Method for producing acetic acid

Patent metadata

Field	Value
Publication number	US-10428005-B2
Application number	US-201715542621-A
Country	US
Kind code	B2
Filing date	May 25, 2017
Priority date	Mar 22, 2017
Publication date	Oct 1, 2019
Grant date	Oct 1, 2019

Abstract

It is intended to provide a method capable of industrially and efficiently producing acetic acid having a good potassium permanganate test value without a large cost.
The method includes a step of distilling an aqueous phase and/or an organic phase of a column top condensate of a lower boiling point component removal column by a crotonaldehyde removal column; and the reflux ratio of the lower boiling point component removal column is not less than 2 (when the aqueous phase is refluxed), and the crotonaldehyde removal column is operated such that at least one of the following conditions (i) to (iii) is satisfied:
(i) the reflux ratio of the distillation column is not less than 0.01; (ii) the ratio of the crotonaldehyde concentration (ppm by mass) in a distillate liquid of the distillation column to the crotonaldehyde concentration (ppm by mass) in a charging mixture (former/latter) is less than 1; and (iii) the ratio of the crotonaldehyde concentration (ppm by mass) in a bottom fraction of the distillation column to the crotonaldehyde concentration (ppm by mass) in a charging mixture (former/latter) is more than 1.

First claim

The invention claimed is:

1. A method for producing acetic acid, comprising:
carbonylating methanol with carbon monoxide in the presence of a catalyst system containing a metal catalyst and methyl iodide, as well as acetic acid, methyl acetate, and water in a reaction vessel to produce acetic acid;
evaporating a reaction mixture obtained by the carbonylation to separate into a vapor stream and a residual liquid stream in an evaporator;
removing a lower boiling point component to separate the vapor stream by a first distillation column into a first overhead stream rich in at least one lower boiling point component selected from methyl iodide and acetaldehyde, and a first acetic acid stream rich in acetic acid, and condensing and separating the first overhead stream to obtain an aqueous phase and an organic phase;
dehydrating the first acetic acid stream by a second distillation column to separate into a second overhead stream rich in water and a second acetic acid stream more enriched with acetic acid than the first acetic acid stream;
recycling at least a portion of the aqueous phase and/or organic phase in the first overhead stream to a reaction vessel; and
separating and removing crotonaldehyde by treating at least another portion of the aqueous phase and/or organic phase by a distillation column;
wherein a potassium permanganate test value of the second acetic acid stream is more than 50 minutes; and
wherein with respect to a reflux ratio of the first distillation column, when only the aqueous phase is refluxed to the first distillation column, a reflux ratio of the aqueous phase is not less than 2, when only the organic phase is refluxed, a reflux ratio of the organic phase is not less than 1, and when both the aqueous phase and the organic phase are refluxed, a total reflux ratio of the aqueous phase and the organic phase is not less than 1.5; and when removing the crotonaldehyde, the distillation column is operated such that all of the following conditions (i) to (iii) are satisfied:
(i) the reflux ratio of the distillation column is not less than 0.01;
(ii) a ratio of a crotonaldehyde concentration in ppm by mass in a distillate liquid of the distillation column to a crotonaldehyde concentration in ppm by mass in a charging mixture, former/latter, is less than 1; and
(iii) a ratio of a crotonaldehyde concentration in ppm by mass in a bottom fraction of the distillation column to the crotonaldehyde concentration in ppm by mass in the charging mixture, former/latter, is more than 1.

2. The method for producing acetic acid according to claim 1 , wherein a reflux ratio of the second distillation column is not less than 0.3.

3. The method for producing acetic acid according to claim 1 , wherein in the second acetic acid stream a crotonaldehyde concentration is not more than 0.98 ppm by mass, and/or a 2-ethyl crotonaldehyde concentration is not more than 1.0 ppm by mass, and/or a butyl acetate concentration is not more than 15 ppm by mass.

4. The method for producing acetic acid according to claim 1 , wherein the catalyst system further contains an ionic iodide.

5. The method for producing acetic acid according to claim 1 , further comprising separating and removing acetaldehyde by distilling at least a portion of the aqueous phase and/or the organic phase obtained by condensing the first overhead stream.

6. The method for producing acetic acid according to claim 5 , wherein at least a portion of a residual liquid after separating and removing acetaldehyde from at least a portion of the aqueous phase and/or the organic phase is recycled to the reaction vessel.

