# US 10,308,564 B2 · Aromatic alkylation using chemically-treated solid oxides

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- Number: US 10,308,564 B2
- Document ID: US10308564B2
- Status: Granted
- Kind: B2
- Application number: 15/438,822
- Filed: 2017-02-22
- Published: 2017-08-17
- Granted: 2019-06-04
- Earliest claimed: 2016-02-17
- Assignees: Chevron Phillips Chemical Company LP
- Applicants: Chevron Phillips Chemical Company LP
- Inventors: Qing Yang; Max P. McDaniel; Uriah J. Kilgore; Mark L. Hlavinka
- Web page: https://patentgrep.com/patent/US10308564B2

## CPC

- C07C 2/68: with halides
- B01J 21/12: Silica and alumina
- B01J 27/053: Sulfates
- B01J 27/10: Chlorides
- B01J 27/12: Fluorides
- B01J 37/0201: {Impregnation}
- B01J 37/0209: {involving a reaction between the support and a fluid}
- B01J 37/24: Chlorinating
- B01J 37/26: Fluorinating
- C07C 2/66: Catalytic processes
- C07C 2521/04: Alumina
- C07C 2521/12: Silica and alumina
- C07C 2527/06: Halogens; Compounds thereof
- C07C 2527/10: Chlorides
- C07C 2527/12: Fluorides
- C07C 2527/125: Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## 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.

## Claims

### 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.

### Claim 2 (depends on 1)

The process of claim 1, wherein the aromatic compound comprises a C6 to C24 hydrocarbon aromatic compound.

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

The process of claim 1, wherein the olefin feedstock comprises at least 75 wt. % C3 to C18 alpha olefins.

### Claim 5 (depends on 1)

The process of claim 1, wherein the olefin feedstock comprises a C2 to C40 alpha olefin.

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 1)

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

### Claim 8 (depends on 1)

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.

### Claim 9 (depends on 1)

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

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 1)

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.

### Claim 12 (depends on 1)

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.

### Claim 13 (depends on 12)

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.

### Claim 14 (depends on 1)

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.

### Claim 15 (depends on 14)

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.

### Claim 16 (depends on 1)

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.

### Claim 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.

### Claim 18 (depends on 17)

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.

### Claim 19 (depends on 17)

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.

### Claim 20 (depends on 19)

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.

### Claim 21 (depends on 19)

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.