Nickel-based catalytic composition, and its use in a process for the oligomerization of olefins

Patent metadata

Field	Value
Publication number	US-9283554-B2
Application number	US-201514694052-A
Country	US
Kind code	B2
Filing date	Apr 23, 2015
Priority date	Apr 28, 2014
Publication date	Mar 15, 2016
Grant date	Mar 15, 2016

Abstract

The invention describes a nickel-based composition. The invention also concerns the use of said composition as a catalytic composition in an olefin oligomerization process.

First claim

The invention claimed is:

1. A composition comprising:
at least one precursor of nickel with an oxidation number of (0) or (+II),
at least one ligand with formula 1a), 1b) or 1c)

 in which
A and A′, which may be identical or different, are independently O, S, NR 3 or a single bond between the phosphorus atom and a carbon atom,
the group R 3 is either a hydrogen atom or an alkyl group, which may or may not be cyclic, which may or may not be substituted and which may or may not contain heteroelements, or an aromatic group, which may or may not be substituted and which may or may not contain heteroelements,
the groups R 1a and R 1b being mutually identical or different and which may or may not be bonded together, are selected from alkyl groups which may or may not be cyclic, which may or may not be substituted and which may or may not contain heteroelements, and aromatic groups which may or may not be substituted and which may or may not contain heteroelements,
the group R 2 is selected from alkyl groups which may or may not be cyclic, which may or may not be substituted and which may or may not contain heteroelements, and aromatic groups which may or may not be substituted and which may or may not contain heteroelements,

with the condition that when a precursor of nickel with an oxidation number of (+II) is in the composition, it is in the presence of a reducing agent or in the presence of a Brönsted base.

2. The composition according to claim 1 , comprising an additional Lewis base.

3. The composition according to claim 2 , in which the additional Lewis base is a phosphine of the type P(A 1 R′ 1a )(A′ 1 R′ 1b )(A″ 1 R′ 1c ) or a phosphinamine of the type (R′ 1a A 1 )(R′ 1b A′ 1 )P—NH(R′ 2 ) or (R′ 1a A 1 )(R′ 1b A′ 1 )P—NH—S(O) 2 (R′ 2 ) in which:
A 1 , A′ 1 and A″ 1 , which may be identical or different, are independently O, S, NR 3 or a single bond between the phosphorus atom and a carbon atom,
the group R 3 is either a hydrogen atom or an alkyl group, which may or may not be cyclic, which may or may not be substituted and which may or may not contain heteroelements, or an aromatic group which may or may not be substituted and which may or may not contain heteroelements,
the groups R′ 1a , R′ 1b and R′ 1c , being mutually identical or different and which may or may not be bonded together, are selected from alkyl groups which may or may not be cyclic, which may or may not be substituted and which may or may not contain heteroelements, and aromatic groups which may or may not be substituted and which may or may not contain heteroelements,
the group R′ 2 is selected from alkyl groups which may or may not be cyclic, which may or may not be substituted and which may or may not contain heteroelements, and aromatic groups which may or may not be substituted and which may or may not contain heteroelements.

4. The composition according to claim 1 , in which the groups R 1a and R 1b , which may be identical or different and which may or may not be bonded together, and the groups R′ 1a , R′ 1b and R′ 1c , which may be indentical or difference and which may or may not be bonded together, are independently selected from alkyl groups containing 1 to 15 carbon atoms and aromatic groups containing 5 to 20 carbon atoms, which may or may not be substituted and which may or may not contain heteroelements.

5. The composition according to claim 1 , in which the groups R 1a and R 1b which may be identical or different, which may or may not be bonded together, and the groups R′ 1 , i.e. R′ 1a , R′ 1b and R′ 1c which may be identical or different, which may or may not be bonded together, are independently selected from methyl, trifluoromethyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, cyclohexyl and adamantyl groups which may or may not be substituted and which may or may not contain heteroelements; and from phenyl, o-tolyl, m-tolyl, p-tolyl, mesityl, 3,5-dimethylphenyl, 4-n-butylphenyl, 4-methoxyphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-isopropoxyphenyl, 4-methoxy-3,5-dimethylphenyl, 3,5-di-tert-butyl-4-methoxyphenyl, 4-chlorophenyl, 3,5-di(trifluoromethyl)phenyl, benzyl, naphthyl, bisnaphthyl, pyridyl, bisphenyl, furanyl and thiophenyl groups, which may or may not be substituted and which may or may not contain heteroelements.

