Green synthesis of glycerol 1,3-bromo- and iodohydrins under solvent-free conditions

Abstract

New eco-friendly conditions for Finkelstein reaction employing homogeneous media or aluminasupported reagents, both solventless, were utilized in the bromohydrins and iodohydrins synthesis from 1,3-dichlorohydrin (1,3-DCH), obtained from glycerol. Thus, the trans-halogenation of glycerol-1,3-dichlorohydrin (1) in homogeneous media, using NaI, NaBr salts and organic additives (TBAI, TBAB), led to the synthesis of four different glycerol halohydrins (2a, 2b, 3a, 3b) in regular to excellent conversions (43-96%) and good selectivities to 3a and 2b. Already, the alumina-supported reagents such as KI, KBr, NaBr were used for glycerol-1,3-dichlorohydrin transhalogenation, in the absence of solvent, producing halohydrin mixtures in high conversions (77-99%) and very good selectivity (82%) to 1,3-diiodo-2-propanol (2b).

Recent Advances in Conversion of Glycerol: A Byproduct of Biodiesel Production to Glycerol Carbonate

“…Halogenation Glycerol 1. Glycerol-1,3-dichlorohydrin through multigrams via Conant's methodology Glycerol 1,3-bromo and iodohydrins [25] 2. Bromo and glycerol iodohydrins via Finkelstein's reaction using NaI, NaBr salts, and organic additives (TBAI and TBAB)…”

Critical Review on Production of Glycerol Carbonate from Byproduct Glycerol through Transesterification

“…Glycerol can be converted into several value-added derivatives such as mono-/di-/triglycerol ester, 1,2 propanediol, mesoxalic acid, glycerol 1,3-bromo- and iodohydrins, dihydroxyacetone, glyceric acid, oxalic acid, tartronic acid, syngas, hydrogen, glycerol carbonate, polyglycerol mono-/di-/tri-GTBE, etc. as summarized in Table . − …”

“…Glycerol 1,3-bromo-and iodohydrins Two step synthesis bromo and iodohydrins from glycerol 1. Glycerol-1,3-dichlorohydrin through multigrams via Conant ́s methodology Santos et al25 2. bromo-and glycerol iodohydrins via Finkelstein reaction using NaI, NaBr salts and organic additives (TBAI, TBAB)…”