Solutions of trialkali metal salts of MGDA with an excess of L-enantiomer, their manufacture and use

Patent metadata

Field	Value
Publication number	US-9873659-B2
Application number	US-201515516589-A
Country	US
Kind code	B2
Filing date	Oct 7, 2015
Priority date	Oct 17, 2014
Publication date	Jan 23, 2018
Grant date	Jan 23, 2018

Abstract

Aqueous solution containing in the range of from 60.5 to 75% by weight of a mixture of trialkalimetal salts of the L-and D-enantiomers of methyl glycine diacetic acid (MGDA), said mixture containing predominantly the respective L-isomer with an enantiomeric excess (ee) in the range of from 3 to 97%, wherein said trialkali metal salts have the general formula (I) [CH 3 —CH(COO)—N(CH 2 —COO) 2 ]K 3−x Na x (I) wherein x is in the range of from zero to 2.9.

First claim

The invention claimed is:

1. An aqueous solution comprising in the range of from 60.5 to 75% by weight of a mixture of trialkali metal salts of the L- and D-enantiomers of methyl glycine diacetic acid (MGDA), said mixture comprising predominantly the respective L-enantiomer with an enantiomeric excess (ee) in the range of from 3 to 97%, wherein said trialkali metal salts have the general formula (I)
[CH 3 —CH(COO)—N(CH 2 —COO) 2 ]K 3−x Na x   (I)

wherein x is in the range of from zero to 2.9.

2. The aqueous solution according to claim 1 , wherein the enantiomeric excess (ee) is in the range of from 12.5 to 75%.

3. The aqueous solution according to claim 1 , further comprising 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, diglycolic acid, propionic acid, acetic acid and their respective alkali metal or mono- or diammonium salts, the percentage referring to the total solids content.

4. The aqueous solution according to claim 1 , wherein said aqueous solution further comprises at least one inorganic salt selected from the group consisting of alkali metal hydroxides and alkali metal carbonates.

5. The aqueous solution according to claim 1 , further comprising a dialkali metal salt of general formula (II)
[CH 3 —CH(COO)—N(CH 2 —COO) 2 ]K 2−y Na y H  (II)

wherein y is in the range of from zero to 2.0.

6. A process for making the aqueous solution of claim 1 , comprising the steps of
(a) dissolving a mixture of L-alanine and its alkali metal salt in water,
(b) converting said mixture of L-alanine and its alkali metal salt with formaldehyde and hydrocyanic acid or alkali metal cyanide to a dinitrile,
(c) saponification of the dinitrile resulting from step (b) in two steps (c1) and (c2) at different temperatures, employing stoichiometric amounts of alkali metal hydroxide or an excess of 1.01 to 1.5 moles of alkali metal hydroxide per molar sum of COOH groups and nitrile groups of the dinitrile from step (b),
wherein said alkali metal salt from step (a) and alkali metal hydroxides from step (c) bear different cations.

7. The process according to claim 6 , 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 175 to 195° C.

8. The process according to claim 6 wherein step (c2) has an average residence time in the range of from 10 to 70 minutes.

9. The process according to claim 6 , 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).

10. The process according to claim 6 wherein step (c2) is carried out at a higher pressure than step (c1).

11. The process according to claim 6 , 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 50 to 150° C. with an average residence time of 30 minutes to 8 hours.

12. A detergent composition comprising 1 to 50% by weight of the aqueous solution according to claim 1 , based on a total solids content of the detergent composition.

13. The aqueous solution according to claim 1 , which is in fully or partially neutralized form, said neutralization being performed with an organic or inorganic acid.

14. A mixture of trialkali metal salts of the L- and D-enantiomers of methyl glycine diacetic acid (MGDA), said mixture comprising predominantly the respective L-enantiomer with an enantiomeric excess (ee) in the range of from 3 to 97%, wherein said trialkali metal salts have the general formula (II)
[CH 3 —CH(COO)—N(CH 2 —COO) 2 ]K 3−x Na x   (II)

wherein x is in the range of from zero to 2.9.

Assignees

• Basf Se

Inventors

• Reinoso Garcia Marta
• Franzke Constanze
• Stamm Armin

Classifications

• C07C229/16 Primary

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

• C11D3/046

  Salts · CPC title

• C07C227/44

  Stabilisation; Use of additives · CPC title

• C07C227/26

  from compounds containing carboxyl groups by reaction with HCN, or a salt thereof, and amines, or from aminonitriles · CPC title

• C11D3/33 Primary

  Amino carboxylic acids · CPC title