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1. One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?

Author

Isaline Bonnin, Raphaël Mereau, Thierry Tassaing, and Karine De Oliveira Vigier

Subjects
catalysis, cellulose, isosorbide, lignocellulosic biomass, Science, Organic chemistry, QD241-441
Abstract

The catalytic conversion of (ligno)cellulose is currently subject of intense research. Isosorbide is one of the interesting products that can be produced from (ligno)cellulose as it can be used for the synthesis of a wide range of pharmaceuticals, chemicals, and polymers. Isosorbide is obtained after the hydrolysis of cellulose to glucose, followed by the hydrogenation of glucose to sorbitol that is then dehydrated to isosorbide. The one-pot process requires an acid and a hydrogenation catalyst. Several parameters are of importance during the direct conversion of (ligno)cellulose such as the acidity, the crystallinity and the particle size of cellulose as well as the nature of the feedstocks. This review highlights all these parameters and all the strategies employed to produce isosorbide from (ligno)cellulose in a one-pot process.

Published
2020
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2. Sustainable Amination of Bio-Based Alcohols by Hydrogen Borrowing Catalysis

Author

Sophie Hameury, Hana Bensalem, and Karine De Oliveira Vigier

Subjects
bio-based alcohol, amination, hydrogen borrowing, Chemical technology, TP1-1185, Chemistry, QD1-999
Abstract

In this review, we aim to give an overview of the use of the Borrowing Hydrogen (BH) methodology with bio-based alcohols. This methodology only forms water as a by-product, thus providing a sustainable way to amines, which have a large range of applications. This process is of particular interest when related to biomass due to the high abundance of alcohol functions in natural compounds. However, natural compounds often comprise multiple chemical functions that can change the reactivity of the substrate. This comprehensive review, comprising both homogeneous and heterogeneous catalysts, aims at summarizing the recent advancements in biomass amination for every class of substrate, highlighting the key parameters governing their reactivity and the remaining scientific hurdles. Even though most substrates have successfully been converted into the corresponding amines, reaction selectivity and functional group tolerance still need to be improved.

Published
2022
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3. Hydrogenation of Xylose to Xylitol in the Presence of Bimetallic Nanoparticles Ni3Fe Catalyst in the Presence of Choline Chloride

Author

Naseeb Ullah, François Jérôme, and Karine De Oliveira Vigier

Subjects
hydrogenation, sugars, deep eutectic solvents, Chemical technology, TP1-1185, Chemistry, QD1-999
Abstract

Hydrogenation of sugars to sugars alcohols is of prime interest for food applications for instance. Xylose obtained from the hemicellulose fraction of lignocellulosic biomass can be hydrogenated to xylitol. Herein, we conducted catalytic hydrogenation reactions in a non-conventional media approach by using choline chloride, a non-toxic naturally occurring organic compound that can form a deep eutectic solvent with xylose. Acknowledging the benefits of cost-effective transition metal-based alloys, Ni3Fe1 bimetallic nanoparticles were utilized as a hetero-catalyst. Under optimized reaction conditions (110 °C, 3 h and 30 bar H2), a highly concentrated feed of xylose (76 wt.%) was converted to 80% of xylitol, showing the benefit of using choline chloride. Overall, the catalytic conversion activity and the product selectivity in the substrate-assisted DES media are relatively high but, the recyclability of the catalyst should be improved in the presence of such media.

Published
2022
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4. Synthesis of Furfuryl Alcohol from Furfural: A Comparison between Batch and Continuous Flow Reactors

Author

Maïté Audemar, Yantao Wang, Deyang Zhao, Sébastien Royer, François Jérôme, Christophe Len, and Karine De Oliveira Vigier

Subjects
continuous flow, batch reactor, furfural, furfuryl alcohol, hydrogenation, Technology
Abstract

Furfural is a platform molecule obtained from hemicellulose. Among the products that can be produced from furfural, furfuryl alcohol is one of the most extensively studied. It is synthesized at an industrial scale in the presence of CuCr catalyst, but this process suffers from an environmental negative impact. Here, we demonstrate that a non-noble metal catalyst (Co/SiO2) was active (100% conversion of furfural) and selective (100% selectivity to furfuryl alcohol) in the hydrogenation of furfural to furfuryl alcohol at 150 °C under 20 bar of hydrogen. This catalyst was recyclable up to 3 cycles, and then the activity decreased. Thus, a comparison between batch and continuous flow reactors shows that changing the reactor type helps to increase the stability of the catalyst and the space-time yield. This study shows that using a continuous flow reactor can be a solution to the catalyst suffering from a lack of stability in the batch process.

Published
2020
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5. Mechanocatalytic Depolymerization of Cellulose With Perfluorinated Sulfonic Acid Ionomers

Author

Ayman Karam, Prince N. Amaniampong, José M. García Fernández, Claudio Oldani, Sinisa Marinkovic, Boris Estrine, Karine De Oliveira Vigier, and François Jérôme

Subjects
cellulose, depolymerization, mechanocatalysis, Aquivion, biomass, Chemistry, QD1-999
Abstract

Here, we investigated that the mechanocatalytic depolymerization of cellulose in the presence of Aquivion, a sulfonated perfluorinated ionomer. Under optimized conditions, yields of water soluble sugars of 90–97% were obtained using Aquivion PW98 and PW66, respectively, as a solid acid catalyst. The detailed characterization of the water soluble fraction revealed (i) the selective formation of oligosaccharides with a DP up to 11 and (ii) that depolymerization and reversion reactions concomitantly occurred during the mechanocatalytic process, although the first largely predominated. More importantly, we discussed on the critical role of water contained in Aquivion and cellulose on the efficiency of the mechanocatalytic process.

Published
2018
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6. Catalytic Conversion of Carbohydrates to Furanic Derivatives in the Presence of Choline Chloride

Author

François Jérôme and Karine De Oliveira Vigier

Subjects
carbohydrates, furanic derivatives, choline chloride, low melting mixture, deep eutectic solvent, Chemical technology, TP1-1185, Chemistry, QD1-999
Abstract

The synthesis of furanic derivatives (5-hydroxymethylfurfural (HMF), furfural…) from carbohydrates is of high interest for a wide range of applications. These reactions are carried out in the presence of various solvents, and among them choline chloride can be used. It is a salt that can form a low melting mixture with a carbohydrate (fructose, glucose…) or a deep eutectic mixture with carboxylic acid. A review of the studies performed in the conversion of carbohydrates to furanic derivatives in the presence of choline chloride is presented here with the advantages and drawbacks of this solvent. Choline chloride can enhance the selectivity to HMF by stabilizing effect and allows the conversion of highly concentrated feed. However, the extraction of the products from these solvents still needs improvement.

Published
2017
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10. Conversion of Ammonia to Hydrazine Induced by High‐Frequency Ultrasound

Author

François Jérôme, Karine De Oliveira Vigier, Anaelle Humblot, Stéphane Streiff, Laurie Grimaud, Audrey Allavena, Prince Nana Amaniampong, Tony Chave, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Sonochimie dans les Fluides Complexes (LSFC), Institut de Chimie Séparative de Marcoule (ICSM - UMR 5257), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Laboratoire Interfaces et Surfaces d'Oxydes (LISO), Service de physique de l'état condensé (SPEC - UMR3680), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay, Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Eco-Efficient Products & Processes Laboratory (E2P2L), and RHODIA-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Work (thermodynamics), Materials science, Aqueous solution, Radical, Hydrazine, General Chemistry, 02 engineering and technology, General Medicine, Photochemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Catalysis, 0104 chemical sciences, Ammonia, chemistry.chemical_compound, chemistry, Degradation (geology), [CHIM]Chemical Sciences, Organic synthesis, 0210 nano-technology
Abstract

International audience; Hydrazine is a chemical of outmost importance in our society, either for organic synthesis or energy purpose. The direct conversion of NH3 to hydrazine is highly appealing but it remains a very difficult task because the degradation of hydrazine is thermodynamically more feasible than the cleavage of the N-H bond of NH3. As a result, any catalyst capable of activating NH3 will thus unavoidably decompose N2H4. Here we show that cavitation bubbles, created by ultrasonic irradiation of aqueous NH3 at a high frequency, act as micro-reactors to activate and convert NH3 to NH species, without assistance of any catalyst, yielding hydrazine at the bubble-liquid interface. The compartmentation of in situ produced hydrazine in the bulk solution, which is maintained close to 30°C, advantageously prevents its thermal degradation, a recurrent problem faced by previous technologies. This work also points towards a path to scavenge •OH radicals by adjusting the NH3 concentration.

