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US3987056A
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Disproportionation of n-aryl-1,2,3,6-tetrahydrophthalimides
Assignee: Phillips Petroleum Co
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Filing: 1973-05-07
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Granted: 1976-10-19
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Expires: 1993-05-07
Abstract
Abstract N-Aryl-1,2,3,6-tetrahydrophthalimides are disproportionated to N-arylphthalimides and N-arylhexahydrophthalimides employing a catalyst of palladium, platinum, or ruthenium, on carbon.
Inventors
- 👤 Raymond L. Cobb
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 07:06
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
139 words
The liquid phase process for preparing (II) N-phenylphthalimides or N-substituted phenylphthalimides and (III) N-phenylhexahydrophthalimides or N-substituted phenylhexahydrophthalimides represented by formulas (II) and (III) ##SPC3## which process comprises contacting (I) N-phenyl-1,2,3,6-tetrahydrophthalimides or N-substituted phenyl-1,2,3,6-tetrahydrophthalimides represented by (I): ##SPC4## wherein each R is independently hydrogen, or an alkyl, cycloalkyl, aryl, alkoxy, halogen, such that at least three R groups are hydrogen, and when two R groups other than hydrogen are present in (I), not more than one of these can be in the 2 or 6 positions, and wherein the total number of carbon atoms in said (I) is in the range of 14 to 24, with a palladium, platinum, ruthenium, or combination thereof -on-carbon catalyst at a contacting temperature of less than about 200° C effective for the conversion of said (I) tetrahydrophthalimide to said (II) phthalimide and (III) hexahydrophthalimide.
Claim 2
Dependent Claim
139 words
The liquid phase process for preparing (II) N-phenylphthalimides or N-substituted phenylphthalimides and (III) N-phenylhexahydrophthalimides or N-substituted phenylhexahydrophthalimides represented by formulas (II) and (III) ##SPC3## which process comprises contacting (I) N-phenyl-1,2,3,6-tetrahydrophthalimides or N-substituted phenyl-1,2,3,6-tetrahydrophthalimides represented by (I): ##SPC4## wherein each R is independently hydrogen, or an alkyl, cycloalkyl, aryl, alkoxy, halogen, such that at least three R groups are hydrogen, and when two R groups other than hydrogen are present in (I), not more than one of these can be in the 2 or 6 positions, and wherein the total number of carbon atoms in said (I) is in the range of 14 to 24, with a palladium, platinum, ruthenium, or combination thereof -on-carbon catalyst at a contacting temperature of less than about 200° C effective for the conversion of said (I) tetrahydrophthalimide to said (II) phthalimide and (III) hexahydrophthalimide.
Claim 3
Dependent Claim
43 words
The process according to claim 1 wherein said contacting temperature is between about 150° and 200° C., and wherein said process employs a palladium or platinum or ruthenium:starting compound (I) weight ratio of approximately 0.01- 2 parts metal to 100 parts starting compound.
Claim 4
Dependent Claim
23 words
The process according to claim 2 wherein said catalyst represents about 0.5 to 20 weight percent palladium, platinum, or ruthenium relative to carbon.
Claim 5
Dependent Claim
37 words
The process according to claim 3 wherein said contacting temperature is about 165° to 185° C. and said metal to starting compound ratio is about 0.03 to 0.3 part of metal per 100 parts of starting compound.
Claim 6
Dependent Claim
13 words
The process according to claim 4 wherein said catalyst comprises palladium on charcoal.
Claim 7
Dependent Claim
29 words
The process according to claim 5 wherein in said (I) each R is hydrogen such that said (I) is N-phenyl-1,2,3,6-tetrahydrophthalimide, and the products are (II) N-phenylphthalimide and (III) N-phenylhexahydrophthalimide.
Claim 8
Dependent Claim
13 words
The process according to claim 4 wherein said catalyst comprises platinum on carbon.
Claim 9
Dependent Claim
13 words
The process according to claim 4 wherein said catalyst comprises ruthenium on carbon.
Claim 10
Dependent Claim
19 words
The process according to claim 2 further employing a diluent which is biphenyl, naphthalene, diphenyl ether, or mixtures thereof.
Claim 11
Dependent Claim
114 words
The liquid phase conversion of a tetrahydrophthalimide represented by (I) ##SPC5## wherein R is hydrogen, or alkyl, cycloalkyl, aryl, alkoxy, or halogen radical, such that at least three R groups are hydrogen and when two R groups other than hydrogen are present in (I), not more than one of these can be in the 2 or 6 positions, to (II) phthalimides and (III) hexahydrophthalimides represented by ##SPC6## wherein said conversion is effectuated by contacting said (I) at a temperature of about 150° to 200° C. with an effective amount of a catalyst consisting essentially of ruthenium-on-carbon, wherein said effective amount of said catalyst is approximately 0.01-2 parts ruthenium per 100 parts starting (I) phthalimide.
Claim 12
Dependent Claim
114 words
The liquid phase conversion of a tetrahydrophthalimide represented by (I) ##SPC5## wherein R is hydrogen, or alkyl, cycloalkyl, aryl, alkoxy, or halogen radical, such that at least three R groups are hydrogen and when two R groups other than hydrogen are present in (I), not more than one of these can be in the 2 or 6 positions, to (II) phthalimides and (III) hexahydrophthalimides represented by ##SPC6## wherein said conversion is effectuated by contacting said (I) at a temperature of about 150° to 200° C. with an effective amount of a catalyst consisting essentially of ruthenium-on-carbon, wherein said effective amount of said catalyst is approximately 0.01-2 parts ruthenium per 100 parts starting (I) phthalimide.
Claim 13
Dependent Claim
72 words
The liquid phase process for preparing (II) N-4-chlorophenylphthalimide and (III) N-4-chlorophenylhexahydrophthalimide which process comprises contacting (I) N-4-chlorophenyl-1,2,3,6-tetrahydrophthalimide with a palladium-on-charcoal catalyst at a contacting temperature in the range of about 165°-185° C. effective for the conversion of said (I) tetrahydrophthalimide to said (II) phthalimide and (III) hexahydrophthalimide, wherein said process employs a palladium: starting compound (I) weight ratio of approximately 0.03 to 0.3 parts metal to 100 parts starting compound by weight.
Claim 14
Dependent Claim
72 words
The liquid phase process for preparing (II) N-4-chlorophenylphthalimide and (III) N-4-chlorophenylhexahydrophthalimide which process comprises contacting (I) N-4-chlorophenyl-1,2,3,6-tetrahydrophthalimide with a palladium-on-charcoal catalyst at a contacting temperature in the range of about 165°-185° C. effective for the conversion of said (I) tetrahydrophthalimide to said (II) phthalimide and (III) hexahydrophthalimide, wherein said process employs a palladium: starting compound (I) weight ratio of approximately 0.03 to 0.3 parts metal to 100 parts starting compound by weight.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-10-19 | 1980-04-19 | 1980-10-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-10-19 | 1984-04-19 | 1984-10-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-10-19 | 1988-04-19 | 1988-10-19 | $7700.00 | Window Closed / Lapsed |