IP Library Granted Patent US 11,685,759
Granted Patent B2
US 11,685,759 · App. 17/286,474 · Granted Jun 27, 2023

Method for obtaining crystalline 2′-fucosyllactose

Inventors: Michael Puhl (Ludwigshafen am Rhein, DE); Sebastian Wloch (Ludwigshafen am Rhein, DE); Peter Oedman (Saint Joseph, MO); Anne-Catrin Letzel (Ludwigshafen am Rhein, DE); Hartwig Schroeder (Ludwigshafen am Rhein, DE); Jacek Malisz (Ludwigshafen am Rhein, DE); Daniel Seibert-Ludwig (Ludwigshafen am Rhein, DE); Emiel Jan Kappert (Ludwigshafen am Rhein, DE); Chung Huan Wong (Ludwigshafen am Rhein, DE); Michael Barros Gross (Ludwigshafen am Rhein, DE); Martin Viertelhaus (Ludwigshafen am Rhein, DE)
Assignee: BASF SE
C07H1/08C07H3/06C07B2200/13
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Quick Facts
Patent No.
US 11,685,759
App. No.
17/286,474
Granted
Jun 27, 2023
Kind
B2
Abstract

The present invention relates to a method for obtaining crystalline 2′-fucosyllactose from a 2′-FL raw material, which contains 2′-FL as a main constituent and at least 0.5% by weight, frequently at least 1% by weight, in particular at least 2% by weight, more particularly at least 5% by weight, and especially at least 8% by weight,based on the total amount of mono-and oligosaccharides in the raw material, of one or more mono- or oligosaccharides different from 2′-FL, where the method comprises a)providing a solution of the 2′-FL raw material in water, which does not contain more than 10% by weight, preferably not more than 7% by weight, more preferably not more than 5% by weight of organic solvents, based on the total amount of water; b) effecting the crystallization of 2′-FL from the solution provided in step a) by inducing conditions of a controlled super saturation in the solution; and c) separating crystalline 2′-FL from the mother liquor, and where during controlled supersaturation in step b) not more than 10% by weight, preferably not more than 7% by weight, more preferably not more than 5% by weight of organic solvents are present, based on the total amount of water present during step b).

Claims (27)

1. Method for selectively obtaining crystalline form A or form B of 2′-fucosyllactose from a 2′-fucosyllactose raw material, which contains 2′-FL as a main constituent and at least 0.5% by weight, based on the total amount of mono-and oligosaccharides in the raw material, of one or more mono-or oligosaccharides different from 2′-fucosyllactose, where the method comprises

a) providing a solution of the 2′-fucosyllactose raw material in water, which does not contain more than 10% by weight of organic solvents, based on the total amount of water;

b) effecting the crystallization of 2′-fucosyllactose at a temperature in the range from 0 to 52° C. by inducing conditions of a controlled supersaturation in the solution, where form A or form B of 2′-fucosyllactose is obtained and a water miscible organic solvent is added to the suspension when the crystallization is almost complete; and

c) separating crystalline form A or form B of 2′-fucosyllactose from the mother liquor;

and where during controlled supersaturation in step b) not more than 10% by weight of organic solvents are present, based on the total amount of water present during step b).

2. The method of claim 1 , where the conditions of a controlled supersaturation are induced in a manner such that the ratio c:c* of the concentration c of dissolved 2′-fucosyllactose to the equilibrium solubility c* of 2′-fucosyllactose under the conditions of controlled supersaturation is from more than 1:1 to 1.5:1, thereby effecting the crystallization of 2′-fucosyllactose.

3. The method of claim 1 , where the controlled supersaturation is induced by removing water and/or by cooling.

4. The method of claim 1 , where the crystallization is effected in the presence of solid 2′-fucosyllactose and is carried out as an evaporation crystallization.

5. The method of claim 1 , where the concentration of dissolved 2′-fucosyllactose under the conditions of controlled supersaturation is in the range from 400 to 750 g/L.

6. The method of claim 1 , where the 2′-fucosyllactose raw material contains at least one oligosaccharide selected from lactose, difucosyllactose, lactulose and fucosylated lactulose.

