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See detailMicrowave – assisted synthesis of carbohydrate compounds, focus on uronic acid derivatives.
Laurent, Pascal ULg; Richel, Aurore ULg; Wathelet, Bernard ULg et al

Poster (2010, May)

At the moment, biorefining is increasingly seen as a promising alternative to petrochemical sector since it targets both the replacement of part of petroleum as a source of energy and the development of ... [more ▼]

At the moment, biorefining is increasingly seen as a promising alternative to petrochemical sector since it targets both the replacement of part of petroleum as a source of energy and the development of chemicals from the biomass, such as detergents, phytopharmaceutics, solvents, plastics, etc. The valorisation of carbohydrates arising from the hydrolysis of renewable feedstocks is therefore an area of outmost interest. In this context, uronic acids such as glucuronic acid (GlcA) or galacturonic acid (GalA) derived from widely available raw material such as hemicellulose or pectins represent important biocompatible and bioresorbable starting material. The quest of highly effective, environmentally friendly and straightforward chemical strategies to transform totally O-unprotected uronic acids into high valuable materials remains actually a particularly challenging task. A new strategy enabling the quantitative “one-pot” production of water-soluble monosubstituted D-glucofuranosidurono-6,3-lactones from unprotected D-glucuronic acid (D-GlcA) involving microwaves and an inexpensive siliceous-based promoter will be described. The use of a heterogeneous acid catalytic systems consisting of sulfuric acid impregnated onto silica (H2SO4/SiG60) or onto carbon (H2SO4/C), offers a green alternative to unrecyclable liquid sulfuric acid and permit the developpment of a truly eco-friendly green process, as these supported acids were readily separated from liquid products, without neutralization, by decantation or filtration, thus minimizing energy consumption and wastes. Faced with environmental concerns, this solventless methodology offers attractive features, including short reaction times, high yields and easy set-up and workup. [less ▲]

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See detailMicrowave-assisted conversion of carbohydrates. State of the art and outlook.
Richel, Aurore ULg; Laurent, Pascal ULg; Wathelet, Bernard ULg et al

in Comptes Rendus Chimie (2011), 14

The valorisation of carbohydrates arising from the hydrolysis of renewable feedstocks (i.e. lignocellulosic biomass) is nowadays an area of outmost interest. In this context, the implementation of fast ... [more ▼]

The valorisation of carbohydrates arising from the hydrolysis of renewable feedstocks (i.e. lignocellulosic biomass) is nowadays an area of outmost interest. In this context, the implementation of fast, expeditious and cost-effective methodologies for the modification of these naturally occurring compounds is becoming a prerequisite. In this sense, the application of microwaves has gained progressive attention in laboratories for making a range of high-added value sugars derivatives scaffolds. Advantages of microwaves are numerous and include enhancement of reaction rates and yields, combined to improved regio-, chemo- and anomeric selectivities. Summary: 1. Introduction 2. Chemical transformations of monosaccharides Regioselective hydroxyls protections/deprotections Derivatisation at the anomeric position Other derivatisations Microwave-assisted click chemistry Synergy between microwaves and heterogeneous catalysis Enzymatic modifications of monosaccharides 3. Effect of microwave heating on polysaccharides Hydrolysis and pretreatment of cellulose Derivatisation of cellulose 4. Scale-up of microwave-promoted reactions 5. Conclusions [less ▲]

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See detailMicrowave-assisted conversion of carbohydrates. State of the art and outlook.
Richel, Aurore ULg; Laurent, Pascal ULg; Wathelet, Bernard ULg et al

Conference (2010, May)

The valorisation of carbohydrates arising from the hydrolysis of renewable feedstocks (i.e. lignocellulosic biomass) is nowadays an area of outmost interest. In this context, the implementation of fast ... [more ▼]

