- Regioselective Ring-Opening of Glycidol to Monoalkyl Glyceryl Ethers Promoted by an [OSSO]-FeIII Triflate Complex
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A FeIII-triflate complex, bearing a bis-thioether-di-phenolate [OSSO]-type ligand, was discovered to promote the ring-opening of glycidol with alcohols under mild reaction conditions (0.05 mol % catalyst and 80 °C). The reaction proceeded with high activity (initial turnover frequency of 1680 h?1 for EtOH) and selectivity (>95 %) toward the formation of twelve monoalkyl glyceryl ethers (MAGEs) in a regioselective fashion (84–96 % yield of the non-symmetric regioisomer). This synthetic approach allows the conversion of a glycerol-derived platform molecule (i.e., glycidol) to high-value-added products by using an Earth-crust abundant metal-based catalyst.
- Monica, Francesco Della,Ricciardi, Maria,Proto, Antonio,Cucciniello, Raffaele,Capacchione, Carmine
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p. 3448 - 3452
(2019/08/01)
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- Optimization of the synthesis of glycerol derived monoethers from glycidol by means of heterogeneous acid catalysis
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We present an efficient and green methodology for the synthesis of glycerol monoethers, starting from glycidol and different alcohols, by means of heterogeneous acid catalysis. A scope of Br?nsted and Lewis acid catalysts were applied to the benchmark reaction of glycidol and methanol. The selected catalysts were cationic exchangers, such as Nafion NR50, Dowex 50WX2, Amberlyst 15 and K10-Montmorillonite, both in their protonic form and exchanged with Al(III), Zn(II) and Fe(III). Thus, total conversions were reached in short times by using 1 and 5% mol catalyst loading and room temperature, without the need for excess glycidol or the presence of a solvent. Finally, these conditions and the best catalysts were successfully applied to the reaction of glycidol with several alcohols such as butanol or isopropanol.
- Pires, Elisabet,García, José Ignacio,Leal-Duaso, Alejandro,Mayoral, José Antonio,García-Peiro, José Ignacio,Velázquez, David
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- Synthesis of Monoalkyl Glyceryl Ethers by Ring Opening of Glycidol with Alcohols in the Presence of Lewis Acids
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The present work deals with the production of monoalkyl glyceryl ethers (MAGEs) through a new reaction pathway based on the reaction of glycidol and alcohols catalyzed by Lewis acid-based catalysts. Glycidol is quantitatively converted with high selectivity (99 %) into MAGEs under very mild reaction conditions (80 °C and 0.01 mol % catalyst loading) in only 1 h using Al(OTf)3 or Bi(OTf)3 as catalyst. The proposed method enhances the choice of possible green synthetic approaches for the production of value-added products such as MAGEs.
- Cucciniello, Raffaele,Ricciardi, Maria,Vitiello, Rosa,Di Serio, Martino,Proto, Antonio,Capacchione, Carmine
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p. 3272 - 3275
(2016/12/16)
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- Thermodynamic characteristics of the sorption of glycerol ethers on stationary phase OV-101
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Retention characteristics, temperature dependences of the retention characteristics, and thermodynamic characteristics of sorption on the nonpolar OV-101 phase are determined for 33 glycerol mono-, di-, and triethers with linear and branched monobasic alc
- Zhabina,Krasnykh,Levanova
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p. 1590 - 1593
(2014/10/16)
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- Etherification of glycerol with ethanol over solid acid catalysts
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Different types of acidic heterogeneous catalysts, including sulfonic resins, zeolites and grafted silicas are used for the synthesis of mono-ethers of glycerol using ethanol as the alcohol. The study shows that the performances of the catalysts are governed by both the acidity and the polarity of their surface. Materials with strong hydrophobic character are not active as they do not allow the adsorption of the glycerol. On the other hand a strong adsorption of glycerol on the polar surfaces leads to low activity as well. The best compromise has been found by using sulfonic-acid polystyrene resins of the Amberlyst family and zeolites with intermediate aluminium contents.
- Pariente, Stephane,Tanchoux, Nathalie,Fajula, Franois
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scheme or table
p. 1256 - 1261
(2010/05/17)
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- Control of Product Selectivity for the Epoxidation of Allyl Alcohol by Variation of the Acidity of the Catalyst TS-1
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The acidity of TS-1 controls the product selectivity for the epoxidation of allyl alcohol with H2O2; base treatment of TS-1 enhances the selectivity to glycidol whereas incorporation of Broensted acid sites enhances the selectivity to the products of solvolysis ring opening reactions.
- Hutchings, Graham J.,Lee, Darren F.
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p. 1095 - 1096
(2007/10/02)
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