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US4529554A
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Process for the preparation of nickel ylides containing ylide ligands with a sulfonated group V component
Assignee: Chevron USA Inc
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Filing: 1980-08-18
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Granted: 1985-07-16
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Expires: 2000-08-18
Abstract
Abstract A process is provided for preparing nickel ylides which are themselves novel compounds 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 consisiting 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 carbon 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; a hydrocarbyl group, such as defined above, carrying halogen, hydroxyl or alkoxy or aryloxy; and a sulfonato group (-SO3-) or an alkyl, aryl, alkenyl, cycloalkyl, aralkyl or alkaryl group carrying a sulfonato group; provided that at least one of R1, R2 and R3 is a sulfonato group or an alkyl, aryl, alkenyl, cycloalkyl, aralkyl or alkaryl, as defined above, 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. The process comprises reacting a ligand defined by the following formula: <IMAGE> with an alpha-substituted ketone or aldehyde or an alpha-substituted thioketone or thioaldehyde defined by the following formula: <IMAGE> to obtain the metal salt defined by the following Formula II: <IMAGE> wherein R1, R2, R3, R7, R8, F and M are as defined above and X is a halogen radical selected from the group consisting of fluorine, chlorine, bromine and iodine, preferably chlorine and bromine, a tosyl group (a tolune sulfonate group), or an acetate group. This metal salt is reacted with a base to obtain the novel ylide defined by the following Formula III: <IMAGE> wherein R1, R2, R3, R7, R8, F and M are as defined above. This ylide is then reacted with (1) a zero valent nickel compound or any nickel compound convertible to a zero valent nickel compound in situ and (2) a ligand having the formula: <IMAGE> wherein R4, R5, R6 and E are as defined above.
Inventors
- 👤 David L. Beach
- 👤 James J. Harrison
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 18:12
CPC Classifications
B; B01; B01J; B01J31/00; B01J31/16; B01J31/22; B01J31/2204; B01J31/226; B01J31/2208; B01J31/2226; B01J31/2247; B01J31/24; B01J31/2404; C; C07; C07C; C07C2/00; C07C2/02; C07C2/04; C07C2/06; C07C2/08; C07C2/26; C07C2/36; C07F; C07F15/00; C07F15/04; C07F9/00; C07F9/02; C07F9/28; C07F9/535; C07F9/5352; C07F9/66; C07F9/70; C07F9/72; C07F9/74; C07F9/90; C07F9/92; C08; C08F; C08F110/00; C08F110/02; B01J2231/00; B01J2231/20; B01J2531/00; B01J2531/80; B01J2531/84; B01J2531/847; B01J2540/00; B01J2540/30; B01J2540/32; B01J31/18; B01J31/1895
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
289 words
A process for preparing a nickel ylide which comprises reacting a sulfonated ligand defined by the following formula: ##STR33## with an alpha-substituted ketone or aldehyde or an alpha-substituted thioketone or thioaldehyde defined by the following formula: ##STR34## to obtain the metal salt defined by the following formula: ##STR35## reacting the metal salt so obtained with a base to obtain the following metal ylide: ##STR36## and then reacting the metal ylide with (1) a ligand defined by the following formula: ##STR37## and (2) a zero valent nickel compound or any nickel compound convertible to a zero valent nickel compound in situ, 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 carbon 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 or aryloxy groups, hydrocarbyl groups carrying halogen, hydroxyl, alkoxy or aryloxy, and a sulfonato group or an alkyl, aryl, alkenyl, cycloalkyl aralkyl or alkaryl group carrying a sulfonato group, provided that at least one of R 1 , R 2 and R 3 is a sulfonato group or an alkyl, aryl, alkenyl, cycloalkyl, alkaryl or aralkyl carrying a sulfonato group; M is sulfur or oxygen; E is phosphorus, arsenic, antimony or nitrogen; F is phosphorus, arsenic or antimony; and X is a halogen radical, a tosyl group or an acetate group.
