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US4293727A
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Process for the oligomerization of ethylene
Assignee: Chevron USA Inc
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Filing: 1980-08-18
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Granted: 1981-10-06
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Expires: 2000-08-18
Abstract
Abstract Ethylene is oligomerized by contacting ethylene under oligomerization conditions with a nickel ylide defined by the following Formula I: <IMAGE> wherein R1, R2, R3, R4, R5, R6, R7 and R8 are either alike or different members selected from the group consisting of hydrogen, alkyl radicals having from about one to about 24 carbon atoms, preferably from about one to about 10 carbon atoms; aryl radicals having from about six to about 20 carbon atoms, preferably from about six to about 10 carbon atoms; alkenyl radicals having from about two to about 30 carbons atoms, preferably from about two to about 20 carbon atoms; cycloalkyl radicals having from about three to about 40 carbon atoms, preferably from about three to about 30 carbon atoms; aralkyl and alkaryl radicals having from about six to about 40 carbon atoms, preferably from about six to about 30 carbon atoms; a halogen radical selected from the group consisting of fluorine, chlorine, bromine and iodine, preferably chlorine; a hydroxyl group; an alkoxy or aryloxy group; and a hydrocarbyl group, such as defined above, carrying halogen, hydroxyl or alkoxy or aryloxy; provided that at least one, preferably from about one to about four, of each of R1 to R8 is a sulfonato group (-SO3-) or an alkyl, aryl, alkenyl, cycloalkyl, aralkyl or alkaryl group carrying a sulfonato group; M is sulfur or oxygen, preferably oxygen; E is phosphorus, arsenic, antimony or nitrogen, preferably phosphorus; and F is phosphorus, arsenic or antimony, preferably phosphorus. This process is characterized by a relatively high reaction rate at low temperatures and pressures and results in the production of relatively high proportions of desirable trimer, tetramer, pentamer, and higher olefinic products.
Inventors
- 👤 David L. Beach
- 👤 James J. Harrison
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 16:40
CPC Classifications
B; B01; B01J; B01J31/00; B01J31/16; B01J31/24; B01J31/2404; B01J31/18; B01J31/1895; B01J31/22; B01J31/2204; B01J31/2208; B01J31/2226; B01J31/2247; C; C07; C07C; C07C2/00; C07C2/02; C07C2/04; C07C2/06; C07C2/08; C07C2/26; C07C2/36; C07F; C07F15/00; C07F15/04; C08; C08F; C08F110/00; C08F110/02; B01J2231/00; B01J2231/20; B01J2531/00; B01J2531/80; B01J2531/84; B01J2531/847; B01J2540/00; B01J2540/30; B01J2540/32; C07C2531/00; C07C2531/16; C07C2531/24
Claims Analysis
Total Claims: 60
Claim 1
Independent Claim
183 words
A process for oligomerizing ethylene which comprises contacting ethylene under oligomerization conditions with a nickel ylide defined by the following formula: ##STR78## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are either alike or different members selected from the group consisting of hydrogen, alkyl radicals having from about one to about 24 carbon atoms, aryl radicals having from about six to about 20 carbon atoms, alkenyl radicals having from about two to about 30 carbons atoms, cycloalkyl radicals having from about three to about 40 carbon atoms, aralkyl and alkaryl radicals having from about six to about 40 carbon atoms, halogen radicals, hydroxyl, alkoxy and aryloxy groups, and hydrocarbyl groups carrying halogen, hydroxyl, alkoxy or aryloxy groups, provided that at least one of each of R 1 to R 8 radicals is a sulfonato group or an alkyl, aryl, alkenyl, cycloalkyl, aralkyl or alkaryl carrying a sulfonato group, M is sulfur or oxygen, E is phosphorus, arsenic, antimony or nitrogen and F is phosphorus, arsenic or antimony.
