Continuous flow nitration of 3-[2-chloro-4-(trifluoromethyl) phenoxy] benzoic acid and its chemical kinetics within droplet-based microreactors

Li, Shenfang; Zhang, Xunli; Ji, Desheng; Wang, Qingqiang; Jin, Nanguo; Zhao, Yuchao

doi:10.1016/j.ces.2022.117657

Cited by 16 publications

(13 citation statements)

References 56 publications

(64 reference statements)

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“…And according to the Arrhenius formula, with the increase in reaction temperature, the reaction rate would increase. In addition, for heterogeneous reactions, the increase in reaction temperature leads to a rise in molecular diffusion coefficient, and the mass transfer between the two phases is better . Thus, the reaction conversion was higher under the same residence time when the reaction temperature T r was higher.…”

Section: Results and Discussionmentioning

confidence: 99%

Study on Continuous Flow Nitration of Naphthalene

Xu,

Chen,

et al. 2023

Org. Process Res. Dev.

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In this work, the continuous flow nitration of naphthalene to 1-nitronaphthalene was systematically studied from the microreactor to mesoscale flow reactor and the safety issues during the reaction process were investigated. The effect of the molar ratio of nitric acid to naphthalene, residence time, reaction temperature, and sulfuric acid strength on the reaction process was comprehensively investigated in the microreactor. Under optimal conditions, the reaction yield could reach 94.96%. Due to the rapid exothermic characteristics of nitration, a quick heat transfer assessment was proposed to obtain the temperature profile during optimal conditions. It was found that the maximum overtemperature during the reaction was only 3.78 °C, which was consistent with the high yield under the optimal conditions. Then a scale-up of the microreactor to production was realized by a dimensionenlarging strategy. In the mesoscale flow reactor, the influence of volumetric flow rates was investigated. The annual output of the flow reactor could reach 2643 kg•a −1 while the highest overtemperature inside the reactor channel well exceeded 17.1 °C. In addition, a conventional semibatch experiment was carried out in the batch calorimeter RC1e to explore the reaction's exothermic characteristics. Finally, the performances of the two reactors were compared, showing that the continuous flow reactor had more advantages than the batch reactor in economic benefit and inherent safety.

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Section: Results and Discussionmentioning

confidence: 99%

Study on Continuous Flow Nitration of Naphthalene

Xu,

Chen,

et al. 2023

Org. Process Res. Dev.

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“…The variation in reactant conversion was probably a result of the effect of the total flow rate on the flow dynamic behaviour of droplet-based microfluidics, such as the geometry of the dispersed droplets, their possible coalescence along the microchannel and the twophase interface property(Figure S4, Sl). [15] Two-phase nitrification occurs mainly at the interface of the two phases, which leads to the thermal effect of nitrification being highly concentrated. Typically, smaller dispersed droplets can be formed at high total flow rates, increasing the surface area of the two phases, and resulting in better mass transfer performance and higher reaction rates.…”

Section: Effects Of Varying Total Flow Rate On Mnb Nitration Stagementioning

confidence: 99%

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

Zhao¹,

Zhang²,

Wei³

et al. 2023

ChemistrySelect

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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 mdinitrobenzene was more than 91 % with a residence time of 4 min at 70 °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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“…Recently, microreactor technology has opened new horizons both in academia and industries, becoming a more sustainable and reliable alternative for safer nitration (Cui et al, 2022;Ducry and Roberge, 2005;Guo et al, 2023;Li et al, 2022;Song et al, 2022a;Song et al, 2022b). Microreactors possess internal channels with micron or submillimeter characteristic dimensions, based on which many advantages have emerged, ranging from excellent mass and heat transfer performance to easy scale-up and potential of full process automation.…”

Section: Introductionmentioning

confidence: 99%

“…As a result, the reaction temperature could be raised moderately to accelerate the reaction rate. For example, Li et al (Li et al, 2017;Li et al, 2022) realized the nitration of 2-ethylhexanol and 3-[2-chloro-4-(trifluoromethyl) phenoxy] benzoic acid at room temperature in continuous flow microreactors. Compared with the commonly used temperature of around 273 K in batch reactors, not only shorter reaction times (seconds or minutes) were acquired in microreactors, but also operating difficulties and energy consumption could be decreased.…”

Section: Introductionmentioning

confidence: 99%

“…Wen et al (Wen et al, 2017) used a microreactor for the continuous nitration of trifluoromethoxybenzene in which the conversion was up to 99.6% and the selectivity of the main product (4-(trifluoromethoxy)nitrobenzene) reached 90.97% within 2.4 min. Furthermore, microreactors have shown advantages in the characterization of nitration kinetics, mainly due to the high degree of controllability over the temperature and concentrations in the multiphase microenvironment (Cui et al, 2022;Li et al, 2017;Li et al, 2022;Song et al, 2022a;Song et al, 2022b).…”

Section: Introductionmentioning

confidence: 99%

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Heterogeneous nitration of nitrobenzene in microreactors: Process optimization and modelling

Jin,

Song,

Yue

et al. 2023

Chemical Engineering Science

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Continuous flow nitration of 3-[2-chloro-4-(trifluoromethyl) phenoxy] benzoic acid and its chemical kinetics within droplet-based microreactors

Cited by 16 publications

References 56 publications

Study on Continuous Flow Nitration of Naphthalene

Study on Continuous Flow Nitration of Naphthalene

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

Heterogeneous nitration of nitrobenzene in microreactors: Process optimization and modelling

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