Process for producing allyl alcohol
View Patent ↗A process for producing allyl alcohol is disclosed. The process comprises reacting propylene, acetic acid, and oxygen to produce a reaction mixture. The reaction mixture is distilled to produce a vapor stream comprising propylene and a liquid stream comprising allyl acetate, acetic acid, acrolein, and allyl diacetate. The liquid stream is distilled to produce a lights stream comprising acrolein; a side draw comprising allyl acetate, acetic acid, and water; and a bottoms stream comprising acetic acid and allyl diacetate. The bottoms stream is distilled to remove a heavies stream comprising allyl diacetate. The side draw is hydrolyzed to produce allyl alcohol.
1. A process for producing allyl alcohol, comprising (a) reacting a feed comprising propylene, acetic acid, and oxygen to produce a reaction mixture; (b) distilling the reaction mixture to produce a vapor stream comprising propylene and a liquid stream comprising allyl acetate, acetic acid, acrolein, and allyl diacetate; (c) distilling the liquid stream to produce a lights stream comprising acrolein; a side draw comprising allyl acetate, acetic acid, and water; and a bottoms stream comprising acetic acid and allyl diacetate; (d) vaporizing the bottoms stream in an acetic acid vaporizer to remove a heavies stream comprising allyl diacetate; and (e) hydrolyzing the side draw to produce allyl alcohol.
2. The process of claim 1 wherein step (a) is performed in the presence of a palladium catalyst.
3. The process of claim 1 wherein step (a) is performed in the presence of a supported palladium catalyst.
4. The process of claim 1 wherein at least a portion of the vapor stream is fed to the acetic acid vaporizer.
5. The process of claim 1 wherein step (a) produces allyl diacetate from propylene with a molar selectivity of 0.01 to 1%.
6. The process of claim 1 wherein step (a) produces allyl diacetate from propylene with a molar selectivity of 0.1 to 0.5%.
7. The process of claim 1 wherein the bottoms stream comprises from 1 to 10 wt % allyl diacetate.
8. The process of claim 1 wherein the heavies stream comprises from 2 to 20 wt % allyl diacetate.
9. The process of claim 1 wherein the heavies stream comprises from 5 to 15 wt % allyl diacetate.
10. The process of claim 1 wherein the acetic acid vaporizer is a trayed distillation column.
11. The process of claim 1 wherein the acetic acid vaporizer is operated at an overhead temperature of 90 to 130° C.
12. The process of claim 1 wherein step (e) is performed in the presence of a solid acid catalyst.
13. The process of claim 12 wherein the solid acid catalyst is an ion-exchange resin.