The valorisation of carbohydrates arising from the hydrolysis of renewable feedstocks (i.e. lignocellulosic biomass) is nowadays an area of outmost interest. In this context, the implementation of fast, expeditous and cost-effective methodologies for the modification of these naturally occurring compounds is becoming a prerequisite. In this sense, the application of microwaves has gained progressive attention in laboratories for making a range of high-added value sugars derivatives scaffolds. Its advantages are numerous and include enhacement of reaction rates and yields combined to improved regio-, chemo- and anomeric selectivities. Since the first publications of Gedye et Giguere in 1986, the use of microwave has progressively emerged as a popular non conventional heating source in the field of organic synthesis.1 Nevertheless, its application in the area of carbohydrate chemistry is less documented.2, 3 Although research in this field is still in its infancy, recourse to microwaves often provides, with remarkable yields and atom efficiency, new carbohydrate-based structures that are not easily available by any another means (or only via painstaking multi-step protocols). This communication proposes therefore selected, recent and non exhaustive illustrations of the application of microwaves to promote famous carbohydrates “model” reactions. The scale-up of such microwave-assisted reactions is also presented. [less ▲]

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See detailMicrowave-Assisted Olefin Metathesis
Nicks, François; Borguet, Yannick ULg; Sauvage, Xavier et al

in Dragutan, Valerian; Demonceau, Albert; Dragutan, Ileana (Eds.) et al Green Metathesis Chemistry (2010)

Since the first reports on the use of microwave irradiation to accelerate organic chemical transformations, a plethora of papers have been published in this field. In most examples, microwave heating has ... [more ▼]

Since the first reports on the use of microwave irradiation to accelerate organic chemical transformations, a plethora of papers have been published in this field. In most examples, microwave heating has been shown to dramatically reduce reaction times, increase product yields, and enhance product purity by reducing unwanted side reactions compared to conventional heating methods. The present contribution aims at illustrating the advantages of this technology in olefin metathesis and, when data are available, at comparing microwave-heated and conventionally heated experiments. [less ▲]

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See detailMicrowave-assisted ruthenium-catalysed atom transfer radical reactions
Delfosse, Sébastien; Richel, Aurore ULg; Wei, H. et al

Conference (2005)

Detailed reference viewed: 22 (1 ULg)
See detailMicrowave-assisted ruthenium-catalysed atom transfer radical reactions
Delfosse, Sébastien; Richel, Aurore ULg; Wei, H. et al

Poster (2005, August)

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See detailMicrowave-Assisted Ruthenium-Catalyzed Reactions
Nicks, Francois ULg; Borguet, Yannick ULg; Delfosse, Sebastien et al

in Australian Journal of Chemistry (2009), 62(3), 184-207

Since the first reports on the use of microwave irradiation to accelerate organic chemical transformations, a plethora of papers has been published in this field. In most examples, microwave heating has ... [more ▼]

Since the first reports on the use of microwave irradiation to accelerate organic chemical transformations, a plethora of papers has been published in this field. In most examples, microwave heating has been shown to dramatically reduce reaction times, increase product yields, and enhance product purity by reducing unwanted side reactions compared with conventional heating methods. The present contribution aims at illustrating the advantages of this technology in homogeneous catalysis by ruthenium complexes and, when data are available, at comparing microwave-heated and conventionally heated experiments. Selected examples refer to olefin metathesis, isomerization reactions, 1,3-dipolar cycloadditions, atom transfer radical reactions, transfer hydrogenation reactions, and H/D exchange reactions. [less ▲]

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See detailMicrowave-Assisted Synthesis of 1,3-Dimesitylimidazolinium Chloride
Hans, Morgan ULg; Delaude, Lionel ULg

in Wipf, Peter (Ed.) Organic Syntheses. Volume 87 (2010)

A procedure for the microwave-assisted synthesis of 1,3-dimesitylimidazolinium chloride on a preparative scale is described starting from simple, commercially available reagents. Prior to a microwave ... [more ▼]

A procedure for the microwave-assisted synthesis of 1,3-dimesitylimidazolinium chloride on a preparative scale is described starting from simple, commercially available reagents. Prior to a microwave-assisted cyclization, it involves the formation of N,N'-dimesitylethane-1,2-diamine dihydrochloride via condensation of glyoxal with two equivalents of mesitylamine, followed by reduction of the intermediate Schiff base with sodium borohydride under acidic conditions. All three steps proceed readily under normal atmosphere. Laboratory grade solvents and reagents taken straight from the bottles do not require any additional purification. The two intermediates and the final product are isolated in high yield and purity by simple filtration and washing and may be used without any further purification for most applications. [less ▲]

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See detailMicrowave-assisted synthesis of D-glucuronic acid derivatives using cost-effective solid acid catalysts
Richel, Aurore ULg; Laurent, Pascal ULg; Wathelet, Bernard ULg et al

in Tetrahedron Letters (2010), 51

Monomode microwave-assisted coupling of D-glucuronic acid with alcohols, in the presence of various impregnated acid catalysts, was successfully performed, affording in almost quantitative yields the ... [more ▼]

