Aromatic alkylation using chemically-treated solid oxides

Patent metadata

Field	Value
Publication number	US-10308564-B2
Application number	US-201715438822-A
Country	US
Kind code	B2
Filing date	Feb 22, 2017
Priority date	Feb 17, 2016
Publication date	Jun 4, 2019
Grant date	Jun 4, 2019

Abstract

The present invention discloses processes for alkylating an aromatic compound, such as benzene or toluene, using a chemically-treated solid oxide. Suitable chemically-treated solid oxides include fluorided silica-coated alumina and fluorided-chlorided silica-coated alumina.

First claim

We claim:

1. A process for alkylating an aromatic compound, the process comprising:
contacting the aromatic compound, an olefin feedstock, and a chemically-treated solid oxide at an alkylation temperature in a range from 0° C. to 60° C. to produce a product comprising an alkylated aromatic compound;
wherein the chemically-treated solid oxide comprises a solid oxide treated with an electron-withdrawing anion, and the electron-withdrawing anion is at least on an exterior surface of the chemically-treated solid oxide.

2. The process of claim 1 , wherein the aromatic compound comprises a C 6 to C 24 hydrocarbon aromatic compound.

3. The process of claim 1 , wherein the aromatic compound comprises benzene, naphthalene, toluene, cumene, xylene, ethylbenzene, or any combination thereof.

4. The process of claim 1 , wherein the olefin feedstock comprises at least 75 wt. % C 3 to C 18 alpha olefins.

5. The process of claim 1 , wherein the olefin feedstock comprises a C 2 to C 40 alpha olefin.

6. The process of claim 1 , wherein the olefin feedstock comprises ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, or any combination thereof.

7. The process of claim 1 , wherein the alkylation temperature is in a range from 20° C. to 60° C.

8. The process of claim 1 , wherein the solid oxide comprises silica, alumina, silica-alumina, silica-coated alumina, aluminum phosphate, aluminophosphate, heteropolytungstate, titania, silica-titania, zirconia, silica-zirconia, magnesia, boria, zinc oxide, any mixed oxide thereof, or any combination thereof.

9. The process of claim 1 , wherein the electron-withdrawing anion comprises sulfate, fluoride, chloride, or any combination thereof.

10. The process of claim 1 , wherein the chemically-treated solid oxide comprises a fluorided solid oxide and/or a sulfated solid oxide.

11. The process of claim 1 , wherein the chemically-treated solid oxide comprises fluorided alumina, chlorided alumina, bromided alumina, sulfated alumina, fluorided silica-alumina, chlorided silica-alumina, bromided silica-alumina, sulfated silica-alumina, fluorided silica-zirconia, chlorided silica-zirconia, bromided silica-zirconia, sulfated silica-zirconia, fluorided silica-titania, fluorided silica-coated alumina, fluorided-chlorided silica-coated alumina, sulfated silica-coated alumina, phosphated silica-coated alumina, or any combination thereof.

12. The process of claim 1 , wherein the product comprises less than or equal to 1 wt. % olefin oligomers, based on the total weight of the product.

13. The process of claim 12 , wherein:
the aromatic compound comprises benzene, naphthalene, toluene, cumene, xylene, ethylbenzene, furan, pyridine, methylpyridine, or any combination thereof; and
the olefin feedstock comprises ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, or any combination thereof.

14. The process of claim 1 , wherein:
a molar ratio of the aromatic compound to the olefin feedstock is in a range from 2:1 to 35:1;
the process has an olefin conversion of at least 80%;
the product comprises less than or equal to 5 wt. % olefin oligomers, based on the total weight of the product; and
the product comprises a molar ratio of mono-alkylated aromatic compounds to multi-alkylated aromatic compounds in a range from 1.2:1 to 25:1.

15. The process of claim 14 , wherein:
the aromatic compound comprises benzene, naphthalene, toluene, cumene, xylene, ethylbenzene, furan, pyridine, methylpyridine, or any combination thereof; and
the olefin feedstock comprises ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, or any combination thereof.

16. The process of claim 1 , wherein:
a molar ratio of the aromatic compound to the olefin feedstock is in a range from 5:1 to 20:1;
the process has an olefin conversion of at least 90%;
the product comprises less than or equal to 1 wt. % olefin oligomers, based on the total weight of the product; and
the product comprises a molar ratio of mono-alkylated aromatic compounds to multi-alkylated aromatic compounds in a range from 3:1 to 25:1.

17. A process for alkylating an aromatic compound, the process comprising:
contacting the aromatic compound, an olefin feedstock, and a chemically-treated solid oxide at an alkylation temperature in a range from 0° C. to 60° C. to produce a product comprising an alkylated aromatic compound;
wherein the chemically-treated solid oxide comprises sulfated alumina, and sulfate is at least on an exterior surface of the sulfated alumina.

18. The process of claim 17 , wherein the product comprises less than or equal to 1 wt. % olefin oligomers, based on the total weight of the product.

19. The process of claim 17 , wherein:
the aromatic compound comprises benzene, naphthalene, toluene, cumene, xylene, ethylbenzene, furan, pyridine, methylpyridine, or any combination thereof; and
the olefin feedstock comprises ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, or any combination thereof.

20. The process of claim 19 , wherein:
a molar ratio of the aromatic compound to the olefin feedstock is in a range from 2:1 to 35:1;
the process has an olefin conversion of at least 80%;
the product comprises less than or equal to 5 wt. % olefin oligomers, based on the total weight of the product; and
the product comprises a molar ratio of mono-alkylated aromatic compounds to multi-alkylated aromatic compounds in a range from 1.2:1 to 25:1.

21. The process of claim 19 , wherein:
a molar ratio of the aromatic compound to the olefin feedstock is in a range from 5:1 to 20:1;
the process has an olefin conversion of at least 90%;
the product comprises less than or equal to 1 wt. % olefin oligomers, based on the total weight of the product; and
the product comprises a molar ratio of mono-alkylated aromatic compounds to multi-alkylated aromatic compounds in a range from 3:1 to 25:1.

Assignees

• Chevron Phillips Chemical Co Lp

Inventors

• Yang Qing
• Mcdaniel Max P
• Kilgore Uriah J
• Hlavinka Mark L

Classifications

• B01J27/053

  Sulfates · CPC title

• C07C2/68 Primary

  with halides · CPC title

• C07C2521/12

  Silica and alumina · CPC title

• B01J27/12

  Fluorides · CPC title

• B01J37/26

  Fluorinating · CPC title