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Process for the production of cyclic carboxylic acid imides

Assignee: Akzo NV
•
Filing: 1972-09-08
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Granted: 1976-06-29
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Expires: 1992-09-08
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Abstract

Abstract In a process for reacting an aromatic or hydroaromatic alicyclic or heterocyclic dicarboxylic acid or its anhydride with an aliphatic or aromatic alicyclic or heterocyclic mono- or di-amine to produce an N-substituted dicarboxylic acid imide with a splitting off of water, the improvement of carrying out the reaction in a liquid solvent mixture consisting essentially of a non-polar organic solvent and a strongly polar organic solvent which together form a ternary azeotrope with water at reaction temperatures between about 40 DEG C. and 160 DEG C. The imide products are generally known for use as intermediates and final products in a number of industries.

Inventors

  • 👤 Anton Toth
  • 👤 Gerhard Meyer

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 04:40
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07D471/00; C07D471/02; C07D471/04

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 162 words
In a process for the production of an N-substituted cyclic carboxylic acid imide by reacting in a solvent at an elevated temperature between about 40°C. and 160°C. A. an ortho-dicarboxylic acid or its anhydride of the formula ##EQU3## wherein A is a divalent radical, selected from amongst phenylene, or phenylene substituted by halogen, nitro, acetamido, lower alkyl, lower alkoxy; tetrahydrophenylene or pyridylene: with B. a mono- or di-amine, selected from amongst alkylamine, alkylenediamine, N-alkyl substituted alkylenediamine of up to 18 carbon atoms; phenyl mono- or diamines which may be substituted by halo, nitro, hydroxy, mercapto, lower alkyl, lower alkoxy, mercaptomethyl, mercaptoethyl, methyl or ethyl carboxylate, sodium or potassium sulfonate, or 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyloxide, 4,4'-diamino diphenylsulfone, 1,5-diaminoanthraquinone, aminopyrazine, 2-aminopyridine, 2-aminothiazole, 2-amino-4-methylpyridine, 6-amino-3-methylpyridine, 2-amino-4-methylpyrimidine, ammeline, 2,6-diaminopyridine, 3-aminopyridine or 4-aminopyridine the improvement of carrying out said reaction in a liquid solvent mixture consisting essentially of a non-polar organic solvent and a strongly polar organic solvent which form a ternary azeotrope with water at the reaction temperature.
Claim 2
Dependent Claim 162 words
In a process for the production of an N-substituted cyclic carboxylic acid imide by reacting in a solvent at an elevated temperature between about 40°C. and 160°C. A. an ortho-dicarboxylic acid or its anhydride of the formula ##EQU3## wherein A is a divalent radical, selected from amongst phenylene, or phenylene substituted by halogen, nitro, acetamido, lower alkyl, lower alkoxy; tetrahydrophenylene or pyridylene: with B. a mono- or di-amine, selected from amongst alkylamine, alkylenediamine, N-alkyl substituted alkylenediamine of up to 18 carbon atoms; phenyl mono- or diamines which may be substituted by halo, nitro, hydroxy, mercapto, lower alkyl, lower alkoxy, mercaptomethyl, mercaptoethyl, methyl or ethyl carboxylate, sodium or potassium sulfonate, or 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyloxide, 4,4'-diamino diphenylsulfone, 1,5-diaminoanthraquinone, aminopyrazine, 2-aminopyridine, 2-aminothiazole, 2-amino-4-methylpyridine, 6-amino-3-methylpyridine, 2-amino-4-methylpyrimidine, ammeline, 2,6-diaminopyridine, 3-aminopyridine or 4-aminopyridine the improvement of carrying out said reaction in a liquid solvent mixture consisting essentially of a non-polar organic solvent and a strongly polar organic solvent which form a ternary azeotrope with water at the reaction temperature.
Claim 3
Dependent Claim 33 words
A process as claimed in claim 1 wherein said liquid solvent mixture consists essentially of xylene and a polar solvent selected from the class consisting of dimethylformamide, dimethylacetamide, dimethylsulfoxide, pyridine, picoline and lutidine.
Claim 4
Dependent Claim 29 words
A process as claimed in claim 1 wherein said liquid solvent mixture consists essentially of toluene and a polar solvent selected from the class consisting of pyridine and picoline.
Claim 5
Dependent Claim 18 words
A process as claimed in claim 1 wherein said liquid solvent mixture consists essentially of benzene and acetonitrile.
Claim 6
Dependent Claim 34 words
A process as claimed in claim 1 wherein the liquid solvent mixture consists essentially of 80 to 90% by volume of the non-polar solvent and 20 to 10% by volume of the polar solvent.
Claim 7
Dependent Claim 19 words
A process as claimed in claim 1 wherein the reaction is carried out at temperatures of 90° to 160°C.
Claim 8
Dependent Claim 86 words
A process as claimed in claim 1 wherein the amine as one reactant is dissolved in the polar solvent, the dicarboxylic acid or its anhydride as the other reactant is dissolved in the non-polar solvent, the two resulting solutions are then joined and the resulting mixture heated to the reaction temperature, water resulting from the reaction is azeotropically distilled with a portion of the solvent, the distillate is then cooled and the aqueous phase is separated therefrom while recycling the organic phase to the reaction mixture.
Claim 9
Dependent Claim 38 words
A process as claimed in claim 7 wherein the reaction mixture is heated to its boiling point during the course of the reaction in order to continuously azeotropically distill off the water with a portion of the solvent.
Claim 10
Dependent Claim 36 words
A process as claimed in claim 7 wherein the non-polar solvent containing the dicarboxylic acid or anhydride reactant is preheated to a temperature of about 40° to 90°C. before being joined with the amine-containing polar solvent.
Claim 11
Dependent Claim 30 words
A process as claimed in claim 9 wherein the reaction is carried out at a temperature of from about 90° to 160°C. after joining the two reactants with their solvents.

References Cited (Backward Citations)

US3072725A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-06-29 1979-12-29 1980-06-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-06-29 1983-12-29 1984-06-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-06-29 1987-12-29 1988-06-29 $7700.00 Window Closed / Lapsed

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