7. The method of claim 1 , where the solution of 2′-fucosyllactose provided in step a) does not contain more than 5000 ppm of solid insoluble material, based on the total weight of the solution.

8. The method of claim 1 , where the aqueous solution of 2′-fucosyllactose provided in step a) is obtained by a fermentation process.

9. The method of claim 1 , where the aqueous solution of 2′-fucosyllactose provided in step a) is fed to a continuously operated crystallization apparatus, which contains an aqueous suspension of 2′-fucosyllactose crystals.

10. The method of claim 9 , where step b) comprises

b1) continuously feeding the aqueous solution of 2′-fucosyllactose to a crystallization apparatus containing an aqueous suspension of 2′-fucosyllactose;

b2) continuously removing water from the aqueous suspension of 2′-fucosyllactose contained in the crystallization apparatus to maintain conditions of controlled supersaturation;

b3) continuously removing the aqueous suspension of 2′-fucosyllactose from the crystallization apparatus.

11. The method of claim 9 , where a portion of the aqueous suspension of 2′-fucosyllactose removed in step b3) is mixed with the aqueous solution of 2′-fucosyllactose of step b1) and the mixture is fed back it into the crystallization apparatus.

12. The method of claim 1 , where the solution of the 2′-fucosyllactose raw material is subjected to a crystallization in batch- or fed-batch operated crystallization apparatus.

13. The method of claim 1 , where the crystallization is carried out at a temperature in the range from 20 to 52° C. in the presence of solid 2′-fucosyllactose and where the crystallization is effected from an aqueous supersaturated solution under the conditions of controlled supersaturation, where the aqueous supersaturated solution has a concentration of dissolved 2′-fucosyllactose in the range from 410 to 630 g/L.

14. The method of claim 1 , where at least a portion of the mother liquor obtained in step c) is subjected to a crystallization of 2′-fucosyllactose by inducing conditions of a controlled supersaturation in the mother liquor.

15. The method of claim 14 , where at least a portion of the mother liquor is mixed with the solution of the 2′-fucosyllactose raw material prior to carrying out step b).

16. The method of claim 1 , which comprises a first crystallization step and a second crystallization step,

where the aqueous solution of the 2′-fucosyllactose raw material provided in step a) is subjected to a crystallization of the second crystallization step,

where in the second crystallization step the crystallization of 2′-fucosyllactose is effected by inducing conditions of a controlled supersaturation in the solution according to step b), where the aqueous suspension of the crystalline 2′-fucosyllactose obtained in the second crystallization step is subjected to a solid-liquid separation to obtain a crystalline 2′-fucosyllactose and a mother liquor,

where the mother liquor obtained in the solid-liquid separation is introduced into the first crystallization step.

17. The method of claim 16 , where the crystalline 2′-fucosyllactose obtained in the first crystallization step is dissolved in the aqueous solution of the 2′-fucosyllactose raw material prior to carrying out the second crystallization step.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 20, 2026
From: BASF SE
To: DSM-FIRMENICH SWITZERLAND AG
Reel/Frame 075726/0732 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 20, 2026
From: DSM-FIRMENICH SWITZERLAND AG
To: DSM IP ASSETS B.V.
Reel/Frame 075726/0756 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 18, 2021
From: PUHL, MICHAEL; WLOCH, SEBASTIAN; OEDMAN, PETER; LETZEL, ANNE-CATRIN; SCHROEDER, HARTWIG; MALISZ, JACEK; SEIBERT-LUDWIG, DANIEL; KAPPERT, EMIEL JAN; WONG, CHUNG HUAN; BARROS GROSS, MICHAEL; VIERTELHAUS, MARTIN
To: BASF SE
Reel/Frame 055951/0516 →
Priority Claims (3)
EP 18201228 · Oct 18, 2018 · regional
EP 18206491 · Nov 15, 2018 · regional
EP 17193228 · Aug 23, 2019 · regional
Continuity (1)
Related Publication 20210388014A1 · Dec 16, 2021