Claim 2
Dependent Claim
289 words
A process for preparing a nickel ylide which comprises reacting a sulfonated ligand defined by the following formula: ##STR33## with an alpha-substituted ketone or aldehyde or an alpha-substituted thioketone or thioaldehyde defined by the following formula: ##STR34## to obtain the metal salt defined by the following formula: ##STR35## reacting the metal salt so obtained with a base to obtain the following metal ylide: ##STR36## and then reacting the metal ylide with (1) a ligand defined by the following formula: ##STR37## and (2) a zero valent nickel compound or any nickel compound convertible to a zero valent nickel compound in situ, 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 carbon 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 or aryloxy groups, hydrocarbyl groups carrying halogen, hydroxyl, alkoxy or aryloxy, and a sulfonato group or an alkyl, aryl, alkenyl, cycloalkyl aralkyl or alkaryl group carrying a sulfonato group, provided that at least one of R 1 , R 2 and R 3 is a sulfonato group or an alkyl, aryl, alkenyl, cycloalkyl, alkaryl or aralkyl carrying a sulfonato group; M is sulfur or oxygen; E is phosphorus, arsenic, antimony or nitrogen; F is phosphorus, arsenic or antimony; and X is a halogen radical, a tosyl group or an acetate group.
Claim 3
Dependent Claim
18 words
A process as defined in claim 1 wherein E and F are both phosphorus and M is oxygen.
Claim 4
Dependent Claim
29 words
A process as defined in claim 1 wherein each of R 1 , R 2 and R 3 is phenyl, one of which is substituted with a sulfonato group.
Claim 5
Dependent Claim
29 words
A process as defined in claim 2 wherein each of R 1 , R 2 and R 3 is phenyl, one of which is substituted with a sulfonato group.
Claim 6
Dependent Claim
28 words
A process as defined in claim 1 wherein each of R 4 , R 5 , R 6 and R 8 is phenyl and R 7 is hydrogen.
Claim 7
Dependent Claim
28 words
A process as defined in claim 2 wherein each of R 4 , R 5 , R 6 and R 8 is phenyl and R 7 is hydrogen.
Claim 8
Dependent Claim
28 words
A process as defined in claim 3 wherein each of R 4 , R 5 , R 6 and R 8 is phenyl and R 7 is hydrogen.
Claim 9
Dependent Claim
28 words
A process as defined in claim 4 wherein each of R 4 , R 5 , R 6 and R 8 is phenyl and R 7 is hydrogen.
Claim 10
Dependent Claim
39 words
A process as defined in claim 1 wherein the reaction between the sulfonated ligand and the ketone or aldehyde is carried out at a temperature of about 20° to about 200° C. for about one to about 24 hours.
Claim 11
Dependent Claim
39 words
A process as defined in claim 1 wherein the reaction between the sulfonated ligand and the ketone or aldehyde is carried out at a temperature of about 50° to about 150° C. for about two to about eight hours.
Claim 12
Dependent Claim
39 words
A process as defined in claim 8 wherein the reaction between the sulfonated ligand and the ketone or aldehyde is carried out at a temperature of about 20° to about 200° C. for about one to about 24 hours.
Claim 13
Dependent Claim
39 words
A process as defined in claim 8 wherein the reaction between the sulfonated ligand and the ketone or aldehyde is carried out at a temperature of about 50° to about 150° C. for about two to about eight hours.
Claim 14
Dependent Claim
42 words
A process as defined in claim 1 wherein said metal salt is converted to the corresponding ylide by reacting with a base at a temperature of from about room temperature to about 200° C. for about one minute to about four hours.
Claim 15
Dependent Claim
41 words
A process as defined in claim 1 wherein said metal salt is converted to the corresponding ylide by reacting with a base at a temperature of from about room temperature to about 50° C. for about one to about two hours.
Claim 16
Dependent Claim
42 words
A process as defined in claim 8 wherein said metal salt is converted to the corresponding ylide by reacting with a base at a temperature of from about room temperature to about 200° C. for about one minute to about four hours.
Claim 17
Dependent Claim
41 words
A process as defined in claim 8 wherein said metal salt is converted to the corresponding ylide by reacting with a base at a temperature of from about room temperature to about 50° C. for about one to about two hours.
