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Citation: ZHAO Xin, YU Hui-Li, GE Ji-Yun. Regioselective Nitration of Toluene in Ionic Liquid Caprolactam-trifluoromethanesulfonic Acid[J]. Chinese Journal of Applied Chemistry, ;2009, 26(8): 905-908. shu

Regioselective Nitration of Toluene in Ionic Liquid Caprolactam-trifluoromethanesulfonic Acid

1.
School of Chemistry and Bioengineering, Suzhou University of Science and Technology, Suzhou 215011

Corresponding author: ZHAO Xin,
Received Date: 16 July 2008
Available Online: 29 September 2008
Fund Project: 建设部科研基金资助项目(2008-K7-29) (2008-K7-29)

A novel ionic liquid(IL) caprolactam-trifluoromethanesulfonic acid([CP]OTf) was prepared with trifluoromethanesulfonic acid and caprolactam as raw materials.The structure of the IL was characterized by ¹H NMR and FTIR,and was used as the catalyst and solvent in the nitration of toluene.The effects of the amount of catalyst,reaction temperature,reaction time,concentration of nitric acid and catalyst recycling on the yield and para-selectivity for the nitration of toluene were investigated with the aid of gas chromatography.The results show that when the nitration temperature was 55 ℃,the reaction time was 6 h,the molar ratio of toluene to 95% nitric acid was 1:1,the amount of catalyst was 15% of the molar amount of toluene,the ortho-para isomer ratio reached 1.12,far below 1.67 by using sulfuric acid,and gave a product yield of 78.41%.IL([CP]OTf) showed high regioselectivity and catalytic activity.The catalyst could be reutilized up to five times with little decrease in activity and regioselectivity.
- toluene,
- ionic liquid,
- nitration,
- caprolactam-trifluoromethanesulfonic acid
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