On the use of propylene carbonate and dimethyl carbonate as green solvents in organic electrosynthesis

Autores
Prudlik, Adrian; Matei, Alexandra; Scherkus, Anton; Bardagi, Javier Ivan; Beil, Sebastian B.; Francke, Robert
Año de publicación
2025
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Electroorganic syntheses are often carried out in polar aprotic solvents such as DMF, acetonitrile, or dichloromethane, which exhibit excellent electrochemical properties, but are highly problematic in terms of sustainability. The propylene carbonate–dimethyl carbonate (PC–DMC) system is a promising alternative with enhanced environmental, health, and safety parameters, and has already found numerous applications in electrochemical energy storage systems. Herein, we present a systematic study on the PC–DMC system as reaction medium for organic electrosyntheses, spanning from the characterization of electrolyte properties to representative test reactions on a preparative scale. Anodic synthesis of diaryliodonium salts, cathodic reduction of ketones, and TEMPO-mediated alcohol oxidations serve as use cases, showing that yields are comparable to the ones obtained in conventional solvents. An interesting feature is the possibility for tuning the physicochemical properties of the reaction medium by varying the PC–DMC ratio, which was shown to impact the catalytic rate of TEMPO-mediated alcohol oxidations and the yield of diaryl iodonium synthesis.
Fil: Prudlik, Adrian. Leibniz-institut Für Katalyse - Likat Rostock; Alemania
Fil: Matei, Alexandra. University of Groningen; Países Bajos
Fil: Scherkus, Anton. Leibniz-institut Für Katalyse - Likat Rostock; Alemania
Fil: Bardagi, Javier Ivan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Beil, Sebastian B.. University of Groningen. Faculty of Mathematics and Natural Sciences; Países Bajos
Fil: Francke, Robert. Leibniz-institut Für Katalyse - Likat Rostock; Alemania
Materia
ELECTROCHEMISTRY
CARBONATES
PC
DCM
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/279120
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/279120
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling On the use of propylene carbonate and dimethyl carbonate as green solvents in organic electrosynthesisPrudlik, AdrianMatei, AlexandraScherkus, AntonBardagi, Javier IvanBeil, Sebastian B.Francke, RobertELECTROCHEMISTRYCARBONATESPCDCMhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Electroorganic syntheses are often carried out in polar aprotic solvents such as DMF, acetonitrile, or dichloromethane, which exhibit excellent electrochemical properties, but are highly problematic in terms of sustainability. The propylene carbonate–dimethyl carbonate (PC–DMC) system is a promising alternative with enhanced environmental, health, and safety parameters, and has already found numerous applications in electrochemical energy storage systems. Herein, we present a systematic study on the PC–DMC system as reaction medium for organic electrosyntheses, spanning from the characterization of electrolyte properties to representative test reactions on a preparative scale. Anodic synthesis of diaryliodonium salts, cathodic reduction of ketones, and TEMPO-mediated alcohol oxidations serve as use cases, showing that yields are comparable to the ones obtained in conventional solvents. An interesting feature is the possibility for tuning the physicochemical properties of the reaction medium by varying the PC–DMC ratio, which was shown to impact the catalytic rate of TEMPO-mediated alcohol oxidations and the yield of diaryl iodonium synthesis.Fil: Prudlik, Adrian. Leibniz-institut Für Katalyse - Likat Rostock; AlemaniaFil: Matei, Alexandra. University of Groningen; Países BajosFil: Scherkus, Anton. Leibniz-institut Für Katalyse - Likat Rostock; AlemaniaFil: Bardagi, Javier Ivan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Beil, Sebastian B.. University of Groningen. Faculty of Mathematics and Natural Sciences; Países BajosFil: Francke, Robert. Leibniz-institut Für Katalyse - Likat Rostock; AlemaniaRoyal Society of Chemistry2025-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/279120Prudlik, Adrian; Matei, Alexandra; Scherkus, Anton; Bardagi, Javier Ivan; Beil, Sebastian B.; et al.; On the use of propylene carbonate and dimethyl carbonate as green solvents in organic electrosynthesis; Royal Society of Chemistry; Green Chemistry (print); 27; 16; 3-2025; 4280-42881463-9262CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://xlink.rsc.org/?DOI=D4GC06199Cinfo:eu-repo/semantics/altIdentifier/doi/10.1039/D4GC06199Cinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-01-14T11:45:09Zoai:ri.conicet.gov.ar:11336/279120instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982026-01-14 11:45:09.92CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv On the use of propylene carbonate and dimethyl carbonate as green solvents in organic electrosynthesis
title On the use of propylene carbonate and dimethyl carbonate as green solvents in organic electrosynthesis
spellingShingle On the use of propylene carbonate and dimethyl carbonate as green solvents in organic electrosynthesis
Prudlik, Adrian
ELECTROCHEMISTRY
CARBONATES
PC
DCM
title_short On the use of propylene carbonate and dimethyl carbonate as green solvents in organic electrosynthesis
title_full On the use of propylene carbonate and dimethyl carbonate as green solvents in organic electrosynthesis
title_fullStr On the use of propylene carbonate and dimethyl carbonate as green solvents in organic electrosynthesis
title_full_unstemmed On the use of propylene carbonate and dimethyl carbonate as green solvents in organic electrosynthesis
title_sort On the use of propylene carbonate and dimethyl carbonate as green solvents in organic electrosynthesis
dc.creator.none.fl_str_mv Prudlik, Adrian
Matei, Alexandra
Scherkus, Anton
Bardagi, Javier Ivan
Beil, Sebastian B.
