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1,2,3-Trimethoxypropane and Glycerol Ethers as Bio-Sourced Solvents from Glycerol. Synthesis by Solvent-Free Phase-Transfer Catalysis and Utilization as an Alternative Solvent in Chemical Transformations

Authors

  • Marc Sutter,

    1. Laboratoire de Catalyse, Synthèse et Environnement (CASYEN), Groupe Lemaire, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), CNRS. UMR5246, Université Lyon 1, Bâtiment Curien-CPE, 3° étage 43 Bd du 11 Novembre 1918, 69622, Villeurbanne Cedex (France), Fax: (+33) 472 431 408
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  • Dr. Wissam Dayoub,

    1. Laboratoire de Catalyse, Synthèse et Environnement (CASYEN), Groupe Lemaire, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), CNRS. UMR5246, Université Lyon 1, Bâtiment Curien-CPE, 3° étage 43 Bd du 11 Novembre 1918, 69622, Villeurbanne Cedex (France), Fax: (+33) 472 431 408
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  • Dr. Estelle Métay,

    1. Laboratoire de Catalyse, Synthèse et Environnement (CASYEN), Groupe Lemaire, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), CNRS. UMR5246, Université Lyon 1, Bâtiment Curien-CPE, 3° étage 43 Bd du 11 Novembre 1918, 69622, Villeurbanne Cedex (France), Fax: (+33) 472 431 408
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  • Dr. Yann Raoul,

    1. Sofiprotéol, 11, rue de Monceau, CS 60003, 75378 Paris Cedex 08 (France)
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  • Prof. Marc Lemaire

    Corresponding author
    1. Laboratoire de Catalyse, Synthèse et Environnement (CASYEN), Groupe Lemaire, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), CNRS. UMR5246, Université Lyon 1, Bâtiment Curien-CPE, 3° étage 43 Bd du 11 Novembre 1918, 69622, Villeurbanne Cedex (France), Fax: (+33) 472 431 408
    • Laboratoire de Catalyse, Synthèse et Environnement (CASYEN), Groupe Lemaire, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), CNRS. UMR5246, Université Lyon 1, Bâtiment Curien-CPE, 3° étage 43 Bd du 11 Novembre 1918, 69622, Villeurbanne Cedex (France), Fax: (+33) 472 431 408
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Abstract

1,2,3-Trimethoxypropane (2), 1-alkoxy-2,3-dimethoxy-propanes, and 1-aryloxy-2,3-dimethoxypropanes were prepared in good yields and selectivity by solid–liquid phase-transfer catalysis in the presence of an inorganic base and an ammonium salt as the phase-transfer catalyst with no additional solvent. No heating was required, and the synthesis was easily performed under atmospheric pressure on a 150 g scale. For the preparation of 2, the conversion of glycerol was complete and the selectivity for the expected glycerol trimethylether was above 95 %. This product was utilized as a solvent in organic reactions such as transesterifications between glycerol and vegetable oil, organometallic reactions (Grignard- and Barbier-type reactions), carbon–carbon coupling reactions (Suzuki, Sonogashira, Heck), and in etherification reactions by dehydrogenative alkylation. The solvent showed interesting properties for the solubilization of polymers.

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