Published
2021

11. Editorial deep eutectic solvents

Author

Karine De Oliveira Vigier and Franҫois Jérôme

Subjects
Chemistry (miscellaneous), Process Chemistry and Technology, Management, Monitoring, Policy and Law, Waste Management and Disposal, Catalysis
Published
2023

12. One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?

Author

Raphaël Méreau, Thierry Tassaing, Isaline Bonnin, Karine De Oliveira Vigier, Institut des Sciences Moléculaires (ISM), and Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Isosorbide, isosorbide, One-pot synthesis, Lignocellulosic biomass, Review, 010402 general chemistry, 7. Clean energy, 01 natural sciences, Catalysis, lcsh:QD241-441, chemistry.chemical_compound, Hydrolysis, lcsh:Organic chemistry, medicine, [CHIM]Chemical Sciences, Organic chemistry, Cellulose, lcsh:Science, lignocellulosic biomass, chemistry.chemical_classification, catalysis, 010405 organic chemistry, Organic Chemistry, food and beverages, Polymer, cellulose, 0104 chemical sciences, Chemistry, chemistry, lcsh:Q, Sorbitol, medicine.drug
Abstract

International audience; The catalytic conversion of (ligno)cellulose is currently subject of intense research. Isosorbide is one of the interesting products that can be produced from (ligno)cellulose as it can be used for the synthesis of a wide range of pharmaceuticals, chemicals, and polymers. Isosorbide is obtained after the hydrolysis of cellulose to glucose, followed by the hydrogenation of glucose to sorbitol that is then dehydrated to isosorbide. The one-pot process requires an acid and a hydrogenation catalyst. Several parameters are of importance during the direct conversion of (ligno)cellulose such as the acidity, the crystallinity and the particle size of cellulose as well as the nature of the feedstocks. This review highlights all these parameters and all the strategies employed to produce isosorbide from (ligno)cellulose in a one-pot process. 1713

Published
2020

14. Synthesis and Properties

Author

François Jérôme and Karine De Oliveira Vigier

Subjects
Surface tension, Viscosity, Chemistry, Thermodynamics, Freezing point
Published
2019

16. Selective Acid-Catalyzed Hydroarylation of Nonactivated Alkenes with Aniline Assisted by Hexafluoroisopropanol

Author

Karine De Oliveira Vigier, Anaelle Humblot, Fan Jiang, François Jérôme, Marc Pera-Titus, Raphael Wischert, and Gongming Peng

Subjects
chemistry.chemical_compound, Aniline, Chemistry, Acid catalyzed, Organic Chemistry, Reactivity (chemistry), Hydroamination, Selectivity, Combinatorial chemistry, Trifluoromethanesulfonate, Ring strain, Catalysis
Abstract

The catalytic hydroarylation of nonactivated alkenes with aniline is a reaction of high interest, aiming at providing C-functionalized aniline derivatives that are important precursors for the fabrication of polyurethanes. However, this reaction remains a longstanding goal of catalysis, as it requires one to simultaneously address two important goals: (1) the very low reactivity of nonactivated alkenes and (2) control of the hydroarylation/hydroamination selectivity. As a result, the hydroarylation of aniline is mostly restricted to activated alkenes (i.e., featuring ring strain, conjugation, or activation with electron-donating or -withdrawing groups). Here we show that the combination of bismuth triflate and hexafluoroisopropanol (HFIP) leads to the formation of highly active catalytic species capable of promoting the hydroarylation of various nonactivated alkenes, such as 1-octene, 1-heptene, and 1-undecene, among others, with aniline with high selectivity (71-92%). Through a combined experimental and computational investigation, we propose a reaction pathway where HFIP stabilizes the rate-determining transition state through a H-bond interaction with the triflate anion, thus assisting the acid catalyst in the hydroarylation of nonactivated alkenes. From a practical point of view, this work opens a catalytic access to C-functionalized aniline derivatives from two cheap and abundant feedstocks in a 100% atom-economical fashion.

Published
2021

18. Hydrogenation of Sugars to Sugar Alcohols in the Presence of a Recyclable Ru/Al 2 O 3 Catalyst Commercially Available

Author

Thierry Tassaing, Isaline Bonnin, François Jérôme, Karine De Oliveira Vigier, Raphaël Méreau, Institut des Sciences Moléculaires (ISM), and Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
010405 organic chemistry, Renewable Energy, Sustainability and the Environment, Chemistry, General Chemical Engineering, General Chemistry, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Catalysis, Environmental Chemistry, Organic chemistry, [CHIM]Chemical Sciences, Sugar, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2021

20. Synergistic Effect of High-Frequency Ultrasound with Cupric Oxide Catalyst Resulting in a Selectivity Switch in Glucose Oxidation under Argon

Author

Yingqiao Wang, Ngoc Han Tran, Duy Quang Dao, Prince Nana Amaniampong, Matthew Sherburne, François Jérôme, Karine De Oliveira Vigier, Quang Thang Trinh, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Fédération de recherche INCREASE (INCREASE), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-LIttoral ENvironnement et Sociétés (LIENSs), La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)-La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Centre National de la Recherche Scientifique (CNRS)-Laboratoire de Chimie des Polymères Organiques (LCPO), Université de Bordeaux (UB)-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Institut Polytechnique de Bordeaux-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Bordeaux (UB)-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Institut Polytechnique de Bordeaux-Centre National de la Recherche Scientifique (CNRS)-Laboratoire de Génie Chimique (LGC), Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Unité de recherche sur les Biopolymères, Interactions Assemblages (BIA), Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Centre de recherche sur l'intégration économique et financière (CRIEF), Université de Poitiers-Université de Poitiers, Nanyang Technological University [Singapour], Physicochimie de la Combustion (PC2), Physicochimie des Processus de Combustion et de l’Atmosphère - UMR 8522 (PC2A), Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), National Research Foundation Singapore, Centre National de la Recherche Scientifique, R?gion Nouvelle-Aquitaine, ANR-16-CE07-0003,CELLOPLASM,Clivage de la liaison béta-1,4 glycosidique de la cellulose par plasma atmospherique non-thermique: mécanisme et application pour la production d'alkylglycosides(2016), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre de Recherche sur l'Intégration Economique et Financière (CRIEF), Université de Poitiers-Université de Poitiers-LIttoral ENvironnement et Sociétés - UMRi 7266 (LIENSs), Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS)-Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes 1 (UR1), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Laboratoire de Chimie des Polymères Organiques (LCPO), Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Laboratoire de Génie Chimique (LGC), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Unité de recherche sur les Biopolymères, Interactions Assemblages (BIA), and Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)

Subjects
Radical, Inorganic chemistry, Oxide, 010402 general chemistry, DFT, 01 natural sciences, 7. Clean energy, Biochemistry, Catalysis, Sonochemistry, Metal, chemistry.chemical_compound, Colloid and Surface Chemistry, Oxidation, Copper oxide, glucuronic acid, ultrasound, [CHIM.CATA]Chemical Sciences/Catalysis, General Chemistry, Glucuronic acid, 0104 chemical sciences, chemistry, visual_art, Gluconic acid, visual_art.visual_art_medium, Selectivity
Abstract

We report here, and rationalize, a synergistic effect between a non-noble metal oxide catalyst (CuO) and high-frequency ultrasound (HFUS) on glucose oxidation. While CuO and HFUS are able to independently oxidize glucose to gluconic acid, the combination of CuO with HFUS led to a dramatic change of the reaction selectivity, with glucuronic acid being formed as the major product. By means of density functional theory (DFT) calculations, we show that, under ultrasonic irradiation of water at 550 kHz, the surface lattice oxygen of a CuO catalyst traps H· radicals stemming from the sonolysis of water, making the ring-opening of glucose energetically unfavorable and leaving a high coverage of ·OH radical on the CuO surface, which selectively oxidizes glucose to glucuronic acid. This work also points toward a path to optimize the size of the catalyst particle for an ultrasonic frequency that minimizes the damage to the catalyst, resulting in its successful reuse.

Published
2019

21. Selective Synthesis of THF-Derived Amines from Biomass-Derived Carbonyl Compounds

Author

Changru Ma, Marc Pera-Titus, Eric Muller, François Jérôme, Shi Jiang, Karine De Oliveira Vigier, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Eco-Efficient Products &Processes Laboratory (E2PL2), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-RHODIA, and Solvay (France)

Subjects
010405 organic chemistry, Biomass, chemistry.chemical_element, [CHIM.CATA]Chemical Sciences/Catalysis, General Chemistry, 010402 general chemistry, Furfural, 01 natural sciences, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, Transformation (genetics), chemistry, Organic chemistry, Aldol condensation, ComputingMilieux_MISCELLANEOUS, Amination, Palladium
Abstract

Selective transformation of biomass or biomass-based feedstocks into value-added amines is highly desirable and constitutes one of the most important challenges in catalysis. As of today, only few ...

