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Continuous synthesis of benzaldehyde by ozonolysis of styrene in a micro-packed bed reactor

Continuous synthesis of benzaldehyde by ozonolysis of styrene in a micro-packed bed reactor Due to the inherent safety and high mass/heat transfer efficiency of microreactor, the continuous micro-reaction technology has been widely applied in hazardous chemistry recently. In this work, a continuous ozonolysis system based on micro-packed bed reactors (µPBRs) was developed with the synthesis of benzaldehyde as a model reaction. The effects of operating variables (e.g., stirring time, molar ozone/olefin ratio, reaction pressure, reaction temperature and liquid residence time) on the olefins conversion and product distribution were investigated. Based on the experimental results, the optimum reaction conditions are as follows: stirring time 1 h, molar ratio of ozone to olefin 1.2, reaction pressure 0.1 MPa, and the reaction temperature ranging from − 15 to 10℃, as opposed to the low temperature (<-50℃) routinely employed for batch operation. In addition, the full conversion of styrene and a benzaldehyde yield of ~ 93% was observed with the liquid residence time of 3.8–30.8 s. Consequently, the flow ozonolysis technique upon µPBRs allows for a sustainable, safe and efficient approach to oxidize olefins to aldehydes/ketones compared to traditional methods. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

Continuous synthesis of benzaldehyde by ozonolysis of styrene in a micro-packed bed reactor

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Publisher
Springer Journals
Copyright
Copyright © Akadémiai Kiadó 2022
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1007/s41981-022-00220-6
Publisher site
See Article on Publisher Site

Abstract

Due to the inherent safety and high mass/heat transfer efficiency of microreactor, the continuous micro-reaction technology has been widely applied in hazardous chemistry recently. In this work, a continuous ozonolysis system based on micro-packed bed reactors (µPBRs) was developed with the synthesis of benzaldehyde as a model reaction. The effects of operating variables (e.g., stirring time, molar ozone/olefin ratio, reaction pressure, reaction temperature and liquid residence time) on the olefins conversion and product distribution were investigated. Based on the experimental results, the optimum reaction conditions are as follows: stirring time 1 h, molar ratio of ozone to olefin 1.2, reaction pressure 0.1 MPa, and the reaction temperature ranging from − 15 to 10℃, as opposed to the low temperature (<-50℃) routinely employed for batch operation. In addition, the full conversion of styrene and a benzaldehyde yield of ~ 93% was observed with the liquid residence time of 3.8–30.8 s. Consequently, the flow ozonolysis technique upon µPBRs allows for a sustainable, safe and efficient approach to oxidize olefins to aldehydes/ketones compared to traditional methods.

Journal

Journal of Flow Chemistry – Springer Journals

Published: Sep 1, 2022

Keywords: Ozonolysis; Micro-packed bed reactors; Styrene; Benzaldehyde; Hazardous chemistry

