Chemical Research in Chinese Universities ›› 2011, Vol. 27 ›› Issue (6): 1010-1013.

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Selective Synthesis of 2,6-Dimethylnaphthalene by Transalkylation in the Presence of Acid Ionic Liquids [Cnmim]Cl-AlCl3

WU Guang, WU Wei*, XIAO Lin-fei and LIU Dan   

  1. Heilongjiang Province College Key Laboratory of Chemical Engineering Process and Technology for High-efficiency Conversion, School of Chemistry and Material Sciences, Heilongjiang University, Harbin 150080, P. R. China
  • Received:2011-04-18 Revised:2011-07-22 Online:2011-11-25 Published:2011-11-07
  • Contact: WU Wei E-mail:weiwu_hlj@163.com
  • Supported by:

    Supported by the National Natural Science Foundation of China(No.21076065), the Natural Science Foundation of Heilongjiang Province of China(No.ZD200820-02), and the Science & Technology Research Foundation of Education Bureau of Heilongjiang Province, China(No.11531266).

Abstract: A highly selective synthesis of 2,6-dimethylnaphthanlene(2,6-DMN) by transalkylation between 2-methylnaphthanlene(2-MN) and 1,2,4,5-tetramethylbenzene(TeMB) was performed with 1-alkyl-3-methylimidazo- lium aluminum chloride([Cnmim]Cl-AlCl3) ionic liquids(ILs) as catalysts. The influences of the alkyl group as the organic cation, the acidic strength of [C4mim]Cl-AlCl3 ILs as well as the reaction conditions on the catalytic performance were investigated. [C4mim]Cl-AlCl3 ILs[x(AlCl3)=71%] exhibited high activity and selectivity toward 2,6-DMN. The selectivity to 2,6-DMN and the 2,6-DMN/2,7-DMN ratio reached up to 68.2% and 3.7:1, respectively. The UV-Vis spectrum of TeMB treated by different ILs shows that the protonated degree of TeMB dependeds on the acidity strength of ILs, which has a significant impact on the reaction results. The high protonated degree of TeMB is advantageous to enhancing the conversion of transalkylation and the large stereo-hindrance effect of TeMB is favorable to improving the selecivity to 2,6-DMN.

Key words: Ionic liquid, 2,6-Dimethylnaphthalene, 1-Alkyl-3-methylimidazolium aluminum chloride, Transalkylation