Process for the production of glycolic acid

Patent metadata

Field	Value
Publication number	US-10640443-B2
Application number	US-201716332853-A
Country	US
Kind code	B2
Filing date	Sep 15, 2017
Priority date	Sep 16, 2016
Publication date	May 5, 2020
Grant date	May 5, 2020

Abstract

A process for the production of glycolic acid or a derivative thereof comprises: reacting formaldehyde with carbon monoxide and water in a carbonylation reactor in the presence of a sulfurcatalyst, said reactor operating under suitable conditions, such that glycolic acid is formed; recovering a first product stream comprising glycolic acid, impurities and a sulfur species in the carbonylation reactor; passing the first product stream to an esterification reactor where it is subjected to esterification to form an alkylglycolate and wherein the esterification is catalysed by the sulfur species recovered in the first product stream; recovering a second product stream comprising the alkylglycolate, sulfur species and impurities from the esterification reactor; separating the sulfur species from the second product stream and recycling it to the carbonylation reactor in step (a) to form a sulphur depleted second product stream; separating the alkylglycolate from the sulphur depleted second product stream in a distillation zone; and recovering the alkylglycolate and converting the alkylglycolate to glycolic acid.

First claim

The invention claimed is:

1. A process for the production of glycolic acid or a derivative thereof comprising:
(a) reacting formaldehyde with carbon monoxide and water in a carbonylation reactor in the presence of a sulfur catalyst to form glycolic acid;
(b) recovering a first product stream comprising glycolic acid, impurities, and a sulfur species in the carbonylation reactor;
(c) passing the first product stream to an esterification reactor where it is subjected to esterification to form an alkylglycolate and wherein the esterification is catalysed by the sulfur species recovered in the first product stream;
(d) recovering a second product stream comprising the alkylglycolate, sulfur species, and impurities from the esterification reactor;
(e) separating the sulfur species from the second product stream and recycling it to the carbonylation reactor to form a sulphur depleted second product stream;
(f) separating the alkylglycolate from the sulphur depleted second product stream in a distillation zone; and
(g) recovering the alkylglycolate and converting the alkylglycolate to glycolic acid.

2. The process according to claim 1 , wherein the alkylglycolate is converted to glycolic acid in an hydrolysis reactor.

3. The process according to claim 1 , wherein the molar ratio of water:formaldehyde is about 4:1.

4. The process according to claim 1 , wherein a solvent is used in the carbonylation reactor.

5. The process according to claim 4 , wherein the solvent is propionic acid or a sulphone.

6. The process according to claim 5 , wherein the solvent is 2,3,4,5-tetrahydrothiophene-1,1-dioxide.

7. The process according to claim 1 , wherein the carbonylation reactor is operated at a temperature in the range of from about 50° C. to about 400° C., and at a pressure in the range of from about 1 to about 1000 bara (about 0.1 to about 100 MPa).

8. The process according to any one of claim 1 , wherein the first product stream is passed to a lights separation zone.

9. The process according to claim 8 , wherein the light separation zone is operated at a reboiler temperature of about 140° C. to about 160° C., an overhead temperature of about 75° C. to about 85° C., and a pressure of about 1.8 bara to about 2.2 bara.

10. The process according to claim 8 , wherein a low boiling point alkanol is supplied to the lights separation zone.

11. The process according to claim 8 , wherein an overhead recovered from the lights separation zone is passed to a water separation zone.

12. The process according to claim 11 , wherein an overhead from the water separation zone is fed to a formaldehyde separation column.

13. The process according to claim 1 , wherein the esterification is carried out at a temperature of from about 90° C. to about 150° C.

14. The process according to claim 1 , wherein the esterification reactor is operated at a pressure of from about 3 bara to about 7 bara.

15. The process according to claim 1 , wherein the sulfur species is removed prior to the sulfur species depleted second product stream being treated to recover the alkyl glycolate.

16. The process according to claim 1 , wherein the sulfur species is separated in an esterification flash drum and recovered in a sulfur species stream.

17. The process according to claim 16 , wherein the esterification flash drum is operated at a temperature of from about 140° C. to about 160° C., and at a pressure of about 1.5 to about 2.0 bara.

18. The process according to claim 16 , wherein the sulfur species is recycled to the carbonylation reactor.

19. The process according to claim 16 , wherein the sulfur species stream is passed to a recycle column.

20. The process according to claim 19 , wherein water is added to the bottom of the recycle column.

21. The process according to claim 1 , wherein the second product stream, or a sulfur-depleted second product stream, is passed to an ester distillation column.

22. The process according to claim 21 , wherein the ester distillation column is carried out at a pressure of about 0.2 bara to about 0.4 bara.

23. The process according to claim 21 , wherein an overhead temperature in the ester distillation column is about 60° C. to about 65° C., and a bottom temperature is about 130° C. to about 140° C.

24. The process according to claim 1 , wherein the alkylglycolate is converted to glycolic acid in a hydrolysis reactor.

25. The process according to claim 24 , wherein the hydrolysis reactor is a reactive distillation column.

26. The process according to claim 24 , wherein a catalyst is added to the reactive distillation column.

27. The process according to claim 1 , wherein the alkylglycolate is converted to glycolic acid by ion exchange.

Assignees

• Johnson Matthey Davy Technologies Ltd

Inventors

• Roberts Dena
• Watson David John
• Swinney John

Classifications

• C07C67/54

  by distillation · CPC title

• C07C51/09 Primary

  from carboxylic acid esters or lactones · CPC title

• C07C69/675

  of saturated hydroxy-carboxylic acids · CPC title

• C07C51/12 Primary

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

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title