Glycerol-based solvents as green reaction media in epoxidations with hydrogen peroxide catalysed by bis[3,5-bis(trifluoromethyl)-diphenyl] diselenide

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

“…In line with our previous QSPR results [48], the hydrogen bond ability of the solvent is the main feature influencing the catalytic activity. Best solvents have to possess good hydrogen bond donor (high E T N ) and reduced hydrogen bond acceptor (low ) abilities.…”

“…In the preliminary studies of the epoxidation of cyclooctene using diselenide 1 as precatalyst and H 2 O 2 as oxidant in different reaction media, solvent properties effects were investigated through QSPR equations relating solvent polarity and hydrophobicity parameters with catalytic activity [48]. Following the conclusions of this study we have chosen three common organic solvents and three glycerol derivatives as representative sample of solvents among those in which the catalytic reaction takes place.…”

“…These solvents present some new and attractive advantages, as there are made from a renewable source, they are (presumably) low toxic, exhibit a low volatility, and possess tuneable physico-chemical properties. We have previously described the use of some of these glycerol-derived solvents in the homogeneously catalyzed epoxidation reaction of cyclooctene, using aqueous hydrogen peroxide as oxidant and bis [3,5-bis(trifluoro-methyl)diphenyl] diselenide as catalyst precursor [48].…”

Glycerol and derived solvents: new sustainable reaction media for organic synthesis

“…56 Although the best results were achieved in 2,2,2-trifluoroethanol (TOF = 491 h À1 ), the use of some glycerol-based ethers bearing fluorinated alkyl chains also allowed fast conversions (TOF = 130-214 h…”

Glycerol derivatives as green reaction mediums

“…The elimination of each hydroxyl group of glycerol by hydrogenolysis can be used to yield 1,3-propanediol and 1,2-propanediol, which are less polar and less viscous solvents (16). Furthermore, each hydroxyl group of glycerol or of the two synthesized propanediols, alone or together, can be transferred into various ether groups (17). For example, 1,3-dialkoxy-2-propanols and 1,2,3-trialkoxypropanes were synthesized by either a symmetrical or an unsymmetrical epoxide ring opening reaction comprising commercially available glycidyl ethers with alcohols.…”