Process for producing 2-butanol from gammavalerolactone

Patent metadata

Field	Value
Publication number	US-10865170-B2
Application number	US-201916508777-A
Country	US
Kind code	B2
Filing date	Jul 11, 2019
Priority date	Jul 13, 2018
Publication date	Dec 15, 2020
Grant date	Dec 15, 2020

Abstract

A process is disclosed for selectively producing 2-butanol from GVL by using at least one transition metal catalyst selected from the group consisting of iron, ruthenium, cobalt, rhodium and iridium.

First claim

The invention claimed is:

1. A process for selective production of 2-butanol from γ-valerolactone (GVL), the process comprising:
a. providing in a reactor at least one transition metal catalyst selected from a group consisting of iron, ruthenium, cobalt, rhodium and iridium;
b. heating a feedstock containing GVL, thereby forming a heated GVL feedstock;
c. forming a reaction mixture by feeding into the reactor:
i. the heated GVL feedstock; and
ii. hydrogen gas; and

d. maintaining a temperature of the reaction mixture in a range of 200−300° C. to allow selective production of reaction products containing 2-butanol,
wherein no water is fed into the reactor during the process.

2. The process of claim 1 , wherein the selectivity of 2-butanol production is at least 50% analysed as GC-MS area-%.

3. The process of claim 1 , wherein the feedstock contains at least 80 wt-% GVL.

4. The process of claim 1 , wherein in the process conditions provide 2-butanol in a liquid phase, wherein a ratio of 2-butanol to 2-methyltetrahydrofuran is at least 2 analysed as GC-MS area-%.

5. The process of claim 1 , wherein the catalyst comprises:
Rh, Ru, or a combination thereof.

6. The process of claim 1 , wherein the catalyst is provided on a support.

7. The process of claim 6 , wherein the support comprises:
Zr oxide, Al oxide, Ti oxide, silica, or a combination thereof.

8. The process of claim 1 , wherein the catalyst comprises:
Rh/ZrO2 or Ru/ZrO2, or a combination thereof.

9. The process of claim 1 , wherein the temperature is maintained in a range 215-270° C. during production of 2-butanol.

10. The process of claim 1 , wherein the temperature is maintained in a range 240-260° C. during production of 2-butanol.

11. The process of claim 1 , wherein in the process conditions provide 2-butanol in a liquid phase, and wherein the liquid phase comprises:
GVL, 2-butanol, 2-methyltetrahydrofuran and 2-pentanol.

12. The process of claim 11 , wherein the liquid phase comprises:
2-butanol, 2-methyltetrahydrofuran, 2-pentanol, 1-pentanol, 2-butanone, pentanoic acid 2-penten-l-ylester, and pentanoic acid pentylester.

13. The process of claim 1 , wherein a pressure selected from a range of 40-100 bar, or a range of 50-90 bar, is maintained inside the reactor during production of 2-butanol.

14. The process of claim 1 , wherein the process is a continuous process.

15. The process of claim 14 wherein at least part of a unreacted GVL present in the liquid phase is recycled into the reactor.

16. The process of claim 1 , wherein the liquid phase contains at least 15% 2-butanol analysed as GC-MS area-%.

17. The process of claim 1 , comprising:
controlling pressure inside the reactor, and converting methane formed during the process to hydrogen gas.

18. The process of claim 1 , comprising:
recovering at least one further reaction product selected from 2-MTHF, 2-butanone, and pentyl pentanoate.

19. The process of claim 1 , wherein GVL is derived from a lignocellulosic source.

20. A method comprising:
applying a catalyst containing at least one transition metal selected from a group consisting of iron, ruthenium, cobalt, rhodium and iridium, in a selective production of 2-butanol from GVL, wherein no water is fed into the method during the selective production of 2-butanol from GVL.

Assignees

• Neste Oyj

Inventors

• Lindblad Marina
• Käldström Mats
• Wallenius Susanna
• Lamminpää Kaisa

Classifications

• C07C29/149 Primary

  with hydrogen or hydrogen-containing gases · CPC title

• B01J23/464

  Rhodium · CPC title

• B01J23/462

  Ruthenium · CPC title

• B01J21/066 Primary

  Zirconium or hafnium; Oxides or hydroxides thereof · CPC title

• C07D307/32

  Oxygen atoms · CPC title