Synthesis of Functionalized Cyclic Carbonates by One‐Pot Reactions of Carbon Dioxide, Epibromohydrin, and Phenols, Thiophenols, or Carboxylic Acids Catalyzed by Ionic Liquids

Abstract

The one‐pot reactions of CO2, epibromohydrin, and phenols, thiophenols, or carboxylic acids catalyzed by 1‐butyl‐3‐[(3‐hydroxyphenyl)methyl]imidazolium bromide were investigated. Three kinds of cyclic carbonates with ether, thioether, or ester groups were synthesized under mild reaction conditions in good‐to‐high yields. Reaction‐mechanism studies indicated that the proton exchange between the alkoxide formed through the ring‐opening reaction of epibromohydrin with 1‐bromo‐3‐phenoxy‐2‐propanol plays a crucial role in this synthetic route. The catalyst 1‐butyl‐3‐[(3‐hydroxyphenyl)methyl]imidazolium bromide was transformed to the corresponding cyclic‐carbonate‐functionalized ionic liquid during the reaction. This transformation did not affect its catalytic performance in the reaction.

Controllable Homogeneity/Heterogeneity Switch of Imidazolium Ionic Liquids for CO2 Utilization

“…The CO 2 cycloaddition upon epoxide is often conducted in elevated temperature, and imidazolium IL plays a role as a homogeneous catalyst in the reaction. Therefore, in order to separate out cyclic carbonate product and recycle the IL catalyst, energy‐intensive methods have been utilized such as vacuum distillation and column chromatography, resulting in extra cost. Basic idea of homogeneity/heterogeneity switch resides in phase separation of IL catalyst by temperature change.…”

Carbonation of Epoxidized Methyl Soyates in Tetrabutylammonium Bromide-Based Deep Eutectic Solvents

“…Because of their advantages of high boiling point, excellent biodegradability and solubility, cyclic carbonates are widely used as a kind of main raw material for polycarbonates 1 and other plastics industries, such as non-isocyanate polyurethanes 2 . Five-membered cyclic carbonates, as a member of the cyclic carbonates, are often used as electrolyte solvents for lithium-ion batteries 3 , plasticizers 4 , environmentally friendly aprotic polar organic solvent 5 , fuel additive 6 , starting materials and intermediates in the manufacture of fine chemicals 7 .…”