# US 10,246,383 B2 · Process for producing paraxylene by methylation of benzene and/or toluene

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,246,383 B2
- Document ID: US10246383B2
- Status: Granted
- Kind: B2
- Application number: 15/702,337
- Filed: 2017-09-12
- Published: 2018-04-12
- Granted: 2019-04-02
- Earliest claimed: 2016-10-06
- Assignees: ExxonMobil Chemical Patents Inc.
- Applicants: ExxonMobil Chemical Patents Inc.
- Inventors: Tan-Jen Chen; Seth M. Washburn
- Web page: https://patentgrep.com/patent/US10246383B2

## CPC

- C07C 2/66: Catalytic processes
- B01J 29/0308: {Mesoporous materials not having base exchange properties, e.g. Si-MCM-41}
- B01J 29/70: of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J 29/7038: {MWW-type, e.g. MCM-22, ERB-1, ITQ-1, PSH-3 or SSZ-25}
- C07C 2/864: {the non-hydrocarbon is an alcohol}
- C07C 2529/70: of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
- Y02P 20/52: using catalysts, e.g. selective catalysts
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A process is described for producing paraxylene, in which an aromatic hydrocarbon feedstock comprising benzene and/or toluene is contacted with an alkylating reagent comprising methanol and/or dimethyl ether in an alkylation reaction zone under alkylation conditions in the presence of an alkylation catalyst to produce an alkylated aromatic product comprising xylenes. The alkylation catalyst comprises a molecular sieve having a Constraint Index ≤5, and the alkylation conditions comprise a temperature less than 500° C. Paraxylene may then be recovered from the alkylated aromatic product.

## Claims

### Claim 1

A process for producing paraxylene, the process comprising:
(a) selectivating an alkylation catalyst consisting essentially of MCM-49 zeolite and alumina binder by contacting the alkylation catalyst with a selectivating agent selected from the group consisting of silicon, steam, and a combination of silicon and steam;
(b) contacting an aromatic hydrocarbon feed comprising toluene with an alkylating reagent comprising methanol and/or dimethyl ether in at least one alkylation reaction zone in the presence of the alkylation catalyst under alkylation conditions comprising a temperature less than 500° C. and a pressure of 700 kPa-a to 7000 kPa-a to produce an alkylated aromatic product comprising xylenes, wherein the at least one alkylation reaction zone comprises a fixed bed of the alkylation catalyst; and
(c) recovering paraxylene from the alkylated aromatic product.

### Claim 2 (depends on 1)

The process of claim 1, wherein the aromatic hydrocarbon feed comprises at least 90 wt % toluene.

### Claim 3 (depends on 2)

The process of claim 2, wherein the alkylating reagent comprises methanol.

### Claim 4 (depends on 3)

The process of claim 3, wherein the alkylation conditions comprise a temperature of at least 250° C.

### Claim 5 (depends on 4)

The process of claim 4, wherein the alkylation conditions comprise a temperature from 250° C. to 450° C.

### Claim 6 (depends on 5)

The process of claim 5, wherein the alkylation conditions comprise a pressure from 3000 kPa-a to 7000 kPa-a.

### Claim 7 (depends on 6)

The process of claim 6, wherein the alkylation conditions comprise a weight hourly space velocity based on the aromatic hydrocarbon feed of 50 to 0.5 hr−1.

### Claim 8 (depends on 7)

The process of claim 7, wherein the alkylated aromatic product comprises at least 80 wt % xylenes.

### Claim 9 (depends on 1)

The process of claim 1, wherein the alkylation conditions comprise a pressure in the range from 2,000 to 7,000 kPa-a.

### Claim 10 (depends on 1)

The process of claim 1, wherein the alkylation conditions comprise a pressure in the range from 3,000 to 5,000 kPa-a.

### Claim 11 (depends on 1)

The process of claim 1, wherein the alkylation conditions comprise a temperature in the range from 300 to 450° C.

### Claim 12

A process for producing paraxylene, the process comprising:
(a) selectivating an alkylation catalyst consisting essentially of MCM-49 zeolite and alumina binder by contacting the alkylation catalyst with a selectivating agent selected from the group consisting of silicon, steam, and a combination of silicon and steam;
(b) contacting an aromatic hydrocarbon feed comprising toluene with an alkylating reagent comprising methanol in at least one alkylation reaction zone in the presence of the alkylation catalyst under alkylation conditions comprising a temperature from about 250° C. to less than about 500° C. and a pressure of 700 kPa-a to 7000 kPa-a to produce an alkylated aromatic product comprising xylenes, wherein the at least one alkylation reaction zone comprises a fixed bed of the alkylation catalyst; and
(c) recovering paraxylene from the alkylated aromatic product.

### Claim 13 (depends on 12)

The process of claim 12, wherein the aromatic hydrocarbon feed comprises at least 90 wt % toluene.

### Claim 14 (depends on 13)

The process of claim 13, wherein the alkylation conditions comprise a temperature from 250° C. to 450° C.

### Claim 15 (depends on 14)

The process of claim 14, wherein the alkylation conditions comprise a pressure from 3000 kPa-a to 7000 kPa-a.

### Claim 16 (depends on 15)

The process of claim 15, wherein the alkylation conditions comprise a weight hourly space velocity based on the aromatic hydrocarbon feed of 50 to 0.5 hr−1.

### Claim 17 (depends on 16)

The process of claim 16, wherein the alkylated aromatic product comprises at least 80 wt % xylenes.

### Claim 18 (depends on 12)

The process of claim 12, wherein the alkylation conditions comprise a pressure in the range from 2,000 to 7,000 kPa-a.

### Claim 19 (depends on 12)

The process of claim 12, wherein the alkylation conditions comprise a pressure in the range from 3,000 to 5,000 kPa-a.

### Claim 20 (depends on 12)

The process of claim 12, wherein the alkylation conditions comprise a temperature in the range from 300 to 450° C.