Monomode microwave-assisted coupling of D-glucuronic acid with alcohols, in the presence of various impregnated acid catalysts, was successfully performed, affording in almost quantitative yields the corresponding monosubstituted b-D-glucofuranosidurono-6,3-lactones in less than 10 min at 85°C. This study evidences the synergy of microwaves and impregnated acid catalysts as a fast and clean strategy in the field of carbohydrate chemistry. [less ▲]

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See detailMicrowave-assisted synthesis of imidazolinium salts
Hans, Morgan; Demonceau, Albert ULg; Delaude, Lionel ULg

in Polymer Preprints (2008), 49(2), 942-943

Imidazolinium salts were prepd. via microwave-assisted cyclocondensation of ethanediamines with triethoxy alkanes or triethoxymethyl benzene. The synthesized imidazolinium salts may be used as NHC ... [more ▼]

Imidazolinium salts were prepd. via microwave-assisted cyclocondensation of ethanediamines with triethoxy alkanes or triethoxymethyl benzene. The synthesized imidazolinium salts may be used as NHC precursors or ionic liqs. [less ▲]

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See detailMicrowave-assisted synthesis of N-heterocyclic carbene precursors
Aidouni, Adila; Demonceau, Albert ULg; Delaude, Lionel ULg

in Synlett (2006), (3), 493-495

A very simple and efficient procedure is reported for the synthesis of 1,3-diarylimidazolinium chlorides by cyclization of N,N'-diarylethylenediamines dihydrochlorides with triethyl ortho-formate under ... [more ▼]

A very simple and efficient procedure is reported for the synthesis of 1,3-diarylimidazolinium chlorides by cyclization of N,N'-diarylethylenediamines dihydrochlorides with triethyl ortho-formate under microwave irradiation. [less ▲]

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See detailMicrowave-assisted synthesis of vinyl esters through ruthenium-catalyzed addition of carboxylic acids to alkynes
Nicks, Francois ULg; Libert, Lionel ULg; Delaude, Lionel ULg et al

in Polymer Preprints (2008), 49(2), 944-945

1-Hexen-2-yl 4-acetoxybenzoate was regioselectively prepd. via microwave-assisted ruthenium-catalyzed addn. of 4-acetoxybenzoic acid to 1-hexyne. Species of catalysts, reaction time and temp. play roles ... [more ▼]

1-Hexen-2-yl 4-acetoxybenzoate was regioselectively prepd. via microwave-assisted ruthenium-catalyzed addn. of 4-acetoxybenzoic acid to 1-hexyne. Species of catalysts, reaction time and temp. play roles in the reaction respect to yields and selectivity, therefore were examd. Microwave effect was obsd. and preferred to the generation of the Markovnikov-type product compared to traditional heating. [less ▲]

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See detailMicrowave-Assisted Synthesis of Vinyl Esters through Ruthenium-Catalyzed Addition of Carboxylic Acids to Alkynes
Nicks, Francois ULg; Libert, Lionel ULg; Delaude, Lionel ULg et al

in Australian Journal of Chemistry (2009), 62(3), 227-231

A rapid and efficient method is described for the selective synthesis of enol esters via the microwave-accelerated addition of carboxylic acids to terminal alkynes. The method employs the readily ... [more ▼]

A rapid and efficient method is described for the selective synthesis of enol esters via the microwave-accelerated addition of carboxylic acids to terminal alkynes. The method employs the readily available [RuCl2(p-cymene)(PPh3)] complex as catalyst without the need of bases, and reactions are complete in 20 min. [less ▲]

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See detailMicrowave-assisted thermochemical and primary hydrolytic conversions of lignocellulosic resources: a review
Richel, Aurore ULg; Jacquet, Nicolas ULg

in Biomass Conversion and Biorefinery (in press)

Faced with the inevitable depletion of fossil resources, agricultural productions have rapidly emerged as promising renewable alternatives. Particularly, the conversion of lignocellulosic materials has ... [more ▼]