Published
2019

22. Catalytic glycosylation of glucose with alkyl alcohols over sulfonated mesoporous carbons

Author

Sébastien Rio, Karine De Oliveira Vigier, Anne Ponchel, Wahiba Ramdani, Ayman Karam, François Jérôme, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), UCCS Équipe Catalyse Supramoléculaire, Unité de Catalyse et Chimie du Solide - UMR 8181 (UCCS), Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille-Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille, and Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, Glycosylation, 010405 organic chemistry, Chemistry, Process Chemistry and Technology, Glycoside, chemistry.chemical_element, [CHIM.CATA]Chemical Sciences/Catalysis, Solid acid, 010402 general chemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, Yield (chemistry), [CHIM]Chemical Sciences, Organic chemistry, Physical and Theoretical Chemistry, Mesoporous material, Carbon, ComputingMilieux_MISCELLANEOUS, Alkyl
Abstract

Herein we investigated the catalytic performances of sulfonated mesoporous carbons in the glycosylation of carbohydrates with alkyl alcohols. Catalytic performances were compared to common solid acid catalysts previously reported for this reaction. Under optimized conditions, the targeted alkyl glycosides were obtained in 85% yield, together with a turn over frequency and a space time yield higher than those of the best heterogeneous catalysts reported so far in such reaction. Furthermore, the presence of mesoporous channels significantly lowered the deactivation rate of the catalyst in comparison to a non-porous sulfonated carbon.

Published
2019

23. Impact of shaping Aquivion PFSA on its catalytic performances

Author

Ana Franco, Karine De Oliveira Vigier, François Jérôme, Sinisa Marinkovic, Ayman Karam, Rafael Luque, Claudio Oldani, Magali Limousin, Boris Estrine, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Universidad de Córdoba [Cordoba], Green Chemistry Department, ARD, l'Innovation Verte, Agro-Industrie Recherches et Développements, Solvay Specialty Polymers, and Departamento de Quimica Organica [Universidad de Cordoba]

Subjects
Reaction conditions, Materials science, 010405 organic chemistry, business.industry, [CHIM.CATA]Chemical Sciences/Catalysis, 010402 general chemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, Reaction rate, Process engineering, business, ComputingMilieux_MISCELLANEOUS
Abstract

Over the last three years, a growing amount of reports highlighted the exceptional catalytic performances of Aquivion PFSA in many challenging chemical reactions. To date, all these studies employed Aquivion PFSA in powder form and the impact of shaping Aquivion PFSA on its catalytic performances has never been reported, although this aspect is of prime importance for implementation on a larger scale. Often considered as a matter of practical interest in the current literature, the shaping of a catalyst is actually mandatory and is clearly a key research topic for catalyst design and chemical engineering. Here, we explored the effect of shaping Aquivion PFSA on (1) its catalytic performances (i.e. yield, reaction rate and space time yield), (2) its ease of recovery at the end of the reaction (i.e. filtration, recyclability) and (3) its deactivation rate. In particular, we found that shaping Aquivion PFSA into micropellets was a good compromise (between powder and macropellets) to maintain acceptable catalytic performances while considerably facilitating the recovery of Aquivion PFSA at the end of the reaction. Last but not least, by properly controlling the reaction conditions, it was possible to limit the deactivation of Aquivion PFSA shaped into micropellets, a recurrent problem in catalytic carbohydrate processing.

Published
2019

25. Organic Acid-Regulated Lewis Acidity for Selective Catalytic Hydroxymethylfurfural Production from Rice Waste: An Experimental–Computational Study

Author

Iris K.M. Yu, Karine De Oliveira Vigier, Zhishan Su, Chi Sun Poon, Yong Sik Ok, François Jérôme, Alex C.K. Yip, Daniel C.W. Tsang, Department of Civil and Environmental Engineering [Hong Kong] (CEE), The Hong Kong Polytechnic University [Hong Kong] (POLYU), University of Canterbury [Christchurch], Sichuan University [Chengdu] (SCU), Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Poitiers-Institut de Chimie du CNRS (INC), Korea University [Seoul], and Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, Maleic acid, Renewable Energy, Sustainability and the Environment, General Chemical Engineering, Oxalic acid, [CHIM.CATA]Chemical Sciences/Catalysis, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Oxalate, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, chemistry, Succinic acid, Environmental Chemistry, Malic acid, 0210 nano-technology, ComputingMilieux_MISCELLANEOUS, Hydroxymethylfurfural, Organic acid, Nuclear chemistry
Abstract

A series of organic acids, including maleic acid (maleicA), malic acid (malicA), succinic acid (SA), and oxalic acid (OA)/oxalate, was evaluated as green additives to promote the selective Al(III)-catalyzed production of hydroxymethylfurfural (HMF) from food waste. The roles of Al(III)–organic acid interactions in altering the catalytic functions were elucidated on the basis of experimental and computational evidence. The catalytic results showed that the Al/OA and Al/oxalate systems gave the slowest glucose conversion among the studied systems. OA/oxalate had such a high affinity for Al(III), that the Lewis acidity of Al(III) (i.e., ability to accept electron pairs) was unfavorably reduced, which was supported by the theoretical calculations of Gibbs free energies considering the Al(III)–OA complexes the most thermodynamically feasible. When rice waste was used as the substrate, which is rich in glucose-based starch, the addition of maleicA to the Al(III) system enhanced the HMF selectivity. The Lewis ac...

Published
2018

26. Ammonia chemistry: Sounds better with ultrasound

Author

Prince N. Amaniampong, Anaelle Humblot, Karine De Oliveira Vigier, and Francois Jerome

Subjects
Acoustics and Ultrasonics, Arts and Humanities (miscellaneous)
Abstract

Hydrazine is a chemical of utmost importance in our society, either for organic synthesis or energy use. The direct conversion of NH3 to hydrazine is highly appealing, but it remains a very difficult task because the degradation of hydrazine is thermodynamically more feasible than the cleavage of the N−H bond of NH3. As a result, any catalyst capable of activating NH3 will thus unavoidably decompose N2H4. Here, we show that cavitation bubbles, created by ultrasonic irradiation of aqueous NH3 at a high frequency, act as microreactors to activate and convert NH3 to NH species, without assistance of any catalyst, yielding hydrazine at the bubble–liquid interface. The compartmentation of in-situ-produced hydrazine in the bulk solution, which is maintained close to 30 °C, advantageously prevents its thermal degradation, a recurrent problem faced by previous technologies. This work also points towards a path to scavenge .OH radicals by adjusting the NH3 concentration.

Published
2022

27. Synergistic effect between nanostructured catalysts and high-frequency ultrasound: Application in biomass conversion to specialty chemicals

Author

Sabine Valange, Prince N. Amaniampong, Karine De Oliveira Vigier, and Francois Jerome

Subjects
Acoustics and Ultrasonics, Arts and Humanities (miscellaneous)
Abstract

Within the context of sustainable chemistry, sonochemistry is now emerging as an alternative unconventional technology in catalysis. While ultrasound-generated radicals can participate in chemical reactions, mastering the reaction selectivity of polyfunctional substrates remains an elusive task. To address this challenge, we designed nanostructured metal oxides with leaf-like morphologies (e.g., CuO) by sonochemical synthesis (20 kHz) and investigated their activity for controlling the selectivity of oxidation reactions under ultrasonic irradiation in aqueous solution. We demonstrated that colocalization of the cavitation event onto the CuO surface active sites enables the direct utilization of radicals generated by cavitation for chemo-selective chemical reactions. In particular, we provided evidence for an alternative reaction pathway in glucose selective oxidation through synergistic cavitation–catalyst interactions at 550 kHz. We showed that the unwanted H• radicals stemming from water sonolysis are trapped by the surface lattice oxygen of CuO, thereby increasing the coverage of •OH radicals on the catalyst surface, and steering the selective oxidation of glucose to glucuronic acid, a valuable chemical whose synthesis remains a formidable challenge in the field of catalysis. This work also highlights that the particle size of the sonocatalyst is a key parameter governing an optimal transfer of radicals from the cavitation bubbles to the catalyst surface.

Published
2022

28. A Combined Experimental-Theoretical Study on Diels-Alder Reaction with Bio-Based Furfural: Towards Renewable Aromatics

Author

Changru Ma, Eric Muller, Karine De Oliveira Vigier, Raphael Wischert, Frédéric Guégan, I van Scodeller, François Jérôme, and Centre National de la Recherche Scientifique (CNRS)

Subjects
Steric effects, Chemistry, General Chemical Engineering, Aromatization, 02 engineering and technology, [CHIM.CATA]Chemical Sciences/Catalysis, 010402 general chemistry, 021001 nanoscience & nanotechnology, Furfural, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, General Energy, Computational chemistry, Reagent, Electrophile, Environmental Chemistry, General Materials Science, Chemical equilibrium, 0210 nano-technology, Selectivity, ComputingMilieux_MISCELLANEOUS, Diels–Alder reaction
Abstract

The synthesis of relevant renewable aromatics from bio-based furfural derivatives and cheap alkenes is carried out by using a Diels-Alder/aromatization sequence. The prediction and the control of the ortho/meta selectivity in the Diels-Alder step is an important issue to pave the way to a wide range of renewable aromatics, but it remains a challenging task. A combined experimental-theoretical approach reveals that, as a general trend, ortho and meta cycloadducts are the kinetic and thermodynamic products, respectively. The nature of substituents, both on the dienes and dienophiles, significantly impacts the feasibility of the reaction, through a modulation on the nucleo- and electrophilicity of the reagents, as well as the ortho/meta ratio. We show that the ortho/meta selectivity at the reaction equilibrium stems from a subtle interplay between charge interactions, favoring the ortho products, and steric interactions, favoring the meta isomers. This work also points towards a path to optimize the aromatization step.

