# US 2013/0158321 A1 · Process for the production of octenes by dimerizing ethylene to form butenes and dimerizing the butenes to form octenes

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- Number: US 2013/0158321 A1
- Document ID: US20130158321A1
- Status: Published application
- Kind: A1
- Application number: 13/716,590
- Filed: 2012-12-17
- Published: 2013-06-20
- Earliest claimed: 2011-12-20
- Assignees: Ifp Energies Nouvelles
- Inventors: Helene OLIVIER-BOURBIGOU; Francois HUGUES; Lionel MAGNA; Pierre-Alain BREUIL
- Web page: https://patentgrep.com/patent/US20130158321A1

## CPC

- C07C 2/24: with metals
- C07C 2/10: with metal oxides
- C07C 2/30: containing metal-to-carbon bond; Metal hydrides
- C07C 2/32: as complexes, e.g. acetyl-acetonates {(complexes of salts of acids of halogen C07C2/20)}
- C07C 2/34: Metal-hydrocarbon complexes
- C07C 2/36: as phosphines, arsines, stilbines or bismuthines
- C07C 5/32: by dehydrogenation with formation of free hydrogen
- C07C 2521/04: Alumina
- C07C 2521/12: Silica and alumina
- C07C 2523/755: Nickel
- C07C 2531/02: containing organic compounds or metal hydrides
- C07C 2531/025: Sulfonic acids
- C07C 2531/04: containing carboxylic acids or their salts
- C07C 2531/12: containing organo-metallic compounds or metal hydrides
- C07C 2531/14: of aluminium or boron
- C07C 2531/18: containing nitrogen, phosphorus, arsenic or antimony
- C07C 2531/22: Organic complexes
- C07C 2531/24: Phosphines
- Y02P 20/52: using catalysts, e.g. selective catalysts
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The present invention describes a process for the production of octenes from ethylene by dimerizing ethylene to butenes and by dimerizing butenes to octenes.

## Claims

### Claim 1

A process for the production of octenes starting from ethylene, employing the following steps:
a) dimerizing ethylene to butenes in the presence of a catalyst;
b) dimerizing the butenes obtained in step a) to octenes in the presence of a catalyst.

### Claim 2 (depends on 1)

A process according to the preceding claim 1, in which the effluent obtained after ethylene dimerization, containing butenes, is sent as is to the butenes dimerization step.

### Claim 3 (depends on 1)

A process according to claim 1, in which the effluent obtained after ethylene dimerization, containing butenes, is sent to a separation section in order to separate the butenes from unreacted ethylene on the one hand, and on the other hand from the oligomers formed during ethylene dimerization.

### Claim 4 (depends on 1)

A process according to the claim 1, in which the ethylene dimerization is carried out in the presence of a titanium-based catalyst.

### Claim 5 (depends on 4)

A process according to claim 4, in which the titanium-based catalyst is composed of an alkyl titanate, an organic ether type additive and an aluminium compound with formula AlR3 or AlR2H in which each of the residues R is a hydrocarbyl radical, and the ether type additive and the alkyl titanate are employed in a molar ratio of 1:0.5 to 10:1.

### Claim 6 (depends on 1)

A process according to claim 1, in which the ethylene dimerization is carried out in the presence of a catalytic system composed of a nickel compound and an aluminium compound.

### Claim 7 (depends on 6)

A process according to claim 6, in which the catalytic system is a mixture of a first compound selected from the group comprising the following formulae: (R3P)2NiY2, (R3PO)2NiX2, (R3AsO)2NiX2, (pyridine)2NiX2, (bipyridine)NiX2, (phenanthroline)NiX2 and a complex formed by a bicyclic nitrogen-containing compound with NiX2, where R is a hydrocarbon group containing up to 20 carbon atoms, X is a halogen, Y is selected from halogens or hydrocarbon groups as defined hereinabove and pyridine, bipyridine and phenanthroline which may or may not be substituted with one or more hydrocarbon groups, and a second compound represented by the formula R′zAlXy, where x and y are whole numbers in the range 1 to 3, R′ is a hydrocarbon group containing up to 20 carbon atoms and X is a halogen.

### Claim 8 (depends on 1)

A process according to claim 1, in which the butenes dimerization is carried out in the presence of a catalytic system in the liquid phase comprising a nickel compound and an aluminium compound.

### Claim 9 (depends on 8)

A process according to claim 8, in which the catalytic system is composed of at least one divalent nickel compound with at least one hydrocarbylaluminium dihalide with formula AlRX2 in which R is a hydrocarbyl radical containing 1 to 12 carbon atoms, X is a chlorine or bromine atom, and at least one organic Bronsted acid, preferably with a pKa of at most 3.

### Claim 10 (depends on 1)

A process according to claim 1, in which the butenes dimerization is carried out in the presence of a catalytic system composed of a nickel complex or a mixture of nickel complexes in a two-phase liquid-liquid medium containing a medium with an ionic nature which is not or is only slightly miscible with the organic phase containing the octenes.

### Claim 11 (depends on 1)

A process according to claim 1, in which the butenes dimerization comprises at least two successive steps, the first being carried out in the presence of a catalytic system in the liquid phase comprising a nickel compound and an aluminium compound, the second being carried out in the presence of a catalytic system comprising a nickel complex or a mixture of nickel complexes in a two-phase liquid-liquid medium containing a medium with an ionic nature which is not or is only slightly miscible with the organic phase containing the octenes.

### Claim 12 (depends on 1)

A process according to claim 1, in which the butenes dimerization is carried out in the presence of a heterogeneous catalyst containing oxides of nickel, silicon and aluminium.

### Claim 13 (depends on 1)

A process according to claim 1, in which the butenes dimerization is carried out in the presence of a heterogeneous catalyst containing nickel, as well as chlorine or sulphur, deposited on alumina.

### Claim 14 (depends on 1)

A process according to claim 1, in which the ethylene is obtained from a fossil source and/or from a renewable source.

### Claim 15 (depends on 1)

A process according to claim 1, in which the ethylene is obtained from ethanol dehydration.