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Synthesis and performance of piperidinium‐based ionic liquids as catalyst for alkylation of p ‐xylene with 1‐hexadecene
Author(s) -
Ge Sujuan,
Zhou Yuming,
Sheng Xiaoli,
Mao Chunfeng,
Zhao Lina,
Xu Jianxing,
Qiu Lei
Publication year - 2021
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.6147
Subject(s) - chemistry , catalysis , ionic liquid , molar ratio , bromide , alkylation , electrospray ionization , fourier transform infrared spectroscopy , mass spectrometry , alkyl , anhydrous , nuclear chemistry , medicinal chemistry , inorganic chemistry , organic chemistry , chemical engineering , chromatography , engineering
Piperidinium‐based ionic liquids (ILs) were synthesized under mild conditions by coordinating N ‐alkyl‐ N ‐methylpiperidinium bromide ([Pip 1,x ]Br) with anhydrous AlCl 3 . The weak basicity of N ‐methylpiperidine had little impact on downstream problems from proton impurities and catalyst poisoning. The results of Fourier transform infrared (FT‐IR), electrospray ionization mass spectrometry (ESI‐MS), and nuclear magnetic resonance ( 27 Al NMR) confirmed that the active components in [Pip 1,x ]Br‐2AlCl 3 ( χ = 0.67) were [Al 3 Cl 9 Br] − and [Al 2 Cl 6 Br] − . Besides, the reaction performance of [Pip 1,8 ]Br‐2AlCl 3 under different conditions was carried out by single‐factor experiment and further confirmed by orthogonal experimental method. Among these reaction conditions, the optimal combination was the reaction temperature of 40°C, ILs/O molar ratio of 0.2:1, px/O molar ratio of 12:1, and the reaction time of 30 min. Furthermore, [Pip 1,8 ]Br‐2AlCl 3 had excellent stability and can be recycled 14 times. It was the high‐efficiency catalytic activity and prominent recyclability that made continuous industrial production possible.