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高等学校化学研究 ›› 2019, Vol. 35 ›› Issue (4): 674-679.doi: 10.1007/s40242-019-8414-0

• Articles • 上一篇    下一篇

Converting Thiophene in Simulated Coking Crude Benzene to N,N-Dimethyl-2-thiophenecarboxamide by Dimethylcarbamyl Chloride Under Mild Conditions

SHEN Xizhou1,2, SONG Hao1, FANG Liuya1, DENG Hang1, GAN Feng1, SHEN Zhi1   

  1. 1. School of Chemical Engineering & amp;Pharmacy, Wuhan Institute of Technology, Wuhan 430205, P. R. China;
    2. Key Laboratory for Green Chemical Process, Ministry of Education, Wuhan Institute of Technology, Wuhan 430073, P. R. China
  • 收稿日期:2018-12-28 修回日期:2019-05-10 出版日期:2019-08-01 发布日期:2019-08-01
  • 通讯作者: SHEN Xizhou E-mail:Xzhoush@163.com

Converting Thiophene in Simulated Coking Crude Benzene to N,N-Dimethyl-2-thiophenecarboxamide by Dimethylcarbamyl Chloride Under Mild Conditions

SHEN Xizhou1,2, SONG Hao1, FANG Liuya1, DENG Hang1, GAN Feng1, SHEN Zhi1   

  1. 1. School of Chemical Engineering & amp;Pharmacy, Wuhan Institute of Technology, Wuhan 430205, P. R. China;
    2. Key Laboratory for Green Chemical Process, Ministry of Education, Wuhan Institute of Technology, Wuhan 430073, P. R. China
  • Received:2018-12-28 Revised:2019-05-10 Online:2019-08-01 Published:2019-08-01
  • Contact: SHEN Xizhou E-mail:Xzhoush@163.com

摘要: Since the content of thiophene in coking crude benzene is high, it is necessary to remove it from coking crude benzene for efficient utilization. In this study, an important intermediate, N,N-dimethyl-2-thiophenecar-boxamide, was synthesized from thiophene and dimethylcarbamyl chloride. The influences of the dosages of dimethylcarbamyl chloride and ZnCl2 catalyst, reaction temperature and time on the removal rate were further explored based on the reaction kinetics. The structure of the target product was characterized by means of MS, 1H NMR and 13C NMR. The removal rate of thiophene was 98.14% after the reaction for 2 h and thiophene was almost removed after the reaction for 3 h under the optimal reaction conditions[a molar ratio of n(thiophene):n(dimethylcarbamyl chloride):n(ZnCl2)=1:12:10, 300 r/min, 318 K and 101.325 kPa]. The acylation of thiophene with dimethylcarbamyl chloride was approximately in accord with the first order kinetic equation at 303-323 K. The activation energy was 53.9850 kJ/mol and the pre-exponential factor was 1.4521×109 h-1.

关键词: Coking crude benzene, F-C acylation, Acyl chloride, Thiophene, Thiophene derivative

Abstract: Since the content of thiophene in coking crude benzene is high, it is necessary to remove it from coking crude benzene for efficient utilization. In this study, an important intermediate, N,N-dimethyl-2-thiophenecar-boxamide, was synthesized from thiophene and dimethylcarbamyl chloride. The influences of the dosages of dimethylcarbamyl chloride and ZnCl2 catalyst, reaction temperature and time on the removal rate were further explored based on the reaction kinetics. The structure of the target product was characterized by means of MS, 1H NMR and 13C NMR. The removal rate of thiophene was 98.14% after the reaction for 2 h and thiophene was almost removed after the reaction for 3 h under the optimal reaction conditions[a molar ratio of n(thiophene):n(dimethylcarbamyl chloride):n(ZnCl2)=1:12:10, 300 r/min, 318 K and 101.325 kPa]. The acylation of thiophene with dimethylcarbamyl chloride was approximately in accord with the first order kinetic equation at 303-323 K. The activation energy was 53.9850 kJ/mol and the pre-exponential factor was 1.4521×109 h-1.

Key words: Coking crude benzene, F-C acylation, Acyl chloride, Thiophene, Thiophene derivative