Synthesis And Process Research Of Triethyleneglycol Divinyl Ether

Triethyleneglycol divinyl ether (DVE-3) as a highly valuable synthon is widely applied in polymerformulations and organic synthesis. Its copolymers and homopolymers have been widely used in fields of lubricants, adhesive, plasticizers, painting, surface protecting materials and so on. However the development of vinyl ethers and their related products are still in infancy, and only few monomers are industrially produced in our country by now. There are rare literatures reported on the synthesis of DVE-3, so the research on it will be interesting and significant.In this paper, an efficient route of preparing DVE-3was investigated according to the previous methods. The desired proudct was generated from iridium-catalyzed transfer vinylation in which triethylene glycol reacted with vinyl acetate.In order to optimize the reaction conditions, we selected the reaction of benzyl alcohol and vinyl acetate as the model reaction. The effect of different catalysts, bases, solvents were evaluated in the transfer vinylation of alcohols to vinyl ethers. As a result, the optimal conditions are using Na2CO3(60mol%) as the base, toluene as the solvent, and2mol%[Ir(cod)Cl]2(cod=1,5-cyclooctadiene) or2mol%[Ir(coe)2Cl]2(coe=cyclooclene) as the catalyst at100℃for14h, and the yield can be obtained in93%.Based on the research of benzyl alcohol, we also got the optimal reaction conditions of DVE-3:Triethylene glycol reacted with vinyl acetate in toluene at100℃for14h using Na2CO3(60mol%) as the base,, and [Ir(cod)Cl]2(4mol%) or [Ir(coe)2Cl]2(4mol%) as the catalyst, the yield was given in50%.At last, a series of experiments were performed and the final results showed that the optimal conditions we obtained could be applied to other alcohols, so the reaction conditions have certain applicability.