Feed sources for butanediol production processes

Patent metadata

Field	Value
Publication number	US-9809518-B2
Application number	US-201615352851-A
Country	US
Kind code	B2
Filing date	Nov 16, 2016
Priority date	Nov 20, 2015
Publication date	Nov 7, 2017
Grant date	Nov 7, 2017

Abstract

Butanediol production processes are described herein. In some embodiments, the processes include contacting an allyl alcohol stream with a hydroformylation catalyst in the presence of a gas stream including carbon monoxide and hydrogen under hydroformylation conditions sufficient to form a hydroformylation product stream including a butanediol intermediate, wherein the allyl alcohol stream includes less than 98 wt. % allyl alcohol.

First claim

What is claimed is:

1. A process comprising:
contacting an allyl alcohol stream with a hydroformylation catalyst comprising rhodium phosphate at a feed concentration of 0.3-3.3 wt. % in the presence of a gas stream comprising carbon monoxide and hydrogen under hydroformylation conditions sufficient to form a hydroformylation product stream comprising a butanediol intermediate, wherein the allyl alcohol stream comprises less than 98 wt. % allyl alcohol.

2. The process of claim 1 , further comprising contacting the butanediol intermediate with a hydrogenation catalyst in the presence of hydrogen under hydrogenation conditions sufficient to form a hydrogenation product stream comprising 1,4-butanediol.

3. The process of claim 2 , characterized by an allyl alcohol conversion of 80-100%.

4. The process of claim 2 , characterized by a selectivity of 65-100%.

5. The process of claim 2 , further comprising recovering 1,4-butanediol from the hydrogenation product stream.

6. The process of claim 1 , wherein the allyl alcohol stream comprises one or more impurities selected from acetone, water, propionaldehyde, n-propanol, C 4+ hydrocarbons, C 1+ oxygenates and combinations thereof.

7. The process of claim 6 , wherein the allyl alcohol stream comprises an acetone concentration in a range of 0 wt. % to 25 wt. % based on the total weight of the allyl alcohol stream, a water concentration in a range of 0 wt. % to 6 wt. % based on the total weight of the allyl alcohol stream, a propionaldehyde concentration in a range of 0 wt. % to 6 wt. % based on the total weight of the allyl alcohol stream, a n-propanol concentration in a range of 0 wt. % to 1 wt. % based on the total weight of the allyl alcohol stream, a C 4+ hydrocarbon concentration in a range of 0 wt. % to 5 wt. % based on the total weight of the allyl alcohol stream and C 1+ oxygenates concentration in a range of 0 wt. % to 11 wt. % based on the total weight of the allyl alcohol stream.

8. The process of claim 1 , wherein the allyl alcohol stream comprises methanol in a methanol concentration of less than 100 ppm.

9. The process of claim 1 , wherein the allyl alcohol stream comprises an acetone concentration of at least 0.25 wt. % based on the total weight of the allyl alcohol stream, a methanol concentration of less than 100 ppm based on the total weight of the allyl alcohol stream, a water concentration of at least 0.1 wt. % based on the total weight of the allyl alcohol stream, a propionaldehyde concentration of at least 0.25 wt. % based on the total weight of the allyl alcohol stream, or combinations thereof.

10. The process of claim 1 , wherein the hydroformylation conditions comprise a hydroformylation temperature in a range of 20° C. to 100° C. and a hydroformylation pressure in a range of 20 psig (137,895 Pa) to 600 psig (4,136,854 Pa).

11. The process of claim 1 , wherein the hydroformylation catalyst comprises a rhodium phosphate with a rhodium:phosphate molar ratio of 1:1-1.2:1.

Assignees

• Lyondell Chemical Tech Lp

Inventors

• White Daniel F
• Alvarez Roberto
• Mandimutsira Beaven S

Classifications

• C07C45/50

  by oxo-reactions · CPC title

• C07C29/141 Primary

  with hydrogen or hydrogen-containing gases · CPC title

• C07C47/19

  containing hydroxy groups (sugars C07H) · CPC title

• C07C31/207

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