Safe, Green, and Efficient Synthesis of m-Dinitrobenzene via Two-Step Nitration in a Continuous-Flow Microreactor

被引:5
作者
Zhao, Wenyuan [1 ]
Zhang, Qi [1 ]
Wei, Wei [1 ]
Xu, Weichang [1 ]
Sun, Wenxuan [1 ]
An, Tingwang [1 ]
Ji, Lu [1 ]
Wang, Hande [1 ]
Zhou, Chuan [1 ]
Yan, Dongmao [1 ]
机构
[1] Shenyang Res Inst Chem Ind, 8 East Shen Liao Rd, Shenyang 110021, Peoples R China
来源
CHEMISTRYSELECT | 2023年 / 8卷 / 14期
基金
中国国家自然科学基金;
关键词
Microreactors; Continuous flow; Nitration; Kilogram-scale; m-dinitrobenzene; NITRIC-ACID; AROMATIC NITRATION; NITROBENZENE; PERFORMANCE; BENZENE;
D O I
10.1002/slct.202204997
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In industry, m-dinitrobenzene is mainly obtained by two-step nitration of benzene, but still faces the problem of being heterogeneous and highly exothermic. In this work, a two-step continuous-flow nitration was developed in a microreactor, combining benzene nitration and mononitrobenzene nitration in series. The waste acid after the mononitrobenzene nitration stage was utilized in the benzene mononitration stage, and the waste acid in the benzene mononitration stage was treated and concentrated for reuse. The whole process consumes almost no sulfuric acid. Under optimal conditions, the yield of dinitrobenzene was more than 99.0 % and the selectivity of m-dinitrobenzene was more than 91 % with a residence time of 4 min at 70 degrees C. In addition, the space-time yield of the continuous microreactor was 800 times higher than the batch reactor. It provides a safe and efficient method for the industrial production of m-dinitrobenzene.
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页数:8
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共 34 条
  • [1] Phenol in Mixed Acid Benzene Nitration Systems
    Afonso, Diogo
    Ribeiro, Alejandro F. G.
    Araujo, Paulo
    Vital, Joaquim
    Madeira, Luis M.
    [J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2018, 57 (46) : 15942 - 15953
  • [2] Mixing performance of unbalanced split and recombine micomixers with circular and rhombic sub-channels
    Ansari, Mubashshir Ahmad
    Kim, Kwang-Yong
    [J]. CHEMICAL ENGINEERING JOURNAL, 2010, 162 (02) : 760 - 767
  • [3] Numerical and Experimental Quantification of the Performance of Microreactors for Scaling-up Fast Chemical Reactions
    Asano, Shusaku
    Yatabe, Shota
    Maki, Taisuke
    Mae, Kazuhiro
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (05) : 807 - 817
  • [4] A microreactor for the nitration of benzene and toluene
    Burns, JR
    Ramshaw, C
    [J]. CHEMICAL ENGINEERING COMMUNICATIONS, 2002, 189 (12) : 1611 - 1628
  • [5] Safe, efficient and selective synthesis of dinitro herbicides via a multifunctional continuous-flow microreactor: one-step dinitration with nitric acid as agent
    Chen, Yizheng
    Zhao, Yuchao
    Han, Mei
    Ye, Chunbo
    Dang, Minhui
    Chen, Guangwen
    [J]. GREEN CHEMISTRY, 2013, 15 (01) : 91 - 94
  • [6] The continuous kilogram-scale process for the synthesis of 2,4,5-trifluorobromobenzene via Gattermann reaction using microreactors
    Deng, Qiulin
    Lei, Qin
    Shen, Ruwei
    Chen, Chao
    Zhang, Lixiong
    [J]. CHEMICAL ENGINEERING JOURNAL, 2017, 313 : 1577 - 1582
  • [7] NITRIC ACID EQUILIBRIA IN WATER-SULFURIC ACID
    DENO, NC
    PETERSON, HJ
    SACHER, E
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1961, 65 (02) : 199 - &
  • [8] Electrophilic aromatic nitration: Understanding its mechanism and substituent effects
    Freire de Queiroz, Jorge
    Walkimar de M. Carneiro, Jose
    Sabino, Adao A.
    Sparrapan, Regina
    Eberlin, Marcos N.
    Esteves, Pierre M.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (16) : 6192 - 6203
  • [9] Dynamics and controllability of droplet fusion under gas-liquid-liquid three-phase flow in a microfluidic reactor
    Hao, Yanyan
    Jin, Nan
    Wang, Qingqiang
    Zhou, Yufei
    Zhao, Yuchao
    Zhang, Xunli
    Lu, Hongying
    [J]. RSC ADVANCES, 2020, 10 (24) : 14322 - 14330
  • [10] A modular microreactor for mixed acid nitration
    Henke, L
    Winterbauer, H
    [J]. CHEMICAL ENGINEERING & TECHNOLOGY, 2005, 28 (07) : 749 - 752