US4482640A
Expired / Lapsed
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Ethylene oligomerization
Assignee: Phillips Petroleum Co
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Filing: 1983-05-02
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Granted: 1984-11-13
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Expires: 2003-05-02
Abstract
Abstract A novel ethylene oligomerization catalyst is provided consisting essentially of a nickel compound, a phosphine compound, and an acid. In addition, an improved ethylene oligomerization process is provided which comprises contacting ethylene with the novel catalyst composition present, in an effective solvent, at a temperature from about 0° C. to about 200° C. As a result of the inventive process, high catalyst productivity and good selectivity to desired oligomeric products are obtained.
Inventors
- 👤 Ronald D. Knudsen
- 👤 Stephen E. Reiter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 18:49
CPC Classifications
C; C07; C07C; C07C2/00; C07C2/02; C07C2/04; C07C2/06; C07C2/08; C07C2/26; C07C2/36; B; B01; B01J; B01J31/00; B01J31/02; B01J31/04; B01J31/16; B01J31/20; B01J31/22; B01J31/2204; B01J31/2208; B01J31/2226; B01J31/223; B01J31/2282; B01J31/2291; B01J31/2295; B01J31/24; B01J31/2404; B01J2231/00; B01J2231/20; B01J2531/00; B01J2531/80; B01J2531/84; B01J2531/847; B01J2540/00; B01J2540/20; B01J2540/22; B01J2540/225; C07C2531/00; C07C2531/02; C07C2531/04; C07C2531/16; C07C2531/20; C07C2531/22; C07C2531/24; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/52
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
187 words
A composition consisting essentially of: (a) at least one nickel compound selected from the group consisting of: bis(1,5-cyclooctadiene)nickel(O), bis(tricyclohexylphosphine)nickel(O), nickel tetracarbonyl, (cyclododecatriene)nickel, and bis(ethylene)(dicyclohexylphosphine)nickel; (b) a phosphine compound of the formula PR 3 wherein R represents H or a C 1 to C 20 hydrocarbyl radical with the proviso that any alkenyl substitution be at least 3 carbon atoms removed from the phosphorus atom and at least one R is not H; and (c) an acid selected from the group consisting of (i) a fluorinated carboxylic acid of the formula R'COOH wherein R' represents a C 1 to C 10 hydrocarbyl radical having at least 1 fluorine (F) atom, (ii) a dicarboxcyclic acid of the formula (R") 2 --X--(COOH) 2 wherein R" independently represents H or a C 1 to C 20 hydrocarbyl or fluorinated hydrocarbyl radical and X is a tetravalent C atom or the tetra-substituted benzene radical C 6 H 2 , (iii) 2-ketobutyric acid and (iv) glycine, such that the molar ratio of (b) to (a) is about 0.01-4.0 to 1 and the molar ratio of (c) to (a) is about 0.01-10.0 to 1.
Claim 2
Dependent Claim
187 words
A composition consisting essentially of: (a) at least one nickel compound selected from the group consisting of: bis(1,5-cyclooctadiene)nickel(O), bis(tricyclohexylphosphine)nickel(O), nickel tetracarbonyl, (cyclododecatriene)nickel, and bis(ethylene)(dicyclohexylphosphine)nickel; (b) a phosphine compound of the formula PR 3 wherein R represents H or a C 1 to C 20 hydrocarbyl radical with the proviso that any alkenyl substitution be at least 3 carbon atoms removed from the phosphorus atom and at least one R is not H; and (c) an acid selected from the group consisting of (i) a fluorinated carboxylic acid of the formula R'COOH wherein R' represents a C 1 to C 10 hydrocarbyl radical having at least 1 fluorine (F) atom, (ii) a dicarboxcyclic acid of the formula (R") 2 --X--(COOH) 2 wherein R" independently represents H or a C 1 to C 20 hydrocarbyl or fluorinated hydrocarbyl radical and X is a tetravalent C atom or the tetra-substituted benzene radical C 6 H 2 , (iii) 2-ketobutyric acid and (iv) glycine, such that the molar ratio of (b) to (a) is about 0.01-4.0 to 1 and the molar ratio of (c) to (a) is about 0.01-10.0 to 1.
Claim 3
Dependent Claim
11 words
A composition according to claim 1 wherein (a) is bis(1,5-cyclooctadiene) nickel(O).
Claim 4
Dependent Claim
26 words
A composition according to claim 1 wherein (b) is one selected from the group consisting of tricyclohexylphosphine, triisobutylphosphine, tri-n-butylphosphine, dicyclohexylphenylphosphine, diethylphenylphosphine, dicyclohexylphosphine, tribenzylphosphine, ortho-tolyldiphenylphosphine, and di(ortho-tolyl)phenylphosphine.
Claim 5
Dependent Claim
10 words
A composition according to claim 3 wherein (b) is dicyclohexylphosphine.
Claim 6
Dependent Claim
10 words
A composition according to claim 2 wherein (b) is dicyclohexylphosphine.
Claim 7
Dependent Claim
11 words
A composition according to claim 5 wherein (c) is trifluoroacetic acid.
Claim 8
Dependent Claim
11 words
a composition according to claim 5 wherein (c) is heptafluorobutyric acid.
Claim 9
Dependent Claim
11 words
A composition according to claim 5 wherein (c) is 2-ketobutyric acid.
Claim 10
Dependent Claim
10 words
A composition according to claim 5 wherein (c) is glycine.
Claim 11
Dependent Claim
27 words
A composition according to claim 5 wherein (c) is one selected from the group consisting of malonic acid, ethylmalonic acid, dimethylmalonic acid, benzylmalonic acid, and diethylmalonic acid.
Claim 12
Dependent Claim
11 words
A composition according to claim 10 wherein (c) is dimethylmalonic acid.
Claim 13
Dependent Claim
32 words
A composition according to claim 1 wherein the molar ratio of (b) to (a) is about 0.5-2.5 to 1 and the molar ratio of (c) to (a) is about 0.01-10.0 to 1.
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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) | 1987-11-13 | 1988-05-14 | 1988-11-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-11-13 | 1992-05-14 | 1992-11-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-11-13 | 1996-05-14 | 1996-11-13 | $7700.00 | Window Closed / Lapsed |