Published
2020

29. Selective dihydroxylation of methyl oleate to methyl-9,10-dihydroxystearate in the presence of a recyclable tungsten based catalyst and hydrogen peroxide

Author

François Jérôme, Nahla Araji, Audrey Moores, Gregory Chatel, Karine De Oliveira Vigier, and Centre National de la Recherche Scientifique (CNRS)

Subjects
Methyl oleate, 010405 organic chemistry, chemistry.chemical_element, 02 engineering and technology, General Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, Tungsten, 021001 nanoscience & nanotechnology, 01 natural sciences, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Transfer agent, Dihydroxylation, Phase (matter), Yield (chemistry), Materials Chemistry, Organic chemistry, 0210 nano-technology, Hydrogen peroxide
Abstract

International audience; The dihydroxylation of fatty methyl esters is of prime importance for the synthesis of surfactants and lubricants. The conversion of methyl oleate (MO) to 98% yield of methyl-9,10-dihydroxysterate (MDHS) was performed in the presence of H2O2 and H3PW12O40 catalyst in absence of a phase transfer agent. The study of the effect of hydrogen peroxide concentration revealed that significant catalytic activity was only achieved for an optimal amount of H2O2. A mechanism for this reaction was proposed where hydrogen peroxide reacts with H3PW12O40 to produce peroxo-phosphotungstate anions, which directly dihydroxylate MO. The recyclability of the catalyst was also studied. To this aim, a recyclable form of the heteropolyacid was synthesized using Cs cations (Cs2.3H0.7PW12O40). This catalyst was recycled up to three cycles without significant loss in catalytic performances.

Published
2020

31. Modeling of Ethylene Glycol Production from Glucose in a Semi‐Continuous Reactor

Author

Ghislain Irakoze, François Jérôme, Yolande Pérès, Michel Delmas, Patrick Cognet, Karine De Oliveira Vigier, Martine Urrutigoïty, Carlos Murillo, Laboratoire de Génie Chimique (LGC), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and INCREASE CNRS federation

Subjects
Process modeling, 010405 organic chemistry, Chemistry, General Chemical Engineering, Continuous reactor, 02 engineering and technology, General Chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 7. Clean energy, Industrial and Manufacturing Engineering, 0104 chemical sciences, Catalysis, modelling, chemistry.chemical_compound, Chemical engineering, semi-continuous reaction, reaction kinetics, [CHIM.COOR]Chemical Sciences/Coordination chemistry, glucose, 0210 nano-technology, Ethylene glycol
Abstract

International audience; A numerical study describes the catalytic conversion of glucose into ethylene glycol (EG) in a semi-batch reactor. This analysis couples a set of power law models (homogeneous reactions) and Langmuir-Hinshelwood-Hougen-Watson (LHHW) equations (hydrogenations). For this purpose, the kinetic parameters of the LHHW expressions are estimated for the reaction conditions. Then, the kinetic model evaluates the influence of the H2 pressure and the catalyst concentrations on the selectivity. The results indicate that the EG yield is increased by setting the temperature and the H2 pressure. In this manner, the process reduces the hexitols and methane production and increases the EG yield. The originality of the work is based on the influence of the H2 pressure and the catalyst concentrations in the model.

Published
2020

32. Selective Hydrogenation of Xylose to Xylitol over Co/SiO 2 Catalysts

Author

Karine De Oliveira Vigier, Sébastien Royer, Andreea Raluca Ifrim, Adrian Ungureanu, Wahiba Ramdani, François Jérôme, Maïté Audemar, Tang Junhui, and Centre National de la Recherche Scientifique (CNRS)

Subjects
010405 organic chemistry, Organic Chemistry, chemistry.chemical_element, [CHIM.CATA]Chemical Sciences/Catalysis, Xylose, 010402 general chemistry, Xylitol, 7. Clean energy, 01 natural sciences, Catalysis, 12. Responsible consumption, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, chemistry, 13. Climate action, Organic chemistry, Physical and Theoretical Chemistry, Cobalt
Abstract

International audience; Xylose can be selectively converted to xylitol in water, with an optimized yield of 98%, in the presence of a simple silica supported metallic cobalt-Co/SiO2-catalyst. This catalyst displays initial outstanding catalytic properties in proper solvent, the best one being pure water. Recyclability studies show a moderate deactivation of the catalyst, while selectivity to xylitol remains almost unchanged after 4 cycles, confirming the promising character of this catalyst formulation for the xylitol production process. Xylose is a product issued from the hydrolysis of beechwood hemicelluloses. Different routes exists for the valorisation of xylose, amongst the selective hydrogenation to xylitol (scheme 1). Xylitol is an extensively used molecule in food, cosmetics, and pharmaceutical industry[1-4]. Xylitol has then been identified as one of the top-twelve value added chemicals that can be obtained from biomass [5]. As an example, xylitol is a valuable water soluble sweetener due to its atypical properties amongst, compared to sucrose, a higher sweetness strength and a lower energy capacity. Today, xylitol is widely incorporated in daily consumed products (chewing gums, chocolates, toothpastes, etc.) [6]. With an estimated market of 340 M$, xylitol is becoming the most popular "natural" sweeteners [7]. Industrial production of xylitol by selective catalytic hydrogenation appears as an economically viable approach. Scheme 1. Hydrogenation of xylose to xylitol. Xylitol can be produced by catalytic hydrogenation in the presence of RANEY® nickel. Reaction is performed in liquid phase, under high hydrogen pressure and temperature in batch-type reactors [8]. Selectivity above 90%, at high conversion degree can be obtained at 80-130°C under 40-70 bar of H2 (5 wt.% catalyst of the xylose mass present at 40-60 wt.% in water) in the presence of RANEY® nickel. Despite the high selectivity and activity reached using this catalyst, with economic advantages related to the use of noble metal free catalysts for the reaction, the intrinsic properties of the nickel, amongst toxicity and limited stability,[8-9] makes the research of efficient catalyst substitutes. Indeed, the use of xylitol for food applications imply the absence of any trace of nickel in final product, nickel being recognized as a carcinogen compound. Most of recent studies were devoted to the study of supported noble metals, such as Ru, Rh and Pd, in monometallic or bimetallic catalytic systems, with the possible adding of dopants as Sn [8-15] Ru appeared as the most efficient. Hernandez-Mejia et al.[16] reported that xylose can be selectively converted to xylitol in the presence of rutile phase TiO2 supported Ru (1 wt.%), despite the low surface area displayed by the rutile support. Authors then reported xylose yields higher than 90%, for a reaction performed in water at

Published
2020

33. Conversion of furfural to tetrahydrofuran-derived secondary amines under mild conditions

Author

Karine De Oliveira Vigier, Eric Muller, François Jérôme, Shi Jiang, Marc Pera-Titus, Centre National de la Recherche Scientifique (CNRS), Eco-Efficient Products &Processes Laboratory (E2PL2), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-RHODIA

Subjects
010405 organic chemistry, Biomass, chemistry.chemical_element, [CHIM.CATA]Chemical Sciences/Catalysis, 010402 general chemistry, Furfural, 01 natural sciences, Pollution, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, chemistry, Bioenergy, Environmental Chemistry, Organic chemistry, [CHIM]Chemical Sciences, Tetrahydrofuran, ComputingMilieux_MISCELLANEOUS, Palladium
Abstract

International audience; The production of amino-containing compounds from biomass is an important goal of research programs. Starting from carbohydrate-based furfural, a simple and highly efficient system was developed for producing a library of secondary and tertiary tetrahydrofurfurylamines under mild conditions (25 °C/1 bar H2) with excellent yields (>90%). Commercially available Pd/Al2O3 proved to be a suitable catalyst and exhibited outstanding performance.

