Process for the preparation of methionine alpha-hydroxy analogues from sugars and derivatives thereof

Patent metadata

Field	Value
Publication number	US-10189778-B2
Application number	US-201615568943-A
Country	US
Kind code	B2
Filing date	Apr 29, 2016
Priority date	Apr 30, 2015
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

Abstract

A process for the preparation of methionine a-hydroxy analogue and derivatives thereof comprising contacting one or more sugars or derivatives thereof with a metallo-silicate composition in the presence of a compound comprising sulphur and a solvent.

First claim

The invention claimed is:

1. A process for the preparation of a methionine α-hydroxy analogue and derivatives thereof of the formula:
R′—S—CH 2 —CH 2 —CHOH—COO—R  (I)

wherein R is selected from the group consisting of H, C 1 -C 8 alkyl, alkaline or alkaline-earth metals; and R′ is selected from the group consisting of H and methyl; and
wherein the process comprises a step of contacting one or more sugars or derivatives thereof selected from the group consisting of glucose, fructose, galactose, mannose, sucrose, xylose, erythrose, erythrulose, threose, glycolaldehyde, methyl vinyl glycolate,vinyl glycolic acid and 2-hydroxyl-α-butyrolactone with a metallo-silicate zeotype material, in the presence of a compound comprising sulphur and a solvent, wherein the metallo-silicate zeotype material has a framework structure selected from the group consisting of BEA, MFI, FAU, MOR, and FER, with a metal and/or metal oxide component.

2. A process according to claim 1 , wherein the compound comprising sulphur is selected from the group consisting of C 1 -C 5 alkyl thiol, C 1 -C 5 alkyl thiol salt, dimethylmercaptan, dimethyl disulphide and hydrogen sulphide.

3. A process according to claim 2 , wherein the compound comprising sulphur is selected from the group consisting of methane thiol, methanethiolate alkaline salts, dimethylmercaptan, dimethyl disulphide, and hydrogen sulphide.

4. A process according to claim 1 , wherein the one or more sugars or derivatives thereof subjected to a pyrolysis step to obtain a pyrolysis product and subsequently the pyrolysis product is contacted with the metallo-silicate zeotype material in the presence of the compound comprising sulphur and the solvent.

5. The process according to claim 1 , wherein the zeotype material is one or more materials selected from the group consisting of Sn-BEA, Sn-MFI, Sn-FAU, Sn-MCM-41 and Sn-SBA-15.

6. The process according to claim 1 , wherein the solvent is selected from one or more of the group consisting of methanol, ethanol, 1-propanol, 1-butanol, 2-propanol, 2-butanol, DMSO and water.

7. The process according to claim 1 , wherein the methionine α-hydroxy analogue and derivatives thereof are selected from the group consisting of 2-hydroxy-4-(methylthio)butanoic acid, salts and esters thereof.

8. The process according to claim 1 , wherein the methionine α-hydroxy analogue and derivatives thereof are selected from the group consisting of 2-hydroxy-4-(methylthio)butanoic acid, 2-hydroxy-4-(methylthio)butanoic acid methyl ester and 2-hydroxy-4-(methylthio)butanoic acid ethyl ester.

9. The process according to claim 1 , wherein the contacting step is performed under heating.

10. The process according to claim 9 , wherein the heating temperature is between 50 and 200° C.

11. The process according to claim 9 , wherein the heating is continued for a period of from 10 minutes to 12 hours.

12. The process according to claim 1 , further comprising performing the contacting step in the presence of one or more basic components selected from the group consisting of a metal salt and polymer resin.

13. The process according to claim 1 , wherein the yield of the methionine α-hydroxy analogue and derivatives thereof are greater than the yield of methyl vinylglycolate (MVG).

14. The process according to claim 1 , wherein the process is a continuous process.

15. The process according to claim 14 , wherein the yield of the methionine α-hydroxy analogue and derivatives thereof is greater than 15%.

16. The process according to claim 14 , wherein the weight hourly space velocity is between 0.005 and 10 h −1 , preferably between 0.1 and 1 h −1 .

17. The process according to claim 1 , wherein the methionine α-hydroxy analogue and derivatives thereof are recovered.

18. The process according to claim 1 , wherein the methionine α-hydroxy analogue and derivatives thereof are recovered by purification.

19. The process according to claim 1 , wherein the methionine α-hydroxy analogue and derivatives thereof are purified by distillation.

20. The process according to claim 7 , wherein the 2-hydroxy-4-(methylthio)butanoic esters are hydrolysed.

21. A process according to claim 1 , wherein the zeotype material includes Sn which at least partially replaces aluminium in the material.

22. A process for the continuous preparation of a methionine α-hydroxy of the formula:
R′—S—CH 2 —CH 2 —CHOH—COO—R  (I)

wherein R is selected from the group consisting of H, C 1 -C 8 alkyl, alkaline or alkaline-earth metals; and R′ is selected from the group consisting of H and methyl; and
wherein the process comprises a step of contacting one or more sugars or derivatives thereof selected from the group consisting of glucose, fructose, galactose, mannose, sucrose, xylose, erythrose, erythrulose, threose, glycolaldehyde, methyl vinyl glycolate, vinyl glycolic acid and 2-hydroxy-α-butyrolactone with a Sn-zeotype material comprising a BEA, MFI, FAU, MOR and FER framework structure, in the presence of a compound comprising sulphur and an alcoholic solvent selected from the group consisting of methanol, ethanol, 1-propanol, 1-butanol, 2-propanol and 2-butanol.

23. A process for the continuous preparation of a methionine α-hydroxy of the formula:
R′—S—CH 2 —CH 2 —CHOH—COO—R  (I)

wherein R is selected from the group consisting of H, C 1 -C 8 alkyl, alkaline or alkaline-earth metals; and R′ is selected from the group consisting of H and methyl; and
wherein the process comprises contacting and heating one or more C 2 -C 6 sugars or C 2 -C 6 sugar derivatives with (1) a metal/ metal oxide containing zeolite material, (2) a compound comprising sulphur, and (3) an alcoholic solvent selected from one of methanol, ethanol, 1-propanol, 1-butanol, 2-propanol and 2-butanol, wherein the zeolite comprises a BEA, MFI, FAU, MOR or FER structure.

Assignees

• Haldor Topsoe As
• Haldor Topsoe As

Inventors

• Sadaba Zubiri Irantzu
• Taarning Esben
• Tzoulaki Despina

Classifications

• C07C323/52 Primary

  the carbon skeleton being acyclic and saturated · CPC title

• C07C321/04

  of an acyclic saturated carbon skeleton · CPC title

• C07C319/14 Primary

  of sulfides · CPC title

• A23L33/175

  Amino acids · CPC title

• A23L33/17

  Amino acids, peptides or proteins · CPC title