Bio-Glycidol Conversion to Solketal over Acid Heterogeneous Catalysts: Synthesis and Theoretical Approach

Abstract

The present work deals with the novel use of heterogeneous catalysts for the preparation of solketal from bio-glycidol. Sustainable feedstocks and mild reaction conditions are considered to enhance the greenness of the proposed process. Nafion NR50 promotes the quantitative and selective acetalization of glycidol with acetone. DFT calculations demonstrate that the favored mechanism consists in the nucleophilic attack of acetone to glycidol concerted with the ring opening assisted by the acidic groups on the catalyst and in the following closure of the five member ring of the solketal.

Hydrogen from Renewables: A Case Study of Glycerol Reforming

“…Over the last decades, fossil fuels and their derivatives have remained the most widely exploited energy source for the world, with 97.6 million barrels/day in 2018 and an expected increase up to 112.2 million barrels/day by 2035 [1]. Environmental apprehension over global warming and the search for new sustainable alternatives to fossil energy have recently given rise to a sector of huge impact from the economic, scientific, and industrial standpoints, based on the use of biomass as feedstocks [2][3][4][5]. This sector, which bases itself on the 12 Principles of Green Chemistry [6], considers it imperative to develop eco-friendly and energy-efficient processes for the sustainable production of fuels and chemicals [7,8].…”

Regioselective Ring‐Opening of Glycidol to Monoalkyl Glyceryl Ethers Promoted by an [OSSO]‐FeIII Triflate Complex

“…The reactionp roceeded with high activity (initial turnover frequency of 1680 h À1 for EtOH) and selectivity( > 95 %) toward the formation of twelve monoalkyl glyceryl ethers (MAGEs) in ar egioselective fashion (84-96 %y ield of the non-symmetric regioisomer). [12][13][14] We have recentlys hown that GLYc an be conveniently obtained as a value-added product from biobasedepichlorohydrin (ECH) productionp lants (EPICEROL process, Solvay), [15] thereby enhancing the environmental sustainability of the entireE CH chain as well as interest towards GLYc onversiont ov aluable chemicals such as polymers, [16] drugs, [17] diols, [18][19][20] solketal, [21,22] and organic carbonates. [1][2][3][4][5][6][7] In particular, since the discoveryo fm anyu seful synthetic strategies that have given access to aw ide variety of chiral epoxides, this reaction has becomeani mportant entry in the toolbox of organic synthesis for obtaining enantiopure molecules.…”

“…[1][2][3][4][5][6][7] In particular, since the discoveryo fm anyu seful synthetic strategies that have given access to aw ide variety of chiral epoxides, this reaction has becomeani mportant entry in the toolbox of organic synthesis for obtaining enantiopure molecules. [12][13][14] We have recentlys hown that GLYc an be conveniently obtained as a value-added product from biobasedepichlorohydrin (ECH) productionp lants (EPICEROL process, Solvay), [15] thereby enhancing the environmental sustainability of the entireE CH chain as well as interest towards GLYc onversiont ov aluable chemicals such as polymers, [16] drugs, [17] diols, [18][19][20] solketal, [21,22] and organic carbonates. [12][13][14] We have recentlys hown that GLYc an be conveniently obtained as a value-added product from biobasedepichlorohydrin (ECH) productionp lants (EPICEROL process, Solvay), [15] thereby enhancing the environmental sustainability of the entireE CH chain as well as interest towards GLYc onversiont ov aluable chemicals such as polymers, [16] drugs, [17] diols, [18][19][20] solketal, [21,22] and organic carbonates.…”

Catalytic Processes for The Valorization of Biomass Derived Molecules

“…The use of an acid heterogeneous catalyst (Nafion NR50) for the synthesis of solketal from bio-glycidol was presented by Cucciniello et al [32]. The Nafion NR50 system was found to be very efficient even at a very low catalyst loading, allowing a quantitative acetalization of glycidol into solketal under relative mild reaction conditions.…”