IP Library Granted Patent US 8,637,699
Granted Patent B2
US 8,637,699 · App. 13/088,145 · Granted Jan 28, 2014

Process for the manufacture of acetic acid

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Quick Facts
Patent No.
US 8,637,699
App. No.
13/088,145
Granted
Jan 28, 2014
Kind
B2
Abstract

The disclosure relates to a process in which methanol is carbonylated in a reaction zone in the presence of a catalyst to obtain a reaction mixture (A) comprising acetic acid, hydrogen iodide, methyl iodide, water and the catalyst. At least a part of the reaction mixture (A) is separated in a flash zone to obtain a vapor stream (B V ) which comprises acetic acid, hydrogen iodide, methyl iodide and water. The vapor stream (B V ) is withdrawn from the flash zone, and the withdrawn vapor stream is then reacted with at least one alkylimidazole to obtain a composition (C) from which acetic acid is separated. By reacting the vapor stream (B V ) with the alkylimidazole at least parts of the hydrogen iodide and methyl iodide contained in (B V ) are bound in form of iodide salts which significantly facilitates the separation of crude acetic acid from the vapor stream (B V ) and the further purification of the crude acetic acid.

Claims (24)

1. A process for producing acetic acid which comprises:

(a) carbonylating methanol in the presence of a catalyst in a reaction zone to obtain a reaction mixture (A) comprising acetic acid, hydrogen iodide, methyl iodide, water and the catalyst;

(b) separating at least a part of the reaction mixture (A) in a flash zone to obtain a liquid stream (B L ) comprising the catalyst, and a vapor stream (B V ) comprising acetic acid, hydrogen iodide, methyl iodide and water, and withdrawing the vapor stream (B V ) from the flash zone;

(c) reacting the withdrawn vapor stream (B V ) with at least one alkylimidazole to obtain a composition (C); and

(d) separating the acetic acid from the composition (C).

2. The process of claim 1 , wherein step (d) comprises

(d 1 ) fractioning the composition (C) in a fractioning zone to obtain a product stream (D P ) comprising the acetic acid and a liquid stream (D L ) comprising water and at least one iodide salt formed by reacting the alkylimidazole with hydrogen iodide or with methyl iodide.

3. The process of claim 2 , wherein the vapor stream (B V ) and the at least one alkylimidazole are reacted in the fractioning zone.

4. The process of claim 2 , wherein the liquid stream (D L ) is recycled to the reaction zone.

5. The process of claim 4 , wherein the liquid stream (D L ) is recycled to the reaction zone by firstly introducing (D L ) into the flash zone to obtain a combination of the liquid streams (D L ) and (B L ), and subsequently recycling at least a part of the combination of (D L ) and (B L ) to the reaction zone.

6. The process of claim 4 , wherein the at least one alkylimidazole is employed in step (c) in an amount sufficient to establish a steady state concentration of from about 2 to about 20% by weight of the iodide salt in the reaction mixture (A).

7. The process of claim 1 , wherein the alkylimidazole is a compound of formula (I)

wherein x is 1, 2 or 3, and each R independently is C 1 -C 6 -alkyl.

8. The process of claim 7 , wherein the alkylimidazole is a compound of formula (Ia)

wherein

R 1 is hydrogen, or C 1 -C 6 -alkyl;

R 2 , R 3 , R 4 each independently, is hydrogen, or C 1 -C 2 -alkyl;

and wherein at least one of R 1 , R 2 , R 3 and R 4 is different from hydrogen, and at least one of R 1 , R 2 , R 3 and R 4 is hydrogen.

9. The process of claim 7 , wherein the alkylimidazole is 1-methylimidazole, 1-ethylimidazole, 1-propylimidazole, 1-isopropylimidazole, 1-(1-butyl)imidazole, 1-(2-butyl)imidazole, 1-isobutylimidazole, 1-tert-butylimidazole, 3-methylimidazole, 3-ethylimidazole, 4-methylimidazole, 4-ethylimidazole, 1,4-dimethylimidazole, 1,4-diethylimidazole, 1-ethyl-4-methylimidazole, 4-ethyl-1-methylimidazole, 2-methyl-1-propylimidazole, 4-methyl-1-propylimidazole, 5-methyl-1-propylimidazole, 2,4-dimethyl-1-propylimidazole, 2,5-dimethyl-1-propylimidazole, 1-isopropyl-2-methylimidazole, 1-isopropyl-4-methylimidazole, 1-isopropyl-5-methylimidazole, 2,4-dimethyl-1-isopropylimidazole, 2,5-dimethyl-1-isopropylimidazole, 1-(1-butyl)-2-methylimidazole, 1-(1-butyl)-4-methylimidazole, 1-(1-butyl)-5-methylimidazole, 1-(1-butyl)-2,4-dimethylimidazole, 1-(1-butyl)-2,5-dimethylimidazole, 1-(2-butyl) -2-methylimidazole, 1-(2-butyl)-4-methylimidazole, 1-(2-butyl)-5-methylimidazole, 1-(2-butyl)-2,4-dimethylimidazole, 1-(2-butyl)-2,5-dimethylimidazole, 1-isobutyl-2-methylimidazole, 1-isobutyl-4-methylimidazole, 1-isobutyl-5-methylimidazole, 2,4-dimethyl -1-isobutylimidazole, 2,5-dimethyl-1-isobutylimidazole, 1-tert-butyl-2-methylimidazole, 1-tert-butyl-4-methylimidazole, 1-tert-butyl-5-methylimidazole, 1-tert -butyl-2,4-dimethylimidazole, or 1-tert-butyl-2,5-dimethylimidazole.

10. The process of claim 1 , wherein the catalyst is a rhodium catalyst.

11. The process of claim 1 , wherein the reaction mixture (A) comprises at least one catalyst stabilizer selected from the group consisting of phosphine oxides and iodides of a metal of Group 1 and 2 of the Periodic Table of the Elements.

12. The process of claim 11 , wherein the stabilizer is triphenylphosphine oxide and/or lithium iodide.

13. The process of claim 1 , wherein the reaction mixture (A) does not comprise a catalyst stabilizer selected from the group consisting of phosphine oxides and iodides of metals of Group 1 and 2 of the Periodic Table of the Elements.

14. The process of claim 1 , wherein the reaction mixture (A) comprises water in a concentration of from about 2% to about 10% by weight.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2014
From: LYONDELL CHEMICAL TECHNOLOGY, L.P.
To: LYONDELLBASELL ACETYLS, LLC
Reel/Frame 033182/0019 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 21, 2014
From: LYONDELL CHEMICAL COMPANY
To: LYONDELL CHEMICAL TECHNOLOGY, L.P.
Reel/Frame 032268/0384 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 18, 2011
From: HALLINAN, NOEL C.; SALISBURY, BRIAN; BRTKO, WAYNE JOSEPH
To: LYONDELL CHEMICAL COMPANY
Reel/Frame 026299/0050 →