Alkylation of anthracene to 2-isopropylanthracene catalyzed by Lewis acid ionic liquids

Abstract

Alkylation of anthracene with 2-chloropropane to 2-isopropylanthracene catalyzed by various Lewis acidic ionic liquids (ILs), such as [Emim]Cl-AlCl 3 , [Emim]Cl-FeCl 3 , [Emim]Cl-ZnCl 2 , [Bmim]Cl-AlCl 3 , and [Omim]Cl-AlCl 3[Emim]C1-A1C1 3 ionic liquid was found to be the most active catalyst in the alkylation. The yield of 2-isopropylanthracene was up to 74.5% and the selectivity of 2-isopropylanthracene was up to 82.9%. The [Emim]C1-A1C1 3 ionic liquid catalyst showed good catalytic activity after running for 6 times. Ease of product separation and the recycling performance of the ionic liquid catalyst is expected to contribute to the development of clean and environmentally friendly strategy for the synthesis of 2-isopropylanthracene.

Structural Effects on the Physico‐Chemical and Catalytic Properties of Acidic Ionic Liquids: An Overview

“…Consistently with the previously discussed work, it was reported [95] that [emim][Cl]/AlCl 3 gave the best results in terms of yield (74.5 %) and selectivity (82.9 %). With increases in the alkyl chain length on the imidazolium ring to butyl and octyl the percentage yields decreased (just as in the previous work) and zero performance was again observed when the metal halide used was ZnCl 2 .…”

Ionic Liquids: From Synthesis to Applications in Solar Cells

“…ILs derived from AlCl 3 , ZnCl 2 , CuCl 2 or FeCl 3 , high yields and selectivities were achieved in all cases, with the chloroaluminate-based ILs giving the highest yields and selectivities. [59] The high sensitivity of chloroaluminate-based ILs to moisture makes recycling and reuse problematic, [60] nonetheless, chloroaluminate-based ILs continue to find niche applications in synthesis, such as in the preparation of β-chlorovinylketones from acetylene. [61] The Diels-Alder cyclization displays a strong endo/exo dependence on the reaction solvent (the ratio has even been used as the basis of a polarity scale).…”

High-pressure phase behavior of CO2+1-butyl-3-methylimidazolium chloride system

“…ILs have gained much attention due to a variety of chemical processes related to their unique properties, such as non-volatility, high thermal stability, non-flammability, high polarity, and wide temperature range for the liquid phase. This allows ILs to be applied as good substitute solvents for conventional volatile solvents in "clean processes" and "green chemistry" [1,2] in many fields including synthesis [3], polymerization [4], catalysis [5][6][7], separation [8], etc.…”