Continuous flow photooxygenation of monoterpenes

Park, Chan Yi; Kim, Young-Joon; Lim, Hyo Jin; Park, Jeong-Hyeon; Kim, Mi Jin; Seo, Seung Woo; Park, Chan Pil

doi:10.1039/c4ra12965b

Cited by 49 publications

(46 citation statements)

References 32 publications

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“…Continuous-flow photooxygenation of ß-pinene under sunlight. 185 Seeberger et al used a capillary FEP reactor (750 µm ID, 14 mL) for photosensitized singlet oxygen oxidation chemistry in flow. 187 The tubing was wrapped tightly around a quartz immersion well (cooled by a thermostat), containing a 450 W medium pressure mercury lamp and a Pyrex filter.…”

Section: Homogeneous Catalysismentioning

confidence: 99%

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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: Homogeneous Catalysismentioning

confidence: 99%

“…185,186 They evaluated two photochemical reactors, i.e., a monochannel reactor and a tube-in-tube reactor. The monochannel microreactor (PEEK tubing, 500 µm ID, 26 µL) was used for small scale optimizations and rapid screening of the reaction scope.…”

Section: Homogeneous Catalysismentioning

confidence: 99%

Liquid phase oxidation chemistry in continuous-flow microreactors

et al. 2016

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“…Prompted by these encouraging results, a multitude of reactor designs -including microfluidic chip reactors [150], falling-film reactors [151], dual-and triplechannel microreactors [152,153], coil-based devices [154,155], gas-permeable micro-capillary films [156], and tube-in-tube membrane devices [157] -were subsequently applied for the generation and subsequent utilization of 1 O 2 in gas/liquid continuous flow regimes using well-known photosensitizers such as Rose Bengal, methylene blue, and porphyrins. Furthermore, it was shown that porphyrins can be immobilized on the channel wall of a glass microreactor to heterogeneously catalyze the formation of the reactive oxygen species [158].…”

Section: Oxidative Carbon-carbon Coupling Reactionsmentioning

confidence: 98%

Aerobic Oxidations in Continuous Flow

Pieber

Kappe

2015

Organometallic Flow Chemistry

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In recent years, the high demand for sustainable processes resulted in the development of highly attractive oxidation protocols utilizing molecular oxygen or even air instead of more uneconomic and often toxic reagents. The application of these sustainable, gaseous oxidants in conventional batch reactors is often associated with severe safety risks and process challenges especially on larger scales. Continuous flow technology offers the possibility to minimize these safety hazards and concurrently allows working in high-temperature/high-pressure regimes to access highly efficient oxidation protocols. This review article critically discusses recent literature examples of flow methodologies for selective aerobic oxidations of organic compounds. Several technologies and reactor designs for biphasic gas/liquid as well as supercritical reaction media are presented in detail.

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“…Until today, such protocols under flow conditions are most advanced with photosensitized oxidations which most recently have matured to great efficacy and versatility by the works of Seeberger et al and Noël et al Prominent examples include the photooxidations of citronellol [35,40–42], indanes [43], monoterpenes [36], furans [42], furfurals [44], thiols [37] and amines [45] as well as the syntheses of ascaridol [46] and artemisinin [47]. Related microreactor setups were applied to biphasic gas/liquid mixtures in the photochlorination of alkylbenzenes [48] and [2 + 2]-cycloadditions with ethylene [49].…”

Section: Introductionmentioning

confidence: 99%

A flow reactor setup for photochemistry of biphasic gas/liquid reactions

Schachtner

Bayer

Wangelin

2016

Beilstein J. Org. Chem.

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SummaryA home-built microreactor system for light-mediated biphasic gas/liquid reactions was assembled from simple commercial components. This paper describes in full detail the nature and function of the required building elements, the assembly of parts, and the tuning and interdependencies of the most important reactor and reaction parameters. Unlike many commercial thin-film and microchannel reactors, the described set-up operates residence times of up to 30 min which cover the typical rates of many organic reactions. The tubular microreactor was successfully applied to the photooxygenation of hydrocarbons (Schenck ene reaction). Major emphasis was laid on the realization of a constant and highly reproducible gas/liquid slug flow and the effective illumination by an appropriate light source. The optimized set of conditions enabled the shortening of reaction times by more than 99% with equal chemoselectivities. The modular home-made flow reactor can serve as a prototype model for the continuous operation of various other reactions at light/liquid/gas interfaces in student, research, and industrial laboratories.

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Continuous flow photooxygenation of monoterpenes

Abstract: Two complementary technologies for the photooxygenation of monoterpenes were developed.

Cited by 49 publications

References 32 publications

Liquid phase oxidation chemistry in continuous-flow microreactors

Liquid phase oxidation chemistry in continuous-flow microreactors

Aerobic Oxidations in Continuous Flow

A flow reactor setup for photochemistry of biphasic gas/liquid reactions

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