Published
2020

34. Synthesis of Furfuryl Alcohol from Furfural: A Comparison between Batch and Continuous Flow Reactors

Author

Christophe Len, Yantao Wang, Deyang Zhao, Karine De Oliveira Vigier, Sébastien Royer, Maïté Audemar, François Jérôme, and Centre National de la Recherche Scientifique (CNRS)

Subjects
Control and Optimization, batch reactor, Batch reactor, Energy Engineering and Power Technology, 010402 general chemistry, Furfural, furfuryl alcohol, 01 natural sciences, 7. Clean energy, lcsh:Technology, Catalysis, Furfuryl alcohol, chemistry.chemical_compound, continuous flow, Hemicellulose, Electrical and Electronic Engineering, Engineering (miscellaneous), ComputingMilieux_MISCELLANEOUS, 010405 organic chemistry, Renewable Energy, Sustainability and the Environment, Chemistry, lcsh:T, furfural, [CHIM.CATA]Chemical Sciences/Catalysis, 0104 chemical sciences, Chemical engineering, Yield (chemistry), Batch processing, hydrogenation, Selectivity, Energy (miscellaneous)
Abstract

Furfural is a platform molecule obtained from hemicellulose. Among the products that can be produced from furfural, furfuryl alcohol is one of the most extensively studied. It is synthesized at an industrial scale in the presence of CuCr catalyst, but this process suffers from an environmental negative impact. Here, we demonstrate that a non-noble metal catalyst (Co/SiO2) was active (100% conversion of furfural) and selective (100% selectivity to furfuryl alcohol) in the hydrogenation of furfural to furfuryl alcohol at 150 °C under 20 bar of hydrogen. This catalyst was recyclable up to 3 cycles, and then the activity decreased. Thus, a comparison between batch and continuous flow reactors shows that changing the reactor type helps to increase the stability of the catalyst and the space-time yield. This study shows that using a continuous flow reactor can be a solution to the catalyst suffering from a lack of stability in the batch process.

Published
2020

35. Selective radical depolymerization of cellulose to glucose induced by high frequency ultrasound

Author

Isabelle Capron, Jonathan Clarhaut, Karine De Oliveira Vigier, Ayman Karam, Tony Chave, Somia Haouache, François Jérôme, Prince Nana Amaniampong, José M. García Fernández, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Physiopathologie des Adaptations Nutritionnelles (PhAN), Université de Nantes - UFR de Médecine et des Techniques Médicales (UFR MEDECINE), Université de Nantes (UN)-Université de Nantes (UN)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Sonochimie dans les Fluides Complexes (LSFC), Institut de Chimie Séparative de Marcoule (ICSM - UMR 5257), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), University of Sevilla, Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Universidad de Sevilla / University of Sevilla, ANR-16-CE07-0003,CELLOPLASM,Clivage de la liaison béta-1,4 glycosidique de la cellulose par plasma atmospherique non-thermique: mécanisme et application pour la production d'alkylglycosides(2016), and Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Poitiers-Institut de Chimie du CNRS (INC)

Subjects
chemistry.chemical_classification, 010405 organic chemistry, Depolymerization, Radical, Glycosidic bond, General Chemistry, 010402 general chemistry, Photochemistry, 01 natural sciences, 0104 chemical sciences, Homolysis, Catalysis, chemistry.chemical_compound, Chemistry, chemistry, Degradation (geology), [CHIM]Chemical Sciences, Cellulose, Selectivity
Abstract

The depolymerization of cellulose to glucose is a challenging reaction and often constitutes a scientific obstacle in the synthesis of downstream bio-based products. Here, we show that cellulose can be selectively depolymerized to glucose by ultrasonic irradiation in water at a high frequency (525 kHz). The concept of this work is based on the generation of H˙ and ˙OH radicals, formed by homolytic dissociation of water inside the cavitation bubbles, which induce the cleavage of the glycosidic bonds. The transfer of radicals on the cellulose particle surfaces prevents the side degradation of released glucose into the bulk solution, allowing maintaining the selectivity to glucose close to 100%. This work is distinguished from previous technologies in that (i) no catalyst is needed, (ii) no external source of heating is required, and (iii) the complete depolymerization of cellulose is achieved in a selective fashion. The addition of specific radical scavengers coupled to different gaseous atmospheres and ˙OH radical dosimetry experiments suggested that H˙ radicals are more likely to be responsible for the depolymerisation of cellulose., Ultrasonic irradiation of cellulose at a high frequency induces its selective depolymerization to glucose at room temperature and atmospheric pressure within only a few minutes.

Published
2020

36. Hydroconversion of 5‐Hydroxymethylfurfural to 2,5‐Dimethylfuran and 2,5‐Dimethyltetrahydrofuran over Non‐promoted Ni/SBA‐15

Author

Eric Marceau, Sébastien Royer, Robert Wojcieszak, Franck Dumeignil, Shuo Chen, François Jérôme, Karine De Oliveira Vigier, Carmen Ciotonea, Unité de Catalyse et Chimie du Solide - UMR 8181 (UCCS), Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ANR-17-CE07-0022,NobleFreeCat,Nanoparticules bimétalliques sans métal noble pour l'hydrogénation des sucres(2017), Université de Lille, CNRS, Centrale Lille, ENSCL, Univ. Artois, Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS], and Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, 2,5-Dimethylfuran, chemistry.chemical_element, 02 engineering and technology, [CHIM.CATA]Chemical Sciences/Catalysis, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Catalysis, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, Nickel, chemistry, Biofuel, 5-hydroxymethylfurfural, Organic chemistry, HMF, hydroconversion, nickel, biofuels, incipient wetness impregnation, Physical and Theoretical Chemistry, 0210 nano-technology, Incipient wetness impregnation, Hydroxymethylfurfural
Abstract

The selective hydroconversion of 5‐hydroxymethylfurfural (HMF) to biofuels is currently highly sought‐for. While the literature has demonstrated that this reaction is possible on promoted Ni catalysts, we show here that a monometallic, non‐promoted Ni/SBA‐15 catalyst, prepared by incipient wetness impregnation, can convert HMF to 2,5‐dimethylfuran (DMF) and to 2,5‐dimethyltetrahydrofuran (DMTHF) at 180 °C, in a consecutive way. Through a control over reaction time, high yields to DMF (71 %, at conversion of 93 %) or DMTHF (97 %, at conversion of 100 %) can be achieved. Kinetic modelling suggests a preferential route to DMF via 5‐methylfurfural (MFFR) as intermediate, though the route via 2,5‐bis(hydroxylmethyl)furan (BHMF) is also present. The favored route in the experimental conditions involves the hydrogenolysis of the hydroxyl group of HMF as first step, followed by the hydrogenation of the aldehyde function, to methylfurfuryl alcohol (MFOL). It is suggested a higher reaction rate of hydrogenation or hydrogenolysis of the side group is linked to the presence of a methyl group in the molecule. No hydrogenation of the furan ring is detected on the intermediates. 12;7

Published
2020

37. Catalyst‐Free Synthesis of Alkylpolyglycosides Induced by High‐Frequency Ultrasound

Author

Yves Blériot, José M. García Fernández, Carmen Ortiz Mellet, Jean-Louis Clément, Prince Nana Amaniampong, Karine De Oliveira Vigier, François Jérôme, Gregory Chatel, Didier Gigmes, Centre National de la Recherche Scientifique (France), Université de Poitiers, Junta de Andalucía, European Commission, Conseil régional d'Aquitaine, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Fédération de recherche INCREASE (INCREASE), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre de Recherche sur l'Intégration Economique et Financière (CRIEF), Université de Poitiers-Université de Poitiers-LIttoral ENvironnement et Sociétés - UMRi 7266 (LIENSs), Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS)-Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes 1 (UR1), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Laboratoire de Chimie des Polymères Organiques (LCPO), Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Laboratoire de Génie Chimique (LGC), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Unité de recherche sur les Biopolymères, Interactions Assemblages (BIA), Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Instituto de Investigaciones Químicas (IIQ), Universidad de Sevilla-Consejo Superior de Investigaciones Científicas [Madrid] (CSIC), Laboratoire de Chimie Moléculaire et Environnement (LCME), Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry]), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-LIttoral ENvironnement et Sociétés (LIENSs), La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)-La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Centre National de la Recherche Scientifique (CNRS)-Laboratoire de Chimie des Polymères Organiques (LCPO), Université de Bordeaux (UB)-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Institut Polytechnique de Bordeaux-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Bordeaux (UB)-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Institut Polytechnique de Bordeaux-Centre National de la Recherche Scientifique (CNRS)-Laboratoire de Génie Chimique (LGC), Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Unité de recherche sur les Biopolymères, Interactions Assemblages (BIA), Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Centre de recherche sur l'intégration économique et financière (CRIEF), Université de Poitiers-Université de Poitiers, Universidad de Sevilla / University of Sevilla-Consejo Superior de Investigaciones Científicas [Madrid] (CSIC), INCREASE, Region Nouvelle Aquitaine, and ANR-16-CE07-0003,CELLOPLASM,Clivage de la liaison béta-1,4 glycosidique de la cellulose par plasma atmospherique non-thermique: mécanisme et application pour la production d'alkylglycosides(2016)

