Process for preparing aminobenzoic acid or an aminobenzoic acid conversion product

Patent metadata

Field	Value
Publication number	US-10968466-B2
Application number	US-201716469746-A
Country	US
Kind code	B2
Filing date	Dec 18, 2017
Priority date	Dec 20, 2016
Publication date	Apr 6, 2021
Grant date	Apr 6, 2021

Abstract

The present invention relates to a process for preparing aminobenzoic acid or an aminobenzoic acid conversion product, comprising the steps of: (I) providing an aqueous solution of aminobenzoic acid using a fermentation process; (II) adsorbing aminobenzoic acid; (III) desorbing aminobenzoic acid at a pH in the range from −0.8 to 3.0, preferably −0.5 to 3.0, more preferably 0.1 to 3.0, very preferably 0.5 to 2.5, very exceptionally preferably 1.0 to 2.0; (IV) obtaining the aminobenzoic acid from the desorbate obtained in step (III); (V) optionally further converting the aminobenzoic acid obtained in step (IV) to an aminobenzoic acid conversion product.

First claim

The invention claimed is:

1. A process for preparing aminobenzoic acid or an aminobenzoic acid conversion product, comprising:
(I) providing an aqueous solution of aminobenzoic acid using a fermentation process, wherein step (I) comprises:
(I-1) fermenting a raw material comprising:
a fermentable carbon-containing compound,

and
a nitrogen-containing compound,

in a fermentation reactor using microorganisms to obtain a fermentation broth; optionally followed by
(I-2) a work-up comprising the following work-up steps:
(α) removing the microorganism from the fermentation broth obtained in step (I-1) and/or
(β) decolorizing the fermentation broth obtained in step (I-1) or, when carrying out step (α), the microorganism-depleted fermentation broth obtained in step (α);
wherein step (I) further comprises:
(I-3) introducing the fermentation broth obtained in step (I-1) or, if carried out, in step (I-2) into a reactor in which aminobenzoic acid is precipitated by mixing with an acidic aqueous solution, the pH of the resulting mixture being adjusted to a value in the range from 3.0 to 4.7; and
(I-4) removing the aminobenzoic acid precipitated in step (I-3) to obtain an aminobenzoic acid-depleted mother liquor;
(II) treating the aqueous solution of aminobenzoic acid, as provided in step (I), which is the aminobenzoic acid-depleted mother liquor obtained in step (I-4), with an adsorbent to load the adsorbent with aminobenzoic acid and to obtain an aminobenzoic acid-depleted material;
(III) treating the aminobenzoic acid-loaded adsorbent from step (II) with an aqueous desorbent of a pH in the range from −0.8 to 3.0 to obtain an aminobenzoic acid-enriched desorbate and an aminobenzoic acid-depleted adsorbent;
(IV) obtaining the aminobenzoic acid from the desorbate obtained in step (III) by using the aminobenzoic acid-enriched desorbate as a constituent of the acidic aqueous solution used in step (I-3); and
(V) optionally further reacting the aminobenzoic acid obtained in step (IV) to give an aminobenzoic acid conversion product.

2. The process of claim 1 , in which step (I) further comprises:
(I-5) purifying the aminobenzoic acid removed in step (I-4).

3. The process of claim 1 , in which the aminobenzoic acid-enriched desorbate obtained in step (III) is used as a constituent of the acidic aqueous solution used in step (I-3), together with an acid selected from the group consisting of hydrochloric acid, sulfuric acid, phosphoric acid and mixtures thereof.

4. The process of claim 1 , in which the pH of the aqueous desorbent is kept constant while step (III) is carried out.

5. The process of claim 1 , in which the pH of the aqueous desorbent passes through a gradient while step (III) is carried out.

6. The process of claim 1 , in which an aqueous solution of the ortho-isomer of aminobenzoate and/or of aminobenzoic acid is provided in step (I).

7. The process of claim 1 , in which the microorganisms used in step (I-1) comprise a species selected from the group consisting of Escherichia coli, Pseudomonas putida, Corynebacterium glutamicum, Ashbya gossypii, Pichia pastoris, Hansenula polymorpha, Yarrowia lipolytica, Zygosaccharomyces bailii and Saccharomyces cerevisiae.

8. The process of claim 1 , comprising step (V), step (V) comprising one of the following reactions:
(V-1) decarboxylating the aminobenzoic acid to give aniline;
(V-2) decarboxylating the aminobenzoic acid to give aniline, followed by acid-catalyzed reaction of the aniline with formaldehyde to form di- and polyamines of the diphenylmethane series;
(V-3) decarboxylating the aminobenzoic acid to give aniline, followed by acid-catalyzed reaction of the aniline with formaldehyde to form di- and polyamines of the diphenylmethane series, followed by reaction with phosgene to form di- and polyisocyanates of the diphenylmethane series;
(V-4) decarboxylating the aminobenzoic acid to give aniline, followed by reaction of the aniline to give an azo compound;
(V-5) reacting the aminobenzoic acid to give an amide; or
(V-6) reacting the aminobenzoic acid to give conductive polymers.

9. The process of claim 8 , comprising step (V-6), wherein the conductive polymer is polyanthranilic acid.

Assignees

• Covestro Deutschland Ag

Inventors

• Jäger Gernot
• Görtz Ivonne
• Lolli Giulio
• Moussa Amgad Salah
• Hamedinger Thomas

Classifications

• C07C209/78

  from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines · CPC title

• C07C245/02

  Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides · CPC title

• C07C227/40 Primary

  Separation; Purification · CPC title

• C12P13/005 Primary

  Amino acids other than alpha- or beta amino acids, e.g. gamma amino acids · CPC title

• C07C231/02

  from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines · CPC title