸中心,提高目的产物4,4'-二异丙基联苯的选择性。

关键词: 丝光沸石, 多级孔, 4-异丙基联苯, 4,4'-二异丙基联苯, 烷基化, 催化, 选择性, 制备

Abstract:

Isopropylation of 4-isopropybiphenyl to 4,4'-diisopropylbiphenyl was carried out over hierarchical mesoporousmordenite zeolites through alkalis modification of H-mordenite zeolite in a fixed-bed reactor. In order to investigate the effects of the pore structure and the acid sites of the zeolite samples on the catalytic properties, the parent and modified zeolite samples were thoroughly characterized with X-ray diffraction (XRD), transmission electron microscopy (TEM), ammonia temperature programmed desorption (NH₃-TPD), and N₂ physical adsorption-desorption. The results showed that the alkalis treatment adapted the pore structure, and the acid strength and amount without obvious destruction to the MOR topological structure. This adaption was contributed to the improvements of 4-isopropybiphenyl conversion and reaction stability. Modifying the sample with alkalis first and then followed by an acid treatment was in favor of removing the extra-framework alumina from the alkalis treatment and adapting the acid sites on the extra surface of the sample, which can successfully improve the selectivity of 4,4'-diisopropylbiphenyl.

Key words: H-mordenite, hierarchical mesoporous, 4-isopropybiphenyl, 4,4'-diisopropylbiphenyl, alkylation, catalysis, selectivity, preparation

中图分类号:

O643.3

刘民, 沈忠明, 郭新闻, 宋春山. 酸碱复合改性丝光沸石催化4-异丙基联苯异丙基化[J]. 化工学报, 2015, 66(9): 3470-3475.

LIU Min, SHEN Zhongming, GUO Xinwen, SONG Chunshan. Isopropylation of 4-isopropybiphenyl to 4,4'-diisopropylbiphenyl over alkalis and acid modified mordenite zeolites[J]. CIESC Journal, 2015, 66(9): 3470-3475.