Faced with the inevitable depletion of fossil resources, agricultural productions have rapidly emerged as promising renewable alternatives. Particularly, the conversion of lignocellulosic materials has nowadays opened new vistas for the production of energy, biofuels and chemicals. In this literature review, microwave technology is described as an original heating source either for the thermochemical conversions (at temperatures up to 400°C) of lignocellulose into biofuels or the pretreatment (below 400°C) and further hydrolysis of lignocellulose into bioethanol and other valuable chemicals. Advantages of microwave approaches include a commonly observed acceleration in reaction rate and improved selectivities and yields. [less ▲]

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See detailMicrowave-assisted transformations of agroresources: an example of green chemistry
Richel, Aurore ULg; Laurent, Pascal ULg; Paquot, Michel ULg

Report (2010)

Faced with the inevitable depletion of fossil resources, agricultural productions have rapidly emerged as a promising renewable alternative. Alongside its traditional involvement in the agro-food, the ... [more ▼]

Faced with the inevitable depletion of fossil resources, agricultural productions have rapidly emerged as a promising renewable alternative. Alongside its traditional involvement in the agro-food, the biomass has nowadays opened new vistas in the non-food sector. Indeed, original products and structures, potentially biodegradable, are proposed as substitutes for conventional petrochemical derivatives. The steady rise of oil prices, on the one hand, and the implementation of a new European legislation (REACH: Registration, Evaluation and Authorization of Chemicals), on the other hand, have only help to boost the academic and industrial research in this area. In this context, microwave-mediated synthesis has progressively emerged as a green chemistry technology. Application of microwaves (MW) as a non conventional heating source finds a plethora of illustrations in the field of organic synthesis. Microwaves usually accelerate chemical processes, while offering improved yields and selectivities. MW heating enables reactions under solventless conditions, providing unique chemical pathways, with special advantages such as ease of manipulation and reduction (or prevention) of pollution "at source". Various reactions and processes can be applied to transform lignocellulosic raw materials into valuable fuels and chemicals. Selected examples of strategical modifications of renewable biomass feedstocks via activation by microwave irradiation are proposed herein. [less ▲]

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See detailMicrowave-assisted transformations of agroresources: an example of green chemistry
Richel, Aurore ULg

in SciTopics-Research summarises by Experts (2010)

Faced with the inevitable depletion of fossil resources, agricultural productions have rapidly emerged as a promising renewable alternative. Alongside its traditional involvement in the agro-food, the ... [more ▼]

Faced with the inevitable depletion of fossil resources, agricultural productions have rapidly emerged as a promising renewable alternative. Alongside its traditional involvement in the agro-food, the biomass has nowadays opened new vistas in the non-food sector. Indeed, original products and structures, potentially biodegradable, are proposed as substitutes for conventional petrochemical derivatives. The steady rise of oil prices, on the one hand, and the implementation of a new European legislation (REACH: Registration, Evaluation and Authorization of Chemicals), on the other hand, have only help to boost the academic and industrial research in this area. In this context, microwave-mediated synthesis has progressively emerged as a green chemistry technology. Application of microwaves (MW) as a non conventional heating source finds a plethora of illustrations in the field of organic synthesis. Microwaves usually accelerate chemical processes, while offering improved yields and selectivities. MW heating enables reactions under solventless conditions, providing unique chemical pathways, with special advantages such as ease of manipulation and reduction (or prevention) of pollution "at source". Various reactions and processes can be applied to transform lignocellulosic raw materials into valuable fuels and chemicals. Selected examples of strategical modifications of renewable biomass feedstocks via activation by microwave irradiation are proposed herein. [less ▲]

Detailed reference viewed: 30 (4 ULg)
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See detailMicrowave-assisted transformations of carbohydrates
Richel, Aurore ULg; Wathelet, Jean-Paul ULg; Paquot, Michel ULg

in SciTopics / Research Summaries by Experts (2010)

Detailed reference viewed: 52 (11 ULg)
See detailMicrowave-assisted transformations of carbohydrates
Richel, Aurore ULg

Report (2010)

This reports deals with the involvment of microwaves for the conversion of renewable feedstocks, and in particlar for the tranfsormation of monosaccharides and cellulose into high added value materials.

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See detailMicrowave-Enhanced Ruthenium Catalysed Atom Transfer Radical Additions
Richel, Aurore ULg; Leclerc, Alain; Demonceau, Albert ULg et al

Poster (2005)

Detailed reference viewed: 16 (6 ULg)