# US 10,246,387 B2 · Process for selectivating catalyst for producing paraxylene by methylation of benzene and/or toluene

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- Number: US 10,246,387 B2
- Document ID: US10246387B2
- Status: Granted
- Kind: B2
- Application number: 15/702,469
- 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
- Web page: https://patentgrep.com/patent/US10246387B2

## CPC

- C07C 15/08: Xylenes
- 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 15/04: Benzene
- C07C 15/06: Toluene
- 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. The alkylation catalyst may be selectivated to produce a higher than equilibrium amount of paraxylene by using a molar ratio of alkylating agent to aromatic of at least 1:4.

## Claims

### Claim 1

A process for producing paraxylene, the process comprising:
(a) selectivating an alkylation catalyst consisting essentially of MCM-49 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 benzene and/or 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. to produce an alkylated aromatic product comprising xylenes; wherein the molar ratio of the alkylating reagent to benzene and/or toluene of at least 1:4 is used at least until the amount of paraxylene as a percentage of the total xylenes produced is equal to or greater than 23 wt. %; and
(b) recovering paraxylene from the alkylated aromatic product.

### Claim 2 (depends on 1)

The process of claim 1, wherein the amount of paraxylene as a percentage of the total xylenes produced is at least 35 wt % of paraxylene, based on the total amount of xylenes.

### Claim 3 (depends on 1)

The process of claim 1, wherein the molar ratio of the alkylating reagent to benzene and/or toluene is 1:2.

### Claim 4 (depends on 3)

The process of claim 3, wherein the aromatic hydrocarbon feed comprises toluene.

### Claim 5 (depends on 4)

The process of claim 4, wherein the aromatic hydrocarbon feed comprises at least 90 wt % toluene.

### Claim 6 (depends on 5)

The process of claim 5, wherein the alkylating reagent comprises methanol.

### Claim 7 (depends on 6)

The process of claim 6, wherein the alkylation conditions comprise a temperature of at least 250° C.

### Claim 8 (depends on 7)

The process of claim 7, wherein the alkylation conditions comprise a temperature from 300° C. to 450° C.

### Claim 9 (depends on 8)

The process of claim 8, wherein the alkylation conditions comprise a pressure from 700 kPa-a to 7000 kPa-a.

### Claim 10 (depends on 9)

The process of claim 9, wherein the alkylation conditions comprise a weight hourly space velocity based on the aromatic hydrocarbon feed of 50 to 0.5 hr−1.

### Claim 11 (depends on 10)

The process of claim 10, wherein the alkylated aromatic product comprises at least 70 wt % xylenes.

### Claim 12 (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 13 (depends on 1)

The process of claim 1, wherein the alkylation conditions comprise a pressure in the range from 2,000 to 5,000 kPa-a.

### Claim 14 (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.