Processes for the preparation of alkylbenzenes

Patent metadata

Field	Value
Publication number	US-12240792-B2
Application number	US-202118042487-A
Country	US
Kind code	B2
Filing date	Aug 20, 2021
Priority date	Aug 24, 2020
Publication date	Mar 4, 2025
Grant date	Mar 4, 2025

Abstract

Processes for alkylating benzene are provided. In embodiments, the process comprises combining benzene, an olefin, and a catalyst composition under conditions to react benzene with the olefin to produce an alkylbenzene, the catalyst composition comprising components selected from the group consisting of an ionic liquid, an acid, and an aromatic; an acid, a base capable of forming an ionic liquid with the acid, and an aromatic; an ionic liquid and an acid; and an acid and a base capable of forming an ionic liquid with the acid. 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 benzene being alkylated.

First claim

What is claimed is:

1. A process for alkylating benzene, the process comprising combining benzene, an olefin, and a catalyst composition under conditions to react benzene with the olefin to produce an alkylbenzene, 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 is not the benzene being alkylated.

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 is selected from an unsubstituted or substituted monocyclic aromatic.

4. The process of claim 1 , wherein the aromatic 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 is selected from benzene, toluene, xylenes, mesitylene, hexamethylbenzene, and a halogenated benzene.

6. The process of claim 1 , wherein the acid is triflic acid, H 2 SO 4 , or tetrafluoroethane sulfonic acid.

7. The process of claim 1 , wherein the ionic liquid comprises an ammonium cation and the ammonium cation has formula NR 4 + , wherein each R is independently selected from alkyl groups.

8. The process of claim 1 , wherein the ionic liquid comprises an imidazolium cation and the imidazolium cation has Formula A

wherein R 1 is hydrogen or alkyl and n is from 0 to 18.

9. The process of claim 1 , wherein the ionic liquid comprises an imidazolium cation and the imidazolium cation has Formula B

wherein R 1 is hydrogen or alkyl and n is 0, 3, 4, or 5.

10. The process of claim 9 , wherein n is 0.

11. The process of claim 1 , wherein the ionic liquid comprises [HSO 4 ] − or [HCF 2 CF 2 SO 3 ] − as an anion.

12. The process of claim 1 , wherein the ionic liquid comprises a cation selected from an ammonium and an imidazolium and [HSO 4 ] − or [HCF 2 CF 2 SO 3 ] − as an anion.

13. A process for alkylating benzene, the process comprising combining benzene, a linear alpha olefin or a mixture of linear alpha olefins, and a catalyst composition under conditions to react benzene with the olefin or the mixture to produce an alkylbenzene, 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 ionic liquid does not comprise a non-metal halide and the catalyst composition is free of a metal halide and the catalyst composition is free of a non-metal halide and the aromatic is not the benzene being alkylated.

14. The process of claim 13 , wherein the aromatic is selected from benzene, toluene, xylenes, mesitylene, hexamethylbenzene, and a halogenated benzene.

15. The process of claim 14 , wherein the acid is triflic acid, H 2 SO 4 , or tetrafluoroethane sulfonic acid.

16. The process of claim 15 , wherein the ionic liquid comprises a cation selected from an ammonium and an imidazolium and [HSO 4 ] − or [HCF 2 CF 2 SO 3 ] − as an anion.

17. The process of claim 1 , wherein the acid is present in the catalyst composition at an amount in a range of from 80 weight % to 98 weight %, wherein weight % refers to (weight of the ionic liquid or the base)/(combined weight of the acid with the weight of the ionic liquid or the base)*100.

18. The process of claim 16 , wherein the acid is present in the catalyst composition at an amount in a range of from 80 weight % to 98 weight %, wherein weight % refers to (weight of the ionic liquid or the base)/(combined weight of the acid with the weight of the ionic liquid or the base)*100.

19. The process of claim 1 , wherein the aromatic is a halogenated benzene.

20. The process of claim 18 , wherein the aromatic is a halogenated benzene.

Assignees

• Univ Kansas
• Univeristy Of Kansas

Inventors

• Shiflett Mark Brandon
• Kore Rajkumar
• Scurto Aaron M

Classifications

• C07C2531/025

  Sulfonic acids · CPC title

• C07C2527/054

  Sulfuric acid or other acids with the formula H2Sn03n+1 · CPC title

• C07C2531/02

  containing organic compounds or metal hydrides · CPC title

• C07C2/62 Primary

  with acids · CPC title

• C07C2/70 Primary

  with acids · CPC title