IP Library Granted Patent US 11,384,038
Granted Patent B2
US 11,384,038 · App. 16/068,472 · Granted Jul 12, 2022

Process for the preparation of ethylene glycol from sugars

Inventors: Christian Mårup Osmundsen (Gentofte, DK); Esben Taarning (Frederiksberg, DK); Morten Boberg Larsen (Smørum, DK)
Assignee: HALDOR TOPSØE A/S
C07C29/141B01J21/18B01J23/72C07C27/00C07C27/04C07C31/202B01J19/24Y02P20/129Y02P20/52
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Quick Facts
Patent No.
US 11,384,038
App. No.
16/068,472
Granted
Jul 12, 2022
Kind
B2
Abstract

A process for the preparation of ethylene glycol and other C 1 -C 3 hydroxy compounds comprising the steps of hydrogenating a composition comprising C 1 -C 3 oxygenate compounds in the gas phase in the presence of a copper on carbon catalyst.

Claims (31)

1. A process for the preparation of ethylene glycol, comprising the steps of:

a) providing an oxygenate feed composition comprising a C 1 -C 3 oxygenate compound, wherein the composition comprising C 1-3 -oxygenate compounds comprises glycolaldehyde and at least one of glyoxal and carboxylic acid, and

b) providing a hydrogenation catalyst material comprising Cu on carbon, then

c) reacting the composition of step a) with hydrogen in the presence of the catalyst of step b) and under conditions to provide gas phase hydrogenation of the oxygenate compound to obtain a hydrogenation product composition comprising ethylene glycol, and then

d) recovering the hydrogenation product composition.

2. The process according to claim 1 , wherein the process is performed under continuous conditions.

3. The process according to claim 1 , wherein the oxygenate feed composition of step a) is brought into the gas phase by atomizing the oxygenate feed using an atomization nozzle.

4. The process according to claim 1 , wherein the oxygenate feed composition comprises glycolaldehyde, glyoxal and at least one of the C 1 -C 3 oxygenate compounds selected from the group consisting of pyruvaldehyde, acetol and formaldehyde.

5. The process according to claim 1 , wherein the oxygenate feed composition of step a) is brought into the gas phase prior to step c).

6. The process according to claim 1 , wherein the hydrogenation catalyst material of step b) has a loading of Cu on carbon in the range of from 0.1 to 70 weight percent.

7. The process according to claim 1 , wherein step c) is conducted under an initial hydrogen partial pressure of at least 0.5 bar.

8. The process according to claim 1 , wherein the initial oxygenate molar fraction in step c) is from 0.01 to 0.5.

9. The process according to claim 1 , wherein step c) is conducted under a total pressure of from 0.8-500 bar.

10. The process according to claim 1 , wherein step c) is conducted under a temperature in the range of from 100-400° C.

11. The process according to claim 1 , wherein step c) of reacting the oxygenate feed composition with hydrogen in the presence of the hydrogenation catalyst material is conducted in a chemical reactor.

12. The process according to claim 11 , wherein the oxygenate feed composition is fed to the chemical reactor at a ratio of flow rate by weight of oxygenate feed composition of step a) to weight of catalytic material of step b) in the range of from 0.001 to 1000 g C 1 -C 3 oxygenate compounds per g catalyst per hour.

13. The process according to claim 1 , wherein the hydrogenation product composition of d) is subjected to a purification step.

14. The process according to claim 1 , wherein unreacted hydrogen recovered after step d), is recycled to step c).

15. The process according to claim 1 , wherein the process is conducted in a Berty reactor, a packed bed reactor, a fixed bed reactor, a multi-tubular reactor or a fluid bed reactor.

16. A process for the preparation of ethylene glycol, comprising the steps of:

i. providing a feedstock solution of a sugar composition;

ii. exposing the feedstock of a) to thermolytic fragmentation to produce a fragmentation product composition comprising a C 1 -C 3 oxygenate compound; and

iii. optionally conditioning the fragmentation product composition; and then

iv. subjecting the fragmentation product composition of step ii) or iii) to the process according to claim 1 , wherein the fragmentation product composition is the oxygenate feed composition of step a).

17. The process according to claim 16 , wherein the sugar composition is selected from fructose, xylose, glucose, mannose, galactose, sucrose, and lactose.

18. The process according to claim 16 , wherein the feedstock solution of step i) is a solution of a sugar in a solvent comprising from 20-95 wt % of sugar.

19. The process according to claim 16 , wherein the solvent comprises one or more of the compounds selected from the group consisting of water, methanol, ethanol, ethylene glycol and propylene glycol.

20. The process according to claim 1 , wherein step c) is conducted under a total pressure of from 0.8-10 bar, wherein step c) is conducted under a temperature in the range of from 150-400° C., wherein the hydrogenation product composition of step d) comprises ethylene glycol.

21. The process according to claim 1 , wherein the oxygenate feed composition comprises glycolaldehyde and glyoxal.

22. The process according to claim 1 , wherein the oxygenate feed composition comprises glycolaldehyde and a carboxylic acid.

23. The process according to claim 1 , wherein the oxygenate feed composition comprises glycolaldehyde and a carboxylic acid selected from the group consisting of acetic acid, formic acid, lactic acid and glycolic acid.

Assignments (2)
CHANGE OF NAME Recorded Dec 19, 2023
From: HALDOR TOPSØE A/S
To: TOPSOE A/S
Reel/Frame 066076/0685 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 23, 2018
From: OSMUNDSEN, CHRISTIAN MARUP; TAARNING, ESBEN; LARSEN, MORTEN BOBERG
To: HALDOR TOPSØE A/S
Reel/Frame 046673/0789 →
Priority Claims (1)
DK PA 2016 00006 · Jan 7, 2016 · national
Continuity (1)
Related Publication 20190010103A1 · Jan 10, 2019