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US4128574A
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Method for making organic polycarboxylic acids
Assignee: General Electric Co
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Filing: 1976-10-04
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Granted: 1978-12-05
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Expires: 1996-10-04
Abstract
Abstract A method is described for making organic polycarboxylic acids or anhydrides, such as aromatic ether bis(phthalic acid)s, based on a cyclic imide-cyclic anhydride exchange reaction at elevated temperatures in the presence of water. In addition to making organic polycarboxylic acid, organic imides are also generated.
Inventors
- 👤 Ronald L. Markezich
- 👤 Tohru Takekoshi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 16:47
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/44; C07D207/444; C07D207/448; C07C; C07C51/00; C07C51/54; C07C51/567; C07D209/00; C07D209/02; C07D209/44; C07D209/48
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
298 words
A method which comprises, (1) heating at a temperature of at least 100° C. in the presence of water, a mixture comprising a first organic imide of the formula, ##STR24## and a first organic anhydride, or polycarboxylic acid precursor thereof of the formula, ##STR25## for a time sufficient to effect an imide-anhydirde exchange to produce a mixture comprising a second organic imide of the formula, ##STR26## and a second polycarboxylic acid or anhydride thereof of the formula, ##STR27## (2) effecting the separation of the second organic imide or second polycarboxylic acid or anhydride from the mixture of (1), where Q and Q 1 are the same or different monovalent radicals selected from R 1 --, R 1 O--, R 1 S--, the same or different divalent radicals selected from --O--, --S--, --R 2 --, --O--R 2 --O--, --S--R 2 --S-- and --OR 2 XR 2 O--, and Q and Q 1 can have different valences, X is selected from ##STR28## and y is equal to 0 to 5 inclusive, R and R 4 are selected from the same or different polyvalent organic radicals, R 1 is selected from C.sub.(6-13) monovalent aromatic radicals, and C.sub.(1-8) alkyl radicals, R 2 is selected from C.sub.(6-13) divalent aromatic organic radicals and C.sub.(1-8) alkylene radicals, R 3 is selected from H and C.sub.(1-20) monovalent organic radicals, D is selected from --O-- and --OH, "a" is a whole number equal to 0 or 1, "b" is an integer equal to 1 or 2 and "c" is an integer equal to 1 or 2, when "a" and "c" are respectively 1, Q is a monovalent radical, and when "a" is 1 and "c" is 2, Q is a divalent radical, and "a", "b" and "c" and "d", "e" and "f" have the same values respectively.
Claim 2
Independent Claim
298 words
A method which comprises, (1) heating at a temperature of at least 100° C. in the presence of water, a mixture comprising a first organic imide of the formula, ##STR24## and a first organic anhydride, or polycarboxylic acid precursor thereof of the formula, ##STR25## for a time sufficient to effect an imide-anhydirde exchange to produce a mixture comprising a second organic imide of the formula, ##STR26## and a second polycarboxylic acid or anhydride thereof of the formula, ##STR27## (2) effecting the separation of the second organic imide or second polycarboxylic acid or anhydride from the mixture of (1), where Q and Q 1 are the same or different monovalent radicals selected from R 1 --, R 1 O--, R 1 S--, the same or different divalent radicals selected from --O--, --S--, --R 2 --, --O--R 2 --O--, --S--R 2 --S-- and --OR 2 XR 2 O--, and Q and Q 1 can have different valences, X is selected from ##STR28## and y is equal to 0 to 5 inclusive, R and R 4 are selected from the same or different polyvalent organic radicals, R 1 is selected from C.sub.(6-13) monovalent aromatic radicals, and C.sub.(1-8) alkyl radicals, R 2 is selected from C.sub.(6-13) divalent aromatic organic radicals and C.sub.(1-8) alkylene radicals, R 3 is selected from H and C.sub.(1-20) monovalent organic radicals, D is selected from --O-- and --OH, "a" is a whole number equal to 0 or 1, "b" is an integer equal to 1 or 2 and "c" is an integer equal to 1 or 2, when "a" and "c" are respectively 1, Q is a monovalent radical, and when "a" is 1 and "c" is 2, Q is a divalent radical, and "a", "b" and "c" and "d", "e" and "f" have the same values respectively.
Claim 3
Dependent Claim
12 words
A method in accordance with claim 1, for making an organic imide.
Claim 4
Dependent Claim
16 words
A method in accordance with claim 1, where the first organic imide is an organic bisimide.
Claim 5
Dependent Claim
21 words
A method in accordance with claim 1, where the imide anhydride exchange results in the production of an imide dicarboxylic acid.
Claim 6
Independent Claim
128 words
A method which comprises (1) heating at a temperature of at least 100° C. in the presence of water, a mixture comprising a bisimide of the formula, ##STR29## and phthalic anhydride or phthalic acid to produce a mixture comprising ##STR30## and an N-organo phthalimide of the formula, ##STR31## (2) effecting the separation of the N-organo phthalimide from the mixture of (1), where Q is a divalent radical selected from --O--, --S--, --R 2 --, --O--R 2 --O--, --S--R 2 --S-- and --OR 2 XR 2 O--, X is selected from --O--, --S--, ##STR32## and y is equal to 0 to 5 inclusive, R 2 is selected from C.sub.(6-13) divalent aromatic organic radicals and C.sub.(1-8) alkylene radicals, and R 3 is selected from H and C.sub.(1-20) monovalent organic radicals.
Claim 7
Independent Claim
128 words
A method which comprises (1) heating at a temperature of at least 100° C. in the presence of water, a mixture comprising a bisimide of the formula, ##STR29## and phthalic anhydride or phthalic acid to produce a mixture comprising ##STR30## and an N-organo phthalimide of the formula, ##STR31## (2) effecting the separation of the N-organo phthalimide from the mixture of (1), where Q is a divalent radical selected from --O--, --S--, --R 2 --, --O--R 2 --O--, --S--R 2 --S-- and --OR 2 XR 2 O--, X is selected from --O--, --S--, ##STR32## and y is equal to 0 to 5 inclusive, R 2 is selected from C.sub.(6-13) divalent aromatic organic radicals and C.sub.(1-8) alkylene radicals, and R 3 is selected from H and C.sub.(1-20) monovalent organic radicals.
Claim 8
Dependent Claim
17 words
A method in accordance with claim 5, where separation of the resulting N-organophthalimide is achieved by distillation.
Claim 9
Dependent Claim
16 words
A method in accordance with claim 5, where Q is ##STR33## and R 3 is methyl.
Claim 10
Dependent Claim
20 words
A method in accordance with claim 5, where the mixture is heated in the presence of a ferric chloride catalyst.
Claim 11
Dependent Claim
15 words
A method in accordance with claim 5, where the mixture is heated under sealed conditions.
Claim 12
Dependent Claim
36 words
A method in accordance with claim 5, where the mixture is distilled after the mixture has been restored to ambient conditions to effect the separation of N-organo phthalimide from a reaction mixture comprising anhydride and ##STR34##
Claim 13
Dependent Claim
19 words
A method in accordance with claim 5, where the separation of the N-alkyl phthalimide is achieved by solvent extraction.
References Cited (Backward Citations)
US4005134A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-12-04 | 1982-06-05 | 1982-12-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-04 | 1986-06-05 | 1986-12-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-04 | 1990-06-05 | 1990-12-05 | $7700.00 | Window Closed / Lapsed |