Claim 18
Dependent Claim
42 words
A process as defined in claim 9 wherein said metal salt is converted to the corresponding ylide by reacting with a base at a temperature of from about room temperature to about 200° C. for about one minute to about four hours.
Claim 19
Dependent Claim
41 words
A process as defined in claim 12 wherein said metal salt is converted to the corresponding ylide by reacting with a base at a temperature of from about room temperature to about 50° C. for about one to about two hours.
Claim 20
Dependent Claim
37 words
A process as defined in claim 1 wherein the ligand, the zero valent nickel compound and the ylide are reacted at a temperature of about 0° to about 100° C. for about one-half to about 48 hours.
Claim 21
Dependent Claim
31 words
A process as defined in claim 1 wherein the ligand, the zero valent nickel compound and the ylide are reacted at about room temperature for about three to about 20 hours.
Claim 22
Dependent Claim
37 words
A process as defined in claim 8 wherein the ligand, the zero valent nickel compound and the ylide are reacted at a temperature of about 0° to about 100° C. for about one-half to about 48 hours.
Claim 23
Dependent Claim
31 words
A process as defined in claim 8 wherein the ligand, the zero valent nickel compound and the ylide are reacted at about room temperature for about three to about 20 hours.
Claim 24
Dependent Claim
37 words
A process as defined in claim 17 wherein the ligand, the zero valent nickel compound and the ylide are reacted at a temperature of about 0° to about 100° C. for about one-half to about 48 hours.
Claim 25
Dependent Claim
31 words
A process as defined in claim 18 wherein the ligand, the zero valent nickel compound and the ylide are reacted to about room temperature for about three to about 20 hours.
Claim 26
Dependent Claim
16 words
A process as defined in claim 1 wherein said zero valent nickel compound is bis(cyclooctadiene) nickel.
Claim 27
Dependent Claim
16 words
A process as defined in claim 8 wherein said zero valent nickel compound is bis(cyclooctadiene) nickel.
Claim 28
Dependent Claim
16 words
A process as defined in claim 9 wherein said zero valent nickel compound is bis(cyclooctadiene) nickel.
Claim 29
Dependent Claim
16 words
A process as defined in claim 12 wherein said zero valent nickel compound is bis(cyclooctadiene) nickel.
Claim 30
Dependent Claim
16 words
A process as defined in claim 13 wherein said zero valent nickel compound is bis(cyclooctadiene) nickel.
Claim 31
Dependent Claim
16 words
A process as defined in claim 16 wherein said zero valent nickel compound is bis(cyclooctadiene) nickel.
Claim 32
Dependent Claim
16 words
A process as defined in claim 17 wherein said zero valent nickel compound is bis(cyclooctadiene) nickel.
Claim 33
Dependent Claim
16 words
A process as defined in claim 18 wherein said zero valent nickel compound is bis(cyclooctadiene) nickel.
Claim 34
Dependent Claim
16 words
A process as defined in claim 19 wherein said zero valent nickel compound is bis(cyclooctadiene) nickel.
Claim 35
Dependent Claim
16 words
A process as defined in claim 22 wherein said zero valent nickel compound is bis(cyclooctadiene) nickel.
Claim 36
Dependent Claim
16 words
A process as defined in claim 23 wherein said zero valent nickel compound is bis(cyclooctadiene) nickel.
Claim 37
Dependent Claim
16 words
A process as defined in claim 24 wherein said zero valent nickel compound is bis(cyclooctadiene) nickel.
Claim 38
Dependent Claim
11 words
A process as defined in claim 26 wherein X is chlorine.
Claim 39
Dependent Claim
11 words
A process as defined in claim 28 wherein X is chlorine.
Claim 40
Dependent Claim
11 words
A process as defined in claim 32 wherein X is chlorine.
Claim 41
Dependent Claim
11 words
A process as defined in claim 36 wherein X is chlorine.
References Cited (Backward Citations)
US2998416A
Cited
US3686159A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-07-15 | 1989-01-14 | 1989-07-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-07-15 | 1993-01-14 | 1993-07-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-07-15 | 1997-01-14 | 1997-07-16 | $7700.00 | Window Closed / Lapsed |