7. The method for producing acetic acid according to claim 1 , wherein in the vapor stream fed to the first distillation column a crotonaldehyde concentration is 0 to 5.0 ppm by mass, and/or a 2-ethyl crotonaldehyde concentration is 0 to 3.0 ppm by mass, and/or a butyl acetate concentration is 0.1 to 13.0 ppm by mass.

8. The method for producing acetic acid according to claim 1 , wherein in the first acetic acid stream a crotonaldehyde concentration is not more than 1.3 ppm by mass, and/or a 2-ethyl crotonaldehyde concentration is not more than 1.0 ppm by mass, and/or a butyl acetate concentration is not more than 15 ppm by mass.

9. The method for producing acetic acid according to claim 1 , wherein a crotonaldehyde concentration in a distillation column charging mixture when removing the crotonaldehyde is 0.01 to 50 ppm by mass.

10. The method for producing acetic acid according to claim 1 , wherein distillation is performed by a batch process when removing the crotonaldehyde.

11. The method for producing acetic acid according to claim 1 , wherein a throughput of the distillation column for removing the crotonaldehyde is 0.0001 to 50 parts by mass with respect to an amount of the vapor stream fed to the first distillation column of 100 parts by mass.

12. The method for producing acetic acid according to claim 1 , wherein in the second acetic acid stream a crotonaldehyde concentration is not more than 0.80 ppm by mass, and/or a 2-ethyl crotonaldehyde concentration is not more than 0.50 ppm by mass, and/or a butyl acetate concentration is not more than 10 ppm by mass.

13. The method for producing acetic acid according to claim 1 , wherein in the vapor stream fed to the first distillation column a crotonaldehyde concentration is 0.01 to 4.0 ppm by mass, and/or a 2-ethyl crotonaldehyde concentration is 0.01 to 2.5 ppm by mass, and/or a butyl acetate concentration is 0.2 to 12.0 ppm by mass.

14. The method for producing acetic acid according to claim 1 , wherein in the first acetic acid stream a crotonaldehyde concentration is not more than 1.0 ppm by mass, and/or a 2-ethyl crotonaldehyde concentration is not more than 0.50 ppm by mass, and/or a butyl acetate concentration is not more than 10 ppm by mass.

15. The method for producing acetic acid according to claim 1 , wherein a crotonaldehyde concentration in a distillation column charging mixture when removing the crotonaldehyde is 0.3 to 30 ppm by mass.

16. The method for producing acetic acid according to claim 1 , wherein a throughput of the distillation column for removing the crotonaldehyde is 0.001 to 30 parts by mass.

17. The method for producing acetic acid according to claim 1 , wherein with respect to a reflux ratio of the first distillation column, when only the aqueous phase is refluxed to the first distillation column, a reflux ratio of the aqueous phase is not less than 3, when only the organic phase is refluxed, a reflux ratio of the organic phase is not less than 1.5, and when both the aqueous phase and the organic phase are refluxed, a total reflux ratio of the aqueous phase and the organic phase is not less than 2.3.

18. The method for producing acetic acid according to claim 1 , wherein in (ii) above, the ratio of the crotonaldehyde concentration in ppm by mass in the distillate liquid of the distillation column to the crotonaldehyde concentration in ppm by mass in the charging mixture, former/latter, is not more than 0.95, and in (iii) above, the ratio of the crotonaldehyde concentration in ppm by mass in the bottom fraction of the distillation column to the crotonaldehyde concentration in ppm by mass in the charging mixture, former/latter, is not less than 1.2.

19. The method for producing acetic acid according to claim 1 , wherein an acetaldehyde concentration in a reaction mixture liquid in the reaction vessel is not more than 500 ppm by mass, and/or a crotonaldehyde concentration in a reaction mixture liquid in th

Assignees

• Daicel Corp

Inventors

• Shimizu Masahiko

Classifications

• C07C51/445

  by steam distillation · CPC title

• B01D3/009

  in combination with chemical reactions · CPC title

• C07C51/12 Primary

  on an oxygen-containing group in organic compounds, e.g. alcohols · CPC title

• C07C51/44

  by distillation · CPC title

• B01D3/143

  by two or more of a fractionation, separation or rectification step · CPC title