Subjects
Glycosylation, Surfactants, General Chemical Engineering, Carbohydrates, Degree of polymerization, 010402 general chemistry, 01 natural sciences, Catalysis, symbols.namesake, chemistry.chemical_compound, Ultrasound, [CHIM]Chemical Sciences, Environmental Chemistry, General Materials Science, ComputingMilieux_MISCELLANEOUS, Alkyl, chemistry.chemical_classification, 010405 organic chemistry, Chemistry, Glycoside, Combinatorial chemistry, 3. Good health, 0104 chemical sciences, General Energy, Alkylpolyglycosides, symbols, Degradation (geology), Fischer glycosidation, High frequency ultrasound
Abstract

The irradiation of concentrated feeds of carbohydrates in alcoholic solution by high-frequency ultrasound (550 kHz) induces the formation of alkylpolyglycosides (APGs). This work is distinct from previous reports in that it does not involve any (bio)catalyst or activating agent, it takes place at only 40 °C, thus avoiding degradation of carbohydrates, and it selectively yields APGs with a degree of polymerization in a window of 2¿7, an important limitation of the popular Fischer glycosylation. This ultrasound-based technology proved successful with a range of different valuable carbohydrates and alkyl alcohols. The elucidation of the structure of all the produced glycosides strongly suggests that 1,6-anhydrosugars formed in situ are key intermediate species., Authors are grateful to the CNRS, the University of Poitiers, the Ministry of Research, the Région Nouvelle Aquitaine, the MINECO (contract nos. SAF2016‐76083‐R and CTQ2015‐64425‐C2‐1‐R), the Junta de Andalucía (contract no. FQM2012‐1467) and the European Community (FEDER) for their financial supports.

Published
2018

38. Selective Conversion of Concentrated Feeds of Furfuryl Alcohol to Alkyl Levulinates Catalyzed by Metal Triflates

Author

Bertrand Doumert, Alban Chappaz, Matthieu Corbet, Karine De Oliveira Vigier, Raphael Wischert, Didier Morvan, Jonathan Lai, Armin T. Liebens, François Jérôme, Xavier Trivelli, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Poitiers-Institut de Chimie du CNRS (INC), Eco-Efficient Products &Processes Laboratory (E2PL2), RHODIA-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Solvay, Institut Michel Eugène Chevreul - FR 2638 (IMEC), Université d'Artois (UA)-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Centrale Lille Institut (CLIL), Unité de Glycobiologie Structurale et Fonctionnelle UMR 8576 (UGSF), Institut National de la Recherche Agronomique (INRA)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), CNRS, French Ministry of research, SOLVAY, Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Eco-Efficient Products & Processes Laboratory (E2P2L), Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Université de Lille-Centre National de la Recherche Scientifique (CNRS), Université de Poitiers-Centre National de la Recherche Scientifique (CNRS), Eco-Efficient Products and Processes Laboratory (E2P2L), Université de Lyon-Centre National de la Recherche Scientifique (CNRS)-Solvay, Fédération M.E. Chevreul, Université de Lille, Sciences et Technologies, Unité de Glycobiologie Structurale et Fonctionnelle - UMR 8576 (UGSF), Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Recherche Agronomique (INRA), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-RHODIA

Subjects
General Chemical Engineering, 02 engineering and technology, 01 natural sciences, 7. Clean energy, Furfuryl alcohol, Catalysis, Alkyl levulinate, Metal, chemistry.chemical_compound, Environmental Chemistry, Organic chemistry, Biomass, Metal triflates, ComputingMilieux_MISCELLANEOUS, Alkyl, chemistry.chemical_classification, 010405 organic chemistry, Renewable Energy, Sustainability and the Environment, Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, General Chemistry, 021001 nanoscience & nanotechnology, Concenterd feed, 0104 chemical sciences, Acid catalysis, visual_art, visual_art.visual_art_medium, 0210 nano-technology
Abstract

International audience; Herein, we describe an efficient and recyclable catalytic system based on metal triflates capable of converting highly concentrated feeds of furfuryl alcohol (30-40 wt %) to alkyl levulinates in excellent yields (>90%). This constitutes a unique and important advance in the field. Indeed, the dilution of feedstocks represent one of the major bottlenecks in catalysis for the industrial deployment of biobased fuels and chemicals in our society. The impact of water in the metal triflates catalytic performances is also discussed. A comparison with a commercialized process (SFOS) shows that this catalytic route is in line with industrial requirements in terms of yield, selectivity, reactor productivity, and capacity. In particular, unprecedented space time yields up to 200 kg m(-3) h(-1) were obtained.

Published
2018

39. Cover Picture: Conversion of Ammonia to Hydrazine Induced by High‐Frequency Ultrasound (Angew. Chem. Int. Ed. 48/2021)

Author

Anaelle Humblot, Prince Nana Amaniampong, Laurie Grimaud, Audrey Allavena, Tony Chave, François Jérôme, Karine De Oliveira Vigier, and Stéphane Streiff

Subjects
Materials science, business.industry, Ultrasound, Hydrazine, INT, General Chemistry, Catalysis, Ammonia, chemistry.chemical_compound, chemistry, Cover (algebra), business, Nuclear chemistry, High frequency ultrasound
Published
2021

41. Amphiphilic dipyridinium-phosphotungstate as an efficient and recyclable catalyst for triphasic fatty ester epoxidation and oxidative cleavage with hydrogen peroxide

Author

Audrey Moores, Gregory Chatel, Karine De Oliveira Vigier, Luis Carlos de la Garza, Department of Chemistry, McGill University, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Poitiers-Institut de Chimie du CNRS (INC), Laboratoire de Chimie Moléculaire et Environnement (LCME), and Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry])

Subjects
010405 organic chemistry, Chemistry, Ricinoleic acid, [CHIM.CATA]Chemical Sciences/Catalysis, 010402 general chemistry, 01 natural sciences, 7. Clean energy, Pollution, 0104 chemical sciences, Turnover number, Catalysis, chemistry.chemical_compound, Transfer agent, Oxidizing agent, Amphiphile, Environmental Chemistry, Organic chemistry, Selectivity, Hydrogen peroxide, ComputingMilieux_MISCELLANEOUS
Abstract

A novel amphiphilic dipyridinium peroxophosphotungstate ion pair was developed as a selective and recyclable catalyst for the triphasic epoxidation of fatty acids and esters with hydrogen peroxide. The synthesis of the catalyst was studied extensively by solid and liquid phase 31P nuclear magnetic resonance (NMR). The oxidation of vegetable oils is of prime importance for the production of lubricants, plasticizers, polymer stabilizers and other olefinic compounds. Based on the oxidizing activity of peroxophosphotungstates, we designed a lipophilic phase transfer agent that renders the active complex insoluble in the reaction media, without having to support it on a matrix. This affords a catalyst combining the activity of homogeneous catalysts and the recyclability of heterogeneous systems. We show that this catalyst is able to fully epoxidize methyl oleate with excellent selectivity, with a turnover frequency of 149 at 60 °C, and can be easily recycled, to reach a record turn over number of 1868. A larger scale experiment on 13 grams and a scope including linoleic and ricinoleic acids were also demonstrated. The catalyst also shows excellent activity and selectivity for the oxidative cleavage of methyl oleate and the oxidation of small olefins.

Published
2017

42. The potency of γ-valerolactone as bio-sourced polar aprotic organic medium for the electrocarboxlation of furfural by CO2

Author

Karine De Oliveira Vigier, Christophe Coutanceau, Florent Boissou, Mehrad Tarighi, Stève Baranton, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Fédération de recherche INCREASE (INCREASE), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-LIttoral ENvironnement et Sociétés (LIENSs), La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)-La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Centre National de la Recherche Scientifique (CNRS)-Laboratoire de Chimie des Polymères Organiques (LCPO), Université de Bordeaux (UB)-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Institut Polytechnique de Bordeaux-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Bordeaux (UB)-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Institut Polytechnique de Bordeaux-Centre National de la Recherche Scientifique (CNRS)-Laboratoire de Génie Chimique (LGC), Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Unité de recherche sur les Biopolymères, Interactions Assemblages (BIA), Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Centre de recherche sur l'intégration économique et financière (CRIEF), Université de Poitiers-Université de Poitiers, Campus France, Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre de Recherche sur l'Intégration Economique et Financière (CRIEF), Université de Poitiers-Université de Poitiers-LIttoral ENvironnement et Sociétés - UMRi 7266 (LIENSs), Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS)-Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes 1 (UR1), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Laboratoire de Chimie des Polymères Organiques (LCPO), Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Laboratoire de Génie Chimique (LGC), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Unité de recherche sur les Biopolymères, Interactions Assemblages (BIA), and Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)

Subjects
integumentary system, Standard hydrogen electrode, General Chemical Engineering, Oxalic acid, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, Furfural, 01 natural sciences, Coupling reaction, 0104 chemical sciences, Analytical Chemistry, Acetic acid, chemistry.chemical_compound, chemistry, Saturated calomel electrode, Electrochemistry, [CHIM]Chemical Sciences, 0210 nano-technology, Voltammetry, ComputingMilieux_MISCELLANEOUS, Nuclear chemistry, Electrode potential
Abstract

