Processes for the acylation of an aromatic compound
Processes for acylating an aromatic compound are provided. In embodiments, such a process comprises combining an aromatic compound, an acylating agent, and a catalyst composition under conditions to induce acylation of the aromatic compound with the acylating agent, the catalyst composition comprising components selected from the group consisting of a sulfonic acid of formula R—SO 3 H, wherein R is a linear alkyl group substituted with one or more halogen atoms; an ionic liquid and an acid; an acid and a base capable of forming an ionic liquid with the acid; an ionic liquid, an acid, and an aromatic; and an acid, a base capable of forming an ionic liquid with the acid, and an aromatic. The ionic liquid does not comprise a metal halide and the catalyst composition is free of a metal halide and the aromatic, if present in the catalyst composition, is not the aromatic compound being acylated.
1 . A process for acylating an aromatic compound, the process comprising combining an aromatic compound, an acylating agent, and a catalyst composition under conditions to induce acylation of the aromatic compound with the acylating agent, the catalyst composition comprising components selected from the group consisting of
(a) an ionic liquid, an acid, and an aromatic; and
(b) an acid, a base capable of forming an ionic liquid with the acid, and an aromatic;
wherein the ionic liquid does not comprise a metal halide and the catalyst composition is free of a metal halide and the aromatic of the catalyst composition is not the aromatic compound being acylated.
2 . The process of claim 1 , wherein the ionic liquid does not comprise a non-metal halide and the catalyst composition is free of a non-metal halide.
3 . The process of claim 1 , wherein the aromatic of the catalyst composition is selected from an unsubstituted or substituted monocyclic aromatic.
4 . The process of claim 1 , wherein the aromatic of the catalyst composition has formula C 6 R 6 , wherein each R is independently selected from hydrogen, a halogen, and an unsubstituted or substituted alkyl group.
5 . The process of claim 1 , wherein the aromatic of the catalyst composition is selected from benzene, toluene, xylenes, mesitylene, hexamethylbenzene, and a halogenated benzene.
6 . The process of claim 1 , wherein the acid is triflic acid or tetrafluoroethane sulfonic acid.
7 . The process of claim 1 , wherein the ionic liquid comprises an imidazolium cation.
8 . The process of claim 7 , wherein the imidazolium cation has Formula B
wherein R 1 is hydrogen or alkyl and n is 0, 3, 4, or 5.
9 . The process of claim 8 , wherein n is 0.
10 . The process of claim 1 , wherein the ionic liquid comprises [HCF 2 CF 2 SO 3 ] − as an anion.
11 . The process of claim 1 , wherein the ionic liquid comprises an imidazolium as a cation and [HCF 2 CF 2 SO 3 ] − as an anion.
12 . The process of claim 1 , wherein the aromatic compound of the catalyst composition is substituted, the acylating agent is an acyl halide, and the aromatic compound is acylated at its para position.
13 . The process of claim 12 , wherein the aromatic compound of the catalyst composition is isobutylbenzene and the acylating agent is acetyl chloride.
14 . The process of claim 1 , wherein a mole ratio of the catalyst composition to the acylating agent is no more than 0.5:1.
15 . The process of claim 1 , wherein the catalyst composition comprises components from (a).
16 . The process of claim 15 , wherein the catalyst composition is represented by [IL] x -[Acid] (100-x) -[Aromatic] y , wherein x is (weight of the ionic liquid)/(combined weight of the ionic liquid and the acid)*100 and ranges from 5 weight % to 20 weight % and further wherein y is (weight of the aromatic of the catalyst composition)/(combined weight of the ionic liquid and the acid)*100 and ranges from 0.1 weight % to 25 weight %.
17 . The process of claim 15 , wherein the aromatic of the catalyst composition is selected from benzene, toluene, xylenes, mesitylene, hexamethylbenzene, and a halogenated benzene.
18 . The process of claim 15 , wherein the ionic liquid comprises an imidazolium as a cation and a sulfonate as an anion.
19 . The process of claim 15 , wherein the acid is a sulfonic acid.
20 . The process of claim 16 , wherein the aromatic of the catalyst composition is hexamethylbenzene; the ionic liquid is N-methyl, N-sulfonic acid imidazolium tetrafluoroethane sulfonate; and the acid is triflic acid or tetrafluoroethane sulfonic acid.