Improved Stability and Shape Selectivity of 2,6-Dimethylnaphthalene by Methylation of Naphthalene with Methanol on Modified Zeolites

DOI: 10.4236/mrc.2014.32004   PDF   HTML     2,994 Downloads   4,936 Views   Citations


2,6-Dimethylnaphthalene (2,6-DMN) is a key intermediate for polyethylene naphthalate synthesis. The selective synthesis of 2,6-DMN from naphthalene and methanol was carried out over different zeolites (HZSM-5, Hβ, HUSY and SAPO-11) modified by 0.1wt% PdO under atmospheric pressure. Among the adopted zeolites, SAPO-11 exhibits exceptional shape-selectivity and stability to synthesize 2,6-dimethylnaphthalene from methylation of naphthalene, due to the special pore structure of SAPO-11 which inosculated better with 2,6-dimethylnaphthalene than with 2,7-dimethylnaphthalene.

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Zhang, Y. , Feng, J. , Lyu, Z. and Li, X. (2014) Improved Stability and Shape Selectivity of 2,6-Dimethylnaphthalene by Methylation of Naphthalene with Methanol on Modified Zeolites. Modern Research in Catalysis, 3, 19-25. doi: 10.4236/mrc.2014.32004.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] He, Z. and Zhu, L. (2001) Prepartion and Application of 2,6-Naphthalene Dicarboxylic Acid and Dimethyl-2, 6Naphthalene Dicarboxylate. Coke Chemical Industries, 94, 51-56.
[2] Chemical Market Reporter, 1999.
[3] Fraenkel, D., Cherniavsky, M., Ittah, B. and Levy, M. (1986) Shape-Selective Alkylation of Naphthalene and Methylnaphthalene with Methanol over H-ZSM-5 Zeolite Catalysts. Journal of Catalysis, 101, 273-283.
[4] Pu, S. and Inui, T. (1996) Synthesis of 2,6-Dimethylnaphthalene by Methylation of Methylnaphthalene on Various Medium and Large-Pore Zoelite Catalysts. Applied Catalysis A, 146, 305-316.
[5] Komatsu, T., Araki, Y. and Namba, S. (1994) Selective Formation of 2,6-Dimethylnaphthalene from 2-Methylnaphthalene on ZSM-5 and Metallosilicates with MFI Structure. Studies in Surface Science and Catalysis, 84, 1821-1828.
[6] Millini, R., Frigerio, F., Bellussi, G., Pazzuconi, G., Perego, C., Pollesel, P. and Romano, U. (2003) A Priori Selection of Shape-Selective Zeolite Catalysts for the Synthesis of 2, 6-Dimethylnaphthalene. Journal of Catalysis, 217, 298-312.
[7] Park, J., Wang, J., Hong, S.I. and Lee, C. (2005) Effect of Dealumination of Zeolite Catalysts on Methylation of 2-Methylnaphthalene in a High-Pressure Fixed-Bed Flow Reactor. Applied Catalysis A, 292, 68-75.
[8] Bai, X., Sun, K., Wu, W., Yan, P. and Yang, J. (2009) Methylation of Naphthalene to Prepare 2, 6-Dimethylnaphthalene over Acid-Dealuminated HZSM-12 Zeolites. Journal of Molecular Catalysis A, 314, 81-87.
[9] Martens, J., Grobet, P. and Jacobs, P. (1990) Catalytic Activity and Si, Al, P Ordering in Microporous Silicoaluminophosphates of the SAPO-5, SAPO-11, and SAPO-37 Type. Journal of Catalysis, 126, 299-305.
[10] Hu, Y., Wang, X., Guo, X., Xu, P. and Li, S. (2004) Hydroisomerization of n-Octane over Pt/SAPO-41 Catalyst. Chinese Journal of Catalysis, 86, 45-51.
[11] Wang, L., Guo, C., Huang, X. and Li, Q. (2002) Synthesis of High Si-Containing SAPO-11 by Post-Si Method. Chemistry Letters, 31, 1012-1013.
[12] Wen, J., Wang, G., Zhang, Y. and Qiu, Z. (2010) Shape-Selective Catalytic Methylation of Naphthalene with Methanol over SAPO-11 Molecular Sieve Catalyst. Petrochemical Technology, 39, 487-491.
[13] Campelo, J.M., Lafont, F. and Marinas, J.M. (1997) Comparison of the Activity and Selectivity of Pt/SAPO-5 and Pt/SAPO-11 in n-Hexane and n-Heptane Hydroconversion. Applied Catalysis A: General, 152, 53-62.
[14] Newsam, J.M., Treacy, M.M.J., Koetsier, W.T. and de Gruyter, C.B. (1988) Structural Characterization of Zeolite Beta. Proceedings of the Royal Society (London) A, 420, 375-405.
[15] Hriljac, J.A., Eddy, M.M., Cheetham, A.K., Donohue, J.A. and Ray, G.J. (1993) Powder Neutron-Diffraction and SI-29 Mas NMR-Studies of Siliceous Zeolite-Y. Journal of Solid State Chemistry, 106, 66-72.
[16] Kokotailo, G.T., Lawton, S.L., Olson, D.H. and Meier, W.M. (1978) Structure of Synthetic Zeolite ZSM-5. Nature, 272, 437-438.
[17] van Koningsveld, H. and Jansen, J.C. (1996) Single Crystal Structure Analysis of Zeolite H-ZSM-5 Loaded with Naphthalene. Microporous Materials, 6, 159-167.
[18] Xie, Y. and Tang, Y. (1990) Spontaneous Monolayer Dispersion of Oxides and Salts onto Surfaces of Supports: Applications to Heterogeneous Catalysis. Advances in Catalysis, 37, 1-43.
[19] Pazzucconi, G., Perego, C., Millini, R. and Frigerio, F. (2000) Process for the Preparation of 2,6-Dimethylnaphthalene Using a MTW Zeolitic Catalyst. US 6147270.
[20] Takagawa, M. and Shigematsu, R. (2000) Process for Producing Highly Pure 2,6-Dimethylnaphthalene. US Pat Appl, US 6072098.
[21] Sikkenga, D., Zaenger, I. and Williams, G. (1991) Preparation of a Dimethylnaphthalene. US Pat Appl, US 5012024.
[22] Fang, Y. and Hu, H. (2006) Shape-Selectivity in 2, 6-Dimethylnaphthalene Synthesis over ZSM-5: Computational Analysis Using Density Functional Theory. Catalysis Communications, 7, 264-267.
[23] Pazzuconi, G., Terzoni, G., Perego, C. and Bellussi, G. (2001) 25-O-03—Selective Alkylation of Naphthalene to 2,6Dimethylnaphthalene Catalyzed by MTW Zeolite. Studies in Surface Science and Catalysis, 135, 4071-4078.

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