Process for oxidation of alkyl aromatic compound to aromatic carboxylic acid

Patent metadata

Field	Value
Publication number	US-9932287-B2
Application number	US-201515117352-A
Country	US
Kind code	B2
Filing date	Feb 19, 2015
Priority date	Feb 20, 2014
Publication date	Apr 3, 2018
Grant date	Apr 3, 2018

Abstract

The present disclosure provides a process for oxidation of p-xylene to terephthalic acid. Recovery of fluid medium and valuable chemicals in carried out using p-xylene as fluid medium which is also the starting material. The recovered stream containing p-xylene, acetic acid and other valuable chemicals is recycled to the oxidation step. The process disclosed in the present disclosure is energy efficient and cost effective.

First claim

The invention claimed is:

1. A process for the oxidation of p-xylene to terephthalic acid comprising the following steps:
a) oxidizing p-xylene using at least one oxidizing agent in the presence of at least one metal salt as a catalyst and at least one promoter in at least one aliphatic carboxylic acid as a fluid medium to obtain a reaction mixture comprising terephthalic acid, oxidation intermediates of terephthalic acid, trimellitic acid, at least one metal salt, the promoter, the aliphatic carboxylic acid and water; wherein the oxidation intermediates of terephthalic acid comprise at least one compound selected from the group consisting of p-tolualdehyde, p-toluic acid and 4-carboxy benzaldehyde;
b) separating a partial amount of the terephthalic acid from the reaction mixture by crystallization and filtration to obtain crude terephthalic acid and a mother liquor; wherein the mother liquor comprises trimellitic acid, the promoter, at least one metal salt, water and the aliphatic carboxylic acid;
c) dividing the mother liquor into a recycle stream and a purge stream; wherein the ratio of the amount of the recycle stream and the purge stream is in the range from 19:1 to 4:1; and recycling the recycle stream to step (a);
d) extracting p-xylene soluble chemicals from the purge stream by adding p-xylene to the purge stream and mixing at a predetermined temperature to obtain a biphasic mixture, which after separation, provides an organic stream and an aqueous stream; wherein the organic stream comprises p-xylene, the aliphatic carboxylic acid and the oxidation intermediates of terephthalic acid, and the aqueous stream comprises the aliphatic carboxylic acid, trimellitic acid, the promoter and at least one metal salt;
e) recycling the organic stream comprising p-xylene, the aliphatic carboxylic acid and the oxidation intermediates of terephthalic acid to step (a); and
f) recovering at least one metal salt from the aqueous stream and recycling the recovered metal salt to step (a);
wherein, the concentration of trimellitic acid in the reaction mixture is below 2000 ppm.

2. The process as claimed in claim 1 , wherein the aliphatic carboxylic acid is acetic acid.

3. The process as claimed in claim 1 , wherein the oxidizing agent is selected from the group consisting of air and oxygen.

4. The process as claimed in claim 1 , wherein the metal salt is selected from the group consisting acetate and bromide salts of Cobalt, Manganese, Chromium, Copper, Nickel, Vanadium, Iron, Molybdenum, Tin, Cerium, Zirconium, Cesium and Titanium.

5. The process as claimed in claim 1 , wherein the metal salt is selected from the group consisting of Cobalt acetate, Manganese acetate, Cobalt bromide and Manganese bromide.

6. The process as claimed in claim 1 , wherein promoter is selected from the group consisting of organic bromide compounds and ionic liquid containing bromide as anion.

7. The process as claimed in claim 1 , wherein the promoter is an ionic liquid containing bromide as anion selected from the group consisting of trihexyltetradecylphosphonium bromide, tetra-n-octylphosphonium bromide, 1-butyl-3-methylimidazolium bromide, 1-hexyl-3-methylimidazolium bromide, 1-butyl-2,3-dimethylimidazolium bromide, 1-methyl-3-octylimidazolium bromide, 1-decyl-3-methylimidazolium bromide, 1-hexadecyl-3-methylimidazolium bromide, 1-methyl-3-octadecylimidazolium bromide, 1,2-dimethyl-3-propylimidazolium bromide, 1-ethyl-3-methylimidazolium bromide, 1-(3-hydroxypropyl)-3-methylimidazolium bromide, N-tributyl-N-methylammonium bromide, N-trimethyl-N-butylammonium bromide, N,N-diethyl-N-methyl-N-propylammonium bromide, N,N-dimethyl-N-ethyl-N-benzyl bromide, N,N-dimethyl-N-ethyl-N-phenylethylammonium bromide, N-ethyl-N-methylpiperidinium bromide, N-propyl-N-methylpiperidinium bromide, N-propyl-N-methylpyrrolidinium bromide, 1-methyl-1-pentylpyrrolidinium bromide, N-butyl-N-methylpyrrolidinium bromide, N-butyl-N-hexylpyrrolidinium bromide and N-butyl-3-methylpyridinium bromide.

8. The process as claimed in claim 1 , wherein the ratio of the amount of the purge stream and the amount of p-xylene in the process step (d) ranges from 1:5 to 2:1.

9. The process as claimed in claim 1 , wherein the predetermined temperature of the process step (d) ranges from 20 to 140° C.

10. The process as claimed in claim 1 , wherein optionally the step of extracting is carried out using multiple extraction technique.

11. The process as claimed in claim 1 , wherein optionally the step of extracting is carried out using concurrent extraction technique, countercurrent extraction technique and combination thereof.

12. The process as claimed in claim 1 , wherein optionally the step of extracting is carried out in at least one reactor selected from the group consisting of continuous stirred flow reactor, static mixture reactor, plug flow reactor, packed bed extraction column and multiple compartment agitated extraction column.

13. The process as claimed in claim 1 , wherein the amount of the aliphatic carboxylic acid extracted in the organic stream is greater than 20% of the total amount in the purge stream.

14. The process as claimed in claim 1 , wherein the amount of trimellitic acid extracted in the organic stream is less than 35% of the total amount in purge stream.

15. The process as claimed in claim 1 , wherein the amount of p-toluic acid extracted in the organic stream is greater than 50% of the total amount in the purge stream and the amount of 4-carboxybenzaldehyde extracted in the organic stream is greater than 50% of the total amount in the purge stream.

Assignees

• Reliance Industries Ltd

Inventors

• Shankaranarayanan Vivek
• Jain Suresh Shantilal
• Aduri Pavankumar
• Terdalkar Rajesh Ratnakar
• Patil Nitin Haribhau
• Uppara Parasuveera

Classifications

• C07C51/48

  by liquid-liquid treatment · CPC title

• C07C51/265 Primary

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

• C07C63/26

  1,4 - Benzenedicarboxylic acid · CPC title

• C07C51/43

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