Processes for producing an acetic acid product having low butyl acetate content

Patent metadata

Field	Value
Publication number	US-9540304-B2
Application number	US-201514874250-A
Country	US
Kind code	B2
Filing date	Oct 2, 2015
Priority date	Nov 14, 2014
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

Abstract

A process for producing an acetic acid product having low butyl acetate content via a carbonylation reaction. The carbonylation reaction is carried out at a temperature from 100 to 300° C., a hydrogen partial pressure from 0.3 to 2 atm, and a rhodium catalyst concentration from 100 to 3000 wppm, based on the weight of the reaction medium. The butyl acetate concentration in the acetic acid product may be controlled by removing acetaldehyde from a stream derived from the reaction medium and/or by adjusting at least one of reaction temperature, hydrogen partial pressure, and metal catalyst concentration.

First claim

We claim:

1. A process for producing an acetic acid product, comprising:
providing a reaction medium comprising acetic acid, methanol, methyl acetate, acetaldehyde, less than or equal to 4.1 wt. % water, a rhodium catalyst, methyl iodide and lithium acetate;
removing acetaldehyde from a stream derived from the reaction medium to form the acetic acid product; and
contacting the acetic acid product with a metal-exchanged ion exchange resin; and
maintaining a butyl acetate concentration in the acetic acid product of less than or equal to 10 wppm and maintaining an iodide concentration in the acetic acid product of less than or equal to 100 wppb wherein the process for producing the acetic acid product is carried out at a hydrogen pressure and wherein the butyl acetate concentration is further maintained by adjusting at least one of reaction temperature, hydrogen partial pressure, and rhodium catalyst concentration in the reaction medium and, wherein the hydrogen partial pressure is from 0.3 to 2 atm.

2. The process of claim 1 , wherein the hydrogen partial pressure is greater than or equal to 0.4 atm.

3. The process of claim 1 , wherein the acetic acid product comprises less than or equal to 250 wppm propionic acid.

4. The process of claim 1 , wherein the acetic acid product comprises a displaced metal selected from the group consisting of silver, mercury, palladium and rhodium, and the displaced metal in the acetic acid product is in an amount of less than or equal to 500 wppb, wherein the displaced metal is a metal used in the ion exchange resins.

5. The process of claim 1 , wherein the acetic acid product comprises a corrosion metal selected from the group consisting of nickel, iron, chromium, and molybdenum, and the corrosion metal in the acetic acid product is in an amount of less than or equal to 1000 wppb.

6. The process of claim 1 , wherein the acetic acid product comprises less than or equal to 50 wppb lithium.

7. The process of claim 1 , wherein the reaction medium comprises methyl acetate in an amount from 0.5 to 30 wt. %, a rhodium catalyst in an amount from 200 to 3000 wppm, lithium iodide in an amount from 1 to 25 wt. %, and methyl iodide in an amount from 1 to 25 wt. %.

8. The process of claim 1 , wherein the removing acetaldehyde comprises:
(a) separating at least a portion of the reaction medium to provide a vapor overhead stream comprising acetic acid and a liquid recycle;
(b) distilling the vapor overhead stream to yield a purified acetic acid product and a first overhead stream comprising methyl iodide, water, acetic acid, methyl acetate, and acetaldehyde;
(c) distilling at least a portion of the first overhead stream to form a second overhead stream and a liquid phase residuum, wherein the second overhead stream is enriched with acetaldehyde with respect to the at least a portion of the first overhead stream; and
(d) extracting the second overhead stream with water to obtain an aqueous acetaldehyde stream comprising acetaldehyde and a raffinate comprising methyl iodide.

9. The process of claim 8 , further comprising condensing and biphasically separating the first overhead stream to form a light liquid phase and a heavy liquid phase, wherein the at least a portion of the first overhead stream distilled in step (c) comprises the light liquid phase.

10. The process of claim 8 , further comprising condensing and biphasically separating the first overhead stream to form a light liquid phase and a heavy liquid phase, wherein the at least a portion of the first overhead stream distilled in step (c) comprises the heavy liquid phase.

11. A process for producing an acetic acid product, comprising:
reacting methanol with carbon monoxide in a reactor having a hydrogen partial pressure from 0.3 to 2 atm to yield a reaction medium comprising acetic acid, methanol, methyl acetate, less than or equal to 4.1 wt. % water, acetaldehyde, a rhodium catalyst, methyl iodide and lithium acetate;
removing acetaldehyde from a stream derived from the reaction medium to form the acetic acid product; and
contacting the acetic acid product with a metal-exchanged ion exchange resin; and
maintaining a butyl acetate concentration in the acetic acid product of less than or equal to 10 wppm and maintaining an iodide concentration in the acetic acid product of less than or equal to 100 wppb.

12. The process of claim 11 , wherein the butyl acetate concentration is further maintained by adjusting at least one of reaction temperature, hydrogen partial pressure, and rhodium catalyst concentration in the reaction medium.

13. The process of claim 12 , wherein the acetic acid product comprises less than or equal to 250 wppm propionic acid.

14. The process of claim 11 , wherein the acetic acid product comprises a displaced metal selected from the group consisting of silver, mercury, palladium and rhodium, and the displaced metal in the acetic acid product is in an amount of less than or equal to 500 wppb, wherein the displaced metal is a metal used in the ion exchange resins.

15. The process of claim 11 , wherein the reaction medium comprises methyl acetate in an amount from 0.5 to 30 wt. %, a rhodium catalyst in an amount from 200 to 3000 wppm, lithium iodide in an amount from 1 to 25 wt. %, and methyl iodide in an amount from 1 to 25 wt. %.

16. A process for producing an acetic acid product, comprising:
providing a reaction medium comprising acetic acid, methanol, methyl acetate, less than or equal to 4.1 wt. % water, acetaldehyde, a rhodium catalyst, methyl iodide and lithium acetate;
removing acetaldehyde from a stream derived from the reaction medium to form the acetic acid product, wherein the acetic acid product comprises a corrosion metal selected from the group consisting of nickel, iron, chromium, and molybdenum, and the corrosion metal in the acetic acid product is in an amount of less than or equal to 1000 wppb; and
contacting the acetic acid product with a metal-exchanged ion exchange resin; and
maintaining a butyl acetate concentration in the acetic acid product of less than or equal to 10 wppm and maintaining an iodide concentration in the acetic acid product of less than or equal to 100 wppb wherein the reaction is carried out at a hydrogen partial pressure from 0.3 to 2 atm.

17. The process of claim 16 , wherein the butyl acetate concentration is further maintained by adjusting at least one of reaction temperature, hydrogen partial pressure, and rhodium catalyst concentration in the reaction medium.

Assignees

• Celanese Int Corp

Inventors

• Liu Yaw-Hwa
• Scates Mark O

Classifications

• C07C51/12 Primary

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

• C07C51/44

  by distillation · CPC title

• C07C53/08

  Acetic acid (pyroligneous acid C10C; preparation of vinegar C12J) · CPC title