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Efficient Photooxygenation Process of Biosourced alpha-Terpinene by Combining Controlled LED-Driven Flow Photochemistry and Rose Bengal-Anchored Polymer Colloids

Radjagobalou, Robbie and Blanco, Jean-François and Petrizza, Luca and Le Bechec, Mickael and Dechy-Cabaret, Odile and Lacombe, Sylvie and Save, Maud and Loubière, Karine Efficient Photooxygenation Process of Biosourced alpha-Terpinene by Combining Controlled LED-Driven Flow Photochemistry and Rose Bengal-Anchored Polymer Colloids. (2020) ACS Sustainable Chemistry & Engineering, 8 (50). 18568-18576. ISSN 2168-0485

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Official URL: https://doi.org/10.1021/acssuschemeng.0c06627

Abstract

This work studies the reactivity of poly(N-vinylcaprolactam-co-vinyl acetate-co-vinylbenzyl Rose Bengal) microgels (VBRB@MG) as heterogeneous photosensitizers in a continuous-flow process for sustainable singlet oxygen sensitized photooxygenation of a bio-based molecule. Experiments were carried out in a LED-driven spiral-shaped microreactor in which slurry Taylor flows were generated, allowing accurate control of irradiation, light absorption and gas-liquid flow conditions. The benchmark photooxygenation of -terpinene was implemented in ethanol to provide a green solvent using air as a safe supply of oxygen. Swollen RB-grafted colloids formed an efficient substrate for converting -terpinene into ascaridole, providing up to high conversion with high selectivity under continuous-flow conditions, and within short residence times of a few minutes. The supported RB exhibited a reactivity similar to that of the free RB. The reactivity of the supported photosensitizer was maintained for several cycles with a reproducible level after 8 months of storage. Under experimental conditions favouring photobleaching of RB, the photobleaching level of RB was lower with the VBRB@MG colloids than with free RB, suggesting that grafting RB molecules onto the colloid can prevent their photodegradation.

Item Type:Article
Audience (journal):International peer-reviewed journal
Uncontrolled Keywords:
Institution:French research institutions > Centre National de la Recherche Scientifique - CNRS (FRANCE)
Université de Toulouse > Institut National Polytechnique de Toulouse - Toulouse INP (FRANCE)
Université de Toulouse > Université Toulouse III - Paul Sabatier - UT3 (FRANCE)
Other partners > Université de Pau et des Pays de l'Adour - UPPA (FRANCE)
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Agence Nationale de la Recherche - ANR
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Deposited On:08 Mar 2022 09:04

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