# US 8,785,705 B2 · Use of a co-feed in the coupling of toluene with a carbon source

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- Number: US 8,785,705 B2
- Document ID: US8785705B2
- Status: Granted
- Kind: B2
- Application number: 13/457,500
- 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; James R. Butler
- Inventors: Sivadinarayana Chinta; Joseph L. Thorman; James R. Butler
- Web page: https://patentgrep.com/patent/US8785705B2

## CPC

- C07C 2/862: {the non-hydrocarbon contains only oxygen as hetero-atoms}
- C07C 2/864: {the non-hydrocarbon is an alcohol}
- C07C 2521/02: Boron or aluminium; Oxides or hydroxides thereof
- C07C 2529/06: Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C 2529/08: of the faujasite type, e.g. type X or Y
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process for making styrene is disclosed that includes providing toluene, a co-feed, and a C1 source to a reactor containing a catalyst, 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. The co-feed can be selected from the group of water, carbon monoxide, hydrogen, 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 comprising X zeolite and at least one promoter selected from the group consisting of Ce, Cu, P, Cs, B, Co, Ga, and combinations thereof, wherein the C1 source is selected from the group consisting of methanol, formaldehyde formalin, trioxane, methylformcel, paraformaldehyde, methylal, dimethyl ether, and combinations thereof; 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 co-feed is selected from the group consisting of carbon monoxide, hydrogen, and combinations thereof.

### Claim 2 (depends on 1)

The process of claim 1, wherein the catalyst comprises B and Cs supported on the X zeolite.

### Claim 3 (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 4 (depends on 1)

The process of claim 1, wherein the co-feed is present in amounts of 0.0001 to 15 wt % of the combined feed of the toluene, co-feed and C1 source.

### Claim 5 (depends on 1)

The process of claim 1, resulting in a toluene conversion from 2to 50%.

### Claim 6 (depends on 1)

The process of claim 1, having a selectivity to styrene from 15to 80%.

### Claim 7 (depends on 1)

The process of claim 1, having a selectivity to ethylbenzene from 15 to 80%.

### Claim 8

A method of making styrene, comprising:
providing a reactor comprising a catalyst comprising X zeolite and at least one promoter selected from the group consisting of Ce, Cu, P, Cs, B, Co, Ga, and combinations thereof;
providing a reactant feed stream comprising toluene and a C1 source selected from the group consisting of methanol, formaldehyde, formalin, trioxane, methylformcel, paraformaldehyde, methylal, dimethyl ether, and combinations thereof;
providing a co-feed selected from the group consisting of carbon monoxide, hydrogen, and combinations thereof; and
reacting the toluene with the C1 source in the presence of the co-feed and the catalyst to form a product stream comprising ethylbenzene and styrene.

### Claim 9 (depends on 8)

The method of claim 8, resulting in a toluene conversion of from 2 to 50%.

### Claim 10 (depends on 8)

The method of claim 8, having a selectivity to styrene from 15 to 80%.

### Claim 11 (depends on 8)

The method of claim 8, having a selectivity to ethylbenzene from 15 to 80%.

### Claim 12

A method of producing styrene comprising:
providing toluene, a co-feed, and a C1 source to a reactor comprising a catalyst;
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 catalyst comprises boron and cesium supported on an X-type zeolite;
wherein the co-feed is selected from the group consisting carbon monoxide, hydrogen, and combinations thereof
wherein the reaction gives a toluene conversion of from 2 to 50%, a selectivity to styrene from 15 to 80%, and a selectivity to ethylbenzene from 15 to 80%.