A solvent-free method for making dioxolane and dioxane from the biorenewables glycerol and furfural catalyzed by oxorhenium(V) oxazoline.
Low catalyst loading of a cationic oxorhenium(V) oxazoline complex, [2-(2'-hydroxyphenyl)-2-oxazolinato(-2)]oxorhenium(v), condenses diols and aldehydes to give 1,3-dioxolanes in excellent yields under neat conditions and reasonably mild temperatures. The reaction is applicable to biomass-derived furfural and glycerol. The resulting cyclic acetals may find use as value-added chemicals and/or oxygenate fuel additives. Differences in the stereoselectivity of the reaction for epoxides versus diols provide insight into the reaction mechanism.
Wegenhart
Benjamin L
BL
Brown Laboratory, Department of Chemistry and the Center for Catalytic Conversion of Biomass to Biofuels (C3Bio), 560 Oval Drive, West Lafayette, Indiana 47907, USA.
Abu-Omar
Mahdi M
MM
D002384:Catalysis; D004146:Dioxanes / Q000138:chemical synthesis* / Q000737:chemistry; D004148:Dioxolanes / Q000138:chemical synthesis* / Q000737:chemistry; D005662:Furaldehyde / Q000737:chemistry*; D005990:Glycerol / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D012211:Rhenium / Q000737:chemistry; D013237:Stereoisomerism
D004146:Dioxanes; D004148:Dioxolanes; D009942:Organometallic Compounds; D010080:Oxazoles; D012211:Rhenium; D005662:Furaldehyde; C025223:1,4-dioxane; D005990:Glycerol; D010100:Oxygen; C010962:formal glycol