SCI和EI收录∣中国化工学会会刊

Chinese Journal of Chemical Engineering ›› 2020, Vol. 28 ›› Issue (8): 2092-2098.DOI: 10.1016/j.cjche.2020.06.001

• Catalysis, Kinetics and Reaction Engineering • Previous Articles     Next Articles

Continuous, homogeneous and rapid synthesis of 4-bromo-3-methylanisole in a modular microreaction system

Pei Xie, Kai Wang, Jian Deng, Guangsheng Luo   

  1. The State Key Laboratory of Chemical Engineering, Department of Chemical Engineering, Tsinghua University, Beijing 100084, China
  • Received:2020-04-15 Revised:2020-05-25 Online:2020-09-19 Published:2020-08-28
  • Contact: Guangsheng Luo
  • Supported by:
    We gratefully acknowledge financial support from National Key R&D Program of China (2017YFB0307102), and National Natural Science Foundation of China (21991100, 21991104)

Continuous, homogeneous and rapid synthesis of 4-bromo-3-methylanisole in a modular microreaction system

Pei Xie, Kai Wang, Jian Deng, Guangsheng Luo   

  1. The State Key Laboratory of Chemical Engineering, Department of Chemical Engineering, Tsinghua University, Beijing 100084, China
  • 通讯作者: Guangsheng Luo
  • 基金资助:
    We gratefully acknowledge financial support from National Key R&D Program of China (2017YFB0307102), and National Natural Science Foundation of China (21991100, 21991104)

Abstract: 4-Bromo-3-methylanisole is mainly used to synthesize black fluorane dye (2-anilino-3-methyl-6- dibutylaminofluorane, ODB-2), which is one of the most important heat and pressure-sensitive dyes in the manufacture of thermal papers. Compared to the industrial heterogeneous batch process, a continuous homogeneous bromination technology in a modular microreaction system has been developed, and 4-bromo-3-methylanisole has been successfully prepared through high-selective mono-bromination of 3-methylanisole with Br2 solution in CHCl3. In optimal conditions, the content of bis-brominated byproducts can be controlled less than 0.5%, which is superior to the industrial standard with 99.5% 3-methylanisole conversion at very short residence time and mild reaction temperature.

Key words: 4-bromo-3-methylanisole, bromination, continuous synthesis, modular microreaction system, mixing enhancement

摘要: 4-Bromo-3-methylanisole is mainly used to synthesize black fluorane dye (2-anilino-3-methyl-6- dibutylaminofluorane, ODB-2), which is one of the most important heat and pressure-sensitive dyes in the manufacture of thermal papers. Compared to the industrial heterogeneous batch process, a continuous homogeneous bromination technology in a modular microreaction system has been developed, and 4-bromo-3-methylanisole has been successfully prepared through high-selective mono-bromination of 3-methylanisole with Br2 solution in CHCl3. In optimal conditions, the content of bis-brominated byproducts can be controlled less than 0.5%, which is superior to the industrial standard with 99.5% 3-methylanisole conversion at very short residence time and mild reaction temperature.

关键词: 4-bromo-3-methylanisole, bromination, continuous synthesis, modular microreaction system, mixing enhancement