Claim 2
Dependent Claim
183 words
A process for oligomerizing ethylene which comprises contacting ethylene under oligomerization conditions with a nickel ylide defined by the following formula: ##STR78## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are either alike or different members selected from the group consisting of hydrogen, alkyl radicals having from about one to about 24 carbon atoms, aryl radicals having from about six to about 20 carbon atoms, alkenyl radicals having from about two to about 30 carbons atoms, cycloalkyl radicals having from about three to about 40 carbon atoms, aralkyl and alkaryl radicals having from about six to about 40 carbon atoms, halogen radicals, hydroxyl, alkoxy and aryloxy groups, and hydrocarbyl groups carrying halogen, hydroxyl, alkoxy or aryloxy groups, provided that at least one of each of R 1 to R 8 radicals is a sulfonato group or an alkyl, aryl, alkenyl, cycloalkyl, aralkyl or alkaryl carrying a sulfonato group, M is sulfur or oxygen, E is phosphorus, arsenic, antimony or nitrogen and F is phosphorus, arsenic or antimony.
Claim 3
Dependent Claim
36 words
A process as defined in claim 1 wherein the sulfonato group is in R 4 , R 5 and/or R 6 and at least one of R 4 , R 5 and R 6 is aryl.
Claim 4
Dependent Claim
22 words
A process as defined in claim 1 wherein the sulfonato group is in R 1 , R 2 and/or R 3 .
Claim 5
Dependent Claim
14 words
A process as defined in claim 1 wherein R 7 comprises a sulfonato group.
Claim 6
Dependent Claim
18 words
A process as defined in claim 1 wherein E and F are both phosphorus and M is oxygen.
Claim 7
Dependent Claim
18 words
A process as defined in claim 2 wherein E and F are both phosphorus and M is oxygen.
Claim 8
Dependent Claim
18 words
A process as defined in claim 3 wherein E and F are both phosphorus and M is oxygen.
Claim 9
Dependent Claim
18 words
A process as defined in claim 4 wherein E and F are both phosphorus and M is oxygen.
Claim 10
Dependent Claim
29 words
A process as defined in claim 6 wherein each of R 4 , R 5 and R 6 is phenyl, one of which is substituted with a sulfonato group.
Claim 11
Dependent Claim
28 words
A process as defined in claim 9 wherein each of R 1 , R 2 , R 3 and R 8 is phenyl and R 7 is hydrogen.
Claim 12
Dependent Claim
29 words
A process as defined in claim 7 wherein each of R 1 , R 2 and R 3 is phenyl, one of which is substituted with a sulfonato group.
Claim 13
Dependent Claim
28 words
A process as defined in claim 11 wherein each of R 4 , R 5 , R 6 and R 8 is phenyl and R 7 is hydrogen.
Claim 14
Dependent Claim
39 words
A process as defined in claim 8 wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 8 is phenyl and R 7 is a sulfonato group.
Claim 15
Dependent Claim
18 words
A process as defined in claim 10 wherein said ylide is in the form of its sodium salt.
Claim 16
Dependent Claim
18 words
A process as defined in claim 12 wherein said ylide is in the form of its sodium salt.
Claim 17
Dependent Claim
18 words
A process as defined in claim 13 wherein said ylide is in the form of its sodium salt.
Claim 18
Dependent Claim
18 words
A process as defined in claim 13 wherein said ylide is in the form of its potassium salt.
Claim 19
Dependent Claim
18 words
A process as defined in claim 13 wherein said ylide is in the form of its ammonium salt.
Claim 20
Dependent Claim
18 words
A process as defined in claim 13 wherein said ylide is in the form of its trimethylammonium salt.
Claim 21
Dependent Claim
35 words
A process as defined in claim 1 wherein said ethylene and said nickel ylide are contacted at a temperature of from about -20° to about 200° C. for about 10 minutes to about 72 hours.
Claim 22
Dependent Claim
34 words
A process as defined in claim 1 wherein said ethylene and said nickel ylide are contacted at a temperature of from about 30° to about 150° C. for about one to about eight hours.
Claim 23
Dependent Claim
35 words
A process as defined in claim 10 wherein said ethylene and said nickel ylide are contacted at a temperature of from about -20° to about 200° C. for about 10 minutes to about 72 hours.
