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Improved Regioselective Di-nitration of Biphenyl over Reusable HBEA-500 Zeolite
Improved Regioselective Di-nitration of Biphenyl over Reusable HBEA-500 Zeolite
Bulletin of the Korean Chemical Society. 2014. Apr, 35(4): 1241-1243
Copyright © 2014, Korea Chemical Society
  • Received : September 17, 2013
  • Accepted : December 29, 2013
  • Published : April 20, 2014
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About the Authors
Yan F. Tai
School of Applied Chemistry and Environmental Engineering, Bengbu College, Bengbu 233000, P.R. China
Cheng Ji
School of Chemical Engineering, Hefei University of Technology, Hefei 230009, P.R. China
Chun J. Shi
School of Applied Chemistry and Environmental Engineering, Bengbu College, Bengbu 233000, P.R. China
Wei Wang
School of Chemical Engineering, Hefei University of Technology, Hefei 230009, P.R. China
Xin H. Peng
School of Chemical Engineering, Hefei University of Technology, Hefei 230009, P.R. China

Abstract
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Experimental
General Procedure of Nitration. All reactions were carried out in a 50 mL one-necked round bottomed flask equipped with a water condenser and a magnetic stirrer. In a typical experiment, a mixture of zeolite HBEA-500 (0.30 g) which was calcined at 550 °C for 2 h in air prior to use, biphenyl (0.61 g, 4 mmol), nitric acid (95%, 0.35 mL, 8 mmol) was stirred in acetic anhydride (5.0 mL) at −5 °C for 24 h. When the reaction was over, 10 mL of dichloro-methane was added, then the zeolites was removed by filtration and the filtrate was washed with water (3 × 10 mL) and 5% aqueous solution of NaHCO 3 (10 mL) and water (3 × 10 mL). The organic phase separated was dried with anhydrous sodium sulfate, and filtrated to give a straw yellow liquid. The isomer distribution and yields of products were estimated from the peak areas based on the internal standard technique using gas chromatography. The straw yellow products with further purification by column chromato-graphy, and were identified by comparison of their analytical data with those of authentic samples.
Catalyst Regeneration. The used zeolite was recovered from the reaction mixture by filtration and washed with dichloromethane. The catalyst was dried at 110 °C for 4 h in the oven and ground into powder, then, calcined at 550 °C for 6 h.
1H-NMR of Nitrated Products: 2-Nitrobiphenyl yellow oil 1 H NMR (400 MHz, CDCl 3 ) δ 7.8 (d, 1H), 7.6 (d, 1H), 7.5 (m, 1H), 7.4 (m, 4H), 7.3 (m, 2H).
4-Nitrobiphenyl White Solid: 1 H NMR (400 MHz, CDCl 3 ) δ 8.3 (m, 2H), 7.7 (m, 2H), 7.6 (d, 2H), 7.5 (d, 2H), 7.4 (d, 1H).
2,2'-Dinitrobiphenyl Yellow Solid: 1 H NMR (400 MHz, CDCl 3 ) δ 8.3 (d, 2H), 7.7 (t, 2H), 7.6 (t, 2H), 7.3 (d, 2H).
2,4'-Dinitrobiphenyl Yellow Solid: 1 H NMR (400 MHz, CDCl 3 ) δ 8.2 (d, 2H), 8.0 (d, 1H), 7.7 (t, 1H), 7.6 (t, 1H), 7.5 (d, 2H), 7.4 (d, 1H).
4,4'-Dinitrobiphenyl Yellow Solid: 1 H NMR (400 MHz, CDCl 3 ) δ 8.4 (d, 4H), 7.7 (d, 4H).
Acknowledgements
Publication cost of this paper was supported by the Korean Chemical Society.
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