Homogeneous continuous flow nitration of O-methylisouronium sulfate and its optimization by kinetic modeling.

IF 2.2 4区 化学 Q2 CHEMISTRY, ORGANIC Beilstein Journal of Organic Chemistry Pub Date : 2024-09-24 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.205
Jiapeng Guo, Weike Su, An Su
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Abstract

Nitration of O-methylisouronium sulfate under mixed acid conditions gives O-methyl-N-nitroisourea, a key intermediate of neonicotinoid insecticides with high application value. The reaction is a fast and highly exothermic process with a high mass transfer resistance, making its control difficult and risky. In this paper, a homogeneous continuous flow microreactor system was developed for the nitration of O-methylisouronium sulfate under high concentrations of mixed acids, with a homemade static mixer eliminating the mass transfer resistance. In addition, the kinetic modeling of this reaction was performed based on the theory of NO2 + attack, with the activation energy and pre-exponential factor determined. Finally, based on the response surface generated by the kinetic model, the reaction was optimized with a conversion of 87.4% under a sulfuric acid mass fraction of 94%, initial reactant concentration of 0.5 mol/L, reaction temperature of 40 °C, molar ratio of reactants at 4.4:1, and a residence time of 12.36 minutes.

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O-甲基异脲硫酸盐的均相连续流硝化及其动力学模型优化。
在混合酸条件下,O-甲基异脲硫酸盐发生硝化反应,生成 O-甲基-N-硝基异脲,这是一种新烟碱类杀虫剂的关键中间体,具有很高的应用价值。该反应是一个快速、高放热、高传质阻力的过程,因此其控制难度大、风险高。本文开发了一种均相连续流微反应器系统,用于在高浓度混合酸条件下硝化 O-甲基异脲硫酸盐,自制的静态混合器消除了传质阻力。此外,还根据 NO2 + 攻击理论对该反应进行了动力学建模,并确定了活化能和预指数因子。最后,根据动力学模型生成的响应面,对该反应进行了优化,在硫酸质量分数为 94%、初始反应物浓度为 0.5 摩尔/升、反应温度为 40 °C、反应物摩尔比为 4.4:1、停留时间为 12.36 分钟的条件下,转化率为 87.4%。
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来源期刊
CiteScore
4.90
自引率
3.70%
发文量
167
审稿时长
1.4 months
期刊介绍: The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
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