Study On Hydrolysis Reactions Of Aromatic Compounds Catalyzed By PEG-based Thermoregulated Ionic Liquid

Hydrolysis was an important reaction of organic synthesis. The most commonly employed procedures for hydrolysis have been used of alkalizes or acidic. There were also investigations into the hydrolysis to speed up the hydrolysis reactions, such as the use of micellar catalysis, the metal salts, microwaves, etc. However, the disadvantages of the traditional hydrolysis were the additional use of base, the long reaction times, high reaction temperatures, and the formation of other by-products and the difficulty of catalyst recovery. Room temperature ionic liquids had recently been widely used for synthesis, catalysis, separation, and novel electrolytes. Novel temperature-dependent ionic liquid biphasic systems had been reported, not only they had been noticed with the advantages of high product yield in the reaction, but also they provided us a novel route for improving product isolation as well as recycling of catalysts.In this article, we reported a novel and efficient procedure for the hydrolysis of organic halides, esters and epoxies with water which catalyzed by Fe2(SO4)3 in the PEG1000-based diatonic ionic liquid and toluene temperature-dependent biphasic system under homogeneous catalysis in aqueous media(PEG1000-DAIL[BF4]/Fe2(S04)3). It was found that this novel method not only enhanced the yield and the selectivity of the products, but also made the operating units easy workup. In this work, excellent yield (96%) and high selectivity (99%) of benzyl alcohol was obtained in 1h by hydrolysis of benzyl chloride catalyzed by PEG1000-DAIL[BF4]/Fe2(S04)3 at the temperature of 110℃. In the experiment of hydrolysis of methyl benzoate, we found that benzoic acid was obtained in 95.1% excellent yield in 2h at the temperature of 105℃.We also found that in the experiment of hydrolysis of styrene oxide, if the temperature was controlled at 120℃for 2.5h, styrene glycol was obtained in 93.4% excellent yield and 99.1% high selectivity. In addition, the catalytic system could be recycled or reused without any appreciable decrease in yields and reaction rates. Moreover the product can be easily isolated by decantation when the hydrolysis was finished and the reactions had been cooled to the room temperature. The excellent recyclability of the catalytic system made this procedure easier and cleaner, and this novel method for hydrolysis was a good example of green chemistry technology.