# US 8,785,706 B2 · Addition of a base to enhance product yield in alkylation reactions

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- Number: US 8,785,706 B2
- Document ID: US8785706B2
- Status: Granted
- Kind: B2
- Application number: 13/457,508
- Filed: 2012-04-27
- Published: 2012-11-22
- Granted: 2014-07-22
- Earliest claimed: 2011-05-22
- Assignees: Fina Technology, Inc.
- Applicants: Sivadinarayana Chinta; Joseph L. Thorman
- Inventors: Sivadinarayana Chinta; Joseph L. Thorman
- Web page: https://patentgrep.com/patent/US8785706B2

## CPC

- B01J 31/26: containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J 29/061: {containing metallic elements added to the zeolite}
- B01J 29/86: Borosilicates; Aluminoborosilicates {(B01J29/005 takes precedence)}
- C07C 2/864: {the non-hydrocarbon is an alcohol}
- B01J 2229/38: Base treatment
- C07C 2529/70: of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process for making styrene including providing toluene, a co-feed, and a C1 source to a reactor containing a catalyst having acid sites and reacting toluene with the C1 source in the presence of the catalyst and the co-feed to form a product stream containing ethylbenzene and styrene, wherein the C1 source is selected from methanol, formaldehyde, formalin, trioxane, methylformcel, paraformaldehyde, methylal, dimethyl ether, and wherein the co-feed removes at least a portion of the acid sites on the catalyst. The co-feed can be selected from the group of aniline, amines, cresol, anisol, and combinations thereof.

## Claims

### Claim 1

A process for making styrene comprising:
providing toluene, a co-feed, and a C1 source to a reactor comprising a catalyst containing acid sites; wherein the catalyst comprises a X-zeolite and Cs; and
reacting toluene with the C1 source in the presence of the catalyst and the co-feed to form a product stream comprising ethylbenzene and styrene;
wherein the C1 source is selected from the group consisting of methanol, formaldehyde, formalin, trioxane, methylformcel, paraformaldehyde, methylal, dimethyl ether, and combinations thereof;
wherein the co-feed is a base compound that reduces the number of active acid sites on the catalyst; wherein the co-feed is selected from the group consisting of aniline, cresol, anisol, and combinations thereof.

### Claim 2 (depends on 1)

The process of claim 1, wherein the co-feed adds basic sites to the catalyst.

### Claim 3 (depends on 1)

The process of claim 1, wherein the co-feed reduces at least a portion of the active acid sites on the catalyst by the molecules of the co-feed occupying spatial volume near the acid sites of the catalyst.

### Claim 4 (depends on 1)

The process of claim 1, wherein the co-feed is added to the catalyst prior to the toluene and the C1 source.

### Claim 5 (depends on 1)

The process of claim 1, wherein the co-feed is simultaneously fed to the reactor with the toluene and the C1 source.

### Claim 6 (depends on 1)

The process of claim 1, wherein the co-feed is present in amounts of from 0.1 to 5.0 wt % based on the total weight of the feed.

### Claim 7 (depends on 1)

The process of claim 1, wherein co-feed is present in amounts of from 0.5 to 1.0 wt % based on the total weight of the feed.

### Claim 8 (depends on 1)

The process of claim 1, comprising a toluene conversion of at least 3 mol %.

### Claim 9 (depends on 1)

The process of claim 1, comprising a selectivity to styrene of at least 10 mol %.

### Claim 10 (depends on 1)

The process of claim 1, comprising a selectivity to ethylbenzene of at least 10 mol %.

### Claim 11

A process of producing styrene comprising:
providing toluene, a co-feed, and a C1 source to a reactor comprising a catalyst containing acid sites; wherein the catalyst comprises a X-zeolite and Cs has been inserted; and
reacting toluene with the C1 source in the presence of the catalyst and the co-feed to form a product stream comprising ethylbenzene and styrene;
wherein the C1 source is selected from the group consisting of methanol, formaldehyde, formalin, trioxane, methylformcel, paraformaldehyde, methylal, dimethyl ether, and combinations thereof;
wherein the co-feed is selected from the group consisting of aniline, cresol, and anisol, and combinations thereof;
wherein the co-feed is present in amounts from 0.1 to 5.0 wt % based on the total weight of the feed and removes at least a portion of the acid sites on the catalyst; and
wherein molecules of the co-feed can occupy spatial volume near the acid sites of the catalyst.