参考文献 20

[1]	Fellmann J, Wentrcek P, Lu P T. Manufacture of 4,4'-diisopropylbiphenyl [P]: US, 5026940. 1991-6-25.
[2]	Zong Zhimin(宗志敏), Jiang Qun(蒋群), Chen Zhongxiu(陈忠秀), Wei Xianyong(魏贤勇). Advance in selective alkylation of arenes [J]. Coal Conversion(煤炭转化), 1998, 21(1): 41-45.
[3]	Priddy D B. Alkylation of biphenyl under mild Friedel-Crafts conditions [J]. Ind. Eng. Chem. Prod. Res. Dev., 1969, 8(3): 239-241.
[4]	Matsuda T, Kikuchi E. Synthesis of symmetrical alkyl-aromatics by use of shape-selective catalysts [J]. Res. Chem. Intermed., 1993, 19(4): 319-332.
[5]	Lee G S, Maj J J, Rocke S C, Garces J M. Shape selective alkylation of polynuclear aromatics with mordenite-type catalysts - a high-yield synthesis of 4,4'-diisopropylbiphenyl [J]. Catal. Lett., 1989, 2(4): 243-247.
[6]	Bandyopadhyay M, Bandyopadhyay R, Tawada S, Kubota Y, Sugi Y. Catalytic performance of silicoaluminophosphate (SAPO) molecular sieves in the isopropylation of biphenyl [J]. Applied Catalysis A-General, 2002, 225(1/2): 51-62.
[7]	Sugi Y, Tawada S, Sugimura T, Kubota Y, Hanaoka T, Matsuzaki T, Nakajima K, Kunimori K. Shape-selective isopropylation of biphenyl over H-mordenites - relationships of bulk products and encapsulated products in the pores [J]. Applied Catalysis A-General, 1999, 189(2): 251-261.
[8]	Selvam T, Mabande G T P, Schwieger W, Sugi Y, Toyama I, Kubota Y, Lee H S, Kim J H. Selective isopropylation of biphenyl to 4,4'-DIPB over mordenite (MOR) type zeolite obtained from a layered sodium silicate magadiite [J]. Catal. Lett., 2004, 94(1/2): 17-24.
[9]	Sugi Y, Tu X L, Matsuzaki T, Hanaoka T A, Kubota Y, Kim J H, Matsumoto M, Nakajima K, Igarashi A. The effect of propylene pressure on shape-selective isopropylation of biphenyl over H-mordenite [J]. Catal. Today, 1996, 31(1/2): 3-10.
[10]	Hayashi M, Tawada S, Kubota Y, Sugi Y, Kim J. Deactivation of external acid sites of H-mordenite by silica-modification in the isopropylation of biphenyl [J]. React. Kinet. Catal. Lett., 2004, 83(2): 329-335.
[11]	Anand C, Sugimura T, Komura K, Kubota Y, Kim J H, Seo G, Vinu A, Sugi Y. The isopropylation of biphenyl over H-mordenite - roles of 3- and 4-isopropylbiphenyls [J]. Korean J. Chem. Eng., 2013, 30(5): 1043-1050.
[12]	Sugi Y, Maekawa H, Hasegawa Y, Ito A, Asai R, Yamamoto D, Komura K, Kubota Y, Kim J H, Seo G. The alkylation of biphenyl over three-dimensional large pore zeolites: the influence of zeolite structure and alkylating agent on the selectivity for 4,4'- dialkylbiphenyl [J]. Catal. Today, 2008, 131(1/2/3/4): 413-422.
[13]	Tzoulaki D, Jentys A, Pérez-Ramírez J, Egeblad K, Lercher J A. On the location, strength and accessibility of Brønsted acid sites in hierarchical ZSM-5 particles [J]. Catal. Today, 2012, 198(1): 3-11.
[14]	Li Sha(李莎), Li Yuping(李玉平), Di Chunyu(狄春雨), Zhang Pengfei(张鹏飞), Pan Ruili(潘瑞丽), Dou Tao(窦涛). Modification and catalyst performance of ZSM-5 zeolite by treatment with TPAOH/NaOH mixed alkali [J]. Journal of Fuel Chemistry and Technology(燃料化学学报), 2012, 40(5): 583-588.
[15]	Groen J C, Moulijn J A, Perez-Ramirez J. Decoupling mesoporosity formation and acidity modification in ZSM-5 zeolites by sequential desilication-dealumination [J]. Microporous Mesoporous Mater., 2005, 87(2): 153-161.
[16]	Zhao Liang, Wang Hongbo, Liu Min, Guo Xinwen, Wang Xiangsheng, Song Chunshan, Liu Hai'ou. Shape-selective methylation of 2-methylnaphthalene with methanol over hydrothermal treated HZSM-5 zeolite catalysts [J]. Chem. Eng. Sci., 2008, 63(21): 5298-5303.
[17]	Suzuki T, Okuhara T. Change in pore structure of MFI zeolite by treatment with NaOH aqueous solution [J]. Microporous Mesoporous Mater., 2001, 43(1): 83-89.
[18]	Perez-Ramirez J, Verboekend D, Bonilla A, Abello S. Zeolite catalysts with tunable Hierarchy factor by pore-growth moderators [J]. Adv. Funct. Mater., 2009, 19(24): 3972-3979.
[19]	de Lucas A, Canizares P, Durán A, Carrero A. Dealumination of HZSM-5 zeolites: effect of steaming on acidity and aromatization activity [J]. Applied Catalysis A-General, 1997, 154(1/2): 221-240.
[20]	Ahn J H, Kolvenbach R, Al-Khattaf S S, Jentys A, Lercher J A. Enhancing shape selectivity without loss of activity-novel mesostructured ZSM5 catalysts for methylation of toluene to p-xylene [J]. Chem. Commun., 2013, 49(90): 10584-10586.

酸碱复合改性丝光沸石催化4-异丙基联苯异丙基化

Isopropylation of 4-isopropybiphenyl to 4,4'-diisopropylbiphenyl over alkalis and acid modified mordenite zeolites

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