Glycerin-only reaction for allyl alcohol production

Patent metadata

Field	Value
Publication number	US-11358920-B2
Application number	US-202117390014-A
Country	US
Kind code	B2
Filing date	Jul 30, 2021
Priority date	Aug 12, 2020
Publication date	Jun 14, 2022
Grant date	Jun 14, 2022

Abstract

A process of producing allyl alcohol by reacting glycerin with ReO3—Al2O3 in the presence of gamma-valerolactone (GVL) in a reactor is described. More specifically, a process to produce allyl alcohol, comprising the step of: a) reacting glycerin with ReO3—Al2O3 in the presence of an inert solvent, GVL, in a reactor, and b) collecting the product comprising allyl alcohol.

First claim

What is claimed is:

1. A process to produce allyl alcohol, comprising the step of:
a) reacting glycerin with ReO 3 —Al 2 O 3 in the presence of an inert solvent in a reactor, wherein the inert solvent is gamma-valerolactone (GVL); and
b) collecting the product comprising allyl alcohol.

2. The process of claim 1 , wherein the process is free of additional reducing agent.

3. The process of claim 1 , wherein the reaction is further carried out in the presence of at least two inert solvents.

4. The process of claim 3 , wherein at least one of the two inert solvents is tetraethylene glycol dimethyl ether (tetraglyme).

5. The process of claim 1 , wherein the molar ratio of the inert solvent to glycerin ranges from 2:1 to 1:2.

6. The process of claim 1 , wherein the reactor is maintained at 180-200° C. for 4 hours.

7. The process of claim 1 , further comprising pretreating the glycerin.

8. The process of claim 7 , wherein the pretreating step comprises washing the glycerin with an acid or treating the glycerin with an ion exchange resin.

9. The process of claim 8 , wherein the ion exchange resin is a macroreticular sulfonated polystyrene-divinylbenzene resin.

10. The process of claim 7 , wherein the pretreating step further comprises washing the glycerin with water.

11. The process of claim 1 , wherein the product comprises a vapor component and a liquid component.

12. The process of claim 11 , further comprising removing the vapor component from the reactor.

13. The process of claim 11 , further comprising distilling the vapor component with a solvent.

14. The process of claim 11 , further comprising removing the ReO 3 —Al 2 O 3 from the liquid component.

15. The process of claim 14 , further comprising separating the gamma-valerolactone from the remaining liquid component by hydrogenation and distillation.

16. The process of claim 1 , wherein the product further comprises acrolein.

17. The process of claim 16 , wherein the acrolein is separated by distillation and subsequently hydrogenated to form n-propanol.

Assignees

• Lyondell Chemical Tech Lp

Inventors

• Yang Xueyong
• White Daniel F
• Arceneaux Chelsee A
• Metkar Pranit S

Classifications

• C07C29/60 Primary

  by elimination of -OH groups, e.g. by dehydration (C07C29/34 takes precedence) · CPC title

• C07C29/84

  by extractive distillation · CPC title

• C07C29/14

  of a —CHO group · CPC title

• C07C29/175

  with simultaneous reduction of an oxo group · CPC title

• C07C45/52

  by dehydration and rearrangement involving two hydroxy groups in the same molecule · CPC title