[en] Highly efficient and chemoselective singlet oxygen oxidation of unprotected methionine was performed in water using a continuous mesofluidic reactor. Sustainable process engineering and conditions were combined to maximize process efficiency and atom-economy, with virtually no waste generation and safe operating conditions. Three water soluble metal-free photosensitizers (Rose Bengal, Methylene Blue, and tetrakis(4-carboxyphenyl)porphyrin) were assessed. The best results were obtained with Rose Bengal (0.1 mol%) at room temperature under white light irradiation and a slight excess of oxygen. Process and reaction parameters were monitored in real-time with in-line NMR. Other classical organic substrates (alpha-terpinene and citronellol) were oxidized under similar conditions with excellent performances.
Disciplines :
Chemistry
Author, co-author :
Emmanuel, Noémie ; Université de Liège > Département de chimie (sciences) > Center for Integrated Technology and Organic Synthesis - CiTOS
Mendoza Gallego, Carlos ; Université de Liège > Department of Chemical Engineering > Génie chimique - Nanomatériaux et interfaces
Winter, Marc; Corning Reactor Technologies, Corning SAS
Horn R, Clemens; Corning SAS
Vizza, Alessandra; Corning Reactor Technologies, Corning SAS
Dreesen, Laurent ; Université de Liège > Département de physique > Biophotonique
Heinrichs, Benoît ; Université de Liège > Department of Chemical Engineering > Génie chimique - Nanomatériaux et interfaces
Monbaliu, Jean-Christophe ; Université de Liège > Département de chimie (sciences) > Center for Integrated Technology and Organic Synthesis - CiTOS
Language :
English
Title :
Scalable Photocatalytic Oxidation of Methionine under Continuous-Flow Conditions
Publication date :
2017
Journal title :
Organic Process Research and Development
ISSN :
1083-6160
eISSN :
1520-586X
Publisher :
ACS Publications, Washington, United States - District of Columbia
French Community of Belgium (ARC grant, iCFlow 15/19-05)
Commentary :
The research was funded through the ARC grant (iCFlow 15/19-05) for Concerted Research Actions, financed by the JCMM gratefully acknowledges financial support from the University of Liège (WG-13/03).
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