Processes for manufacturing aromatic carboxylic acids

Patent metadata

Field	Value
Publication number	US-10843995-B2
Application number	US-201816627214-A
Country	US
Kind code	B2
Filing date	Jun 19, 2018
Priority date	Jun 29, 2017
Publication date	Nov 24, 2020
Grant date	Nov 24, 2020

Abstract

A process for manufacturing a carboxylic acid is provided, in one aspect, the process comprises oxidizing a feedstock comprising a substituted aromatic hydrocarbon to form a liquid-phase aromatic carboxylic acid; crystallizing at least a portion of the liquid-phase aromatic carboxylic acid in the presence of oxygen and an oxidation catalyst in a first crystallizer to form solid aromatic carboxylic acid, under reaction conditions suitable to oxidize unreacted feedstock to form additional aromatic carboxylic acid; and crystallizing at least a portion of the first crystallization effluent in the presence of oxygen and an oxidation catalyst in a second crystallizer to form additional solid aromatic carboxylic acid, under reaction conditions suitable to oxidize unreacted feedstock to form additional aromatic carboxylic acid, wherein the oxygen is present in a gaseous phase inside the second crystallizer in an amount of no more than 11% by volume on a dry basis.

First claim

The invention claimed is:

1. A process for manufacturing an aromatic carboxylic acid, comprising:
oxidizing a feedstock comprising a substituted aromatic hydrocarbon in a reaction zone in the presence of an oxidation catalyst and a solvent to form a reaction mixture comprising a liquid-phase aromatic carboxylic acid, the reaction zone providing a reaction zone effluent comprising the liquid-phase aromatic carboxylic acid;
crystallizing at least a portion of the liquid-phase aromatic carboxylic acid of the reaction zone effluent in the presence of oxygen and an oxidation catalyst in a first crystallizer of a crystallization zone to form solid aromatic carboxylic acid, and oxidizing unreacted and/or partially oxidized feedstock in the reaction zone effluent to form additional aromatic carboxylic acid, the first crystallizer providing a first crystallization effluent;
crystallizing at least a portion of the first crystallization effluent in the presence of oxygen and an oxidation catalyst in a second crystallizer of the crystallization zone to form additional solid aromatic carboxylic acid, and oxidizing unreacted and/or partially oxidized feedstock in the first crystallizer effluent to form additional aromatic carboxylic acid, the second crystallizer providing a second crystallization effluent, wherein a gaseous phase inside the second crystallizer comprises the oxygen in an amount of no more than 11% by volume of the gaseous phase on a dry basis; and feeding an oxygen-containing feed stream to the second crystallizer, the oxygen being present in the oxygen-containing feed stream in an amount of no more than 11% by volume of the feed stream on a dry basis.

2. The process of claim 1 , wherein the oxygen is present in the oxygen-containing feed stream in an amount of no more than 5% by volume of the feed stream on a dry basis.

3. The process of claim 1 , wherein the oxygen is present in the oxygen-containing feed stream in an amount of no more than 2% by volume of the feed stream on a dry basis.

4. The process of claim 1 , further comprising
recovering a reaction off-gas from the reaction zone; and
treating at least a portion of the recovered reaction off-gas in an off-gas treatment zone; wherein at least a portion of the oxygen-containing feed stream is formed in the off-gas treatment zone.

5. The process of claim 4 , wherein treating at least a portion of the recovered reaction off-gas comprises:
separating the reaction off-gas to form a water-rich stream and a monocarboxylic acid solvent-rich stream; and
separating at least a portion of the water-rich stream to form a gas-phase component comprising oxygen, and a liquid-phase component; and
wherein at least a portion of the oxygen of the oxygen-containing feed stream comprises at least a portion of the gas-phase component.

6. The process of claim 1 , wherein the oxidation catalyst in the reaction zone comprises bromine, and wherein the process further comprises scrubbing the gas-phase component to remove bromine, the oxygen of the oxygen-containing feed stream comprising at least a portion of the gas-phase component remaining after said scrubbing.

7. The process of claim 1 , wherein a flue gas is recovered from the first crystallizer through a vent, and at least a portion of the oxygen of the oxygen-containing feed stream comprises at least a portion of the flue gas of the first crystallizer.

8. The process of claim 1 , further comprising feeding a hydrogen peroxide-containing feed stream to the second crystallizer.

9. The process of claim 1 , further comprising crystallizing at least a portion of the second crystallization effluent in a third crystallizer of the crystallization zone to form a third crystallization effluent comprising solid aromatic carboxylic acid.

10. The process of claim 1 , further comprising separating at least a portion of an effluent of a last crystallizer of the crystallization zone to form an aromatic carboxylic acid-rich stream and a solvent-rich stream.

11. The process of claim 10 , further comprising purifying at least a portion of the aromatic carboxylic acid-rich stream in a purification zone comprising a hydrogenation catalyst to form a purification effluent comprising purified aromatic carboxylic acid.

12. The process of claim 1 , wherein:
the aromatic carboxylic acid comprises terephthalic acid; and
the substituted aromatic hydrocarbon of the feedstock comprises para-xylene.

13. The process of claim 1 , wherein the feedstock comprises at least 99% para-xylene.

14. The process of claim 13 , wherein the second crystallization effluent comprises 4-carboxybenzaldehyde in an amount of no more than 4500 ppm on a solid basis, and comprises p-toluic acid in an amount of no more than 750 ppm on a solid basis.

15. The process of claim 1 , wherein the gaseous phase inside the second crystallizer comprises the oxygen in an amount of at least 0.3% by volume of the gaseous phase on a dry basis.

Assignees

• Bp Corp North America Inc

Inventors

• Bitsch-Larsen Anders

Classifications

• C07C51/265 Primary

  having alkyl side chains which are oxidised to carboxyl groups · CPC title

• C07C51/43

  by change of the physical state, e.g. crystallisation · CPC title