Carbonylation process and catalyst system therefor

Patent metadata

Field	Value
Publication number	US-10335774-B2
Application number	US-201615564867-A
Country	US
Kind code	B2
Filing date	Mar 24, 2016
Priority date	Apr 8, 2015
Publication date	Jul 2, 2019
Grant date	Jul 2, 2019

Abstract

A catalyst system for a liquid phase carbonylation reaction comprising a homogeneous acid catalyst component and a porous solid component, in particular for use in the formation of glycolic acid by carbonylation of formaldehyde. The homogeneous acid catalyst component is, for instance, sulphuric acid while the solid component can be unfunctionalized silica. A process for the carbonylation of an aldehyde to form a carboxylic′ acid or derivative thereof is also described. The process comprises the steps of contacting the catalyst with carbon monoxide, water and the aldehyde.

First claim

The invention claimed is:

1. A catalyst system for a liquid phase carbonylation reaction comprising:
a homogeneous acid catalyst selected from sulphuric acid, triflic acid, sulfonic acids, alkyl phosphonic acids, phosphoric acid, and formic acid;
and,
a porous solid component.

2. The catalyst system according to claim 1 , wherein the homogeneous acid catalyst is a sulfonic acid that is selected from methylsulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid, perfluorooctanesulfonic acid, trihydroxysilylpropane sulfonic acid, and trihydroxysilylethylsulfonic acid.

3. The catalyst system according to claim 1 , wherein the solid component has alkyl sulfonic acid groups, hydroxyl groups, or both alkyl sulfonic acid groups and hydroxyl groups on a surface of the solid component, in pores of the solid component, or on both a surface and in pores of the solid component.

4. The catalyst system according to claim 3 , wherein the solid component is a porous silica material.

5. The catalyst system according to claim 1 , wherein the solid component has a surface area of from about 250 to about 900 m 2 /g and a pore volume of from about 0.2 to 1 cc/g.

6. The catalyst system according to claim 1 , wherein the amount of homogeneous acid catalyst component present in the catalyst system is from: about 10 ppm to about 25 wt %; from about 50 ppm to about 20 wt %; from about 1 wt % to about 15 wt %; or from about 2 wt % to about 10 wt %.

7. A process for the carbonylation of an aldehyde to form a carboxylic acid or derivative thereof comprising the steps of contacting the catalyst system of claim 1 with carbon monoxide, water, and the aldehyde.

8. The process according to claim 7 for the production of glycolic acid by the reaction of carbon monoxide, water, and formaldehyde.

9. The process according to claim 8 , wherein the water is present in an amount from the stoichiometric requirement to a molar ratio of about 4:1 water:formaldehyde.

10. The process according to claim 8 , wherein the reaction is carried out in the presence of a solvent.

11. The process according to claim 10 , wherein the solvent is, water, a carboxylic acid, or a sulfone.

12. The process according to claim 10 , wherein the solvent is glycolic acid or polyglycolide.

13. The process according to claim 8 , wherein the process is carried out at a temperature of from about 50° C. to about 400° C.

14. The process according to claim 8 , wherein the process is carried out a pressure of from about 1 to about 1000 bara.

15. The process according to claim 8 , wherein the amount of homogeneous acid catalyst component present in the catalyst system may be varied during the process.

16. The process according to claim 8 , wherein the process is carried out in a continuous flow configuration or batch-wise.

17. The process according to claim 8 , wherein the process is carried out at a temperature of from about 100° C. to about 250° C.

18. The process according to claim 8 , wherein the process is carried out a pressure of from about 10 to 200 bara.

Assignees

• Johnson Matthey Davy Technologies Ltd

Inventors

• Jackson Simon Wayne
• Snaith Adam Armour
• Tuck Michael William Marshall
• Watson David John

Classifications

• B01J21/08 Primary

  Silica · CPC title

• B01J2229/37

  Acid treatment · CPC title

• B01J14/00 Primary

  Chemical processes in general for reacting liquids with liquids; Apparatus specially adapted therefor (B01J8/00, B01J19/08 take precedence) · CPC title

• C07C51/12

  on an oxygen-containing group in organic compounds, e.g. alcohols · CPC title

• B01J27/02 Primary

  Sulfur, selenium or tellurium; Compounds thereof · CPC title