Claim 24
Dependent Claim
34 words
A process as defined in claim 10 wherein said ethylene and said nickel ylide are contacted at a temperature of from about 30° to about 150° C. for about one to about eight hours.
Claim 25
Dependent Claim
35 words
A process as defined in claim 12 wherein said ethylene and said nickel ylide are contacted at a temperature of from about -20° to about 200° C. for about 10 minutes to about 72 hours.
Claim 26
Dependent Claim
34 words
A process as defined in claim 12 wherein said ethylene and said nickel ylide are contacted at a temperature of from about 30° to about 150° C. for about one to about eight hours.
Claim 27
Dependent Claim
35 words
A process as defined in claim 13 wherein said ethylene and said nickel ylide are contacted at a temperature of from about -20° to about 200° C. for about 10 minutes to about 72 hours.
Claim 28
Dependent Claim
34 words
A process as defined in claim 13 wherein said ethylene and said nickel ylide are contacted at a temperature of from about 30° to about 150° C. for about one to about eight hours.
Claim 29
Dependent Claim
35 words
A process as defined in claim 14 wherein said ethylene and said nickel ylide are contacted at a temperature of from about -20° to about 200° C. for about 10 minutes to about 72 hours.
Claim 30
Dependent Claim
34 words
A process as defined in claim 14 wherein said ethylene and said nickel ylide are contacted at a temperature of from about 30° to about 150° C. for about one to about eight hours.
Claim 31
Dependent Claim
35 words
A process as defined in claim 15 wherein said ethylene and said nickel ylide are contacted at a temperature of from about -20° to about 200° C. for about 10 minutes to about 72 hours.
Claim 32
Dependent Claim
34 words
A process as defined in claim 15 wherein said ethylene and said nickel ylide are contacted at a temperature of from about 30° to about 150° C. for about one to about eight hours.
Claim 33
Dependent Claim
35 words
A process as defined in claim 16 wherein said ethylene and said nickel ylide are contacted at a temperature of from about -20° to about 200° C. for about 10 minutes to about 72 hours.
Claim 34
Dependent Claim
34 words
A process as defined in claim 16 wherein said ethylene and said nickel ylide are contacted at a temperature of from about 30° to about 150° C. for about one to about eight hours.
Claim 35
Dependent Claim
35 words
A process as defined in claim 17 wherein said ethylene and said nickel ylide are contacted at a temperature of from about -20° to about 200° C. for about 10 minutes to about 72 hours.
Claim 36
Dependent Claim
34 words
A process as defined in claim 17 wherein said ethylene and said nickel ylide are contacted at a temperature of from about 30° to about 150° C. for about one to about eight hours.
Claim 37
Dependent Claim
35 words
A process as defined in claim 18 wherein said ethylene and said nickel ylide are contacted at a temperature of from about -20° to about 200° C. for about 10 minutes to about 72 hours.
Claim 38
Dependent Claim
34 words
A process as defined in claim 18 wherein said ethylene and said nickel ylide are contacted at a temperature of from about 30° to about 150° C. for about one to about eight hours.
Claim 39
Dependent Claim
35 words
A process as defined in claim 19 wherein said ethylene and said nickel ylide are contacted at a temperature of from about -20° to about 200° C. for about 10 minutes to about 72 hours.
Claim 40
Dependent Claim
34 words
A process as defined in claim 19 wherein said ethylene and said nickel ylide are contacted at a temperature of from about 30° to about 150° C. for about one to about eight hours.
Claim 41
Dependent Claim
56 words
A process as defined in claim 1 wherein said ethylene and said ylide are contacted in a solvent, and metal ylide being present in the range of about 0.0001 to about 10 moles per liter of solvent and the ethylene being present in the range of about 0.001 to about 20 moles per liter of solvent.
Claim 42
Dependent Claim
56 words
A process as defined in claim 1 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.001 to about 1 mole per liter of solvent and the ethylene being present in the range of about 0.01 to about 10 moles per liter of solvent.
