Isomerization of alkyl naphthalene and refining of 2-methylnaphthalene

doi:10.1016/j.cjche.2016.08.022

›› 2017, Vol. 25 ›› Issue (2): 149-152.DOI: 10.1016/j.cjche.2016.08.022

• Selected Papers from the International Chemical Separation Technology Conference (ICSTC) • 上一篇下一篇

Isomerization of alkyl naphthalene and refining of 2-methylnaphthalene

Hao Sun, Saijian Shi, Zhenggui Gu

School of Chemistry and Materials Science, Jiangsu Provincial Key Laboratory of Materials Cycling and Pollution Control, Nanjing Normal University, Nanjing 210023, China

收稿日期:2016-08-08 修回日期:2016-08-25 出版日期:2017-02-28 发布日期:2017-03-14
通讯作者: Zhenggui Gu
基金资助:
Supported by the Key Discipline Construction of 211 Project IV in China (No. 1843202543), Research Innovation Program for College Graduates of Jiangsu Province (No. KYLX15_0728) and Science and Technology Program of Jiangsu Province (No. BY2012003).

Isomerization of alkyl naphthalene and refining of 2-methylnaphthalene

Hao Sun, Saijian Shi, Zhenggui Gu

School of Chemistry and Materials Science, Jiangsu Provincial Key Laboratory of Materials Cycling and Pollution Control, Nanjing Normal University, Nanjing 210023, China

Received:2016-08-08 Revised:2016-08-25 Online:2017-02-28 Published:2017-03-14
Supported by:
Supported by the Key Discipline Construction of 211 Project IV in China (No. 1843202543), Research Innovation Program for College Graduates of Jiangsu Province (No. KYLX15_0728) and Science and Technology Program of Jiangsu Province (No. BY2012003).

摘要/Abstract

摘要： A preparation process of 2-methylnaphthalene (2-MN) was proposed by isomerization, side-stream distillation and extractive distillation. The isomerization of alkyl naphthalene was catalyzed by acid-treated HBEA zeolites, and the 2-MN selectivity of isomerization was 92.70%. Side-stream distillation and extractive distillation were investigated by simulation, and effects of operation parameters on 2-MN were studied. Further, the simulated results were verified by experiment. Under the optimal condition, the mass fraction of 2-MN reached to 98.09% in the product, and the yield was 83.84% in refining process.

关键词: Side-stream distillation, Extractive distillation, Isomerization, 2-Methylnaphthalene, Simulation, Catalyst

Abstract: A preparation process of 2-methylnaphthalene (2-MN) was proposed by isomerization, side-stream distillation and extractive distillation. The isomerization of alkyl naphthalene was catalyzed by acid-treated HBEA zeolites, and the 2-MN selectivity of isomerization was 92.70%. Side-stream distillation and extractive distillation were investigated by simulation, and effects of operation parameters on 2-MN were studied. Further, the simulated results were verified by experiment. Under the optimal condition, the mass fraction of 2-MN reached to 98.09% in the product, and the yield was 83.84% in refining process.

Key words: Side-stream distillation, Extractive distillation, Isomerization, 2-Methylnaphthalene, Simulation, Catalyst

Hao Sun, Saijian Shi, Zhenggui Gu. Isomerization of alkyl naphthalene and refining of 2-methylnaphthalene[J]. , 2017, 25(2): 149-152.

