Mixtures of MGDA enantiomers, and process for making such mixtures

Patent metadata

Field	Value
Publication number	US-9802884-B2
Application number	US-201415021398-A
Country	US
Kind code	B2
Filing date	Sep 5, 2014
Priority date	Sep 13, 2013
Publication date	Oct 31, 2017
Grant date	Oct 31, 2017

Abstract

Mixture of L- and D-enantiomers of methyl glycine diacetic acid (MGDA) or its respective mono-, di or trialkali metal or mono-, di- or triammonium salts, said mixture containing predominantly the respective L-isomer with an enantiomeric excess (ee) in the range of from 10 to 75%.

First claim

The ivention claimed is:

1. A mixture of L- and D-enantiomers of methyl glycine diacetic acid (MGDA) or its respective mono-, di or trialkali metal or mono-, di- or triammonium salts, the mixture comprising predominantly the respective L-isomer with an enantiomeric excess (ee) in the range of from 10 to 75%.

2. The mixture according to claim 1 , the enantiomers being selected from the trisodium salts of MGDA.

3. The mixture according to claim 1 , the mixture being predominantly the L-isomer with an enantiomeric excess (ee) in the range of from 12.5 to 60%.

4. The mixture according to claim 1 , comprising of from 0.1 to 10% by weight of one or more optically inactive impurities, at least one of the impurities being selected from the group consisting of iminodiacetic acid, formic acid, glycolic acid, propionic acid, acetic acid and their respective alkali metal or mono-, di- or triammonium salts.

5. An aqueous solution comprising of from 40 to 60% by weight of a mixture according to claim 1 .

6. The aqueous solution according to claim 5 , wherein the aqueous solution is free from organic polymer.

7. The aqueous solution according to claim 5 , wherein the aqueous solution additionally comprises at least one inorganic salt selected from the group consisting of alkali metal hydroxides and alkali metal carbonates.

8. A process for making a mixture according to claim 1 , comprising
(a) dissolving a mixture of L-alanine and its alkali metal salt in water,
(b) converting the mixture of L-alanine and its alkali metal salt with formaldehyde and hydrocyanic acid or alkali metal cyanide to a dinitrile,
(c) performing saponification of the dinitrile resulting from (b) in two steps (c1) and (c2) at different temperatures, 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 of the dinitrile from (b).

9. The process according to claim 8 , wherein (c1) is carried out at a temperature in the range of from 20 to 80° C. and (c2) is carried out at a temperature in the range of from 175 to 195° C.

10. The process according to claim 8 , wherein (c2) has an average residence time in the range of from 20 to 60 minutes.

11. The process according claim 8 , wherein (c2) is carried out with an excess of base of 1.01 to 1.2 moles of hydroxide per molar sum of COOH and nitrile groups of the dinitrile from (b).

12. The process according to claim 8 , wherein (c2) is carried out at a higher pressure than (c1).

13. The aqueous solution according to claim 5 , wherein the aqueous solution is suitable for the manufacture of laundry detergent compositions and of detergent compositions for cleaners.

14. The aqueous solution according to claim 1 , wherein the aqueous solution is suitable in fully or partially neutralized form for the manufacture of laundry detergent compositions or of detergent compositions for cleaners, the neutralization being performed with an inorganic acid.

15. The aqueous solution according to claim 1 , wherein the aqueous solution is suitable in fully or partially neutralized form for the manufacture of laundry detergent compositions or of detergent compositions for cleaners, the neutralization being performed with an organic acid.

Assignees

• Basf Se

Inventors

• Reinoso Garcia Marta
• Hartmann Markus
• Schmidt Kati
• Rauls Matthias
• Schmidt Thomas
• Klingelhoefer Paul
• Oftring Alfred
• Kadam Somnath Shivaji

Classifications

• C07C229/16

  to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids · CPC title

• C07C253/00

  Preparation of carboxylic acid nitriles (of cyanogen or compounds thereof C01C3/00) · CPC title

• C07C227/18 Primary

  by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters · CPC title

• C11D3/33

  Amino carboxylic acids · CPC title

• C07C229/24 Primary

  having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid · CPC title