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Facile catalyst recycling by thermomorphic behaviour avoiding organic solvents: a reactive ionic liquid in the homogeneous Pd-catalysed telomerisation of the renewable β-myrcene
Catalysis Science & Technology ( IF 5 ) Pub Date : 2020/02/03 , DOI: 10.1039/c9cy02569c
Michael Terhorst 1, 2, 3, 4, 5 , Anna Kampwerth 1, 2, 3, 4, 5 , Amelie Marschand 1, 2, 3, 4, 5 , Dieter Vogt 1, 2, 3, 4, 5 , Andreas J. Vorholt 5, 6, 7 , Thomas Seidensticker 1, 2, 3, 4, 5
Affiliation  

For the first time, the reactive ionic liquid N,N-dimethyl ammonium N,N-dimethyl carbamate (dimcarb) was used as a polar solvent in the palladium-catalyzed telomerisation of the renewable monoterpene β-myrcene. By doing so, it was possible to avoid any volatile organic solvents. Moreover, the special decomposition behaviour of the reactive ionic liquid dimcarb could be exploited to the extent that dimethyl amine was used as a reagent in the reaction. Accordingly, non-symmetrical C20-chain dimethyl amines were produced from β-myrcene and dimethylamine liberated by dimcarb, achieving selectivities higher than 80%. Detailed investigations revealed the thermomorphic behaviour of the reaction mixture consisting only of dimcarb, β-myrcene and the catalytic system. The advantageous temperature-dependent phase behaviour resulted in one liquid phase occurring at the reaction temperature and two liquid phases upon cooling. Consequently, a virtually pure organic product phase could be separated from the polar catalyst-containing dimcarb phase. Immobilization of the catalyst in the polar reactive ionic liquid phase was ensured by the use of sulfonated triphenylphosphine derivatives. Subsequently, the separated catalyst-containing dimcarb phase was successfully reused in 14 consecutive recycling runs with only minimal leaching of both the catalyst and dimcarb, reaching a total turnover number of 12 000.

中文翻译:

避免有机溶剂的热态行为,可轻松回收催化剂:可再生β-月桂烯在均相Pd催化的端粒化反应中的反应性离子液体

活性离子液体NN-二甲基铵NN-二甲基氨基甲酸酯(dimcarb)首次在钯催化可再生单萜β-月桂烯的端粒化反应中用作极性溶剂。这样,可以避免任何挥发性有机溶剂。此外,在二甲胺用作反应试剂的范围内,可以利用反应性离子液体昏灭威的特殊分解行为。因此,非对称C 20β-月桂烯和由二甲威释放的二甲基胺可生产链状二甲基胺,选择性高于80%。详细的研究揭示了仅由二甲威,β-月桂烯和催化体系组成的反应混合物的热形态行为。有利的与温度有关的相行为导致在反应温度下出现一个液相,并且在冷却时出现两个液相。因此,实际上纯的有机产物相可以与含极性催化剂的二甲威相分离。通过使用磺化的三苯基膦衍生物确保了催化剂在极性反应性离子液相中的固定化。后来,
更新日期:2020-03-26
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