Synthesis of p-nitrophenol under normal pressure with A-1 phase transfer catalysis

Abstract

p-nitrophenol is synthesized using p-nitrochlorobenzene and sodium hydroxide with phase transfer catalyst. Several reaction factors, such as catalyst type, the amounts of catalysts and sodium hydroxide, the concentration of sodium hydroxide solution as well as reaction time, affect greatly the yield of p-nitrophenol. The optimum reaction conditions are as follows: A-1 used as phase transfer catalyst whose consumption is 6% (mole fraction) of p-nitrochlorobenzene; the molar ratio of sodium hydroxide to p-nitrochlorobenzene is 3:1; the concentration of sodium hydroxide solution is 50% (mass fraction). Nitrobenzene, whose molar amount is 2.45 times as much as that of p-nitrochlorobenzene; reaction time is 7 h at 140 °C under normal pressure. The final yield of p-nitrophenol is 83.6%.

Keywords

phase transfer catalysis / p-nitrophenol / synthesis

References

[1] XuJing. Nitrobenzene series product exploitation and development[J]. Hunan Chemical Engineering, 1989, 2: 15-24(in Chinese)

[2] BajS. Study of the reaction of sodium cumyl peroxide with haloaromatic compounds under PTC conditions[J]. Polish J Chem, 1993, 67: 1967-1972

[3] QinShen-yong, ZhangKe-shen. Preparation of p-nitrophenol by hydrolysis of p-nitrochlorobenzene[J]. Sichuan Chemical Engineering, 1994, 1: 11-13(in Chinese)

[4] YuQian, ChengYi-wen, ZhangKe-hua. Determination of p-nitrophenol by gas chromatographic[J]. Chromatographic, 1996, 14(4): 298-299(in Chinese)

[5] YeKai-wen. Study for synthesis of p-nitrophenol[J]. Jiangshu Chemical Engineering, 1997, 25(4): 28-29(in Chinese)

[6] FdldmanDavid, Rabinovitz, Mordecai. Nucleophicicity vs basity of the hydroxide ion under extractive phase transfer catalysis conditions[J]. Tetrahedron Lett, 1997, 30(44): 6091-6094

[7] LuYi-jin. Synthesis of new phase transfer catalysis[J]. Journal of Zhejiang University, 1990, 1(24): 46-52(in Chinese)