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Imidazolium-Based Ionic Liquids as Efficient Reagents for the C-O Bond Cleavage of Lignin.

Identifieur interne : 000E30 ( Main/Exploration ); précédent : 000E29; suivant : 000E31

Imidazolium-Based Ionic Liquids as Efficient Reagents for the C-O Bond Cleavage of Lignin.

Auteurs : Marina Thierry [France] ; Amel Majira [France] ; Bruce Pégot [France] ; Laurent Cezard [France] ; Flavien Bourdreux [France] ; Gilles Clément [France] ; François Perreau [France] ; Stéphanie Boutet-Mercey [France] ; Patrick Diter [France] ; Giang Vo-Thanh [France] ; Catherine Lapierre [France] ; Paul-Henri Ducrot [France] ; Emmanuel Magnier [France] ; Stéphanie Baumberger [France] ; Betty Cottyn [France]

Source :

RBID : pubmed:29048734

Descripteurs français

English descriptors

Abstract

The demethylation of lignin in ionic liquids (ILs) was investigated by using pure lignin model monomers and dimers together with dioxane-isolated lignins from poplar, miscanthus, and maize. Different methylimidazolium ILs were compared and the samples were treated with two different heating processes: microwave irradiation and conventional heating in a sealed tube. The conversion yield and influence of the treatment on the lignin structure were assessed by 31 P NMR spectroscopy, size-exclusion chromatography, and thioacidolysis. The acidic methylimidazolium IL [HMIM]Br was shown to be an effective combination of solvent and reagent for the demethylation and depolymerization of lignin. The relatively mild reaction conditions, the clean work-up, and the ability to reuse the IL makes the described procedure an attractive and new green method for the conversion of lignin to produce phenol-rich lignin oligomers.

DOI: 10.1002/cssc.201701668
PubMed: 29048734


Affiliations:


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Le document en format XML

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<name sortKey="Baumberger, Stephanie" sort="Baumberger, Stephanie" uniqKey="Baumberger S" first="Stéphanie" last="Baumberger">Stéphanie Baumberger</name>
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<title level="j">ChemSusChem</title>
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<term>Chromatography, Gel (MeSH)</term>
<term>Demethylation (MeSH)</term>
<term>Green Chemistry Technology (methods)</term>
<term>Hydrolysis (MeSH)</term>
<term>Imidazoles (chemistry)</term>
<term>Indicators and Reagents (chemistry)</term>
<term>Ionic Liquids (chemistry)</term>
<term>Lignin (chemistry)</term>
<term>Magnetic Resonance Spectroscopy (methods)</term>
<term>Microwaves (MeSH)</term>
<term>Poaceae (chemistry)</term>
<term>Polymerization (MeSH)</term>
<term>Populus (chemistry)</term>
<term>Zea mays (chemistry)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr">
<term>Chromatographie sur gel (MeSH)</term>
<term>Déméthylation (MeSH)</term>
<term>Hydrolyse (MeSH)</term>
<term>Imidazoles (composition chimique)</term>
<term>Indicateurs et réactifs (composition chimique)</term>
<term>Lignine (composition chimique)</term>
<term>Liquides ioniques (composition chimique)</term>
<term>Micro-ondes (MeSH)</term>
<term>Poaceae (composition chimique)</term>
<term>Polymérisation (MeSH)</term>
<term>Populus (composition chimique)</term>
<term>Spectroscopie par résonance magnétique (méthodes)</term>
<term>Technologie de la chimie verte (méthodes)</term>
<term>Zea mays (composition chimique)</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en">
<term>Imidazoles</term>
<term>Indicators and Reagents</term>
<term>Ionic Liquids</term>
<term>Lignin</term>
</keywords>
<keywords scheme="MESH" qualifier="chemistry" xml:lang="en">
<term>Poaceae</term>
<term>Populus</term>
<term>Zea mays</term>
</keywords>
<keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr">
<term>Imidazoles</term>
<term>Indicateurs et réactifs</term>
<term>Lignine</term>
<term>Liquides ioniques</term>
<term>Poaceae</term>
<term>Populus</term>
<term>Zea mays</term>
</keywords>
<keywords scheme="MESH" qualifier="methods" xml:lang="en">
<term>Green Chemistry Technology</term>
<term>Magnetic Resonance Spectroscopy</term>
</keywords>
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<term>Spectroscopie par résonance magnétique</term>
<term>Technologie de la chimie verte</term>
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<term>Chromatography, Gel</term>
<term>Demethylation</term>
<term>Hydrolysis</term>
<term>Microwaves</term>
<term>Polymerization</term>
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<term>Chromatographie sur gel</term>
<term>Déméthylation</term>
<term>Hydrolyse</term>
<term>Micro-ondes</term>
<term>Polymérisation</term>
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<div type="abstract" xml:lang="en">The demethylation of lignin in ionic liquids (ILs) was investigated by using pure lignin model monomers and dimers together with dioxane-isolated lignins from poplar, miscanthus, and maize. Different methylimidazolium ILs were compared and the samples were treated with two different heating processes: microwave irradiation and conventional heating in a sealed tube. The conversion yield and influence of the treatment on the lignin structure were assessed by
<sup>31</sup>
P NMR spectroscopy, size-exclusion chromatography, and thioacidolysis. The acidic methylimidazolium IL [HMIM]Br was shown to be an effective combination of solvent and reagent for the demethylation and depolymerization of lignin. The relatively mild reaction conditions, the clean work-up, and the ability to reuse the IL makes the described procedure an attractive and new green method for the conversion of lignin to produce phenol-rich lignin oligomers.</div>
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<Day>15</Day>
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<Volume>11</Volume>
<Issue>2</Issue>
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<Title>ChemSusChem</Title>
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<ArticleTitle>Imidazolium-Based Ionic Liquids as Efficient Reagents for the C-O Bond Cleavage of Lignin.</ArticleTitle>
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<AbstractText>The demethylation of lignin in ionic liquids (ILs) was investigated by using pure lignin model monomers and dimers together with dioxane-isolated lignins from poplar, miscanthus, and maize. Different methylimidazolium ILs were compared and the samples were treated with two different heating processes: microwave irradiation and conventional heating in a sealed tube. The conversion yield and influence of the treatment on the lignin structure were assessed by
<sup>31</sup>
P NMR spectroscopy, size-exclusion chromatography, and thioacidolysis. The acidic methylimidazolium IL [HMIM]Br was shown to be an effective combination of solvent and reagent for the demethylation and depolymerization of lignin. The relatively mild reaction conditions, the clean work-up, and the ability to reuse the IL makes the described procedure an attractive and new green method for the conversion of lignin to produce phenol-rich lignin oligomers.</AbstractText>
<CopyrightInformation>© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation>
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<LastName>Thierry</LastName>
<ForeName>Marina</ForeName>
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<Affiliation>Institut Jean-Pierre Bourgin, INRA, Agro Paris Tech, CNRS, Université Paris Saclay, 78000, Versailles, France.</Affiliation>
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<Affiliation>ICMMO, UMR CNRS 8182, Université Paris-Sud 11, 91405, Orsay, France.</Affiliation>
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<LastName>Cottyn</LastName>
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