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US4518814A Expired / Lapsed US ⏱️ 0.0 years remaining

Ethylene oligomeration

Assignee: Phillips Petroleum Co
•
Filing: 1984-08-24
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Granted: 1985-05-21
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Expires: 2004-08-24
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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 2026-11-02 03:15
CPC Classifications
C; C07; C07C; C07C2/00; C07C2/02; C07C2/04; C07C2/06; C07C2/08; C07C2/26; C07C2/36; B; B01; B01J; B01J31/00; B01J31/16; B01J31/22; B01J31/2204; B01J31/2208; B01J31/2226; B01J31/223; B01J31/2239; B01J31/2282; B01J31/2295; B01J31/24; B01J31/2404; B01J2231/00; B01J2231/20; B01J2531/00; B01J2531/80; B01J2531/84; B01J2531/847; B01J2540/00; B01J2540/20; B01J2540/22; 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: 7
Claim 1
Independent Claim 385 words
An improved process for the oligomerization of ethylene comprising contacting said ethylene with a catalyst composition in the liquid phase present in at least one solvent selected from the groups consisting of: (i) an aromatic hydrocarbon of the formula ##STR11## wherein R"' represents a C 1 to C 6 alkyl radical and n is 0, 1, 2, 3, or 4; (ii) an alcohol of the formula (R iv ) 3 COH wherein R iv independently represents H or a C 1 to C 12 alkyl, cycloalkyl, aryl, alkaryl, or aralkyl radical with the proviso that at least one R iv is not hydrogen; (iii) an amide of the formula ##STR12## wherein each R v independently represents H or a C 1 to C 10 alkyl, cycloalkyl, aryl, aralkyl, or alkaryl radical with the proviso that at least one R v is not H; (iv) a C 2 to C 20 ether; (v) a C 2 to C 20 ester; (vi) a C 3 to C 20 ketone; (vii) a C 2 to C 20 nitrile; and (viii) a C 6 to C 20 chlorinated aromatic, the catalyst 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 independently 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 carboxcyclic 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 at a temperature of from about 0° C. to about 200° C.
Claim 2
Dependent Claim 385 words
An improved process for the oligomerization of ethylene comprising contacting said ethylene with a catalyst composition in the liquid phase present in at least one solvent selected from the groups consisting of: (i) an aromatic hydrocarbon of the formula ##STR11## wherein R"' represents a C 1 to C 6 alkyl radical and n is 0, 1, 2, 3, or 4; (ii) an alcohol of the formula (R iv ) 3 COH wherein R iv independently represents H or a C 1 to C 12 alkyl, cycloalkyl, aryl, alkaryl, or aralkyl radical with the proviso that at least one R iv is not hydrogen; (iii) an amide of the formula ##STR12## wherein each R v independently represents H or a C 1 to C 10 alkyl, cycloalkyl, aryl, aralkyl, or alkaryl radical with the proviso that at least one R v is not H; (iv) a C 2 to C 20 ether; (v) a C 2 to C 20 ester; (vi) a C 3 to C 20 ketone; (vii) a C 2 to C 20 nitrile; and (viii) a C 6 to C 20 chlorinated aromatic, the catalyst 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 independently 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 carboxcyclic 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 at a temperature of from about 0° C. to about 200° C.
Claim 3
Dependent Claim 20 words
A process according to claim 1 carried out at a temperature of from about 20° C. to about 125° C.
Claim 4
Dependent Claim 11 words
A process according to claim 1 wherein said solvent is toluene.
Claim 5
Dependent Claim 25 words
A process according to claim 1 wherein said solvent is one selected from the group consisting of ethanol, sec-butanol, t-butanol, iso-butanol and 2-butanol, and 2-hexanol.
Claim 6
Dependent Claim 29 words
A process according to claim 3 wherein said solvent consists of toluene and at least one selected from the group consisting of N,N-dimethylformamide, diphenylformamide, acetamide, dimethyl acetamide, and phthalimide.
Claim 7
Dependent Claim 34 words
A process according to claim 3 wherein said solvent consists of toluene and at least one selected from the group consisting of diphenyl ether, 1,2-dimethoxyethane, acetonitrile, acetone, methyl ethyl ketone, ethyl acetate, and chlorobenzene.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-05-20 1988-11-19 1989-05-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-05-20 1992-11-19 1993-05-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-05-20 1996-11-19 1997-05-21 $7700.00 Window Closed / Lapsed

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