References

  • The medicinal chemist’s toolbox: an analysis of reactions used in the pursuit of drug candidates[J]
    Roughley, SD; Jordan, AM
  • Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: an organometallic ozonolysis[J]
    Travis, BR; Narayan, RS; Borhan, B
  • The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst[J]
    Bumler, C; Bauer, C; Kempe, R
  • AIBN-catalyzed oxidative cleavage of gem-disubstituted alkenes with O2 as an oxidant[J]
    Wang, GZ; Li, XL; Dai, JJ
  • Selective copper(II)-catalyzed aerobic oxidative cleavage of aromatic gem-disubstituted alkenes to carbonyl compounds under neutral and mild conditions[J]
    Hossain, MM; Shyu, S-G
  • Noble metal-free V2O5/g-C3N4 composites for selective oxidation of olefins using hydrogen peroxide as an oxidant[J]
    Zou, H; Xiao, G; Chen, K
  • Magnetically recoverable porphyrin-based nanocatalysts for the effective oxidation of olefins with hydrogen peroxide: a comparative study[J]
    Rayati, S; Moradi, D; Nejabat, F
  • Magnetic cobalt ferrite nanoparticles as an efficient catalyst for oxidation of alkenes[J]
    Kooti, M; Afshari, M
  • Ruthenium-catalyzed oxidative cleavage of olefins to aldehydes[J]
    Yang, D; Zhang, C
  • Ozonolysis Applications in Drug Synthesis[J]
    Ornum, SG; V, Champeau, RM; Pariza, R
  • An overview of ozonation associated with nano-filtration as an effective procedure in treating dye effluents from textile industries with the help of a bubble column reactor[J]
    Sukanchan, P
  • Flow Distribution and Ozonolysis in Gas-Liquid Multichannel Microreactors[J]
    Wada, Y; Schmidt, MA; Jensen, KF
  • Ozonolysis in solvent/water mixtures: direct conversion of alkenes to aldehydes and ketones[J]
    Schiaffo, CE; Dussault, PH
  • Direct conversion of terminal alkenes to aldehydes via ozonolysis reaction in rotating zigzag bed[J]
    Liang, Z; Wei, T; Xie, J
  • Scalable, sustainable and catalyst-free continuous flow ozonolysis of fatty acids[J]
    Atapalkar, RS; Athawale, PR; Reddy, DS
  • One-pot oxidative cleavage of olefins to synthesize carboxylic acids by a telescoped ozonolysis–oxidation process[J]
    Cochran, BM
  • ’Reductive ozonolysis’ via a new fragmentation of carbonyl oxides[J]
    Schwartz, C; Raible, J; Mott, K
  • Fragmentation of Carbonyl Oxides by N-Oxides: An Improved Approach to Alkene Ozonolysis[J]
    Schwartz, C; Raible, J; Mott, K
  • Synthesis of Ethyl Benzoate by Ozonolysis of Styrene in the Presence of Ethanol[J]
    Gaifutdinova, EK; Beresnev, VV
  • Intensified ozonolysis of lignins in a spray reactor: insights into product yields and lignin structure[J]
    Silverman, JR; Danby, AM; Subramaniam, B
  • Pyridine Is an Organocatalyst for the Reductive Ozonolysis of Alkenes[J]
    Charnley, RW; Fisher, T; Johnson, J
  • Highly efficient biphasic ozonolysis of alkenes using a high-throughput film-shear flow reactor[J]
    Kendall, AJ; Barry, JT; Seidenkranz, DT
  • Reaction Mechanism and in Situ ATR Spectroscopic Studies of the 1-Decene Ozonolysis in Micro- and Semibatch Reactors[J]
    Steinfeldt, N; Bentrup, U; Jahnisch, K
  • A quantitative investigation of the ozonolysis reaction. XVIII. A kinetic study of the ozone attack on phenylethylenes[J]
    Henry, H; Zador, M; Fliszar, S
  • Flow ozonolysis using a semipermeable Teflon AF-2400 membrane to effect gas-liquid contact[J]
    O’brien, M; Baxendale, IR; Ley, SV
  • Continuous flow ozonolysis in a laboratory scale reactor[J]
    Irfan, M; Glasnov, TN; Kappe, CO
  • Efficient depolymerization of lignin to biobased chemicals using a two-step approach involving ozonation in a continuous flow microreactor followed by catalytic hydrotreatment[J]
    Figueirêdo, MB; Keij, F; Hommes, A
  • Ozonolysis of quinoline and quinoline derivatives in a Corning low flow reactor[J]
    Lee, K; Lin, H; Jensen, KF
  • Automated measurements of gas-liquid mass transfer in micropacked bed reactors[J]
    Zhang, J; Teixeira, AR; Jense, KF
  • Hydrodynamics of gas–liquid flow in micropacked beds: Pressure drop, liquid holdup, and two-phase model[J]
    Zhang, J; Teixeira, AR; Kögl, LT
  • Toward a Continuous-Flow Synthesis of Boscalid®[J]
    Glasnov, TN; Kappe, CO
  • Hydrodynamic effects on three phase micro-packed bed reactor performance–gold–palladium catalysed benzyl alcohol oxidation[J]
    Al-Rifai, N; Galvanin, F; Morad, M
  • Intensified and safe ozonolysis of fatty acid methyl esters in liquid CO2 in a continuous reactor[J]
    Lundin, MD; Danby, AM; Akien, GR
  • A new and convenient method for converting olefins to aldehydes[J]
    Pappas, JJ; Keaveney, WP; Gancher, E
  • Development of a Commercial Process to Prepare AMG 232 Using A Green Ozonolysis-Pinnick Tandem Transformation[J]
    Cochran, BM; Corbett, MT; Correll, TL
  • Valorization of grass lignins: Swift and selective recovery of pendant aromatic groups with ozone[J]
    Danby, AM; Lundin, MD; Subramaniam, B
  • A highly efficient synthesis of benzaldehyde by ozonolysis of styrene in a rotating packed bed[J]
    Gao, W; Du, L; Li, P
  • Solubility of Ozone in Organic Solvents[J]
    Panich, NM; Ershov, BG
  • Their Advantages, Disadvantages, and Alternatives in Organic and Medicinal Chemistry[J]
    Jordan, A; Stoy, P; Sneddon, HF; Chlorinated Solvents
  • Transformations of Peroxide Products of Alkene Ozonolysis[J]
    Myasoedova, YV; Nazarov, IS; Ishmuratov, GY
  • Transformations of peroxide products of olefins ozonolysis[J]
    Ishmuratov, GY; Legostaeva, YV; Botsman, LP
  • Synthetic studies related to oral β-lactam antibiotics[J]
    Yoshioka, M
  • Ozonolysis of some complex organic substrates in flow[J]
    Roydhouse, MD; Motherwell, WB; Constantinou, A
  • The Reactions Of Ozone With Organic Compounds[J]
    Bailey, PS
  • Mechanism of Ozonolysis[J]
    Criegee, R
  • The production of biobased nonanal by ozonolysis of fatty acids[J]
    Omonov, TS; Kharraz, E; Foley, P