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Synthesis of Cross‐linked Ionic Poly(styrenes) and their Application as Catalysts for the Synthesis of Carbonates from CO 2 and Epoxides
Author(s) -
Bobbink Felix D.,
Van Muyden Antoine P.,
Gopakumar Aswin,
Fei Zhaofu,
Dyson Paul J.
Publication year - 2017
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201600461
Subject(s) - catalysis , cycloaddition , styrene , polystyrene , ionic liquid , polymer , epoxide , chemistry , polymerization , polymer chemistry , ionic bonding , materials science , organic chemistry , copolymer , ion
A series of dicationic styrene‐functionalized imidazolium‐based salts, in which the two imidazolium rings are bridged by a functionalized spacer, are prepared. The salts are polymerized to afford cross‐linked imidazolium‐based ionic polystyrene materials, which, owing to the presence of the functionalized spaces, should be highly active organocatalysts for the cycloaddition of CO 2 to epoxides to afford cyclic carbonates (CCE reaction). The catalytic activities of the polymers are evaluated in the CCE reaction. The most active catalyst incorporates a diol functionality and is active at 80 °C and a pressure of 4 bar at a loading of 5 mol %, which is comparable to the most active organocatalysts. Moreover, high yields can be obtained under atmospheric pressure upon increasing the temperature to 120 °C. Under harsher conditions, the catalyst is highly active at a loading one order of magnitude lower, highlighting the importance of benchmark conditions for the CCE reaction. Moreover, the polymer catalysts are advantageous because they can be used at low catalyst loadings, the carbonate product is easily isolated in pure form, and loss of activity of the recovered polymer catalyst is not observed during reuse.