# US 5,705,725 A · Aromatic alkali metal alkene addition process

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- Number: US 5,705,725 A
- Document ID: US5705725A
- Status: Granted
- Kind: A
- Application number: 07/770,004
- Filed: 1991-10-02
- Granted: 1998-01-06
- Earliest claimed: 1991-10-02
- Assignees: Phillips Petroleum Company
- Inventors: Ted M. Pettijohn; Mark E. Lashier; Henry L. Hsieh
- Web page: https://patentgrep.com/patent/US5705725A

## CPC

- C07C 2/30: containing metal-to-carbon bond; Metal hydrides
- C07C 2/72: Addition to a non-aromatic carbon atom of hydrocarbons containing a six-membered aromatic ring
- C07C 2531/12: containing organo-metallic compounds or metal hydrides
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process is provided comprising: (a) contacting a hydrocarbyl lithium with an alkali metal hydrocarbyloxide in the presence of an aromatic compound; and thereafter (b) recovering an aromatic alkali metal compound; and thereafter (c) contacting said aromatic alkali metal compound with an alpha-olefin. Optionally, a catalytic support is also present during steps a, b, and c.

## Claims

### Claim 1

A process to produce isobutylbenzene consisting essentially of:
contacting n-butyl lithium and potassium t-butoxide in the presence of toluene and propylene and recovering said isobutylbenzene.

### Claim 2

A process to produce a single alkene addition product said process comprising contacting:
a hydrocarbyl lithium; with
an alkali metal hydrocarbyloxide wherein said alkali metal is selected from the group consisting of sodium, potassium, cesium, rubidium, and mixtures of two or more thereof;
in the presence of an aromatic compound wherein said aromatic compound has the following formula ##STR2## wherein each R group is independently selected from the group consisting of hydrogen, alkyl radicals, aryl radicals, and alkylaryl radicals; and
in the presence of an alpha-olefin; and
recovering said single alkene addition product.

### Claim 3 (depends on 2)

A process according to claim 2 wherein said contacting is carried out in the presence of a catalytic support.

### Claim 4 (depends on 3)

A process according to claim 3 wherein said catalytic support is selected from the group consisting of alkali metal carbonates, silicas, aluminas, silica-aluminas, alumina-phosphates and mixtures of two or more thereof.

### Claim 5 (depends on 3)

A process according to claim 3 wherein said catalytic support consists essentially of potassium carbonate.

### Claim 6 (depends on 2)

A process according to claim 2 wherein said hydrocarbyl lithium is selected from the group consisting of methyl lithium, ethyl lithium, propyl lithium, butyl lithium, pentyl lithium, hexyl lithium, and mixtures of two or more thereof.

### Claim 7 (depends on 2)

A process according to claim 2 wherein said hydrocarbyl lithium consists of n-butyl lithium.

### Claim 8 (depends on 2)

A process according to claim 2 wherein said alkali metal hydrocarbyloxide is selected from the group consisting of sodium methoxide, sodium ethoxide, potassium methoxide, potassium ethoxide, potassium propyloxide, potassium butoxide, potassium pentoxide, and mixtures of two or more thereof.

### Claim 9 (depends on 2)

A process according to claim 2 wherein said alkali metal hydrocarbyloxide consists essentially of potassium butoxide.

### Claim 10 (depends on 2)

A process according to claim 2 wherein said aromatic compound is selected from the group consisting of toluene, 1,2-dimethyl benzene, 1,3-dimethyl benzene, 1,4-dimethyl benzene, 1,3,5-trimethyl benzene, and mixtures of two or more thereof.

### Claim 11 (depends on 2)

A process according to claim 2 wherein said aromatic compound consists of toluene.

### Claim 12 (depends on 2)

A process according to claim 2 wherein said alpha-olefin is selected from the group consisting of ethylene, propylene, 1-butene, isobutylene, 3-methyl-1-butene, 1-pentene, 3-methyl-1-pentene, 4-methyl-1-pentene, 1-hexene, 3-ethyl-1-hexene, 1-octene, 1-decene, and mixtures of two or more thereof.

### Claim 13 (depends on 2)

A process according to claim 2 wherein said alpha-olefin consists of propylene.

### Claim 14 (depends on 3)

A process according to claim 3 wherein said catalytic support consists essentially of silica-alumina.