Claim 43
Dependent Claim
56 words
A process as defined in claim 10 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.0001 to about 10 moles per liter of solvent and the ethylene being present in the range of about 0.001 to about 20 moles per liter of solvent.
Claim 44
Dependent Claim
56 words
A process as defined in claim 10 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.001 to about 1 mole per liter of solvent and the ethylene being present in the range of about 0.01 to about 10 moles per liter of solvent.
Claim 45
Dependent Claim
56 words
A process as defined in claim 12 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.0001 to about 10 moles per liter of solvent and the ethylene being present in the range of about 0.001 to about 20 moles per liter of solvent.
Claim 46
Dependent Claim
56 words
A process as defined in claim 12 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.001 to about 1 mole per liter of solvent and the ethylene being present in the range of about 0.01 to about 10 moles per liter of solvent.
Claim 47
Dependent Claim
56 words
A process as defined in claim 13 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.0001 to about 10 moles per liter of solvent and the ethylene being present in the range of about 0.001 to about 20 moles per liter of solvent.
Claim 48
Dependent Claim
56 words
A process as defined in claim 13 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.001 to about 1 mole per liter of solvent and the ethylene being present in the range of about 0.01 to about 10 moles per liter of solvent.
Claim 49
Dependent Claim
56 words
A process as defined in claim 14 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.0001 to about 10 moles per liter of solvent and the ethylene being present in the range of about 0.001 to about 20 moles per liter of solvent.
Claim 50
Dependent Claim
56 words
A process as defined in claim 14 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.001 to about 1 mole per liter of solvent and the ethylene being present in the range of about 0.01 to about 10 moles per liter of solvent.
Claim 51
Dependent Claim
56 words
A process as defined in claim 15 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.0001 to about 10 moles per liter of solvent and the ethylene being present in the range of about 0.001 to about 20 moles per liter of solvent.
Claim 52
Dependent Claim
56 words
A process as defined in claim 15 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.001 to about 1 mole per liter of solvent and the ethylene being present in the range of about 0.01 to about 10 moles per liter of solvent.
Claim 53
Dependent Claim
56 words
A process as defined in claim 16 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.0001 to about 10 moles per liter of solvent and the ethylene being present in the range of about 0.001 to about 20 moles per liter of solvent.
Claim 54
Dependent Claim
56 words
A process as defined in claim 16 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.001 to about 1 mole per liter of solvent and the ethylene being present in the range of about 0.01 to about 10 moles per liter of solvent.
Claim 55
Dependent Claim
56 words
A process as defined in claim 17 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.0001 to about 10 moles per liter of solvent and the ethylene being present in the range of about 0.001 to about 20 moles per liter of solvent.
Claim 56
Dependent Claim
56 words
A process as defined in claim 17 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.001 to about 1 mole per liter of solvent and the ethylene being present in the range of about 0.01 to about 10 moles per liter of solvent.
Claim 57
Dependent Claim
56 words
A process as defined in claim 18 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.0001 to about 10 moles per liter of solvent and the ethylene being present in the range of about 0.001 to about 20 moles per liter of solvent.
Claim 58
Dependent Claim
56 words
A process as defined in claim 18 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.001 to about 1 mole per liter of solvent and the ethylene being present in the range of about 0.01 to about 10 moles per liter of solvent.
Claim 59
Dependent Claim
56 words
A process as defined in claim 19 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.0001 to about 10 moles per liter of solvent and the ethylene being present in the range of about 0.001 to about 20 moles per liter of solvent.
Claim 60
Dependent Claim
56 words
A process as defined in claim 19 wherein said ethylene and said ylide are contacted in a solvent, the metal ylide being present in the range of about 0.001 to about 1 mole per liter of solvent and the ethylene being present in the range of about 0.01 to about 10 moles per liter of solvent.
References Cited (Backward Citations)
US2998416A
Cited
US3686159A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1984-10-05 | 1985-04-06 | 1985-10-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-05 | 1989-04-06 | 1989-10-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-05 | 1993-04-06 | 1993-10-06 | $7700.00 | Window Closed / Lapsed |