Citation: Xiaoming Yan, Xuan Ding, Yu Pan, Xiaowei Xu, Ce Hao, Wenji Zheng, Gaohong He. Quaternary-ammonium-immobilized polystyrenes as efficient and reusable heterogeneous catalysts for synthesis of cyclic carbonate: Effects of linking chains and pendent hydroxyl group[J]. Chinese Journal of Catalysis, ;2017, 38(5): 862-871. doi: 10.1016/S1872-2067(17)62819-5 shu

Quaternary-ammonium-immobilized polystyrenes as efficient and reusable heterogeneous catalysts for synthesis of cyclic carbonate: Effects of linking chains and pendent hydroxyl group

Xiaoming Yan ^a,b, ,
Xuan Ding ^a ,
Yu Pan ^a ,
Xiaowei Xu ^a ,
Ce Hao ^a ,
Wenji Zheng ^a ,
Gaohong He ^a,b

a. State Key Laboratory of Fine Chemicals, Research and Development Center of Membrane Science and Technology, School of Petroleum and Chemical Engineering, Dalian University of Technology, Panjin 124221, Liaoning, China;
b. State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024, Liaoning, China

Received Date: 14 February 2017
Revised Date: 16 March 2017

Fund Project: This work was supported by the National Natural Science Foundation of China (21406031, 21476044, U1663223), the Changjiang Scholars Program (T2012049), the State Key Laboratory of Fine Chemicals (KF1507), Dalian High-Level Talent Support Program (2015R056), Education Department of the Liaoning Province of China (LT2015007), and Fundamental Research Funds for the Central Universities (DUT16TD19).

Spherical polystyrene-supported ammonium salts containing different linking chains between the support and ammonium groups were prepared as efficient and easily reusable heterogeneous catalysts for the cycloadditions of CO₂ and epoxides. The effects of the length of the linking chains and a hydroxyl group pendent on the linking chain on the catalytic performance of ionic liquid immobilized catalysts and their mechanisms were studied through experiments and density functional theory calculations. It was found that, compared with a short linking chain, a long chain can make the halogen anion more negative and provide a larger contact area of the catalysts with the reactants, thus enhancing the reaction kinetics. The hydroxyl group can stretch the C–O bonds of the epoxides, promoting the reaction thermodynamics. As a result, for the cycloaddition of propylene oxide, the yield of propylene carbonate is much higher for the catalyst with a long linking chain (yield: 91.4%) compared with the yield for that with a short chain (yield: 70.9%), and is further increased in the presence of pendent hydroxyl groups (yield: 98.5%). The catalyst also shows a high catalytic activity even at mild temperature and good reusability (yield: ≥ 96% for 10 cycles), and the selectivity is always above 99%.
- Cycloaddition,
- Ammonium,
- Long alkyl chain,
- Hydroxyl group,
- Heterogeneous catalyst
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