# US 10,766,834 B2 · Transalkylation processes and catalyst compositions used therein

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- Number: US 10,766,834 B2
- Document ID: US10766834B2
- Status: Granted
- Kind: B2
- Application number: 15/899,096
- Filed: 2018-02-19
- Published: 2018-09-06
- Granted: 2020-09-08
- Earliest claimed: 2017-03-06
- Assignees: ExxonMobil Chemical Patents Inc.
- Applicants: ExxonMobil Chemical Patents Inc.
- Inventors: Brett T. Loveless; Daniel J. Benedict; Kathleen M. Keville; Juan D. Henao; Matthew S. Ide
- Web page: https://patentgrep.com/patent/US10766834B2

## CPC

- C07C 6/10: in hydrocarbons containing no six-membered aromatic rings
- B01J 29/08: of the faujasite type, e.g. type X or Y
- B01J 29/18: of the mordenite type
- B01J 29/7007: {Zeolite Beta}
- B01J 29/7038: {MWW-type, e.g. MCM-22, ERB-1, ITQ-1, PSH-3 or SSZ-25}
- C07C 6/126: {of more than one hydrocarbon}
- C07C 15/04: Benzene
- C07C 15/073: Ethylbenzene
- C07C 2529/08: of the faujasite type, e.g. type X or Y
- C07C 2529/18: of the mordenite type
- C07C 2529/70: of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
- C07C 2529/80: Mixtures of different zeolites
- 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

Disclosed are selectivated transalkylation catalyst compositions and methods of making the same. The selectivated transalkylation catalyst compositions have a zeolite framework structure of MWW, FAU, BEA*, or MOR, or mixtures thereof, and are selectivated with a selectivating solution. The selectivating solution includes a dissolved ion of at least one element in Group 1, Group 2, Group 15, Group 16, or Group 17 of the Periodic Table. Also disclosed are processes of producing ethylbenzene and cumene using the selectivated transalkylation catalyst compositions.

## Claims

### Claim 1

A process for producing ethylbenzene comprising:
(a) providing a selectivated transalkylation catalyst composition;
(b) providing a stream comprising poly-alkylated benzene and a stream comprising benzene, wherein said stream comprising poly-alkylated benzene comprises di-ethylbenzene; and
(c) contacting said stream comprising poly-alkylated benzene with said stream comprising benzene in presence of the selectivated transalkylation catalyst composition under at leas partially liquid phase transalkylation conditions to produce a transalkylation effluen stream comprising said ethylbenzene,
wherein a method for making said selectivated transalkylation catalyst composition comprises:
(i) contacting an untreated transalkylation catalyst composition with a selectivating solution to form said selectivated transalkylation catalyst, said transalkylation catalyst composition comprising a zeolite in acid form and having an MWW framework structure, said selectivating solution comprises water and a cation or an anion of an element in Group 1, Group 2, or Group 17 of the Periodic Table, wherein said selectivated transalkylation catalyst composition has a higher selectivity to ethylbenzene than the selectivity of said transalkylation catalyst composition that has not been contacted with said selectivating solution when the catalysts are compared under equivalent transalkylation conditions,
wherein said element in Group 1 is sodium or potassium, said element in Group 2 is calcium, and said element in Group 17 is chlorine,
wherein said selectivating solution comprises dissolved ions which include one or more of the following elements: calcium in an amount from 600 to 750 milligrams per liter (mg/L), sodium in an amount from 400 to 500 mg/L, potassium in an amount from 40 to 80 mg/L, and chlorine in an amount from 650 to 850 mg/L,
wherein step (i) comprises contacting said untreated transalkylation catalyst composition with said selectivating solution for 1 hour or more at a temperature in a range of 20° C. to 95° C. and at a pH of the selectivating solution in a range of 6.5 to 8.0.

### Claim 2 (depends on 1)

The process of claim 1, wherein said selectivated transalkylation catalyst composition produces a lower amount of xylene by-product of an ethylbenzene process than said transalkylation catalyst composition that has not been contacted with a selectivating solution when the catalysts are compared under equivalent transalkylation conditions.

### Claim 3 (depends on 1)

The process of claim 1, further comprising:
(ii) drying said selectivated transalkylation catalyst composition with an inert gas for 1 hour or more at ambient pressure and at temperature of less than 300° C.

### Claim 4 (depends on 3)

The process of claim 3, wherein said inert gas comprises nitrogen, oxygen, air or a mixture thereof.

### Claim 5 (depends on 1)

The process of claim 1, further comprising:
(iii) contacting said selectivated transalkylation catalyst with benzene for 1 hour or more.

### Claim 6 (depends on 1)

The process of claim 1, further comprising:
(d) separating said transalkylation effluent stream to recover an ethylbenzene stream.

### Claim 7 (depends on 1)

The process of claim 1, wherein said at least partially liquid phase transalkylation conditions include a temperature of 150 to 260° C. and a pressure of 696 to 4137 kPa-a (101 to 600 psia).

### Claim 8 (depends on 7)

The process of claim 7, further comprising:
(e) contacting a benzene stream with an alkylating agent stream under alkylation conditions and in presence of an alkylation catalyst to produce an alkylation effluent which comprises a mono-alkylated benzene and said poly-alkylated benzene.

### Claim 9 (depends on 8)

The process of claim 8, further comprising:
(f) separating said alkylation effluent to recover a poly-alkylated benzene stream; and
(g) supplying said poly-alkylated benzene stream to step (b).

### Claim 10 (depends on 8)

The process of claim 8, wherein said alkylating agent stream comprises ethylene.

### Claim 11 (depends on 8)

The process of claim 8, wherein said alkylation conditions are at least partially liquid phase conditions and include a temperature of 10° C. to 400° C. and a pressure of up to about 25000 kPa, and a WHSV based on weight of said alkylating agent from about 0.1 hr−1 to about 100 hr−1.

### Claim 12 (depends on 1)

The process of claim 1, wherein said stream comprising benzene further comprises impurities, said stream comprising benzene is contacted with a guard bed material to remove at least a portion of said impurities, and said guard bed material comprises a large pore zeolite having a framework structure type selected from the group consisting of FAU, *BEA, MWW, MOR and mixtures thereof.

### Claim 13 (depends on 1)

The process of claim 1, wherein said zeolite which has said MWW framework structure is selected from the group consisting of MCM-22, PSH-3, SSZ-25, MCM-36, MCM-49, MCM-56, ERB-1, EMM-10, EMM-10-P, EMM-12, EMM-13, UZM-8, UZM-8HS, UZM-37, MIT-1, ITQ-1, ITQ-2, ITQ-30 and mixtures of two or more thereof.

### Claim 14 (depends on 13)

The process of claim 13, wherein said zeolite which has said MWW framework structure is MCM-22.