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Synthesis of 2,2,4-trimethyl-1,2-H-dihydroquinoline (TMQ) over selected organosulfonic acid silica catalysts: Selectivity aspects
Molecular Catalysis ( IF 3.9 ) Pub Date : 2018-05-25 , DOI: 10.1016/j.mcat.2018.05.016
J. Nowicki , K. Jaroszewska , E. Nowakowska-Bogdan , M. Szmatoła , J. Iłowska

This paper presents investigation on the synthesis of 2,2,4-trimethyl-1,2-H-dihydroquinoline (TMQ) as a result of the reaction of aniline and both acetone and mesityl oxide in the presence of selected sulfonic acid silica catalysts. Condensation of aniline with acetone is very complex process with the formation of significant number of side products, both desirable and undesirable considering the final product (TMQ). In acidic conditions and elevated reaction temperature the reactivity of main raw materials (aniline, acetone) is significantly high, what causes the formation of many side by-products lowering the selectivity of this reaction. In this paper the reaction of aniline with acetone in the presence of heterogeneous acidic silica catalysts were investigated in more detail and discussed. The results were confirmed by GC/MS analysis, that the presence of TMQ isomers and other by-products significantly affected the formation of final product. The formation of previously not described structural isomer of TMQ has been also demonstrated.



中文翻译:

在选定的有机磺酸二氧化硅催化剂上合成2,2,4-三甲基-1,2- H-二氢喹啉(TMQ):选择性方面

本文介绍了2,2,4-三甲基-1,2- H的合成-二氢喹啉(TMQ)是苯胺与丙酮和异丁烯二氧化物在选择的磺酸二氧化硅催化剂存在下反应的结果。苯胺与丙酮的缩合是非常复杂的过程,会形成大量副产物,考虑到最终产物(TMQ),这是合乎需要的和不合需要的。在酸性条件和升高的反应温度下,主要原料(苯胺,丙酮)的反应性非常高,这导致形成许多副产物,从而降低了该反应的选择性。在本文中,对非均相酸性二氧化硅催化剂存在下苯胺与丙酮的反应进行了更详细的研究。结果通过GC / MS分析得到证实,TMQ异构体和其他副产物的存在显着影响了最终产物的形成。还已经证明了先前未描述的TMQ的结构异构体的形成。

更新日期:2018-05-25
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