Scalable Photocatalytic Oxidation of Methionine under Continuous-Flow Conditions

Emmanuel, Noémie; Mendoza Gallego, Carlos; Winter, Marc; Horn R, Clemens; Vizza, Alessandra; Dreesen, Laurent; Heinrichs, Benoît; Monbaliu, Jean-Christophe

doi:10.1021/acs.oprd.7b00212

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Article (Scientific journals)

Scalable Photocatalytic Oxidation of Methionine under Continuous-Flow Conditions

Emmanuel, Noémie; Mendoza Gallego, Carlos; Winter, Marc et al.

2017 • In Organic Process Research and Development, 21, p. 1435-1438

Peer Reviewed verified by ORBi

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https://hdl.handle.net/2268/212966

DOI
10.1021/acs.oprd.7b00212

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Keywords :

Flow Chemistry; Continuous-flow process; Photocatalytic oxidation; Singlet oxygen; Sulfoxides; Sustainable conditions

Abstract :

[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

Volume :

Pages :

1435-1438

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

http://pubs.acs.org/doi/abs/10.1021/acs.oprd.7b00212

Funders :

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).

Available on ORBi :

since 15 July 2017

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