Mixtures of chelating agents including an L-enantiomer-rich MGDA, and process for making such mixtures

Patent metadata

Field	Value
Publication number	US-10189772-B2
Application number	US-201615554492-A
Country	US
Kind code	B2
Filing date	Mar 1, 2016
Priority date	Mar 11, 2015
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

Abstract

Mixtures comprise (A) 90 to 99.9% by weight of 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, said mixture containing predominantly the respective L-enantiomer with an enantiomeric excess (ee) in the range of from 10 to 99%, and (B) in total 0.1 to 10% by weight of the diacetic acid derivative of at least one amino acid selected from valine, leucine, isoleucine, and tyrosine, as free acids or respective mono-, di- or trialkali metal or mono-, di- or triammonium salts, percentages referring to the sum from (A) and (B).

First claim

The invention claimed is:

1. A mixture, comprising:
(A) 90 to 99.9% by weight of 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, said mixture containing predominantly the respective L-enantiomer with an enantiomeric excess (ee) in the range of from 10 to 99%, and
(B) in total 0.1 to 10% by weight of a diacetic acid derivative of at least one amino acid selected from the group consisting of valine, leucine, isoleucine, and tyrosine, as free acids or respective mono-, di- or trialkali metal or mono-, di- or triammonium salts,
wherein the percentages refer to the sum from (A) and (B).

2. The mixture according to claim 1 , wherein the enantiomers of (A) are selected from the trisodium salts of MGDA.

3. The mixture according to claim 1 , wherein mixture (A) is predominantly the L-enantiomer with an enantiomeric excess (ee) in the range of from 12.5 to 85%.

4. The mixture according to claim 1 , containing in the range 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. The mixture according to claim 1 , wherein (B) is selected from the group consisting of a mixture of enantiomers of valine.

6. An aqueous solution, containing in the range of from 43 to 70% by weight of a mixture according to claim 1 .

7. The aqueous solution according to claim 6 , wherein said aqueous solution additionally contains 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 of claim 1 , wherein said process comprises
(a) dissolving a mixture of L-alanine and at least one further amino acid selected from the group consisting of valine, leucine, isoleucine, and tyrosine in water or an aqueous solution of an alkali metal hydroxide,
(b) converting the respective dissolved amino acids and their respective alkali metal salts with formaldehyde and hydrocyanic acid or alkali metal cyanide to the respective dinitriles,
(c) saponification of the dinitriles resulting from step (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 step (b).

9. The process according to claim 8 , wherein step (c1) is carried out at a temperature in the range of from 20 to 80° C. and step (c2) is carried out at a temperature in the range of from 80 to 200° C., the temperature in step (c2) being higher than in step (c1).

10. The process according to claim 8 , wherein step (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 step (b).

11. A laundry detergent composition or a detergent composition for a cleaner, comprising:
the aqueous solution according to claim 6 .

12. The laundry detergent composition or the detergent composition for the cleaner according to claim 11 ,
wherein said aqueous solution is in fully or partially neutralized form after neutralizing with an inorganic acid.

13. The laundry detergent composition or the detergent composition for the cleaner according to claim 11 ,
wherein said aqueous solution is in fully or partially neutralized form after neutralizing with an organic acid.

14. A method for producing a laundry detergent composition or a detergent composition for a cleaner, comprising:
fully or partially neutralizing the aqueous solution according to claim 6 with an inorganic acid.

15. A method for producing a laundry detergent composition or a detergent composition for a cleaner, comprising:
fully or partially neutralizing the aqueous solution according to claim 6 with an organic acid.

Assignees

• Basf Se

Inventors

• Franzke Constanze
• Jaekel Frank
• Sueling Carsten

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

• C11D3/33 Primary

  Amino carboxylic acids · CPC title

• C07B2200/07

  Optical isomers · 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

• C11D3/0047

  pH regulated compositions · CPC title