The reductive electro-carboxylation of furfural at a Pt/C electrode was studied in a bio-sourced γ-valerolactone (GVL) solvent using linear scan voltammetry, in situ infrared spectroscopy (in situ FTIRS) under electrode potential control and by chrono-amperometry (CA) with analysis of reaction products. In situ FTIRS measurements indicated that GVL reacted at the electrode in the absence of furfural and/or of CO2, while the solvent became much less reactive in the presence of furfural and/or of CO2. It was also found that CO2 was activated from the high cathodic potential of −0.8 V vs SCE (saturated calomel electrode) and that it reacted with furfural. CA measurements at a cell voltage of 2.0 V, corresponding to a cathode potential higher than −1.66 V vs. SHE (standard hydrogen electrode), were performed for 24 h in the presence of CO2 at the cathode. Gas chromatography coupled with mass spectroscopy (GC–MS) analyses revealed the formation of 2-hydroxyvaleric acid (reaction between GVL and residual water) and oxalic acid (coupling reaction of CO2) as main reaction products in the absence of furfural in the reaction medium. In the presence of furfural in the reaction medium, 2-hydroxyvaleric acid and oxalic acid were detected as traces, whereas a new carboxylated specie, 2-furyl(hydroxy)acetic acid, corresponded by far to the main reaction product (ca. 82%). 1H NMR and LC-MS analyses confirmed the formation of this last compound. Under the experimental conditions described in this article, the electro-activation of CO2 could be performed at high cathode potential in GVL, leading in presence of furfural to the formation of the α-hydroxy-acid.

Published
2019

43. Catalytic oxidative dehydrogenation of malic acid to oxaloacetic acid

Author

Virginie Belliere-Baca, Antonio Pineda, Didier Morvan, Karine De Oliveira Vigier, François Jérôme, Asmaa Drif, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Adisseo France S.A.S

Subjects
chemistry.chemical_classification, 010405 organic chemistry, Decarboxylation, [CHIM.CATA]Chemical Sciences/Catalysis, 010402 general chemistry, 01 natural sciences, Pollution, 0104 chemical sciences, Catalysis, Amino acid, chemistry.chemical_compound, chemistry, Oxaloacetic acid, Yield (chemistry), Environmental Chemistry, Organic chemistry, Dehydrogenation, Malic acid, Pyruvic acid, ComputingMilieux_MISCELLANEOUS
Abstract

Here we report the oxidative dehydrogenation of malic acid to oxaloacetic acid, a key precursor in the fabrication of amino acids, over Pt–Bi/C catalysts. Under optimized conditions, we discovered that OAA was selectively produced with up to 60% conversion (i.e. 60% yield). The recurrent unwanted decarboxylation of OAA to pyruvic acid was circumvented by successfully conducting the catalytic reaction at 25 °C. A comparison with the classical Fenton oxidation reaction is discussed.

Published
2019

44. Front Cover: A Combined Experimental–Theoretical Study on Diels‐Alder Reaction with Bio‐Based Furfural: Towards Renewable Aromatics (ChemSusChem 1/2021)

Author

Changru Ma, Karine De Oliveira Vigier, I van Scodeller, Eric Muller, Frédéric Guégan, François Jérôme, and Raphael Wischert

Subjects
Materials science, business.industry, General Chemical Engineering, Biomass, Bio based, Furfural, Renewable energy, chemistry.chemical_compound, General Energy, Front cover, chemistry, Diels alder, Environmental Chemistry, Organic chemistry, General Materials Science, business, Diels–Alder reaction
Published
2020

45. Electro-Carboxylation of Furfural By CO2 in γ-Valerolactone

Author

Karine De Oliveira-Vigier, Stève Baranton, Christophe Coutanceau, and Florent Boissou

Subjects
chemistry.chemical_compound, Valerolactone, Carboxylation, Chemistry, Organic chemistry, Furfural
Abstract

The continuous rise of global warming and depletion of fossil fuel resources has led to the development of new ways of valorization of non petro-sourced chemicals. In this objective, it is important to develop electrochemical valorization processes of CO2, a greenhouse gas, for the synthesis of valuable molecules. When the CO2 electroreduction is performed in aqueous media, the competitive HER will decrease the energetic efficiency and the rapid deactivation of reaction intermediates will lead to side products such as CO, formic acid, oxalic acid and small chain hydrocarbons [1]. To circumvent these issues and create value added chemicals, reductive electro-carboxylation reactions can be performed in polar aprotic solvents (DMF, DMSO, acetonitrile or NMP) in the presence of tetraalkylammonim bromide or chloride as electrolytes [2]. In this work, we focused on non-aqueous bio-sourced solvent, the γ-valerolactone (GVL), to perform a carboxylation reaction of bio-sourced molecules like furfural by electroreduction of CO2. The reductive electro-carboxylation of furfural was studied at a Pt/C electrode was studied in a bio-sourced GVL with tributylmethylammonium chloride (TBMACl) as electrolyte. The solvent behavior in the CO2 reduction potential range was studied by in situ FTIRS measurements which indicated that GVL reacted at the electrode in the absence of furfural and/or of CO2, while the presence of furfural and/or of CO2 made the solvent much less reactive. The electrochemical study showed that the CO2 electroreduction started at from the high cathodic potential of −0.8 V vs SCE (saturated calomel electrode) and the coupling of electrochemistry with in situ FTIRS demonstrated that it reacted with furfural. The reductive electro-carboxylation was then performed in an electrolysis cell. The cell voltage was maintained at 2.0 V (corresponding to a cathode potential of -1.9 V vs. SCE) for 24 h. In absence of furfural, gas chromatography coupled with mass spectroscopy (GC–MS) analyses revealed the formation of oxalic acid (coupling reaction of CO2) as main reaction product. In the presence of furfural in the reaction medium, a new carboxylated specie, 2-furyl(hydroxy)acetic acid, was identified as the main reaction product. 1H NMR and LC-MS analyses further confirmed the formation of this compound, demonstrating the potentialities of bio-sourced solvents for reduction electro-carboxylation of a bio-sourced molecule by reduction of CO2[3]. [1] Y. Hori, Electrochemical CO2 reduction on metal electrodes, in: C. Vayenas, R. White, M. Gamboa-Aldeco (Eds.), Modern Aspects of Electrochemistry, 42, Springer, NewYork 2008, pp. 89–189 [2] R. Matthesses, J. Fransaer, K. Binnemans, D.E. De Vos, Electrocarboxylation: towards sustainable and efficient synthesis of valuable carboxylic acids, Beilstein J. Org.Chem. 10 (2004) 2484–2500. [3] Florent Boissou, S. Baranton, M. Tarighi, K. De Oliveira Vigier, C. Coutanceau, The potency of γ-valerolactone as bio-sourced polar aprotic organic medium for the electrocarboxlation of furfural by CO2. J. Electroanal. Chem. 848 (2019) 113257

Published
2020

46. Heterogeneously-acid catalyzed oligomerization of glycerol over recyclable superacid Aquivion ® PFSA

Author

Karine De Oliveira Vigier, Armin T. Liebens, Nassim Sayoud, Jonathan Lai, François Jérôme, Claudio Oldani, and Ayman Karam

Subjects
010405 organic chemistry, Process Chemistry and Technology, Regioselectivity, Context (language use), 010402 general chemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, Hammett acidity function, chemistry, Nafion, Glycerol, Organic chemistry, Superacid, Physical and Theoretical Chemistry, Selectivity
Abstract

This manuscript explores the catalytic activity, selectivity and stability of Aquivion ® PFSA PW98 in the oligomerization of glycerol. Aquivion ® PFSA PW98 is a solid superacid catalyst with a Hammett acidity function of −12. Furthermore, the perfluorinated structure allows this polymer to stand quite high operating temperature (up to 150–160 °C) without loss in mechanical and chemical integrity which is of huge interest for glycerol conversion. In this context, we discovered that Aquivion ® PFSA PW98 was nearly fully selective to oligoglycerols up to 80% conversion of glycerol. The oligomerization degree of oligoglycerol and the regioselectivity of the reaction (linear vs branched and cyclic isomers) were fully analyzed by means of GC and SEC chromatographies. In contrast to conventional solid acid catalysts, Aquivion ® PFSA PW98 was found highly robust in glycerol and was sucessfully recycled at least 10 times without apparent decrease in activity or selectivity. A comparison with Nafion NR 50 is also included to shed light on the potential of Aquivion ® PFSA PW98 for acid-catalyzed conversion of glycerol.

