Method for producing a crystalline solid from glycine-N,N-diacetic acid derivatives with sufficiently reduced hygroscopicity

Patent metadata

Field	Value
Publication number	US-9376649-B2
Application number	US-201013391397-A
Country	US
Kind code	B2
Filing date	Aug 25, 2010
Priority date	Aug 26, 2009
Publication date	Jun 28, 2016
Grant date	Jun 28, 2016

Abstract

The present invention relates to a process for preparing a crystalline solid from glycine-N,N-diacetic acid derivatives (e.g., MGDA) of sufficiently low hygroscopicity, which is characterized in that at least one crystalline compound of the formula I is introduced as seed, and a spray granulation is carried out with at least one compound of the formula I, preferably followed by a heat treatment.

First claim

The invention claimed is:

1. A process for preparing a crystalline solid, the process comprising spray granulating an aqueous solution of a liquid raw material on a crystalline seed material to obtain the crystalline solid, and
heat-aftertreating the crystalline solid,
wherein the crystalline seed material, the liquid raw material, and the crystalline solid each comprise a glycine-N,N-diacetic acid derivative of formula (I)

wherein R is:
a C 1 to C 30 alkyl or a C 2 to C 30 alkenyl, optionally having up to 5 substituents selected from a hydroxyl group, a formyl group, a C 1 to C 4 alkoxy group, a phenoxy group and a C 1 to C 4 alkoxycarbonyl group and optionally having up to 5 nonadjacent oxygen atoms;
an alkoxylate moiety of formula (II)
—(CH 2 ) k —O—(A 1 O) m -(A 2 O) n —Y  (II)

in which A 1 and A 2 each independently are 1,2-alkylene groups having 2 to 4 C atoms, Y is hydrogen, C 1 to C 12 alkyl, phenyl or C 1 to C 4 alkoxycarbonyl, k is 1, 2 or 3, and m and n are each integers of 0 to 50, a sum of m+n being at least 4;
a phenylalkyl group having 1 to 20 C atoms in the alkyl part of the group;
a five- or six-membered, unsaturated or saturated, heterocyclic ring having up to three heteroatoms from the group consisting of nitrogen, oxygen, and sulfur, which may additionally be benzofused, it being possible for any phenyl ring and heterocyclic ring of R additionally to have up to three substituents selected from the group consisting of a C 1 to C 4 alkyl group, a hydroxyl group, a carboxyl group, a sulfo group and a C 1 to C 4 alkoxycarbonyl group; or
R is a radical of formula (III)

where A is a C 1 to C 12 alkylene bridge or a chemical bond, and each M independently is hydrogen, an alkali metal, an alkaline earth metal, ammonium or substituted ammonium in a corresponding stoichiometric amount.

2. The process according to claim 1 , wherein the process is performed in a granulator and the process further comprises removing a part of the crystalline solid from the granulator, grinding the crystalline solid to obtain additional crystalline seed material, and introducing the additional crystalline seed material into the granulator.

3. The process according to claim 1 , wherein R is C 1 to C 20 alkyl, C 2 to C 20 alkenyl or a radical of formula (III)

4. The process according to claim 1 , wherein the glycine-N,N-diacetic acid derivative is α-alanine-N,N-diacetic acid (MGDA) or an alkali metal salt, an ammonium salt or a substituted amine salt thereof.

5. The process of claim 1 , wherein R is C 1 to C 20 alkyl.

6. The process of claim 1 , wherein R is C 2 to C 20 alkenyl.

7. The process of claim 1 , wherein R is an alkoxylate moiety of formula (II)
—(CH 2 ) k —O—(A 1 O) m -(A 2 O) n —Y  (II).

8. The process of claim 1 , wherein R is a radical of formula (III)

9. The process of claim 8 , wherein A is hexamethylene, octamethylene, 1,2-ethylene, or 1,4-butylene.

10. The process of claim 1 , wherein the spray granulating comprises an air feed temperature of 90-160° C.

11. The process of claim 1 , wherein the spray granulating comprises an air departure temperature of 40-110° C.

12. The process of claim 1 , wherein the crystalline solid temperature obtained by the spray granulating is 40-110° C.

13. The process of claim 1 , wherein the spray granulating comprises a spraying air temperature of 70-110° C.

14. The process of claim 1 , wherein the spray granulating comprises a spraying air pressure of 1-6 bar.

15. The process of claim 1 , wherein the liquid raw material is at a temperature of 50-95° C.

16. The process of claim 1 , wherein the crystalline seed material is present on a fluidized bed and the fluidized bed has a temperature of 50-90° C.,
and the heat aftertreating comprises raising the bed temperature to 90-130° C. over a period of about an hour, and holding the bed temperature at 90-130° C. for about an hour.

17. The process of claim 1 , wherein the obtained crystalline solid preserves its consistency as a powder or granules over a period of at least one day when stored at 25° C. and a relative humidity of 76%.

18. A process for preparing a crystalline solid, the process comprising spraying a crystalline seed material with a liquid raw material to obtain the crystalline solid,
wherein the crystalline seed material, the liquid raw material, and the crystalline solid each comprise a glycine-N,N-diacetic acid derivative of formula (I)

wherein R is:
a C 1 to C 30 alkyl or a C 2 to C 30 alkenyl, optionally having up to 5 substituents selected from a hydroxyl group, a formyl group, a C 1 to C 4 alkoxy group, a phenoxy group and a C 1 to C 4 alkoxycarbonyl group and optionally having up to 5 nonadjacent oxygen atoms;
an alkoxylate moiety of formula (II)
—(CH 2 ) k —O-(A 1 O) m -(A 2 O) n —Y  (II)

in which A 1 and A 2 each independently are 1,2-alkylene groups having 2 to 4 C atoms, Y is hydrogen, C 1 to C 12 alkyl, phenyl or C 1 to C 4 alkoxycarbonyl, k is 1, 2 or 3, and m and n are each integers of 0 to 50, a sum of m+n being at least 4;
a phenylalkyl group having 1 to 20 C atoms in an alkyl part of the group;
a five- or six-membered, unsaturated or saturated, heterocyclic ring having up to three heteroatoms from the group consisting of nitrogen, oxygen, and sulfur, which may additionally be benzofused, it being possible for any phenyl ring and heterocyclic ring of R additionally to have up to three substituents selected from the group consisting of a C 1 to C 4 alkyl group, a hydroxyl group, a carboxyl group, a sulfo group and a C 1 to C 4 alkoxycarbonyl group; or
R is a radical of formula (III)

where A is a C 1 to C 12 alkylene bridge or a chemical bond, and each M independently is hydrogen, an alkali metal, an alkaline earth metal, ammonium or substituted ammonium in a corresponding stoichiometric amount; and heat-aftertreating the crystalline solid.

Assignees

• Baranyai Andreas
• Basf Se

Inventors

• Baranyai Andreas

Classifications

• C11D7/3245

  Aminoacids · CPC title

• 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

• C07C227/42 Primary

  Crystallisation · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• C11D3/33 Primary

  Amino carboxylic acids · CPC title