Epoxidation of cyclooctene and cyclohexene with hydrogen peroxide catalyzed by bis[3,5-bis(trifluoromethyl)-diphenyl] diselenide: Recyclable catalyst-containing phases through the use of glycerol-derived solvents

García-Marín, Héctor; Toorn, John C. van der; Mayoral, José A.; Garcı́a, José I.; Arends, Isabel W. C. E.

doi:10.1016/j.molcata.2010.10.027

Cited by 17 publications

(9 citation statements)

References 53 publications

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“…Fluorinated glycerol derivatives exhibited good catalytic activity in the epoxidation of cyclooctene and cyclohexene with hydrogen peroxide in an aqueous system and prevented epoxide hydrolysis to a great extent, particularly in the case of cyclohexene, as described by the same authors (García-Marín et al, 2011).…”

Section: Glycerol Derivativessupporting

confidence: 55%

Catalysis in glycerol: a survey of recent advances

et al. 2015

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There is currently a significant increase in the use of glycerol as a renewable solvent for catalytic reactions. Glycerol has often been the solvent of choice in both homogeneous and heterogeneous catalyses, despite its high viscosity at ambient temperature and the low solubility of highly hydrophobic reagents found in glycerol. Its biodegradability and non-toxicity have led to reports of improved reaction performance and selectivity, as well as easier product separation and effective catalyst recycling. All relevant advances in this emerging field of "green" catalysis are thoroughly reviewed below.

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Section: Glycerol Derivativessupporting

confidence: 55%

Catalysis in glycerol: a survey of recent advances

et al. 2015

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“…The high performance of [F, 0, F] in the transglycosylation reaction was realized by Bayon et al 43 and Sandoval et al 44 with significant improvement on the selectivity and yield over traditional organic solvents. Aldea et al 45 observed better results in the Kharasch-Sosnovsky allylic oxidation of cycloalkenes, and Garcia-Marin et al 46 obtained similar results in the epoxidation of cyclooctene in [F, 0, F]. Aldea et al 47 reported high yield of enantioselective conjugate reduction of ethyl (E)-3-phenylbut-2-enoate in [F, 0, F].…”

Section: Evaluating the Green Metrics Of Tfge Synthesismentioning

confidence: 97%

Glycerol‐derived solvents containing two or three distinct functional groups enabled by trifluoroethyl glycidyl ether

et al. 2021

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Conversion of epichlorohydrin to glycidyl ethers creates versatile precursors that can be transformed into a variety of molecular species with glycerol skeletons, enabling the design of molecules with highly tailored functionalities. The synthesis of 2,2,2-trifluoroethyl glycidyl ether (TFGE, IUPAC name: 2-[(2,2,2-trifluoroethoxy) methyl]oxirane, CAS# 1535-91-7) was optimized to provide high yield/selectivity and good "green metrics." TFGE was then used as a platform molecule in the synthesis of asymmetric glycerol 1,3-diether-2-alcohol derivatives, which were subsequently transformed to 1,2,3-triethers or 1,3-diether-2-ketones. The density, viscosity, and CO 2 solubility of each molecule were measured and compared with those of other glycerol-derived compounds as well as compounds with similar functional groups. Furthermore, quantum chemical calculations were performed to understand the structure-property-performance relationships of these molecules for CO 2 absorption. Based on the results in this work, we foresee that TFGE (and similar glycidyl ethers) would offer great flexibility in molecular design of green solvents and precursors to more complex compounds.

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“…Thus, fluorinated glycerol derivatives, such as the closely related 1,3-bis(2,2,2trifluoroethoxy)propan-2-ol [3F.0.3F], have been successfully used as reaction media in epoxidation and enzymatic reactions. 38,[47][48][49]…”

Section: Scope Of the Synthesis With Different Bases And Alcoholsmentioning

confidence: 99%

“…Some of them, like the fluoroalkyl glycerol ethers, have special properties that made them suitable for the substitution of ionic liquids in some catalytic applications. [36][37][38] Another key point is the toxicological profile of these compounds, an aspect that is currently under study in our group. 39,40 Last, but not least, the synthetic procedures to obtain this family of glycerol derivatives should meet as much as possible the principles of Green Chemistry and, in order to be of practical applicability, they should also meet economic criteria.…”

Section: Introductionmentioning

confidence: 99%