Process for the separation of 1,4-butanediol and co-products

Patent metadata

Field	Value
Publication number	US-9932284-B2
Application number	US-201414892436-A
Country	US
Kind code	B2
Filing date	May 28, 2014
Priority date	May 31, 2013
Publication date	Apr 3, 2018
Grant date	Apr 3, 2018

Abstract

The present invention provides a process for the recovery of 1,4-butanediol and at least one co-product selected from γ-butyrolactone, n-butanol and tetrahydrofuran from an aqueous stream, said process comprising the steps of providing the aqueous stream, providing a first solvent stream, combining said aqueous stream with said first solvent stream and recovering at least a portion of the 1,4-butanediol and at least a portion of at least one of the co-products by liquid-liquid extraction.

First claim

The invention claimed is:

1. A process for the recovery of 1, 4-butanediol and at least one co-product selected from γ-butyrolactone, n-butanol and tetrahydrofuran from an aqueous stream, said process comprising the steps of providing the aqueous stream, providing a first solvent stream, combining said aqueous stream with said first solvent stream and recovering at least a portion of the 1, 4-butanediol and at least a portion of at least one of the co-products by liquid-liquid extraction wherein at least one co-product is tetrahydrofuran.

2. The process according to claim 1 , wherein the aqueous stream is derived from a reaction product stream from a process for the production of 1, 4-butanediol and/or THF.

3. The process according to claim 1 , wherein at least a portion of the 1, 4-butanediol and at least a portion of at least one of the co-products present are recovered by liquid-liquid extraction by a process comprising the steps of extracting at least a portion of the 1, 4-butanediol and at least a portion of at least one of the co-products present into the solvent and separating a first 1, 4-butanediol, co-products and solvent rich stream, leaving a first residual stream wherein at least one co-product is tetrahydrofuran.

4. The process according to claim 3 , wherein the 1, 4-butanediol, co-products and solvent rich stream is then separated into a 1, 4-butanediol rich stream, a solvent rich stream and separate streams each rich in one of the co-products present by distillation.

5. The process according to claim 1 , wherein at least a portion of the 1, 4-butanediol and at least a portion of each of the co-products present are recovered by liquid-liquid extraction by a process comprising extracting at least a portion of the 1, 4-butanediol into a solvent stream to provide a first 1, 4-butanediol and solvent rich stream; extracting at least a portion of the THF, if present, into a solvent stream to provide a first THF and solvent rich stream; extracting at least a portion of the γ-butyrolactone, if present, into a solvent stream to provide a first γ-butyrolactone and solvent rich stream; and extracting at least a portion of the n-butanol, if present, into a solvent stream to provide a first n-butanol and solvent rich stream, leaving a residual stream.

6. The process according to claim 1 , wherein the solvent is an amine.

7. The process according to claim 6 , wherein the solvent is a tertiary amine.

8. The process according to claim 6 , wherein the solvent is selected from the group consisting of dimethyl-cyclohexyl amine, methyl cyclohexyl amine, N-methyl piperidine, triethylamine, tripropylamine, or a combination thereof.

9. The process according to claim 1 , wherein the solvent is an alcohol.

10. The process according to claim 9 , wherein the solvent is selected from n-butanol, n-pentanol and octanols.

11. The process according to claim 3 , wherein any residual stream is recycled to the process in which the 1, 4-butanediol was formed.

Assignees

• Shell Oil Co

Inventors

• Fischer Kai Jürgen
• Koot Wouter
• Wadman Sipke Hidde
• Lange Jean Paul Andre Marie Joseph Gishlain

Classifications

• C07C31/12

  containing four carbon atoms · CPC title

• C07D307/33

  in position 2, the oxygen atom being in its keto or unsubstituted enol form · CPC title

• C07D307/08

  Preparation of tetrahydrofuran · CPC title

• C07C29/86 Primary

  by liquid-liquid treatment · CPC title

• C07C31/207

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