参考文献

[1] L.D. Lillwitz, Production of dimethyl-2,6-naphthalenedicarboxylate:Precursor to polyethylene naphthalene, Appl. Catal. A 221(2001) 337-358.
[2] A. Arkhireyeva, S. Hashemi, Fracture behaviour of polyethylene naphthalene (PEN), Polymer 43(2001) 289-300.
[3] S.B. Pu, T. Inui, Synthesis of 2,6-dimethylnaphthalene by methylation of methylnaphthalene on various medium and large-pore zeolite catalysts, Appl. Catal. A 146(1996) 305-306.
[4] H. Sun, L. Jiang, Z.G. Gu, Extract methylnaphthalene from C₁₀ aromatics with sidetrack distillation and continuous crystallisation, Mater. Res. Innov. 19(2015) 573-578.
[5] Z. Popova, M. Yankov, L. Dimitrov, I. Chervenkov, Isomerization and disproportionation of 1-MN on zeolites, React. Kinet. Catal. Lett. 52(1994) 51-58.
[6] E. Fedorynska, P. Winiarek, Isomerization of alkylaromatic hydrocarbons on nickelboron-alumina catalysts, React. Kinet. Catal. Lett. 54(1995) 73-79.
[7] T. Komatsu, J.H. Kim, T. Yashima, MFI-type metallosilicates as useful tools to clarify what determines the shape selectivity of ZSM-5 zeolites, ACS Symp. Ser. 738(1999) 162-180.
[8] M. Neubera, H.G. Kargeb, J.Weitkampc, I.R. spectroscopic characterization of zeolite catalysts for the shape selective conversion of polynuclear aromatics, Catal. Today 3(1988) 11-22.
[9] Y. Takagi, T. Nobusawa, T. Suzuki, Prevention and estimation of catalytic deactivation in isomerization of 1-methylnaphthalene, Kagaku Kogaku Ronbunshu 21(1995) 1096-1103.
[10] H. Teng, J. Wang, X.Q. Ren, D.M. Chen, Disproportionation of toluene by modified ZSM-5 zeolite catalysts with high shape-selectivity prepared using chemical liquid deposition with tetraethyl orthosilicate, Chin. J. Chem. Eng. 19(2011) 292-298.
[11] C. Zhang, X.W. Guo, C.S. Song, S.Q. Zhao, X.S.Wang, Effects of steam and TEOS modification on HZSM-5 zeolite for 2,6-dimethylnaphthalene synthesis by methylation of 2-methylnaphthalene with methanol, Catal. Today 149(2010) 196-201.
[12] G.Y. Bai, J. Han, H.H. Zhang, C. Liu, X.W. Lan, F. Tian, Z. Zhao, H. Jin, Friedel-crafts acylation of anisole with octanoic acid over acid modified zeolites, RSC Adv. 4(2014) 27116-27121.
[13] Z.H. Chen, Y.F. Feng, T.X. Tong, A.W. Zeng, Effects of acid-modified HBEA zeolites on thiophene acylation and the origin of deactivation of zeolites, Appl. Catal. A 482(2014) 92-98.
[14] R.E. Rooks, M.F. Malone, M.F. Doherty, A geometric design method for side-stream distillation columns, Ind. Eng. Chem. Res. 35(1996) 3653-3664.
[15] R.P. Brito, M.F. Fossy,M.R.Maciel, Dynamic behaviour of side-streamdistillation columns for the separation of binary azeotropes mixtures, Comput. Chem. Eng. 23(1999) 175-178.
[16] C. Gutiérrez-Antonio, A. Jiménez-Gutiérrez, Design of side-stream azeotropic distillation columns, Chem. Eng. Res. Des. 85(2007) 1384-1389.
[17] J.Y. Zhang, A.X. Hu, Y. Wang, X.H. Xiao, J.B. Guo, X.F. Luo, The separation of catechol from carbofuran phenol by extractive distillation, Chin. J. Chem. Eng. 17(2009) 42-46.
[18] S.L. Xu, H.Y. Wang, A new entrainer for separation of tetrahydrofuran-water azeotropic mixture by extractive distillation, Chem. Eng. Process. 45(2006) 954-958.
[19] M. Matsukata, M. Ogura, T. Osaki, M. Nomura, E. Kikuchi, Conversion of dry gel to microporous crystals in gas phase, Top. Catal. 9(1999) 77-92.
[20] B.L. Yang, J.Wu, G.S. Zhao, H.J.Wang, S.Q. Lu, Multiplicity analysis in reactive distillation column using ASPEN PLUS, Chin. J. Chem. Eng. 14(2006) 301-308.
[21] H.Z. Gu, Z.G. Gu, H. Sun, Study on extractive distillation of m-diethylbenzene from the isomer mixture, Comput. Appl. Chem. 32(2015) 489-492(in Chinese).
[22] H.J. Wang, L. Pang, C. Yang, Y.H. Liu, Production of glycerol carbonate via reactive distillation and extractive distillation:An experimental study, Chin. J. Chem. Eng. 23(2015) 1469-1474.
[23] H. Tian, S.Y. Zhao, H.D. Zheng, Z.X. Huang, Optimization of coproduction of ethyl acetate and n-butyl acetate by reactive distillation, Chin. J. Chem. Eng. 23(2015) 667-674.

Isomerization of alkyl naphthalene and refining of 2-methylnaphthalene

Isomerization of alkyl naphthalene and refining of 2-methylnaphthalene

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