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US4273712A
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Method for making aromatic ether imides
Assignee: General Electric Co
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Filing: 1979-05-09
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Granted: 1981-06-16
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Expires: 1999-05-09
Abstract
Abstract A method for making aromatic ether imides is provided by effecting the displacement of reactive radicals on a phthalimide nucleus with a mono- or bis-alkali metal phenoxide in the presence of a nonpolar solvent and a phase transfer catalyst, such as a tetra-ammonia salt. The aromatic ether imides made by the present invention are useful intermediates for making aromatic ether anhydrides and aromatic bis(ether anhydrides).
Inventors
- 👤 Frank J. Williams, III
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 05:37
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/582
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
272 words
A method for making aromatic ether imides of the formula, ##STR9## which comprises (A) heating at 25° to 150° C. under substantially anhydrous conditions, a mixture consisting essentially of substituted phthalimide of the formula, ##STR10## and an alkali metal phenoxide salt of the formula, R.sup.1 --OM).sub.a, in the presence of a nonpolar organic solvent and an effective amount of a phase transfer catalyst of the formula, (R.sup.2).sub.4 QY, (B) agitating the resulting mixture with a precipitating or extractive organic solvent for the resulting bisimide or allowing the mixture to cool and (C) recovering the bisimide from the mixture of (B), where R is a monovalent group selected from hydrogen, a C.sub.(1-8) alkyl group, a C.sub.(6-13) aryl group and a and a C.sub.(6-13) haloaryl group, R 1 is an aromatic group selected from the group consisting of a C.sub.(6-30) aromatic carbocyclic group, a halogenated C.sub.(6-30) aromatic carbocyclic group and an alkylated C.sub.(6-30) aromatic carbocyclic group and a divalent organic group of the formula, ##STR11## where X is a member selected from the group consisting of divalent groups of the formula, ##STR12## --O--, and --S--, m is 0 or 1, y is a whole number from 1 to 5, R 2 is selected from a C.sub.(1-16) alkyl radical and a C.sub.(6-13) aromatic carbocyclic radical, Q is a Group Va element selected from N and P, Y is a halogen or carbethoxy radical, X 1 is a member selected from the group consisting of nitro and halo, and a is an integer equal to 1 or 2, and when a is 1, R 1 is monovalent and when a is 2, R 1 is divalent.
Claim 2
Independent Claim
272 words
A method for making aromatic ether imides of the formula, ##STR9## which comprises (A) heating at 25° to 150° C. under substantially anhydrous conditions, a mixture consisting essentially of substituted phthalimide of the formula, ##STR10## and an alkali metal phenoxide salt of the formula, R.sup.1 --OM).sub.a, in the presence of a nonpolar organic solvent and an effective amount of a phase transfer catalyst of the formula, (R.sup.2).sub.4 QY, (B) agitating the resulting mixture with a precipitating or extractive organic solvent for the resulting bisimide or allowing the mixture to cool and (C) recovering the bisimide from the mixture of (B), where R is a monovalent group selected from hydrogen, a C.sub.(1-8) alkyl group, a C.sub.(6-13) aryl group and a and a C.sub.(6-13) haloaryl group, R 1 is an aromatic group selected from the group consisting of a C.sub.(6-30) aromatic carbocyclic group, a halogenated C.sub.(6-30) aromatic carbocyclic group and an alkylated C.sub.(6-30) aromatic carbocyclic group and a divalent organic group of the formula, ##STR11## where X is a member selected from the group consisting of divalent groups of the formula, ##STR12## --O--, and --S--, m is 0 or 1, y is a whole number from 1 to 5, R 2 is selected from a C.sub.(1-16) alkyl radical and a C.sub.(6-13) aromatic carbocyclic radical, Q is a Group Va element selected from N and P, Y is a halogen or carbethoxy radical, X 1 is a member selected from the group consisting of nitro and halo, and a is an integer equal to 1 or 2, and when a is 1, R 1 is monovalent and when a is 2, R 1 is divalent.
Claim 3
Dependent Claim
13 words
A method in accordance with claim 1, utilizing an alkali metal monophenoxide salt.
Claim 4
Dependent Claim
13 words
A method in accordance with claim 1, utilizing an alkali metal diphenoxide salt.
Claim 5
Dependent Claim
19 words
A method in accordance with claim 1, where the alkali metal salt is the anhydrous disodium salt of bisphenol-A.
Claim 6
Dependent Claim
33 words
A method in accordance with claim 1, where the alkali metal phenoxide salt is made by azeotroping water from a mixture of toluene and the hydrated form of the alkali metal phenoxide salt.
Claim 7
Dependent Claim
30 words
A method in accordance with claim 1, where the alkali metal phenoxide salt is formed in situ from an aqueous mixture of the alkali metal hydroxide and the corresponding phenol.
Claim 8
Dependent Claim
30 words
A method in accordance with claim 1, where the alkali metal phenoxide salt is made from a mixture of an alkali metal alkoxide and the corresponding monohydric or dihydric phenol.
Claim 9
Dependent Claim
16 words
A method in accordance with claim 1, where Y in the phase transfer catalyst is chloride.
Claim 10
Dependent Claim
17 words
A method in accordance with claim 1, where the phase transfer catalyst is methyl tricapryl ammonium chloride.
Claim 11
Dependent Claim
13 words
A method in accordance with claim 1, where the substituted phthalimide is 3-nitro-N-methylphthalimide.
Claim 12
Dependent Claim
14 words
A method in accordance with claim 1, where the substituted phthalimide is 4-fluoro-N-methyl phthalimide.
Claim 13
Dependent Claim
17 words
A method in accordance with claim 1, where the substituted phthalimide is a nitro-N-methyl or N-phenyl phthalimide.
Claim 14
Dependent Claim
20 words
A method in accordance with claim 1, where the alkali metal phenoxide is an alkali bisphenoxide of a dihydric sulfone.
Claim 15
Dependent Claim
20 words
A method in accordance with claim 1, where the alkali metal phenoxide is an alkali bisphenoxide of a dihydric sulfide.
Claim 16
Independent Claim
76 words
A method for making an ether phthalimide of the formula, ##STR13## which comprises (A) heating at 25° C. to 150° C. under substantially anhydrous conditions 4-nitro-N-methylphthalimide and the disodium salt of bisphenol-A in the presence of toluene and an effective amount of tetrabutyl ammonium bromide, (B) agitating the resulting mixture with a precipitating or extractive organic solvent for said bisimide or allowing the mixture to cool and (C) recovering the bisimide from the mixture of (B).
Claim 17
Independent Claim
76 words
A method for making an ether phthalimide of the formula, ##STR13## which comprises (A) heating at 25° C. to 150° C. under substantially anhydrous conditions 4-nitro-N-methylphthalimide and the disodium salt of bisphenol-A in the presence of toluene and an effective amount of tetrabutyl ammonium bromide, (B) agitating the resulting mixture with a precipitating or extractive organic solvent for said bisimide or allowing the mixture to cool and (C) recovering the bisimide from the mixture of (B).
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) | 1984-06-15 | 1984-12-15 | 1985-06-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-06-15 | 1988-12-15 | 1989-06-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-06-15 | 1992-12-15 | 1993-06-16 | $7700.00 | Window Closed / Lapsed |