6. The composition according to claim 3 , in which the groups R 2 and the groups R′ 2 , which may be identical or different, are independently selected from alkyl groups containing 1 to 15 carbon atoms and aromatic groups containing 5 to 20 carbon atoms, which may or may not be substituted and which may or may not contain heteroelements.

7. The composition according to claim 3 , in which the groups R 2 and the groups R′ 2 , which may be identical or different, are independently selected from methyl, trifluoromethyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, cyclohexyl and adamantyl groups, which may or may not be substituted and which may or may not contain heteroelements; and from phenyl, o-tolyl, m-tolyl, p-tolyl, mesityl, 3,5-dimethylphenyl, 4-n-butylphenyl, 4-methoxyphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-isopropoxyphenyl, 4-methoxy-3,5-dimethylphenyl, 3,5-ditert-butyl-4-methoxyphenyl, 4-chlorophenyl, 3,5-bis(trifluoromethyl)phenyl, benzyl, naphthyl, bisnaphthyl, pyridyl, bisphenyl, furanyl and thiophenyl groups, which may or may not be substituted and which may or may not contain hetero elements.

8. The composition according to claim 1 , in which the nickel precursor with oxidation number (0) is selected from nickel(0)bis(cycloocta-1,5-diene), nickel(0)bis(cycloocta-1,3-diene), nickel(0)bis(cyclooctatetraene), nickel(0)bis(cycloocta-1,3,7-triene), bis(o-tolylphosphito) nickel(0) (ethylene), nickel(0)tetrakis(triphenylphosphite), nickel(0)tetrakis(triphenylphosphine) and nickel (0)bis(ethylene), alone or as a mixture thereof.

9. The composition according to claim 1 , in which the nickel precursor with oxidation number (+II) is selected from nickel (II) chloride, nickel(dimethoxyethane) chloride(II), nickel(II) bromide, nickel(II)(dimethoxyethane) bromide, nickel((II)) fluoride, nickel(II) iodide, nickel((II)) sulphate, nickel((II)) carbonate, nickel((II))dimethylglyoxime, nickel((II)) hydroxide, nickel((II)) hydroxyacetate, nickel(II) oxalate, nickel((II)) carboxylates, 2-ethylhexanoate, nickel((II)) phenates, nickel((II)) acetate, nickel(II) trifluoroacetate, nickel((II))triflate, nickel(II) acetylacetonate, nickel((II)) hexafluoroacetylacetonate, allylnickel(II) chloride, allylnickel(II) bromide, methallylnickel(II) chloride dimer, allylnickel(II) hexafluorophosphate, methallylnickel(II) hexafluorophosphate, biscyclopentadienyl nickel(II), bisallyl nickel(II) and bismethallyl nickel(II); in their hydrated or non-hydrated form, alone or as a mixture thereof.

10. The composition according to claim 1 , further comprising an activating agent selected from the group consisting of tris(hydrocarbyl)aluminium compounds, chlorine-containing or bromine-containing hydrocarbylaluminium compounds, aluminoxanes, organo-boron compounds, and organic compounds which are capable of donating or accepting a proton, alone or as a mixture thereof.

11. The composition according to claim 1 , in which the molar ratio between the ligand and the nickel precursor is in the range of 0.05 to 10.

12. A catalyst comprising a composition according to claim 1 .

13. A process for oligomerizing an olefinic feed, comprising bringing said feed into

Assignees

• IFP Energies Nouvelles
• Univ Amsterdam

Inventors

• Boulens Pierre
• Breuil Pierre-Alain
• Reek Joost
• Olivier-Bourbigou Helene

Classifications

• B01J2231/20

  Olefin oligomerisation or telomerisation · CPC title

• B01J31/0267 Primary

  Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen · CPC title

• C07C2531/18

  containing nitrogen, phosphorus, arsenic or antimony · CPC title

• C07C2531/24

  Phosphines · CPC title

• C07C2/32

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