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US5233115A
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Ethylene oligomerization
Assignee: Phillips Petroleum Co
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Filing: 1992-12-09
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Granted: 1993-08-03
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Expires: 2012-12-09
Abstract
Abstract An ethylene oligomerization process is provided wherein ethylene is contacted with a nickel(II) halide compound, a phosphine compound, and a carboxylate compound in a solvent to produce a precursor reaction mixture, followed by contacting ethylene with the precursor reaction mixture and a borohydride compound to produce a product reaction mixture comprising the desired oligomerization product.
Inventors
- 👤 An-hsiang Wu
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 14:58
CPC Classifications
C; C07; C07C; C07C2/00; C07C2/02; C07C2/04; C07C2/06; C07C2/08; C07C2/26; C07C2/36; C07C2527/00; C07C2527/06; C07C2527/128; C07C2531/00; C07C2531/16; C07C2531/24; C07C2531/26; C07C2531/28; C07C2531/30; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/52
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
182 words
A process for oligomerizing ethylene to an oligomerization product comprising: (a) contacting ethylene, a nickel(II) halide compound, a phosphine compound of the formula PR 3 where each R independently represents H or a C 1 to C 20 hydrocarbyl radical and where at least one R is not H, and a carboxylate compound of the formula R'COOM where R' is a C 1 to C 10 fluorinated hydrocarbyl radical having at least one fluorine atom and M is an alkali metal, wherein the ethylene is in a gaseous phase and the nickel(II) halide compound, phosphine compound, and carboxylate compound are in a solvent and in a liquid phase, thereby producing a precursor reaction mixture in a liquid phase; and (b) contacting, after step (a), ethylene in a gaseous phase, the precursor reaction mixture, and a borohydride compound of the formula M'BH 4-n R n " where n=1, 2, or 3, M' is an alkali metal, and each R" independently represents a C 1 to C 20 hydrocarbyl radical, thereby producing a product reaction mixture in a liquid phase comprising the oligomerization product.
Claim 2
Dependent Claim
182 words
A process for oligomerizing ethylene to an oligomerization product comprising: (a) contacting ethylene, a nickel(II) halide compound, a phosphine compound of the formula PR 3 where each R independently represents H or a C 1 to C 20 hydrocarbyl radical and where at least one R is not H, and a carboxylate compound of the formula R'COOM where R' is a C 1 to C 10 fluorinated hydrocarbyl radical having at least one fluorine atom and M is an alkali metal, wherein the ethylene is in a gaseous phase and the nickel(II) halide compound, phosphine compound, and carboxylate compound are in a solvent and in a liquid phase, thereby producing a precursor reaction mixture in a liquid phase; and (b) contacting, after step (a), ethylene in a gaseous phase, the precursor reaction mixture, and a borohydride compound of the formula M'BH 4-n R n " where n=1, 2, or 3, M' is an alkali metal, and each R" independently represents a C 1 to C 20 hydrocarbyl radical, thereby producing a product reaction mixture in a liquid phase comprising the oligomerization product.
Claim 3
Dependent Claim
46 words
A process as recited in claim 1 wherein step (a) is carried out at a pressure of about 5 to about 5000 psig, at a temperature of about 0° C. to about 100° C., and for a time of about 1 minute to about 2 hours.
Claim 4
Dependent Claim
46 words
A process as recited in claim 2 wherein step (a) is carried out at a pressure of about 20 to about 1000 psig, at a temperature of about 20° C. to about 75° C., and for a time of about 3 minutes to about 30 minutes.
Claim 5
Dependent Claim
46 words
A process as recited in claim 1 wherein step (b) is carried out at a pressure of about 5 to about 5000 psig, at a temperature of about 25° C. to about 125° C., and for a time of about 1 minute to about 15 hours.
Claim 6
Dependent Claim
46 words
A process as recited in claim 4 wherein step (b) is carried out at a pressure of about 200 to about 1000 psig, at a temperature of about 50° C. to about 100° C., and for a time of about 15 minutes to about 5 hours.
Claim 7
Dependent Claim
17 words
A process as recited in claim 1 wherein the nickel(II) halide compound is a nickel(II) chloride compound.
Claim 8
Dependent Claim
16 words
A process as recited in claim 6 wherein the nickel(II) chloride compound is nickel(II) chloride hexahydrate.
Claim 9
Dependent Claim
13 words
A process as recited in claim 1 wherein the phosphine compound is dicyclohexylphosphine.
Claim 10
Dependent Claim
14 words
A process as recited in claim 1 wherein the carboxylate compound is potassium trifluoroacetate.
Claim 11
Dependent Claim
32 words
A process as recited in claim 1 wherein in the borohydride compound of the formula M'BH 4-n R n ", n=3 and R" is a C 1 to C 12 alkyl radical.
Claim 12
Dependent Claim
14 words
A process as recited in claim 10 wherein the borohydride compound is sodium triethylborohydride.
Claim 13
Dependent Claim
50 words
A process as recited in claim 1 wherein the molar ratio of (i) the phosphine compound, (ii) the carboxylate compound, and (iii) the borohydride compound, respectively, to the nickel(II) halide compound are as follows: (i) about 0.1-5 to 1; (ii) about 0.1-5 to 1; and (iii) about 1-10 to 1.
Claim 14
Dependent Claim
30 words
A process as recited in claim 1 wherein the solvent is a C 1 to C 12 hydroxylated hydrocarbon selected from the group consisting of an alcohol and a phenol.
Claim 15
Dependent Claim
13 words
A process as recited in claim 13 wherein the solvent is an alcohol.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-08-02 | 1997-02-01 | 1997-08-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-08-02 | 2001-02-01 | 2001-08-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-08-02 | 2005-02-01 | 2005-08-03 | $7700.00 | Window Closed / Lapsed |