Preparation of acetic acid
View Patent ↗A method for removing aldehyde impurities from an acetic acid stream is disclosed. The method comprises reacting an acetic acid stream containing aldehyde impurities with a hydroxyl compound to form corresponding acetals. The acetals are subsequently removed from the acetic acid by, e.g., distillation.
1. A method for reducing an aldehyde impurity from acetic acid stream, said method comprising:
(a) reacting methanol and carbon monoxide in the presence of a carbonylation catalyst, a catalyst stabilizer, methyl iodide, water and methyl acetate to produce an acetic acid stream comprising the catalyst, the catalyst stabilizer, methyl iodide, methyl acetate, water, acetic acid, and an aldehyde impurity;
(b) flashing at least a portion of the acetic acid stream to a vapor stream comprising acetic acid, water, methyl acetate, methyl iodide and the aldehyde impurity, and a liquid stream comprising the catalyst and the catalyst stabilizer;
(c) recycling the liquid stream to the reaction of step (a);
(d) separating the vapor stream by distillation into an acetic acid product stream comprising acetic acid and water, and an overhead stream comprising methyl iodide, water, methyl acetate, acetic acid, and the aldehyde impurity;
(e) condensing the overhead stream to produce a light, aqueous phase comprising water, acetic acid, and methyl acetate, and a heavy, organic phase comprising methyl iodide and the aldehyde impurity;
(f) reacting at least a portion of the heavy, organic phase with a hydroxyl compound selected from the group consisting of C 4-10 alcohols, glycols, and glycerin to convert the aldehyde impurity to an acetal having a higher boiling point than acetic acid;
(g) recycling the treated heavy phase of step (f) to the distillation of step (d), wherein the acetal goes with the acetic acid product stream as a heavy impurity; and
(h) separating the acetal from the acetic acid product stream of step (g) by distillation.
2. The method of claim 1 , wherein the catalyst is a rhodium catalyst.
3. The method of claim 1 , wherein the catalyst stabilizer is selected from the group consisting of pentavalent Group VA oxides, metal iodide salts, and mixtures thereof.
4. The method of claim 1 , wherein the catalyst stabilizer is a phosphine oxide.
5. The method of claim 1 , wherein the catalyst stabilizer is triphenylphosphine oxide.
6. The method of claim 1 , wherein the water concentration of step (a) is 10 wt % or less based on the total acetic acid stream.
7. The method of claim 1 , wherein the water concentration of step (a) is 6 wt % or less based on the total weight of the acetic acid stream.
8. The method of claim 1 , wherein the aldehyde impurity is acetaldehyde.
9. The method of claim 1 , wherein the hydroxyl compound is a glycol selected from the group consisting of ethylene glycol, propylene glycol, 1,4-butanediol, 1,3-butanediol, 1,5-pentanediol, 1,6-hexanediol, 2-methyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, cyclohexane-1,4-dimethanol, neopentyl glycol, and mixtures thereof.
10. The method of claim 1 , wherein the hydroxyl compound is ethylene glycol.
11. The method of claim 1 , wherein the reaction of step (f) is performed in the presence of an acid catalyst.
12. The method of claim 11 , wherein the catalyst is an acidic ion exchange resin.
13. The method of claim 1 , where the reaction of step (f) is performed at a temperature within the range of about 20° C. to about 135° C.
14. The method of claim 1 , wherein the reaction of step (f) is performed at a temperature within the range of about 20° C. to about 50° C.
15. The method of claim 1 , wherein the heavy phase of step (e) comprises from 60 wt % to 90 wt % of methyl iodide, 1 wt % to 10 wt % of acetic acid, 5 wt % to 15 wt % of methyl acetate, 1 wt % to 10 wt % of an alkane, 1 wt % or less of water, and 2 wt % or less of the aldehyde impurity.