Ozonolysis of some complex organic substrates in flow

Roydhouse, Mark D.; Motherwell, William B.; Constantinou, Achilleas; Gavriilidis, Asterios; Wheeler, Rob C.; Down, K.; Campbell, Ian B.

doi:10.1039/c3ra00125c

Cited by 40 publications

(33 citation statements)

References 31 publications

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“…Ozonolysis of 2-(3-methoxyoxetan-3-yl)furan to its oxetane acid in a Vapourtec cooled reaction module. 283 Sun et al have reported on the ozone degradation of pentachlorophenol in a T-junction microchannel reactor (400 µm x 500 µm, 14 µL). 284 The authors have performed a systematic study to the ozone mass transfer characteristics in different gas-liquid flow regimes.…”

Section: Ozonolysis In Flowmentioning

confidence: 99%

Liquid phase oxidation chemistry in continuous-flow microreactors

et al. 2016

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Continuous-flow liquid phase oxidation chemistry in microreactors receives a lot of attention as the reactor provides enhanced heat and mass transfer characteristics, safe use of hazardous oxidants, high interfacial areas, and scale-up potential. In this review, an up-to-date overview of both technological and chemical aspects of liquid phase oxidation chemistry in continuous-flow microreactors is given. A description of mass and heat transfer phenomena is provided and fundamental principles are deduced which can be used to make a judicious choice for a suitable reactor. In addition, the safety aspects of continuous-flow technology are discussed. Next, oxidation chemistry in flow is discussed, including the use of oxygen, hydrogen peroxide, ozone and other oxidants in flow. Finally, the scale-up potential for continuous-flow reactors is described.

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Section: Ozonolysis In Flowmentioning

confidence: 99%

Liquid phase oxidation chemistry in continuous-flow microreactors

et al. 2016

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“…1-Decene and ethyl sorbate were used as substrates for the ozonolysis reaction with concentrations ranging from 0.05 M to 0.28 M, while tridecane was used as internal standard due to its slow oxidation rate with ozone [8]. Triethylphosphite and triphenylphosphine 0.28 M in ethyl acetate solutions were used as quench agents [8,14]. Nitrogen and oxygen gas cylinders were purchased from Airgas.…”

Section: Discussionmentioning

confidence: 99%

“…Irfan et al performed ozonolysis of several substrates in a commercial flow reactor (O-Cube, ThalesNano, Hungary) from 0°C to ambient temperature and flow rates in the range 0.2-2.0 mL/min, achieving isolated yields of 72-90% [12]. Most recently, Roydhouse et al demonstrated the use of Vapourtec technology coupled with an ozone generator to perform ozonolysis of complex organic substrates in flow, observing good conversion (49-99%) to the corresponding aldehydes and ketones using an in-flow quench of triphenylphosphine [13,14].…”

Section: Introductionmentioning

confidence: 99%

Mass Transfer Characteristics of Ozonolysis in Microreactors and Advanced-Flow Reactors

Nieves‐Remacha¹,

Jensen²

2015

J Flow Chem

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Ozonolysis of alkenes in liquid phase is conducted from micro scales to milli scales using a multichannel microreactor, a Corning low-flow reactor (LFR), and a Corning advanced-flow reactor (AFR). For the mass transfer limited test case of ozonolysis of 1-decene, maximum conversions that depend on the ozone availability in the gas phase are achieved regardless of the operating conditions, proving an excellent mass transfer in all three reactors. Ozonolysis of Sudan Red 7B dye provides visualization of the completion of the reaction in the glass-made AFR and LFR. Overall mass transfer coefficients are estimated to be on the order of 1/s in both the LFR and AFR, increasing with both liquid and gas flow rates. These values are within the same range observed in microchannels and one order of magnitude larger than in other conventional contactors.

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“…The operation of ozonolysis on large scales always involves a certain amount of trepidation due the highly reactive nature of the intermediate molozonides and ozonides. While the application of flow-technology may alleviate the associated safety concerns, [16,17] the Wittig olefination to produce 10 was not highly chemoselective. Therefore, we elected to modify a procedure described by Cignarella and co-workers [18] to generate the indanone 12, which could subsequently undergo the stereo-defining Noyori asymmetric transfer hydrogenation.…”

Section: Synthetic Studiesmentioning

confidence: 99%