# US 4,398,049 A · Oligomerization catalyst and process

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- Number: US 4,398,049 A
- Document ID: US4398049A
- Status: Granted
- Kind: A
- Application number: 06/425,347
- Filed: 1982-09-28
- Granted: 1983-08-09
- Earliest claimed: 1979-09-03
- Assignees: Institut Francais du Petrole
- Inventors: Dominique Le Pennec; Dominique Commereuc; Yves Chauvin
- Web page: https://patentgrep.com/patent/US4398049A

## CPC

- C07C 53/16: Halogenated acetic acids
- C07C 2/30: containing metal-to-carbon bond; Metal hydrides
- C07C 53/126: Acids containing more than four carbon atoms
- C07C 53/18: containing fluorine
- C07C 53/19: Acids containing three or more carbon atoms
- C07C 53/21: containing fluorine
- C07C 2531/04: containing carboxylic acids or their salts
- C07C 2531/14: of aluminium or boron
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A catalyst composition is manufactured by admixing a hydrocarbyl aluminum halide of a nickel compound of the formula (R.sub.1 COO)(R.sub.2 COO)Ni, where R.sub.1 is hydrocarbyl with at least 5 carbon atoms and R.sub.2 is haloalkyl of 1-3 carbon atoms. Olefins such as ethylene, propylene and butenes can be oligomerized, for example, dimerized and trimerized, with the above catalyst composition.

## Claims

### Claim 1

A process of oligomerizing C.sub.1-5 monoolefins, comprising contacting the olefins with a catalyst composition consisting essentially of at least one hydrocarbyl aluminum halide and at least one nickel compound having the formula (R.sub.1 COO) (R.sub.2 COO)Ni, wherein R.sub.1 is a hydroxy-substituted or unsubstituted C.sub.5-20 hydrocarbyl radical; and R.sub.2 is a haloalkyl group having the formula C.sub.m H.sub.p X.sub.q, wherein m is 1,2 or 3 p is zero or an integer; q is an integer; and p+q=2m+1; the molar ratio of the hydrocarbyl aluminum halide to the nickel compound being from 1:1 to 50:1, said contacting being effected at a temperature of -20.degree. C. to 80.degree. C. and a pressure sufficient to maintain the olefins in the liquid or condensed phase, at least in major part.

### Claim 2 (depends on 1)

A process according to claim 1, wherein the amount of the catalyst composition in the liquid phase of the oligomerization reaction, expressed as nickel, is 5-500 ppm by weight.

### Claim 3 (depends on 1)

A process according to claim 1, wherein R.sub.1 is C.sub.5-20 alkyl, and R.sub.2 is trifluoromethyl or trichloromethyl.

### Claim 4 (depends on 1)

A process according to claim 1, wherein the hydrocarbyl aluminum halide has the formula Al.sub.2 R.sub.x Y.sub.y, wherein R is C.sub.1-12 hydrocarbyl; Y is halogen; x and y are each 2, 3 or 4; and X+y=6; and wherein the molar ratio of the hydrocarbyl aluminum halide to the nickel compound is from 2:1 to 20:1.

### Claim 5 (depends on 4)

A process according to claim 4, wherein R is C.sub.1-12 alkyl; Y is chlorine, x is 3; and y is 3.

### Claim 6 (depends on 4)

A process according to claim 4, wherein R is C.sub.1-12 alkyl; Y is chlorine; x is 2; and y is 4.

### Claim 7 (depends on 3)

A process according to claim 3, wherein the hydrocarbyl aluminum halide has the formula Al.sub.2 R.sub.x Y.sub.y ; wherein R is C.sub.1-12 alkyl; Y is chlorine; x is 2 or 3; and y is 6-x.

### Claim 8 (depends on 3)

A process according to claim 3, wherein the hydrocarbyl aluminum halide has the formula Al.sub.2 R.sub.x Y.sub.y, wherein R is C.sub.1-12 alkyl; Y is chlorine; x is 2; and y is 4.

### Claim 9 (depends on 7)

A process according to claim 7, wherein R.sub.2 of the nickel compound is trifluoromethyl.

### Claim 10 (depends on 3)

A process according to claim 3, wherein R.sub.1 COO in said nickel compound is 2-ethylhexanoate, heptanoate, myristate, 4-methylvalerate, decanoate or octoate.

### Claim 11 (depends on 1)

A process according to claim 1, wherein the hydrocarbyl aluminum halide is ethyl aluminum sesquichloride, dichloroethylaluminum, dichloroisobutylaluminum, chlorodiethylaluminum, chlorodiisobutylaluminum, or mixtures thereof.