Feed sources for allyl alcohol production processes

Patent metadata

Field	Value
Publication number	US-9914684-B2
Application number	US-201615352771-A
Country	US
Kind code	B2
Filing date	Nov 16, 2016
Priority date	Nov 20, 2015
Publication date	Mar 13, 2018
Grant date	Mar 13, 2018

Abstract

Allyl alcohol production processes are generally described herein. One or more of the processes generally include contacting a propylene oxide stream with an isomerization catalyst under isomerization conditions sufficient to form an isomerization product stream including allyl alcohol, wherein the propylene oxide stream includes a total impurity concentration of at least 100 ppm. One or more of the processes generally includes purging at least a portion of a stream from one or more separation unit(s).

First claim

What is claimed is:

1. A process comprising:
contacting a propylene oxide stream with an isomerization catalyst comprising lithium phosphate under isomerization conditions sufficient to form an isomerization product stream comprising allyl alcohol,
recovering allyl alcohol from the isomerization product stream to form an allyl alcohol stream comprising introducing the isomerization product stream into a first column adapted to separate propylene oxide from allyl alcohol comprising a top a bottom, and in the range of 36 to 49 theoretical stages, and wherein the impure propylene oxide stream is introduced to the first column at one or more theoretical stages in the range of the 17 th to the 28 th stage, counted from the bottom to the top of the first column,
forming a first overhead stream comprising propylene oxide and a first bottoms stream comprising allyl alcohol and purging at least a portion of the first overhead stream to form a first purge stream when the concentration of propylene oxide in the first overhead stream is 90 wt. % or less, based on the total weight of the first overhead stream; and
transferring the first bottoms stream to a second column adapted to separate methanol from allyl alcohol and form a second overhead stream comprising methanol and a second bottoms stream comprising allyl alcohol;
contacting the allyl alcohol stream with a hydroformylation catalyst in the presence of a gas stream comprising carbon monoxide and hydrogen under hydroformylation conditions sufficient to form a hydroformylation product comprising a hydrogenation feed comprising a butane diol intermediate; and
contacting the hydrogenation feed comprising the butane diol intermediate with hydrogenation catalyst in the presence of hydrogen under hydrogenation conditions comprising the hydrogenation catalyst contacting the hydrogenation feed at a concentration of 0.1-15 wt. % to form a hydrogenation product stream comprising 1,4-butane diol;
wherein the propylene oxide stream comprises a total impurity concentration of at least 100 ppm.

2. The process of claim 1 , wherein the propylene oxide stream contacts the isomerization catalyst within an isomerization reactor and the recovering comprises:
introducing the isomerization product stream into a first column adapted to separate methanol from allyl alcohol and form a first overhead stream comprising methanol and propylene oxide and a first bottoms stream comprising allyl alcohol;
transferring the first overhead stream to a second column adapted to separate methanol from propylene oxide and form a second overhead stream comprising propylene oxide and a second bottoms stream comprising methanol; and
transferring the second overhead stream to the isomerization reactor.

3. The process of claim 2 , wherein the first bottoms stream comprises less than 25 ppm methanol.

4. The process of claim 2 , wherein the second bottoms stream comprises less than 25 ppm methanol.

5. The process of claim 1 , wherein the propylene oxide stream comprises a methyl formate concentration in a range of 0 wt. % to 1 wt. % based on the total weight of the propylene oxide stream.

6. The process of claim 1 , wherein the propylene oxide stream comprises a methanol concentration in a range of 0 wt. % to 5 wt. % based on the total weight of the propylene oxide stream.

7. The process of claim 1 , wherein the propylene oxide stream comprises an acetone concentration in a range of 0 wt. % to 20 wt. % based on the total weight of the propylene oxide stream.

8. The process of claim 1 , wherein the propylene oxide stream comprises a water concentration in a range of 0 wt. % to 5 wt. % based on the total weight of the propylene oxide stream.

9. The process of claim 1 , wherein the propylene oxide stream comprises a propionaldehyde concentration in a range of 0 wt. % to 1 wt. % based on the total weight of the propylene oxide stream.

10. The process of claim 1 , wherein the isomerization conditions comprise an isomerization temperature in a range of 200° C. to 300° C. and an isomerization pressure in a range of 0 psig (0 Pa) to 30 psig (206,843 Pa).

11. The process of claim 1 , wherein the isomerization catalyst comprises lithium phosphate.

12. The process of claim 1 , wherein the recovering allyl alcohol comprises separating methanol from the allyl alcohol to form the allyl alcohol stream, wherein the allyl alcohol stream comprises less than 25 ppm methanol.

13. The process of claim 1 wherein the purging is a continuous operation.

14. The process of claim 1 , wherein the hydrogenation catalyst contacts the hydrogenation feed at a concentration of 0.2-10 wt. %.

15. The process of claim 1 wherein the purging is a batch operation.

Assignees

• Lyondell Chemical Tech Lp

Inventors

• Gaur Sarthak
• Mandimutsira Beaven S
• White Daniel F
• Dubner Walter S

Classifications

• C07C29/56 Primary

  by isomerisation · CPC title

• C07C29/141

  with hydrogen or hydrogen-containing gases · CPC title

• C07C47/19

  containing hydroxy groups (sugars C07H) · CPC title

• C07C45/50

  by oxo-reactions · CPC title

• C07C31/207

  1,4-Butanediol; 1,3-Butanediol; 1,2-Butanediol; 2,3-Butanediol · CPC title