# US 11,078,138 B2 · Sugar hydrogenolysis with molybdenum co-catalyst selective for producing glycols

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- Number: US 11,078,138 B2
- Document ID: US11078138B2
- Status: Granted
- Kind: B2
- Application number: 16/968,154
- Filed: 2019-01-29
- Published: 2020-11-19
- Granted: 2021-08-03
- Earliest claimed: 2018-02-09
- Assignees: Archer Daniels Midland Company
- Applicants: Archer Daniels Midland Company
- Inventors: Chi Cheng Ma; James Brazdil
- Web page: https://patentgrep.com/patent/US11078138B2

## CPC

- C07C 29/132: by reduction of an oxygen containing functional group
- C07C 29/141: with hydrogen or hydrogen-containing gases
- B01J 21/18: Carbon
- B01J 23/28: Molybdenum
- B01J 23/30: Tungsten
- B01J 23/46: Ruthenium, rhodium, osmium or iridium
- B01J 23/6525: {Molybdenum}
- C07C 29/60: by elimination of -OH groups, e.g. by dehydration (C07C29/34 takes precedence)
- Y02P 20/52: using catalysts, e.g. selective catalysts
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A hydrogenolysis process is disclosed for directly converting a sugar feed comprised of a high fructose feedstock, a high sucrose feedstock, or a combination of these to a mixed lower polyols product including both propylene glycol and ethylene glycol. The process provides greater propylene glycol selectivity than ethylene glycol selectivity such that the propylene glycol is present to a greater extent than the ethylene glycol in the mixed lower polyols product. The sugar feed and a source of hydrogen are supplied to a reaction vessel and reacted in the presence of a hydrogenolysis catalyst comprising molybdenum (Mo) and ruthenium (Ru).

## Claims

### Claim 1

A process for directly converting a sugar feed comprised of fructose, dextrose or sucrose to a mixed lower polyols product including both propylene glycol and ethylene glycol, comprising supplying the sugar feed and a source of hydrogen to a reaction vessel and reacting the sugar feed and hydrogen in the presence of a hydrogenolysis catalyst comprising Mo and Ru to provide propylene glycol preferentially to ethylene glycol in the mixed lower polyols product.

### Claim 2 (depends on 1)

The process of claim 1, wherein the Mo is present at 0.5 to 10% by weight of the sugar feed.

### Claim 3 (depends on 1, 2)

The process of claim 1 or claim 2, wherein the Ru is present at 3-7% by weight of the hydrogenolysis catalyst.

### Claim 4 (depends on 1)

The process of claim 1, wherein the hydrogenolysis catalyst comprises a support material.

### Claim 5 (depends on 4)

The process of claim 4, wherein the support material comprises carbon.

### Claim 6 (depends on 4)

The process of claim 4, wherein the support material is selected from the group consisting of a carbon based support material, activated carbon, zirconium oxide, titanium oxide, niobium oxide, tin oxide, lanthanum oxide, tungsten oxide, silicon carbide, silicon oxycarbide, titanium carbide, titanium oxycarbide, zirconium oxycarbide, tungsten carbide, tungsten oxycarbide, and combination of any thereof.

### Claim 7 (depends on 6)

The process of claim 6, wherein the Mo is present at about 9-10% by weight of the sugar feed.

### Claim 8 (depends on 7)

The process of claim 7, wherein the Ru is present at about 5% by weight of the hydrogenolysis catalyst.

### Claim 9 (depends on 8)

The process of claim 8, wherein the Mo is in the form of molybdate.

### Claim 10 (depends on 9)

The process of claim 9, wherein the Mo is in the form of potassium molybdate.

### Claim 11 (depends on 10)

The process of claim 10, wherein the Mo is in the form of potassium molybdate in the range of 3-10% by weight of the sugar feed.

### Claim 12 (depends on 1)

The process of claim 1, wherein the sugar feed is placed in contact with the catalyst at a liquid hourly space velocity of between velocity of 0.2 hr−1 to 2 hr −1.

### Claim 13 (depends on 12)

The process of claim 12, further comprising maintaining a reaction temperature of between 180 to 250 degrees C.

### Claim 14 (depends on 13)

The process of claim 13, further comprising maintaining a hydrogen pressure of 600 to 2500 psi.

### Claim 15 (depends on 14)

The process of claim 14, wherein the reaction vessel is a sealed hydrogenolysis reactor, and the process is conducted for a period of time in the range of 1 hour to 10 hours.

### Claim 16 (depends on 14)

The process of claim 14, wherein the sugar feed is an aqueous fructose solution.

### Claim 17 (depends on 14)

The process of claim 14, wherein the sugar feed is an aqueous sucrose solution.

### Claim 18 (depends on 14)

The process of claim 14, wherein the sugar feed is an aqueous dextrose solution.