Nitration process of 2-(2,4-dichlorophenyl)-4-(difluoromethyl)-5-methyl-1,2,4-triazol-3-one in a microreactor

IF 2 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Flow Chemistry Pub Date : 2023-11-09 DOI:10.1007/s41981-023-00289-7
Jian-yang Cao, Jing Hou, Le-wu Zhan, Bin-dong Li
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Abstract

In a continuous flow microreactor system, a continuous nitration process of 2-(2,4-dichloro-5-nitrophenyl)-4-(difluoromethyl)-5-methyl-1,2,4-triazol-3-one which is the key intermediate for the synthesis of important triazolinone herbicide Sulfentrazone was developed. The effects of molar ratio of mixed acids, molar ratio of nitric acid to substrate, reaction temperature, total flow rate and residence time in the microreactor on nitration reaction were studied. The results showed that when the flow rate of the material was 60 mL/min, the molar ratio of nitrate to sulfur mixed acid was 1:6, the molar ratio of nitric acid to raw material was 1.1:1, the reaction temperature was 60 ℃, and the residence time was 30 s, the product can be obtained in 97% yield. Compared with the results of nitration process using traditional batch reactors, the use of continuous flow microreactors improved reaction efficiency and achieved higher yields. A characterization kinetics study was conducted on this reaction, and the pre-exponential-factor and activation energy for 2-(2,4-dichlorophenyl)-4-(difluoromethyl)-5-methyl-1,2,4-triazol-3-one nitration were obtained. The activation energy of the reaction is 40.204 kJ/mol. The continuous flow microreactor system greatly increased liquid-liquid two phases mass transfer efficiency, while accurately controlling the reaction temperature and residence time in the reactor.

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微反应器中 2-(2,4-二氯苯基)-4-(二氟甲基)-5-甲基-1,2,4-三唑-3-酮的硝化过程
在连续流微反应器系统中,开发了 2-(2,4-二氯-5-硝基苯基)-4-(二氟甲基)-5-甲基-1,2,4-三唑-3-酮的连续硝化工艺,该工艺是合成重要的三唑酮类除草剂磺草酮的关键中间体。研究了混合酸的摩尔比、硝酸与底物的摩尔比、反应温度、总流量和在微反应器中的停留时间对硝化反应的影响。结果表明,当物料流速为 60 mL/min、硝硫混合酸摩尔比为 1:6、硝酸与原料摩尔比为 1.1:1、反应温度为 60 ℃、停留时间为 30 s 时,产品收率可达 97%。与使用传统间歇反应器进行硝化过程的结果相比,使用连续流微反应器提高了反应效率,并获得了更高的产率。对该反应进行了表征动力学研究,得到了 2-(2,4-二氯苯基)-4-(二氟甲基)-5-甲基-1,2,4-三唑-3-酮硝化反应的预指数和活化能。反应的活化能为 40.204 kJ/mol。连续流微反应器系统大大提高了液液两相的传质效率,同时精确控制了反应器中的反应温度和停留时间。
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来源期刊
Journal of Flow Chemistry
Journal of Flow Chemistry CHEMISTRY, MULTIDISCIPLINARY-
CiteScore
6.40
自引率
3.70%
发文量
29
审稿时长
>12 weeks
期刊介绍: The main focus of the journal is flow chemistry in inorganic, organic, analytical and process chemistry in the academic research as well as in applied research and development in the pharmaceutical, agrochemical, fine-chemical, petro- chemical, fragrance industry.
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