PROCESS FOR MAKING MIXTURES OF ENANTIOMERS, AND MIXTURES OF ENANTIOMERS

• US 20180237728A1
• Filed: 03/02/2016
• Published: 08/23/2018
• Est. Priority Date: 03/12/2015
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: FRANZKE, Constanze, REINOSO GARCIA, Marta, BAUMANN, Robert, GREINDL, Thomas
• Granted Patent: US 10,619,125 B2
• Time in Patent Office: Days
• CPC Class Codes: C07C 227/18 by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
• CPC Class Codes: C07C 229/16 to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
• CPC Class Codes: C07C 229/24 having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
• CPC Class Codes: C07C 253/00 Preparation of carboxylic acid nitriles of cyanogen or compounds thereof C01C3/00
• CPC Class Codes: C07C 253/06 from N-formylated amino compounds
• CPC Class Codes: C07C 255/25 Aminoacetonitriles
• CPC Class Codes: C11D 3/33 Amino carboxylic acids

Abstract

Process for preparation of a mixture of methyl glycine diacetic acid (MGDA) or its respective mono-, di-, trialkali metal salt or its respective mono-, di- or tri-ammonium salt or mixtures thereof, and glutamic acid diacetic acid (GLDA) or its respective mono-, di-, tri-, or tetra-alkali metal or mono-, di-, tri- or tetra-ammonium salt or mixtures thereof, wherein said process com-prises the steps of: (a) dissolution in water of (a1) alanine in its L- or D-enantiomeric form or its respective monoalkali metal salt or mixtures thereof, and (a2) glutamic acid as L- or D-enantiomer or its respective mono-, or dialkali metal or mixtures thereof, wherein the molar ratio of alanine to glutamic acid is in the range of from 1:9 to 9:1, (b) converting the mixture obtained in step (a) with formaldehyde and hydrocyanic acid or alkali metal cyanide to the corresponding dinitriles, (c) saponification of the dinitriles resulting from step (b).

Claims

1. A process for preparing a composition comprising methyl glycine di acetic acid (MGDA) or its respective mono-, di-, trialkali metal salt or its respective mono-, di- or tri-ammonium salt or mixtures thereof, and glutamic acid diacetic acid (GLDA) or its respective mono-, di-, tri-, or tetra-alkali metal or mono-, di-, tri- or tetra-ammonium salt or mixtures thereof, the process comprising:

(a) dissolving in water

(a1) alanine in its L- or D-enantiomeric form or its respective monoalkali metal salt or mixtures thereof, and

(a2) glutamic acid as L- or D-enantiomer or its respective mono-, or dialkali metal or mixtures thereof,

wherein a molar ratio (a1) to (a2) of alanine to glutamic acid is in the range of from 1;

9 to 9;

1, to obtain a mixture;

(b) converting the mixture with formaldehyde and hydrocyanic acid or alkali metal cyanide to dinitriles; and

(c) saponifying the dinitriles, to obtain the composition.

2. The process according to claim 1, wherein the saponifying (c) is carried out in two steps (c1) and (c2) at different temperatures.

3. The process according to claim 1, wherein the saponifying (c) is carried out by employing stoichiometric amounts of hydroxide or an excess of 1.01 to 1.5 moles of hydroxide per molar sum of COOH groups and nitrile groups in the converting (b).

4. The process according to claim 1, wherein a solids content of the composition is in the range of from 40 to 70% by weight.

5. The process according to claim 1, wherein the molar ratio of (a1) to (a2) is in the range of from 2.5:

7.5 to 7.5;

2.5.

6. The process according to claim 1, wherein the composition comprises a mixture of L- and D-enantiomers of MGDA or its respective mono-, di- or tri-alkali metal or mono-, di- or tri-ammonium salt or mixtures thereof comprising predominantly the respective L-isomer with an enantiomeric excess (ee) in the range of from 10 to 95%, and L- and D-enantiomers of GLDA or its respective mono-, di-, tri-, or tetra-alkali metal or mono-, di-, tri- or tetra-ammonium salt or mixtures thereof.

7. The process according to claim 1, wherein the saponification (c) is carried out with sodium hydroxide or potassium hydroxide.

8. The process according to claim 1, wherein the converting (b) is carried out at a temperature in the range of 10 to 45°

C.

9. The process according to claim 2, wherein the saponifying (c1) is carried out at a temperature in the range of from 10 to 80°

C., and the saponifying (c2) is carried out at a temperature in the range of from 90 to 195°

C.

10. The process according to claim 2, wherein the saponifying (c2) has an average residence time in the range of from 15 to 360 minutes.

13. An aqueous solution, comprising the composition of claim 1, wherein the aqueous solution has a solids content in the range of from 40 to 70% by weight.

14. A solution, comprising MGDA and GLDA, wherein the solution is obtained from a composition formed by the process of claim 1.

15. A composition formed from the aqueous solution of claim 13, said composition being a laundry detergent composition or a detergent composition for cleaners.

11. A composition, comprising L and D-enantiomers of MGDA or its respective mono-, di- or tri-alkali metal or mono-, di- or tri-ammonium salt or mixtures thereof containing predominantly the respective L-isomer with an enantiomeric excess (ee) in the range of from 10 to 95%, and L- and D-enantiomers of GLDA or its respective mono-, di-, tri-, or tetra-alkali metal or mono-, di-, tri- or tetra-ammonium salt or mixtures thereof.

12. The composition according to claim 11, wherein a molar ratio of MGDA to GLDA or their respective salts is in the range of from 1:

9 to 9;

1.