Francke, Robert
author Prudlik, Adrian
author_facet Prudlik, Adrian
Matei, Alexandra
Scherkus, Anton
Bardagi, Javier Ivan
Beil, Sebastian B.
Francke, Robert
author_role author
author2 Matei, Alexandra
Scherkus, Anton
Bardagi, Javier Ivan
Beil, Sebastian B.
Francke, Robert
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv ELECTROCHEMISTRY
CARBONATES
PC
DCM
topic ELECTROCHEMISTRY
CARBONATES
PC
DCM
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Electroorganic syntheses are often carried out in polar aprotic solvents such as DMF, acetonitrile, or dichloromethane, which exhibit excellent electrochemical properties, but are highly problematic in terms of sustainability. The propylene carbonate–dimethyl carbonate (PC–DMC) system is a promising alternative with enhanced environmental, health, and safety parameters, and has already found numerous applications in electrochemical energy storage systems. Herein, we present a systematic study on the PC–DMC system as reaction medium for organic electrosyntheses, spanning from the characterization of electrolyte properties to representative test reactions on a preparative scale. Anodic synthesis of diaryliodonium salts, cathodic reduction of ketones, and TEMPO-mediated alcohol oxidations serve as use cases, showing that yields are comparable to the ones obtained in conventional solvents. An interesting feature is the possibility for tuning the physicochemical properties of the reaction medium by varying the PC–DMC ratio, which was shown to impact the catalytic rate of TEMPO-mediated alcohol oxidations and the yield of diaryl iodonium synthesis.
Fil: Prudlik, Adrian. Leibniz-institut Für Katalyse - Likat Rostock; Alemania
Fil: Matei, Alexandra. University of Groningen; Países Bajos
Fil: Scherkus, Anton. Leibniz-institut Für Katalyse - Likat Rostock; Alemania
Fil: Bardagi, Javier Ivan. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Beil, Sebastian B.. University of Groningen. Faculty of Mathematics and Natural Sciences; Países Bajos
Fil: Francke, Robert. Leibniz-institut Für Katalyse - Likat Rostock; Alemania
description Electroorganic syntheses are often carried out in polar aprotic solvents such as DMF, acetonitrile, or dichloromethane, which exhibit excellent electrochemical properties, but are highly problematic in terms of sustainability. The propylene carbonate–dimethyl carbonate (PC–DMC) system is a promising alternative with enhanced environmental, health, and safety parameters, and has already found numerous applications in electrochemical energy storage systems. Herein, we present a systematic study on the PC–DMC system as reaction medium for organic electrosyntheses, spanning from the characterization of electrolyte properties to representative test reactions on a preparative scale. Anodic synthesis of diaryliodonium salts, cathodic reduction of ketones, and TEMPO-mediated alcohol oxidations serve as use cases, showing that yields are comparable to the ones obtained in conventional solvents. An interesting feature is the possibility for tuning the physicochemical properties of the reaction medium by varying the PC–DMC ratio, which was shown to impact the catalytic rate of TEMPO-mediated alcohol oxidations and the yield of diaryl iodonium synthesis.
publishDate 2025
dc.date.none.fl_str_mv 2025-03
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/279120
Prudlik, Adrian; Matei, Alexandra; Scherkus, Anton; Bardagi, Javier Ivan; Beil, Sebastian B.; et al.; On the use of propylene carbonate and dimethyl carbonate as green solvents in organic electrosynthesis; Royal Society of Chemistry; Green Chemistry (print); 27; 16; 3-2025; 4280-4288
1463-9262
CONICET Digital
CONICET
url http://hdl.handle.net/11336/279120
identifier_str_mv Prudlik, Adrian; Matei, Alexandra; Scherkus, Anton; Bardagi, Javier Ivan; Beil, Sebastian B.; et al.; On the use of propylene carbonate and dimethyl carbonate as green solvents in organic electrosynthesis; Royal Society of Chemistry; Green Chemistry (print); 27; 16; 3-2025; 4280-4288
1463-9262
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://xlink.rsc.org/?DOI=D4GC06199C
info:eu-repo/semantics/altIdentifier/doi/10.1039/D4GC06199C
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1854320844087492608
score 13.113929

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