Process for the production of ethylene glycol and heterogeneous catalyst composition

Patent metadata

Field	Value
Publication number	US-11358129-B2
Application number	US-201916977748-A
Country	US
Kind code	B2
Filing date	Mar 14, 2019
Priority date	Mar 14, 2018
Publication date	Jun 14, 2022
Grant date	Jun 14, 2022

Abstract

The invention relates to a process for the production of ethylene glycol including the steps of:(i) reacting, in a reactor, at a temperature in the range from equal to or more than 170° C. to equal to or less than 270° C., at least a portion of a carbohydrate source in the presence of hydrogen, a solvent, a homogeneous catalyst, which homogeneous catalyst contains tungsten, and a heterogeneous catalyst, which heterogeneous catalyst contains one or more transition metals from groups 8, 9 and 10 of the Periodic Table of the Elements, yielding ethylene glycol and a spent heterogeneous catalyst;(ii) regenerating the spent heterogeneous catalyst by removing at least a portion of deposited tungsten species from the spent heterogeneous catalyst, yielding a regenerated heterogeneous catalyst; and(iii) using at least a portion of the regenerated heterogeneous catalyst as heterogeneous catalyst in the reaction of step (i).The invention further relates to a regenerated heterogeneous catalyst composition obtainable therein.

First claim

The invention claimed is:

1. A process for the production of ethylene glycol including the steps of:
(i) reacting, in a reactor, at a temperature in the range from equal to or more than 170° C. to equal to or less than 270° C., at least a portion of a carbohydrate source in the presence of hydrogen, a solvent, a homogeneous catalyst, which homogeneous catalyst contains tungsten, and a heterogeneous catalyst, which heterogeneous catalyst contains one or more transition metals selected from groups 8, 9 and 10 of the Periodic Table of the Elements, yielding ethylene glycol and a spent heterogeneous catalyst;
(ii) regenerating the spent heterogeneous catalyst by removing at least a portion of deposited tungsten species from the spent heterogeneous catalyst, yielding a regenerated heterogeneous catalyst; and
(iii) using at least a portion of the regenerated heterogeneous catalyst as heterogeneous catalyst in the reaction of step (i);
wherein at least a portion of the deposited tungsten species is removed from the spent heterogeneous catalyst by washing of the spent heterogeneous catalyst with a washing liquid, wherein the washing liquid comprises ethylene glycol, propylene glycol, butylene glycol or a mixture thereof.

2. The process according to claim 1 , wherein the homogeneous catalyst contains tungsten which tungsten is present as a tungsten compound or tungsten derived from a tungsten compound.

3. The process according to claim 1 , wherein the homogeneous catalyst contains recycled tungsten species recovered, directly or indirectly, from the effluent of the reactor.

4. The process according to claim 1 , wherein the homogeneous catalyst contains or consists of a complex of hexavalent tungsten and pentavalent tungsten.

5. The process according to claim 1 , wherein the molar ratio of moles tungsten to moles transition metal, all calculated as metal, of the spent heterogeneous catalyst is higher than the molar ratio of moles tungsten to moles transition metal, all calculated as metal, of the heterogeneous catalyst as introduced to the reactor.

6. The process according to claim 1 , wherein step (ii) comprises:
washing the spent heterogeneous catalyst with the washing liquid to yield a washed, regenerated, heterogeneous catalyst;
drying the washed, regenerated, heterogeneous catalyst to yield a dried, regenerated, heterogeneous catalyst.

7. The process according to claim 1 , wherein the washing of the spent heterogeneous catalyst with the washing liquid is carried out at a temperature in the range from equal to or more than 150° C. to equal to or less than 250° C.

8. The process according to claim 1 , wherein the washing of the spent heterogeneous catalyst comprises two or more washing steps.

9. The process according to claim 1 , wherein step (ii) comprises:
recovering at least a portion of the spent heterogeneous catalyst from the reactor;
removing at least a portion of deposited tungsten species from the spent heterogeneous catalyst to thereby produce a regenerated heterogeneous catalyst;
recycling at least a portion of the regenerated heterogeneous catalyst to the reactor.

10. The process according to claim 9 , wherein step (ii) comprises:
recovering periodically or continuously at least a portion of the spent heterogeneous catalyst from the reactor;
removing periodically or continuously at least a portion of deposited tungsten species from such spent heterogeneous catalyst to thereby produce a regenerated heterogeneous catalyst;
recycling periodically or continuously at least a portion of the regenerated heterogeneous catalyst to the reactor.

11. The process according to claim 1 , wherein step (ii) is carried out in the absence of hydrogen.

12. The process according to claim 1 , wherein the tungsten species contain tungsten dioxide and/or tungsten trioxide.

13. The process according to claim 1 , wherein the average weight percentage of tungsten, calculated as metal, of the regenerated heterogeneous catalyst is lower than the average weight percentage of tungsten, calculated as metal, of the spent heterogeneous catalyst.

14. The process according to claim 1 , wherein step (i) comprises reacting, in a reactor, at a temperature in the range from equal to or more than 170° C. to equal to or less than 270° C., at least a portion of a carbohydrate source,
in the presence of hydrogen; a solvent; and a homogeneous catalyst, which homogeneous catalyst contains tungsten; and
in the presence of:
(a) a heterogeneous catalyst, which heterogeneous catalyst contains one or more transition metals from groups 8, 9 and 10 of the Periodic Table of the Elements and which heterogeneous catalyst contains no or essentially no tungsten; and/or
(b) a regenerated heterogeneous catalyst, which regenerated heterogeneous catalyst contains tungsten and one or more transition metals from groups 8, 9 and 10 of the Periodic Table of the Elements.

Assignees

• Avantium Knowledge Centre Bv

Inventors

• Singh Jagdeep
• Dekker Paula
• Van Der Waal Jan Cornelis
• Mckay Benjamin

Classifications

• B01J23/462

  Ruthenium · CPC title

• B01J21/18

  Carbon · CPC title

• B01J23/96 Primary

  of catalysts comprising metals, oxides or hydroxides of the noble metals · CPC title

• C07C29/132 Primary

  by reduction of an oxygen containing functional group · CPC title

• C07C31/20

  Dihydroxylic alcohols · CPC title