Published
2016

47. Fast and solvent free polymerization of carbohydrates induced by non-thermal atmospheric plasma

Author

Karine De Oliveira Vigier, Michaël Nigen, Jean-Michel Tatibouët, Abdellatif Barakat, Joakim Delaux, Elodie Fourré, Loyda Atencio, José M. García Fernández, François Jérôme, Ingénierie des Agro-polymères et Technologies Émergentes (UMR IATE), Institut national d’études supérieures agronomiques de Montpellier (Montpellier SupAgro), Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Centre international d'études supérieures en sciences agronomiques (Montpellier SupAgro)-Université Montpellier 2 - Sciences et Techniques (UM2)-Université de Montpellier (UM)-Institut National de la Recherche Agronomique (INRA), Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), IIQ Instituto de Investigaciones Quimicas, Spanish National Research Council (CSIC), Institut national d’études supérieures agronomiques de Montpellier (Montpellier SupAgro)-Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Centre international d'études supérieures en sciences agronomiques (Montpellier SupAgro)-Université Montpellier 2 - Sciences et Techniques (UM2)-Université de Montpellier (UM)-Institut National de la Recherche Agronomique (INRA), Université de Poitiers-Centre National de la Recherche Scientifique (CNRS), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-Université Montpellier 2 - Sciences et Techniques (UM2)-Centre international d'études supérieures en sciences agronomiques (Montpellier SupAgro)-Université de Montpellier (UM)-Institut national d’études supérieures agronomiques de Montpellier (Montpellier SupAgro), Institut National de la Recherche Agronomique (France), Ministerio de Economía y Competitividad (España), Junta de Andalucía, European Commission, Universidad de Sevilla, and Centre National de la Recherche Scientifique (France)

Subjects
Molar mass, Hydrodynamic radius, Aqueous solution, 010405 organic chemistry, Chemistry, 02 engineering and technology, 021001 nanoscience & nanotechnology, 01 natural sciences, Pollution, 0104 chemical sciences, 12. Responsible consumption, Catalysis, Solvent, Chemical engineering, Polymerization, Yield (chemistry), Environmental Chemistry, Organic chemistry, [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering, 0210 nano-technology, Chemical decomposition
Abstract

Non-thermal atmospheric plasma (NTAP) is a physical technology that has been previously employed for surface treatment (cleaning, coating, erosion, etc.) and water or air depollution. We show here that, beyond surface effects, NTAP is capable of enabling the complete and fast polymerization of various mono- and disaccharides in the solid state within only a few minutes and at low temperature (40-80 °C). NTAP-induced polymerization involves a radical mechanism and yields water soluble polysaccharides with a mean molar mass of up to 100000 g mol and a mean hydrodynamic radius of 3 nm. Although polymerization reactions promoted by NTAP occurs in a random manner, the α-1,6 and β-1,6 linkages are however dominant. Furthermore, we discovered that NTAP is highly selective, strongly favoring glycosylation over other chemical transformations in the bulk. Under our working conditions, glycosyl units are preserved that constitute the repeating units of the polysaccharide product. No chemical degradation (e.g. intramolecular dehydration reactions) was observed, allowing a white powder to be recovered with a yield higher than 93 wt%. From a practical point of view, NTAP has great potential for breakthrough in the production of polysaccharides, notably because it does not require the use of a solvent or catalyst, thus by-passing the traditional post-treatment of aqueous effluents and catalyst recycling characteristic of biotechnological polysaccharide production. Its efficiency at low temperature also prevents carbohydrates from degradation. Finally, NTAP proceeds on an on/off switch basis, allowing the polymerization reaction to be started and stopped quasi instantaneously., This study was funded by the CNRS, INRA and the French Ministry of Research, including the PhD grant of J. Delaux. This study was also supported by the Spanish Ministerio de Economía y Competitividad (contract numbers SAF2013-44021-R and CTQ2010-15848), the Junta de Andalucía (contract number FQM2012-1467) and the European Regional Development Funds (FEDER and FSE). The authors are grateful to the technical assistance from the research support services of the University of Sevilla (CITIUS), INRA-NANTES and IC2MP. The authors also expressed their sincere thanks to members of the FR CNRS INCREASE 3707 consortium for fruitful discussions and scientific advices.

Published
2016

48. Oxidative cyclization of linoleic acid in the presence of hydrogen peroxide and phosphotungstic acid

Author

Audrey Moores, Gregory Chatel, François Jérôme, Karine De Oliveira Vigier, Nahla Araji, and Centre National de la Recherche Scientifique (CNRS)

Subjects
linoleic acid, medicine.drug_class, Linoleic acid, hydrogen peroxide, 010402 general chemistry, Heterogeneous catalysis, 01 natural sciences, Catalysis, chemistry.chemical_compound, Transfer agent, THF derivatives 2, medicine, Organic chemistry, Phosphotungstic acid, Physical and Theoretical Chemistry, Hydrogen peroxide, 010405 organic chemistry, Process Chemistry and Technology, [CHIM.CATA]Chemical Sciences/Catalysis, 0104 chemical sciences, chemistry, Yield (chemistry), Antiprotozoal, tungsten catalyst, heteropolyacids
Abstract

International audience; The synthesis of THF and tetrahydro-2H-pyrane is of interest due to the applications of such molecules as antitumour, pesticidal, antiprotozoal and antimicrobial agents for instance. Here, an original approach was performed to prepare these derivatives starting from linoleic acid in the presence of hydrogen peroxide and phosphotungstic acid in the absence of a phase transfer agent. A maximum cyclic compounds yield of 99% was obtained under mild conditions of temperature. A heterogeneous catalyst was synthesized by exchanging proton by Cs to obtain Cs2,3H0,7PW12O40 that was recycled up to 3 cycles. It is one of the best yield to these products observed in the literature from fatty acids.

Published
2020

49. Synthesis of Renewable meta ‐Xylylenediamine from Biomass‐Derived Furfural

Author

Didier Morvan, Eric Muller, Ivan Scodeller, Karine De Oliveira Vigier, François Jérôme, Samir Mansouri, Raphael Wischert, Solvay (France), Laboratoire Hétéroéléments et Coordination (DCPH), École polytechnique (X)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Eco-Efficient Products &Processes Laboratory (E2PL2), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-RHODIA

Subjects
Biomass, Diamines, Xylenes, 010402 general chemistry, Furfural, 01 natural sciences, Catalysis, Benzaldehyde, chemistry.chemical_compound, Benzylamine, Isomerism, Organic chemistry, Furaldehyde, Amination, ComputingMilieux_MISCELLANEOUS, Cycloaddition Reaction, 010405 organic chemistry, business.industry, Aromatization, food and beverages, General Medicine, General Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, 0104 chemical sciences, Renewable energy, chemistry, Quantum Theory, business
Abstract

We report the synthesis of biomass-derived functionalized aromatic chemicals from furfural, a building block nowadays available in large scale from low-cost biomass. The scientific strategy relies on a Diels-Alder/aromatization sequence. By controlling the rate of each step, it was possible to produce exclusively the meta aromatic isomer. In particular, through this route, we describe the synthesis of renewably sourced meta-xylylenediamine (MXD). Transposition of this work to other furfural-derived chemicals is also discussed and reveals that functionalized biomass-derived aromatics (benzaldehyde, benzylamine, etc.) can be potentially produced, according to this route.

Published
2018

50. Sustainable Biofuels and Chemicals Production Using Ionic Liquids

Author

Karine De Oliveira Vigier, Nahla Araji, Sabine Valange, Gregory Chatel, Prince Nana Amaniampong, Ronan Behling, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Fédération de recherche INCREASE (INCREASE), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-LIttoral ENvironnement et Sociétés (LIENSs), La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)-La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Poitiers-Institut national des sciences de l'Univers (INSU - CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Centre National de la Recherche Scientifique (CNRS)-Laboratoire de Chimie des Polymères Organiques (LCPO), Université de Bordeaux (UB)-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Institut Polytechnique de Bordeaux-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Bordeaux (UB)-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Institut Polytechnique de Bordeaux-Centre National de la Recherche Scientifique (CNRS)-Laboratoire de Génie Chimique (LGC), Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Unité de recherche sur les Biopolymères, Interactions Assemblages (BIA), Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Centre de recherche sur l'intégration économique et financière (CRIEF), Université de Poitiers-Université de Poitiers, Laboratoire de Chimie Moléculaire et Environnement (LCME), Université Savoie Mont Blanc (USMB [Université de Savoie] [Université de Chambéry]), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre de Recherche sur l'Intégration Economique et Financière (CRIEF), Université de Poitiers-Université de Poitiers-LIttoral ENvironnement et Sociétés - UMRi 7266 (LIENSs), Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS)-Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rennes 1 (UR1), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Laboratoire de Chimie des Polymères Organiques (LCPO), Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Polytechnique de Bordeaux-Ecole Nationale Supérieure de Chimie, de Biologie et de Physique (ENSCBP)-Université de Bordeaux (UB)-Laboratoire de Génie Chimique (LGC), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Unité de recherche sur les Biopolymères, Interactions Assemblages (BIA), and Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)

Subjects
0301 basic medicine, Waste management, Chemistry, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, 03 medical and health sciences, chemistry.chemical_compound, 030104 developmental biology, Biofuel, Ionic liquid, [CHIM]Chemical Sciences, Production (economics), ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

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