Production method for 1,4-butanediol

Patent metadata

Field	Value
Publication number	US-10487032-B2
Application number	US-201414560714-A
Country	US
Kind code	B2
Filing date	Dec 4, 2014
Priority date	Jun 5, 2012
Publication date	Nov 26, 2019
Grant date	Nov 26, 2019

Abstract

An object of the present invention is to provide high-quality 1,4BG capable of working out to a raw material of PBT with good color tone, by efficiently removing and refining impurities mixed when producing a biomass-derived 1,4BG on an industrial scale and the present invention relates to a production method of refined 1,4BG, where a crude 1,4BG-containing solution is obtained from refined raw material 1,4BG obtained by removing bacterial cells, salt contents and water from the fermentation culture medium, through a step of removing high-boiling-point components and/or low-boiling-point components by distillation and/or a step of converting an unsaturated compound to a hydride and the target product is obtained as a side stream in a further distillation step.

First claim

The invention claimed is:

1. A method for producing refined 1,4-butanediol having a concentration of a cyclic carbonyl compound having a carbon atom number of 5 or 6 of 12 ppm by mass or less, comprising biologically producing 1,4-butanediol in a culture medium for fermentation of an organism capable of producing 1,4-butanediol, at least partially removing each of a bacterial cell, a salt content and water from said fermentation culture medium to obtain a refined raw material 1,4-butanediol-containing solution, obtaining therefrom a crude 1,4-butanediol-containing solution through the following steps (b′) and (c) and optionally the following steps (a) and (b), refining said crude 1,4-butanediol-containing solution through the following step (d) and obtaining said refined 1,4-butanediol having a concentration of a cyclic carbonyl compound having a carbon atom number of 5 or 6 of 12 ppm by mass or less:
Step (a):
a step of distilling said refined raw material 1,4-butanediol-containing solution in a distillation column to remove components which are contained in said refined raw material 1,4-butanediol-containing solution and higher in the boiling point than 1,4-butanediol;

Step (b):
a step of distilling said refined raw material 1,4-butanediol-containing solution in a distillation column to remove components which are contained in said refined raw material 1,4-butanediol-containing solution and lower in the boiling point than 1,4-butanediol;

Step (b′):
a step of bringing said refined raw material 1,4-butanediol-containing solution, optionally after treatment in one or both of steps (a) and (b), into contact with a base;

Step (c):
a hydrogenating step of at least partially converting unsaturated compounds contained in said refined raw material 1,4-butanediol-containing solution obtained from step (b′) into a hydride via hydrogenation; and

Step (d):
a step of distilling said crude 1,4-butanediol-containing solution in a distillation column, withdrawing the refined 1,4-butanediol from a side stream and obtaining said refined 1,4-butanediol having a concentration of a cyclic carbonyl compound having a carbon atom number of 5 or 6 of 12 ppm by mass or less.

2. The method as claimed in claim 1 , wherein the concentration of a cyclic carbonyl compound having a carbon atom number of 5 or 6 in the refined 1,4-butanediol obtained in said step (d) is 2-10 ppm by mass.

3. The method as claimed in claim 1 , comprising step (a) and further comprising the following step (e):
Step (e):
a step of distilling components higher in the boiling point than 1,4-butanediol, which are separated in said step (a), in a distillation column and thereby separating and recovering 1,4-butanediol.

4. The method as claimed in claim 1 , wherein the water concentration in the refined raw material 1,4-butanediol-containing solution immediately before passing through any one step of said steps (a) to (c) or through the step (b′) is from 0.01 to 20 mass % and the pH thereof is 5 or more.

5. The method as claimed in claim 1 , wherein in the hydrogenation step of said step (c), hydrogenation is performed using a solid catalyst having a nickel-containing metal supported on at least either kieselguhr or silica.

6. The method as claimed in claim 1 , wherein the base in said step (b′) is a solid base.

7. The method as claimed in claim 1 , comprising said step (b), wherein the components lower in the boiling point than 1,4-butanediol in said step (b) contain 1-acetoxy-4-hydroxybutane and the 1-acetoxy-4-hydroxybutane concentration in the crude 1,4-butanediol-containing solution after the removal of said components lower in the boiling point than 1,4-butanediol is from 0.1 to 50 ppm by mass.

8. The method as claimed in claim 1 , comprising said step (b), wherein a bottom temperature of the distillation column in said step (b) is from 120 to 200° C.

9. The method as claimed in claim 1 , comprising said step (a), wherein a bottom temperature of the distillation column in said step (a) is from 150 to 200° C.

10. The method as claimed in claim 1 , comprising said step (a), wherein the components higher in the boiling point than 1,4-butanediol in said step (a) contain 2-pyrrolidone and the 2-pyrrolidone concentration in the crude 1,4-butanediol-containing solution after the removal of said components higher in the boiling point than 1,4-butanediol is 20 ppm by mass or less.

11. The method as claimed in claim 1 , comprising said step (a), wherein a heating source of the distillation column in said step (a) contacts substantially only with a bottom liquid but involves no contact with a gas-phase part.

12. The method as claimed in claim 1 , wherein a gamma-butyrolactone concentration in the overhead distillate of the distillation column in said step (d) is higher than the gamma-butyrolactone concentration in the refined 1,4-butanediol withdrawn from a side stream.

13. The method as claimed in claim 1 , comprising a step of controlling the carbonyl value in the refined raw material 1,4-butanediol-containing solution immediately before passing through any one step of said steps (a) to (c) or through the step (b′), to be 2.5 mgKOH/g or less.

14. The method as claimed in claim 1 , wherein in at least one step of said steps (b) to (d), the carbonyl value in said refined raw material 1,4-butanediol-containing solution is reduced.

15. The method as claimed in claim 1 , comprising step (a) and step (b).

16. The method as claimed in claim 1 , comprising step (a).

17. The method as claimed in claim 1 , comprising step (b).

18. The method as claimed in claim 1 , wherein the concentration of a cyclic carbonyl compound having a carbon atom number of 5 or 6 in the refined 1,4-butanediol obtained in said step (d) is 10 ppm by mass or less.

19. The method as claimed in claim 1 , wherein the concentration of a cyclic carbonyl compound having a carbon atom number of 5 or 6 in the refined 1,4-butanediol obtained in said step (d) is 2-6 ppm by mass.

Assignees

• Mitsubishi Chem Corp
• Genomatica Inc

Inventors

• Utsunomiya Masaru
• Izawa Yusuke
• Konishi Norikazu
• Tanaka Kota
• Matsuzono Shinichiro
• Suzuki Takayuki
• Japs Michael
• Burk Mark
• Clark Warren

Classifications

• B01D3/002

  by continuous methods · CPC title

• B01D3/143

  by two or more of a fractionation, separation or rectification step · CPC title

• C07C29/80 Primary

  by distillation · CPC title

• C12P7/18

  polyhydric · CPC title

• C07C29/90

  using hydrogen only · CPC title