The batch reaction experiments have been made for the first time to investigate the effect of ionic structure on the reactivity and selectivity of the trioxane-forming reaction catalyzed by a Brønsted-acidic ionic liquid (IL). The ILs considered include 1-cyclohexyl-2-pyrrolidinone trifluoromethanesulfonate ([NCyP][TfO]), 1-cyclohexyl-2-pyrrolidinone benzenesulfonate ([NCyP][BSA]), 1-cyclohexyl-2-pyrrolidinone p-toluenesulfonate ([NCyP][p-TSA]), 1-octyl-2-pyrrolidinone 2,4-dinitrobenzenesulfonate ([NOP][DNBSA]), 1-octyl-2-pyrrolidinone benzenesulfonate ([NOP][BSA]), 1-octyl-2-pyrrolidinone methanesulfonate ([NOP][MSA]), and 1-octyl-2-pyrrolidinone hydrogen sulfate ([NOP][HSO4]). It is found that the yield and the selectivity of trioxane in the reaction solution correlate closely with the charge density of the anion of the corresponding ILs. Variation of the cation structure from [NCyP]+ to [NOP]+ exerts little influence on the yield and the selectivity of trioxane in the reaction solution. The continuous production experiments have been made to investigate the performance of [NOP][MSA], [NOP][DNBSA], [NCyP][TfO], and H2SO4 as an extraction distillation agent. Such effect of [NCyP][TfO] considerably overides that of H2SO4. The competitive green catalyst in production of trioxane is thus presented.

Novel brønsted-acidic ionic liquids as catalysts for synthesizing trioxane

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.