Process for preparing esters of lactic acid, and 2-hydroxy-3-butenoic acid or alpha-hydroxy methionine analogues from sugars

Patent metadata

Field	Value
Publication number	US-2017334844-A1
Application number	US-201515525450-A
Country	US
Kind code	A1
Filing date	Nov 12, 2015
Priority date	Nov 28, 2014
Publication date	Nov 23, 2017
Grant date	—

Abstract

A continuous flow process for the preparation of one or more esters of lactic acid and 2-hydroxy-3-butenoic acid or α-hydroxy methionine analogues from a sugar in the presence of a solid Lewis acid catalyst and a solvent comprising an organic solvent and water. The invention provides a means for stabilizing a Lewis acid catalyst for use in a continuous reaction process wherein the water is present in an amount of up to or equal to 10 vol. % of the organic solvent.

First claim

1 . A continuous flow process for the preparation of one or more esters of lactic acid and 2-hydroxy-3-butenoic acid or an α-hydroxy methionine analogue from a sugar in the presence of a solid Lewis acid catalyst and a solvent comprising an organic solvent and water, wherein the water is present in an amount of up to or equal to 10 vol. % of the organic solvent.

2 . A process according to claim 1 , wherein a compound comprising sulfur is present in addition to a solid Lewis acid catalyst and a solvent comprising an organic solvent and water if an α-hydroxy methionine analogue is desired.

3 . A process according to claim 2 , wherein the compound comprising sulfur is selected from the group consisting of C 1 -C 5 alkyl thiol, C 1 -C 5 alkyl thiol salts, dimethylmercaptan and dimethyl disulfide.

4 . A process according to claim 1 , wherein the yield of the one or more lactic acid esters decreases by up to 0.25% per hour on stream on average.

5 . A process according to claim 1 , wherein the yield of the one or more lactic acid esters decreases by up to 0.10% per hour on average.

6 . A process according to claim 1 , wherein the yield of the one or more lactic acid esters decreases by up to 5% after 50 hours on stream.

7 . A process according to claim 1 , wherein the yield of the one or more lactic acid esters is greater than 40% after 50 hours on stream.

8 . A process according to claim 1 , wherein the solid Lewis acid catalyst is calcined after 450 hours.

9 . A process according to claim 1 , wherein the solid Lewis acid catalyst framework structure is selected from the group consisting of BEA, MFI, FAU, MOR, FER, MWW, MCM-41 and SBA-15.

10 . A process according to claim 1 , wherein the solid Lewis acid comprises an active metal selected from one or more of the group consisting of Sn, Ti, Pb, Zr, Ge and Hf.

11 . A process according to claim 1 , wherein the solid Lewis acid catalyst is selected from the group consisting of Sn-BEA, Sn-MFI, Sn-FAU, Sn-MOR, Sn-MWW, Sn-MCM-41 and Sn-SBA-15.

12 . A process according to claim 1 , wherein the solid Lewis acid catalyst comprises Sn and the loss of Sn from the solid Lewis acid catalyst is less than or equal to 0.11% of the initial amount of Sn per hour on stream.

13 . A process according to claim 1 , wherein the solid Lewis acid catalyst comprises Sn and the loss of Sn from the solid Lewis acid catalyst is less than 8% of the initial amount of Sn after 50 hours on stream.

14 . A process according to claim 1 , wherein the yield of 2-hydroxy-3-butenoic acid ester is greater than 12% after 50 hours on stream.

15 . A process according to claim 1 , wherein the yield of α-hydroxy methionine analogue ester is greater than 20% after 10 hours on stream.

16 . A process according to claim 1 , wherein the sugar is selected from one or more of the group consisting of glucose, fructose, mannose, sucrose, xylose, erythrose, erythrulose, threose and glycolaldehyde.

17 . A process according to claim 1 , wherein an alkaline earth metal or alkali metal ion is present in the process.

18 . A 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 and isopropanol.

19 . A process according to claim 1 , wherein the temperature of the process is from 140° C. to 200° C.

20 . A process according to claim 1 , wherein at least a fraction of the water is introduced to the solvent by mixing the organic solvent with an aqueous sugar solution.

21 . A process according to claim 1 , wherein the aqueous sugar solution is a sugar syrup with a sugar dry matter content of 30% or higher.

Assignees

• Haldor Topsee As
• Haldor Topsoe As

Inventors

• Sadaba Zubiri Irantzu
• Taarning Esben

Classifications

• C07C69/732

  of unsaturated hydroxy carboxylic acids · CPC title

• C07C69/68

  Lactic acid esters · CPC title

• C07C319/18 Primary

  by addition of thiols to unsaturated compounds · CPC title

• C07C67/44

  by oxidation-reduction of aldehydes, e.g. Tishchenko reaction · CPC title

• C07C67/475

  by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of [IMAGE cpc-sch-C07C-0963.gif] groups between different molecules · CPC title