Chemical Industry and Engineering Progree

• 精细化工 • Previous Articles     Next Articles

Synthesis of 2-chloro-4-fluoro-5-nitrophenyl ethyl carbonate

ZHAO Deming1,ZHU Sanqi1,ZHANG Jianting1,JIN Ningren1,XU Xinhua2,WANG Dahui2   

  1. 1College of Chemical Engineering and Materials,Zhejiang University of Technology;
    2College of Environmental and Resource Scinences,Zhejiang University
  • Online:2010-07-05 Published:2010-07-05

2-氯-4-氟-5-硝基苯基碳酸乙酯的合成

赵德明1,竺三奇1,张建庭1,金宁人1,徐新华2,汪大翚2   

  1. 1浙江工业大学化学工程与材料学院,浙江 杭州 310032;2浙江大学环境与资源学院

Abstract: Through acylation and nitration reactions,2-chloro-4-fluoro-5-nitrophenyl ethyl carbonate was synthesized from 2-choro-4-fluorophenol,ethyl chloroformate and fuming nitric acid. Influencing factors,reaction mechanism and kinetics of acylation and nitration reactions were investigated. Proper experimental conditions for acylation reaction were found as:n(2-choro-4-fluorophenol)∶n(ethyl chloroformate)=1∶1.06,pH 6.8—7.0,reaction temperature 25 ℃ and reaction time 2 h. The optimal nitration reaction conditions were found as:n(HNO3)∶n(2-chloro-4-fluorophenyl ethyl carbonate)=1∶1.25,reaction time 2 h,reaction temperature 20 ℃. The purity of 2-choro-4- fluoro-5-nitrophenyl ethyl ester was 99.21% as determined by HPLC,and the total yield of 2- choro-4-fluoro-5-nitrophenyl ethyl ester based on 2-choro-4-fluorophenol was 92.95%. The molecular structure of 2-chloro-4-fluorophenyl ethyl carbonate and 2-choro-4-fluoro-5-nitrophenyl ethyl ester were exactly identified by 1H-NMR,FT-IR and elementary analysis.

摘要: 采用2-氯-4-氟苯酚为原料,水为溶剂,经氯甲酸乙酯酰化,得到2-氯-4-氟苯基碳酸乙酯,后经混酸硝化,最终得到2-氯-4-氟-5-硝基苯基碳酸乙酯。研究了合成2-氯-4-氟苯基碳酸乙酯和2-氯-4-氟-5-硝基苯基碳酸乙酯的生产工艺条件,并对其反应机理和硝化反应动力学进行了分析。实验结果表明酰化反应较佳条件为:n(2-氯-4-氟苯酚)∶n(氯甲酸乙酯)=1∶1.06,pH值为6.8~7.0,反应温度25 ℃,反应时间2 h;硝化反应的较佳条件为:n(硝酸)∶n(2-氯-4-氟苯基碳酸乙酯)=1∶1.25,温度为15 ℃下滴加发烟硝酸,混酸中浓硫酸的质量分数为80%,反应时间2 h,反应温度20 ℃。以2-氯-4-氟苯酚计两步总收率为92.95%,2-氯-4-氟-5-硝基苯基碳酸乙酯的HPLC纯度为99.21%。2-氯-4-氟苯基碳酸乙酯和2-氯-4-氟-5-硝基苯基碳酸乙酯产品结构经1H-NMR、FT-IR和元素分析表征确认。

京ICP备12046843号-2;京公网安备 11010102001994号
Copyright © Chemical Industry and Engineering Progress, All Rights Reserved.
E-mail: hgjz@cip.com.cn
Powered by Beijing Magtech Co. Ltd