# US 10,865,170 B2 · Process for producing 2-butanol from gammavalerolactone

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- Number: US 10,865,170 B2
- Document ID: US10865170B2
- Status: Granted
- Kind: B2
- Application number: 16/508,777
- Filed: 2019-07-11
- Published: 2020-01-16
- Granted: 2020-12-15
- Earliest claimed: 2018-07-13
- Assignees: Neste Oyj
- Applicants: Neste Oyj
- Inventors: Marina Lindblad; Mats Käldström; Susanna Wallenius; Kaisa Lamminpää
- Web page: https://patentgrep.com/patent/US10865170B2

## CPC

- B01J 21/066: {Zirconium or hafnium; Oxides or hydroxides thereof}
- C07C 29/149: with hydrogen or hydrogen-containing gases
- B01J 23/462: {Ruthenium}
- B01J 23/464: {Rhodium}
- C07C 31/12: containing four carbon atoms
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## 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.

## Claims

### Claim 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.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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-%.

### Claim 5 (depends on 1)

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

### Claim 6 (depends on 1)

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

### Claim 7 (depends on 6)

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

### Claim 8 (depends on 1)

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

### Claim 9 (depends on 1)

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

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 1)

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.

### Claim 12 (depends on 11)

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.

### Claim 13 (depends on 1)

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.

### Claim 14 (depends on 1)

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

### Claim 15 (depends on 14)

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

### Claim 16 (depends on 1)

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

### Claim 17 (depends on 1)

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

### Claim 18 (depends on 1)

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

### Claim 19 (depends on 1)

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

### Claim 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.