IP Library Granted Patent US 9,005,444
Granted Patent B2
US 9,005,444 · App. 12/992,843 · Granted Apr 14, 2015

Separation of rebaudioside A from stevia glycosides using chromatography

Inventors: Chen-Chou Chiang (Plymouth, MN); Jeffrey C. Evans (St. Michael, MN); John Joseph Hahn (Maple Grove, MN); An Amanda Jules Heylen (Zemst, BE); Andrew Keith Ohmes (Jordan, MN); Alexander Patist (Shakopee, MN); Troy Allen Rhonemus (Plymouth, MN); Jenna Stangler (Otsego, MN); Christopher Austin Tyler (Minnetonka, MN); Ronny Leontina Marcel Vercauteren (Beveren, BE)
Assignee: Cargill, Incorporated
C07H1/08
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Quick Facts
Patent No.
US 9,005,444
App. No.
12/992,843
Granted
Apr 14, 2015
Kind
B2
Abstract

Disclosed are methods for the chromatographic separation of rebaudioside A from stevioside in glycoside solutions that are derived from stevia. The chromatographic separation may be an adsorb/desorb type of chromatographic separation or a fractionation type of chromatographic separation.

Claims (33)

1. A method of separating rebaudioside A from stevioside using chromatography, the method comprising the steps of:

(a) providing a glycoside solution comprising rebaudioside A; stevioside; and a solvent;

(b) providing an adsorbent comprising a polystyrene divinylbenzene support functionalized with tertiary amines, quaternary amines, or both tertiary and quaternary amines; and

(c) contacting the adsorbent with the glycoside solution in order to separate at least a portion of the rebaudioside A from the stevioside thereby resulting in the formation of a purified rebaudioside A solution.

2. The method of claim 1 , wherein the method of separating comprises adsorb/desorb chromatography.

3. The method of claim 2 , wherein the adsorb/desorb chromatography comprises the steps of

(a) providing a glycoside solution comprising rebaudioside A; stevioside; and a solvent;

(b) providing an adsorbent comprising a polystyrene divinylbenzene support functionalized with tertiary amines, quaternary mines, or both tertiary and quaternary amines;

(c) providing an elution solvent;

(d) contacting the adsorbent with the glycoside solution and elution solvent so that at least a portion of the stevioside adsorbs onto the adsorbent enriching the glycoside solution in rebaudioside A and resulting in the formation of a purified rebaudioside A composition that is eluted from the adsorbent along with the elution solvent; and

(e) optionally, desorbing the stevioside from the adsorbent.

4. The method of claim 3 , wherein the elution solvent comprises about 20% weight or less ethanol; and about 80% weight or greater water.

5. The method of claim 3 , wherein the elution solvent comprises about 50% weight or less ethanol; and about 50% weight or greater water.

6. The method of claim 1 , wherein the method of separating comprises fractionation chromatography.

7. The method of claim 6 , wherein the fractionation chromatography comprises the steps of:

(a) providing a glycoside solution comprising rebaudioside A; stevioside; and a solvent;

(b) providing an adsorbent comprising a polystyrene divinylbenzene support functionalized with tertiary amines, quaternary mines, or both tertiary and quaternary amines; and

(c) contacting the adsorbent with the glycoside solution so that at least a portion of the stevioside adsorbs onto the adsorbent and so that at least a portion of the rebaudioside A adsorbs onto the adsorbent; wherein the rebaudioside A propagates through the adsorbent at a faster rate than the stevioside; and

(d) collecting a purified rebaudioside A solution from the adsorbent.

8. The method of claim 7 , wherein the solvent comprises about 20% weight or greater ethanol and about 80% weight or less water.

9. The method of claim 7 , wherein the solvent comprises about 25% to about 35% weight ethanol and about 65% to about 75% water.

10. The method of claim 7 , wherein the solvent comprises water and wherein the adsorbent is a strongly acidic cationic exchange resin.

11. The method of claim 7 , wherein the glycoside solution further comprises one or more glycoside selected from rebaudioside B and rebaudioside D; and wherein the method provides a separation between stevioside, rebaudioside A, rebaudioside B, and rebaudioside D.

12. The method of claim 11 , wherein the method provides a separation between stevioside, rebaudioside A, rebaudioside B, and rebaudioside D.

13. The method of claim 6 , wherein the fractionation chromatography is performed using a simulated moving bed.

14. The method of claim 1 , wherein the adsorbent has a surface area of about 900 m2/gram or greater.

15. The method of claim 1 , wherein the adsorbent is functionalized with tertiary amines.

16. The method of claim 1 , wherein the adsorbent is functionalized with quaternary amines.

17. The method of claim 1 , wherein the glycoside solution is a mother liquor from a rebaudioside A crystallization process.

18. The method of claim 1 , wherein the purified rebaudioside A solution has a purity that is about 10% or greater as compared to a purity of the glycoside solution.

19. The method of claim 1 , wherein the purified rebaudioside A solution comprises, on a dry solids basis, about 60% weight to about 80% weight rebaudioside A.

20. The method of claim 1 , wherein the glycoside solution further comprises one or more glycosides selected from rebaudioside B, rebaudioside C, rebaudioside D, rebaudioside E, rebaudioside F, and dulcoside.

21. The method of claim 20 , wherein the glycoside solution comprises one or more glycosides selected from rebaudioside B and rebaudioside D.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2011
From: EVANS, JEFFREY C.; HAHN, JOHN JOSEPH; PATIST, ALEXANDER; RHONEMUS, TROY ALLEN; CHIANG, CHEN-CHOU; HEYLEN, AN AMANDA JULES; OHMES, ANDREW KEITH; STANGLER, JENNA; TYLER, CHRISTOPHER AUSTIN; VERCAUTEREN, RONNY LEONTINA MARCEL
To: CARGILL, INCORPORATED
Reel/Frame 025850/0320 →
Continuity (2)
Provisional Application 61127382 · May 13, 2008
Related Publication 20110087011A1 · Apr 14, 2011