IP Library Granted Patent US 10,144,687
Granted Patent B2
US 10,144,687 · App. 14/147,885 · Granted Dec 4, 2018

Method for producing 1,4-butanediol

Inventors: Yusuke Izawa (Mie, JP); Masaru Utsunomiya (Tokyo, JP); Kouta Tanaka (Mie, JP); Norikazu Konishi (Mie, JP)
Assignee: Mitsubishi Chemical Corporation
C07C29/80C07C29/88
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Quick Facts
Patent No.
US 10,144,687
App. No.
14/147,885
Granted
Dec 4, 2018
Kind
B2
Abstract

An object of the present invention is to provide an industrially advantageous production method of 1,4BG, ensuring that generation of THF in the crude 1,4BG can be also suppressed and at the same time, the concentration of 2-(4-hydroxybutoxy)-tetrahydrofuran can be reduced. The present invention relates to a method for producing 1,4-butanediol, comprising heating crude 1,4-butanediol containing from 0.01 to 0.5 wt % of 2-(4-hydroxybutoxy)-tetrahydrofuran and from 1 to 25 wt % of water at 80° C. or more in the presence of an amine to obtain purified 1,4-butanediol.

Claims (24)

1. A method for producing 1,4-butanediol, the method comprising heating a crude 1,4-butanediol containing from 0.01 to 0.5 wt % of 2-(4-hydroxybutoxy)-tetrahydrofuran and from 2 to 25 wt % of water at 80° C. or more in the presence of an amine to obtain a purified 1,4-butanediol.

2. A method for producing 1,4-butanediol, the method comprising heating a crude 1,4-butanediol containing from 0.01 to 0.5 wt % of 2-(4-hydroxybutoxy)-tetrahydrofuran at 80° C. or more in the presence of an amine and water in an amount of 2 to 25 wt % based on the crude 1,4-butanediol to obtain a purified 1,4-butanediol.

3. The method according to claim 1 , wherein pH of the crude 1,4-butanediol is 7 or more.

4. The method according to claim 1 , wherein an amount of the amine is from 1 ppm by weight to 1 wt % based on the crude 1,4-butanediol.

5. The method according to claim 1 , wherein the crude 1,4-butanediol is heated at 80° C. or more in a distillation column.

6. The method according to claim 1 , further comprising distilling the purified 1,4-butanediol.

7. The method according to claim 2 , wherein pH of the crude 1,4-butanediol is 7 or more.

8. The method according to claim 2 , wherein an amount of the amine is from 1 ppm by weight to 1 wt % based on the crude 1,4-butanediol.

9. The method according to claim 2 , wherein the crude 1,4-butanediol is heated at 80° C. or more in a distillation column.

10. The method according to claim 2 , further comprising distilling the purified 1,4-butanediol.

11. The method of claim 1 , wherein the amount of water ranges from 7 to 25 wt %.

12. The method of claim 2 , wherein the amount of water ranges from 7 to 25 wt %.

13. The method of claim 1 , wherein the amine comprises a compound of formula (1):

wherein:

each of R 1 to R 3 is independently a hydrogen atom, an alkyl group, an aryl group or an amino group; and

each of R 1 to R 3 may optionally have a substituent,

with the proviso that a case where all of R 1 to R 3 are a hydrogen atom is excluded.

14. The method of claim 2 , wherein the amine comprises a compound of formula (1):

wherein:

each of R 1 to R 3 is independently a hydrogen atom, an alkyl group, an aryl group or an amino group; and

each of R 1 to R 3 may optionally have a substituent,

with the proviso that a case where all of R 1 to R 3 are a hydrogen atom is excluded.

15. The method of claim 1 , wherein the amine compound comprises an anion exchange resin.

16. The method of claim 2 , wherein the amine compound comprises an anion exchange resin.

Assignments (3)
CHANGE OF NAME Recorded Sep 5, 2017
From: MITSUBISHI RAYON CO., LTD.
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 043750/0834 →
MERGER Recorded Sep 4, 2017
From: MITSUBISHI CHEMICAL CORPORATION
To: MITSUBISHI RAYON CO., LTD.
Reel/Frame 043750/0207 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2014
From: IZAWA, YUSUKE; UTSUNOMIYA, MASARU; TANAKA, KOUTA; KONISHI, NORIKAZU
To: MITSUBISHI CHEMICAL CORPORATION
Reel/Frame 032147/0058 →
Priority Claims (1)
JP 2011-148328 · Jul 4, 2011 · national
Continuity (2)
Continuation PCTJP2012067011 · Jul 3, 2012
Related Publication 20140116872A1 · May 1, 2014