Nickel-based catalytic composition and method of oligomerization of olefins using said composition

Patent metadata

Field	Value
Publication number	US-9545623-B2
Application number	US-201213604038-A
Country	US
Kind code	B2
Filing date	Sep 5, 2012
Priority date	Sep 8, 2011
Publication date	Jan 17, 2017
Grant date	Jan 17, 2017

Abstract

The present invention describes a novel catalytic composition comprising at least one nickel complex, said complex being obtained from a mixture comprising at least one nickel precursor A with at least one imino-imidazole ligand B and a method of oligomerization of olefins using said catalytic composition.

First claim

The invention claimed is:

1. A catalytic composition comprising at least one nickel complex, said complex being obtained from a mixture comprising:
at least one nickel precursor A, with
at least one imino-imidazole ligand B of formula (I)

in which R 1 , R 2 , R 3 and R 4 are identical or different and are hydrogen, linear or branched alkyl, aryl, aralkyl or alkaryl having up to 12 carbon atoms and optionally containing heteroelements, R 1 and R 2 not forming an aromatic ring; E 1 is —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 , —CH 2 CH 2 CH 2 CH 2 —, 1,2-phenylene, trans-1,2-cyclopentane, trans-1,2-cyclohexane, 2,3-butane, 1,1′-biphenyl, 1,1′-binaphthyl or —Si(Me) 2 -; D 1 is hydrogen, an ether of formula —OR 5 , a thioether of formula —SR 6 , an amine of formula —N(R 7 ) 2 or a phosphine of formula —P(R 8 ) 2 where R 5 , R 6 , R 7 and R 8 are methyl, ethyl or phenyl groups.

2. The catalytic composition according to claim 1 in which R 1 , R 2 , R 3 and R 4 are hydrogen, methyl, ethyl, isopropyl, isobutyl, tent-butyl, cyclohexyl, phenyl or benzyl.

3. The catalytic composition according to claim 1 in which R 1 , R 2 and R 4 are hydrogen.

4. The catalytic composition according to claim 1 in which R 3 is methyl.

5. The catalytic composition according to claim 1 in which E 1 is divalent —CH 2 CH 2 -or divalent 1,2-phenylene.

6. The catalytic composition according to claim 1 in which said nickel precursor A used in the catalytic composition according to the invention is nickel(II) chloride, nickel(II) chloride (dimethoxyethane), nickel(II) bromide, nickel(II) bromide (dimethoxyethane), nickel(II) fluoride, nickel(II) iodide, nickel(II) sulphate, nickel(II) carbonate, nickel(II) dimethylglyoxime, nickel(II) hydroxide, nickel(II) hydroxyacetate, nickel(II) oxalate, a nickel(II) carboxylate, a nickel phenate, nickel(II) acetate, nickel(II) trifluoroacetate, nickel(II) triflate, nickel(II) acetylacetonate, nickel(II) hexafluoroacetylacetonate, nickel bis(cycloocta-1,5-diene), nickel bis(cycloocta-1,3-diene), nickel bis(cyclooctatetraene), nickel bis(cycloocta-1,3,7-triene), bis(o-tolylphosphito)nickel(ethylene), nickel tetrakis(triphenylphosphite), nickel bis(ethylene), π-allylnickel(II) chloride, π-allylnickel(II) bromide, methallylnickel(II) chloride dimer, η 3 -allylnickel(II) hexafluorophosphate, η 3 -methallylnickel(II) hexafluorophosphate or nickel(II) 1,5-cyclooctadienyl, in hydrated or unhydrated form, alone or in a mixture, optionally complexed with a Lewis base.

7. The catalytic composition according to claim 1 in which the catalytic composition contains a compound C activating agent, that is a tris(hydrocarbyl)aluminium compound, a chlorinated or brominated hydrocarbylaluminium compound, an aluminoxane, an organic compound capable of acting as a proton donor, or an organoboron compound, alone or in a mixture.

8. The catalytic composition according to claim 1 in which said nickel complex of the catalytic composition is prepared in the presence of a solvent.

9. A method of oligomerization of olefins having from 2 to 10 carbon atoms, comprising subjecting said olefins to oligomerization conditions in the presence of a catalytic composition according to claim 1 .

10. The method according to claim 9 in which the olefins are ethylene, propylene, an n-butene or an n-pentene, alone or in a mixture, pure or diluted.

11. The method according to claim 9 in which said method is a method of oligomerization of ethylene.

12. The method according to claim 11 in which said method is a method of dimerization of ethylene.

13. The catalytic composition according to claim 6 , wherein said nickel precursor A is 2-ethylhexanoate.

14. The catalytic composition according to claim 1 in which said nickel complex of the catalytic composition is prepared in the absence of a solvent.

Assignees

• Breuil Pierre-Alain
• Boudier Adrien
• Magna Lionel
• Olivier-Bourbigou Helene
• Ifp Energies Now

Inventors

• Breuil Pierre-Alain
• Boudier Adrien
• Magna Lionel
• Olivier-Bourbigou Helene

Classifications

• C07C2/32

  as complexes, e.g. acetyl-acetonates {(complexes of salts of acids of halogen C07C2/20)} · CPC title

• C07C2531/22

  Organic complexes · CPC title

• C07C11/08

  with four carbon atoms · CPC title

• B01J31/1815 Primary

  with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine · CPC title

• C07C2/34

  Metal-hydrocarbon complexes · CPC title