Helically coiled segmented flow tubular reactor for the hydroformylation of long-chain olefins in a thermomorphic multiphase system

Jokiel, Michael; Kaiser, Nicolas Maximilian; Kováts, Péter; Mansour, Michael; Zähringer, Katharina; Nigam, K.D.P.; Sundmacher, Kai

doi:10.1016/j.cej.2018.09.221

Cited by 27 publications

(9 citation statements)

References 22 publications

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“…This was the motivation of for further studies concerning this subject (e.g. Jokiel et al 2019;Mansour et al 2020b) and also for this present experimental investigation.…”

Section: Introductionmentioning

confidence: 63%

Experimental characterization of mixing and flow field in the liquid plugs of gas–liquid flow in a helically coiled reactor

2021

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Flow mixing of two miscible liquids with the addition of gas bubbles is a process often found in industrial chemical apparatus for the production of primary matter. The ongoing optimization of such processes also involves the transformation of batch to continuous mode operation. In that case, the use of helically coiled tubes is an interesting alternative, since those reactors have narrow residence time distributions, very good radial mixing properties and excellent mass transfer can be realized between gases and liquids. For these reasons, in this study the mixing of two miscible liquids with addition of air bubbles in gas–liquid flows has been characterized in a horizontal helically coiled reactor in the laminar flow regime at $${\text{Re}}_{{{\text{total}}}} = 300 \ldots 1088$$ Re total = 300 … 1088 . Eight different superficial liquid velocities and five superficial gas velocities were investigated. In order to characterize mixing in the liquid plugs between two bubbles, laser-induced fluorescence of resorufin was used and particle image velocimetry has been employed to characterize the flow field. Pseudo-3D-visualizations of the resorufin concentration and the Q-criterion, representing the mixing efficiency and vorticity, respectively, were established for individual liquid plugs from the time-resolved measurement results. A time-resolved mixing coefficient, as well as a mean mixing coefficient obtained from multiple liquid plugs, is calculated from the fluorescence images for all examined flow conditions. The experimental results clearly show an increase in the mixing coefficient compared to single-phase conditions, caused by the bubbles. However, distinct mixing pattern, depending on the flow structure, can be recognized on different locations inside the liquid plug. Compared to a stationary case without air bubbles, mixing is worse behind the bubbles and increases inside the plug, reaching a maximum mixing coefficient in front of the next bubble. Overall the mixing coefficient is always increased by the presence of the bubbles. Pseudo-3D-visualizations of the Q-criterion and the vorticity show the presence of secondary vortices right in front of the bubbles, shifted to the outer tube walls, and in addition to the steady Dean vortices. In small plugs, these secondary vortices appear in the whole plug and increase the mixing coefficient drastically. Graphical Abstract

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“…This was the motivation of for further studies concerning this subject (e.g. Jokiel et al 2019;Mansour et al 2020b) and also for this present experimental investigation.…”

Section: Introductionmentioning

confidence: 63%

Experimental characterization of mixing and flow field in the liquid plugs of gas–liquid flow in a helically coiled reactor

2021

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“…Comparing all three cases, the last two allowed longer residence times and higher conversion, reducing the need of recycling the reagent. Furthermore, the PFR-CSTR system was experimentally constructed and configured [ 562 ]. A solution of 1-dodecene ( 656 ) in n- decane was mixed with the rhodium catalyst and the ligand (BiPhePhos) in DMF and then the biphasic system was streamed through the PFR.…”

Section: Reviewmentioning

confidence: 99%

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta¹,

Sharley²,

Baxendale³

2021

Beilstein J. Org. Chem.

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Due to their intrinsic physical properties, which includes being able to perform as volatile liquids at room and biological temperatures, fragrance ingredients/intermediates make ideal candidates for continuous-flow manufacturing. This review highlights the potential crossover between a multibillion dollar industry and the flourishing sub-field of flow chemistry evolving within the discipline of organic synthesis. This is illustrated through selected examples of industrially important transformations specific to the fragrances and flavours industry and by highlighting the advantages of conducting these transformations by using a flow approach. This review is designed to be a compendium of techniques and apparatus already published in the chemical and engineering literature which would constitute a known solution or inspiration for commonly encountered procedures in the manufacture of fragrance and flavour chemicals.

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“…Recently, the hydroformylation of long-chain olefins, which can be produced from renewable feedstocks, was carefully investigated in order to design an efficient process using homogeneous catalysis. − The process is based on a temperature-controlled switchable solvent system called a thermomorphic multicomponent system (TMS) enabling the reaction and the separation of the product from the catalyst. N , N -Dimethylformamide (DMF) was proposed initially as a promising solvent candidate by chemical intuition and was later identified as one of the best performing solvents from a thermodynamic point of view. , However, DMF is a developmental toxic substance, and is included in the REACH list of components of very high concern.…”

Section: Introductionmentioning

confidence: 99%

Systematic Green Solvent Selection for the Hydroformylation of Long-Chain Alkenes

Linke

McBride

Sundmacher

2020

ACS Sustainable Chem. Eng.

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When selecting solvents, not only thermodynamic criteria but also environmental, health, and safety (EHS) properties should be considered. To this end, we present a fully automated solvent selection approach for the homogeneous catalyzed hydroformylation of 1-decene in a temperature-dependent thermomorphic multicomponent system (TMS) using the conductor-like screening model for real solvents (COSMO-RS). The state-of-the-art TMS uses N,N-dimethylformamide (DMF) as the catalyst carrier, which is developmentally toxic, thereby demanding replacement. In order to evaluate the EHS properties holistically, 30 predictive EHS models for 15 different properties are considered in the solvent selection framework, as well as the reliability of the predictions. From a database containing approximately 7800 molecules, the most promising candidates are identified. The best solvent among them, diethyl sulfoxide (DESO), is predicted as outperforming DMF as a catalyst solvent in the hydroformylation. The evidence suggests that DESO may be a broadly applicable environmentally benign substitute solvent for DMF.

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Helically coiled segmented flow tubular reactor for the hydroformylation of long-chain olefins in a thermomorphic multiphase system

Cited by 27 publications

References 22 publications

Experimental characterization of mixing and flow field in the liquid plugs of gas–liquid flow in a helically coiled reactor

Experimental characterization of mixing and flow field in the liquid plugs of gas–liquid flow in a helically coiled reactor

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Systematic Green Solvent Selection for the Hydroformylation of Long-Chain Alkenes

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