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First Evidence of the Double-Bond Formation by Deoxydehydration of Glycerol and 1,2-Propanediol in Ionic Liquids

[Image: see text] Deoxydehydration (DODH) reaction of glycerol (GL) and 1,2-propanediol (1,2-PD), in ionic liquids (ILs), catalyzed by methyltrioxorhenium (MTO) and Re(2)O(7), was studied in detail. To better understand the ability of ILs to improve the catalytic performance of the rhenium catalyst,...

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Autores principales: Mascitti, Andrea, Scioli, Giuseppe, Tonucci, Lucia, Canale, Valentino, Germani, Raimondo, Di Profio, Pietro, d’Alessandro, Nicola
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9386840/
https://www.ncbi.nlm.nih.gov/pubmed/35990467
http://dx.doi.org/10.1021/acsomega.2c01803
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author Mascitti, Andrea
Scioli, Giuseppe
Tonucci, Lucia
Canale, Valentino
Germani, Raimondo
Di Profio, Pietro
d’Alessandro, Nicola
author_facet Mascitti, Andrea
Scioli, Giuseppe
Tonucci, Lucia
Canale, Valentino
Germani, Raimondo
Di Profio, Pietro
d’Alessandro, Nicola
author_sort Mascitti, Andrea
collection PubMed
description [Image: see text] Deoxydehydration (DODH) reaction of glycerol (GL) and 1,2-propanediol (1,2-PD), in ionic liquids (ILs), catalyzed by methyltrioxorhenium (MTO) and Re(2)O(7), was studied in detail. To better understand the ability of ILs to improve the catalytic performance of the rhenium catalyst, several experiments, employing eight different cations and two different anions, were carried out. Among the anions, bis(trifluoromethylsulfonyl)imide (TFSI) appears to be more appropriate than PF(6)(–), for its relatively lower volatility of the resulting IL. Regarding the choice of the most appropriate cation, the presence of a single aromatic ring seems to be a necessary requirement for a satisfying and convenient reactivity. With the aim to extend the recyclability of the catalyst, experiments involving the readdition of polyol to the terminal reaction mixture were carried out. Worthy of interest is the fact that the presence of the IL prevents the inertization process of the catalyst, allowing us to obtain the alkene also after a readdition of fresh polyol.
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spelling pubmed-93868402022-08-19 First Evidence of the Double-Bond Formation by Deoxydehydration of Glycerol and 1,2-Propanediol in Ionic Liquids Mascitti, Andrea Scioli, Giuseppe Tonucci, Lucia Canale, Valentino Germani, Raimondo Di Profio, Pietro d’Alessandro, Nicola ACS Omega [Image: see text] Deoxydehydration (DODH) reaction of glycerol (GL) and 1,2-propanediol (1,2-PD), in ionic liquids (ILs), catalyzed by methyltrioxorhenium (MTO) and Re(2)O(7), was studied in detail. To better understand the ability of ILs to improve the catalytic performance of the rhenium catalyst, several experiments, employing eight different cations and two different anions, were carried out. Among the anions, bis(trifluoromethylsulfonyl)imide (TFSI) appears to be more appropriate than PF(6)(–), for its relatively lower volatility of the resulting IL. Regarding the choice of the most appropriate cation, the presence of a single aromatic ring seems to be a necessary requirement for a satisfying and convenient reactivity. With the aim to extend the recyclability of the catalyst, experiments involving the readdition of polyol to the terminal reaction mixture were carried out. Worthy of interest is the fact that the presence of the IL prevents the inertization process of the catalyst, allowing us to obtain the alkene also after a readdition of fresh polyol. American Chemical Society 2022-08-01 /pmc/articles/PMC9386840/ /pubmed/35990467 http://dx.doi.org/10.1021/acsomega.2c01803 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Mascitti, Andrea
Scioli, Giuseppe
Tonucci, Lucia
Canale, Valentino
Germani, Raimondo
Di Profio, Pietro
d’Alessandro, Nicola
First Evidence of the Double-Bond Formation by Deoxydehydration of Glycerol and 1,2-Propanediol in Ionic Liquids
title First Evidence of the Double-Bond Formation by Deoxydehydration of Glycerol and 1,2-Propanediol in Ionic Liquids
title_full First Evidence of the Double-Bond Formation by Deoxydehydration of Glycerol and 1,2-Propanediol in Ionic Liquids
title_fullStr First Evidence of the Double-Bond Formation by Deoxydehydration of Glycerol and 1,2-Propanediol in Ionic Liquids
title_full_unstemmed First Evidence of the Double-Bond Formation by Deoxydehydration of Glycerol and 1,2-Propanediol in Ionic Liquids
title_short First Evidence of the Double-Bond Formation by Deoxydehydration of Glycerol and 1,2-Propanediol in Ionic Liquids
title_sort first evidence of the double-bond formation by deoxydehydration of glycerol and 1,2-propanediol in ionic liquids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9386840/
https://www.ncbi.nlm.nih.gov/pubmed/35990467
http://dx.doi.org/10.1021/acsomega.2c01803
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