Process for purifying astaxanthin and canthaxanthin

Patent metadata

Field	Value
Publication number	US-10017466-B2
Application number	US-201515516216-A
Country	US
Kind code	B2
Filing date	Oct 1, 2015
Priority date	Oct 2, 2014
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

The present invention relates to a process for purifying the xanthophylls astaxanthin and canthaxanthin.
The process comprises suspending the xanthophyll in an organic solvent or solvent mixture, treating the suspension of the xanthophyll in the organic solvent or solvent mixture at elevated temperature, and subsequent separation off of the xanthophyll from the solvent by a solid-liquid separation, wherein the organic solvent is selected from ketones of the general formula (I) and mixtures of ketones of the general formula (I)

where R 1 is C 1 -C 4 alkyl and R 2 is selected from C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, phenyl and benzyl, wherein the phenyl rings in the two last-mentioned radicals are unsubstituted or can have 1 or 2 methyl groups, or R 1 and R 2 together are linear C 4 -C 6 alkylene, which can bear 1, 2 or 3 methyl groups as substituents.

First claim

The invention claimed is:

1. A process for purifying a xanthophyll selected from the group consisting of astaxanthin and canthaxanthin, comprising
a) suspending the xanthophyll in an organic solvent or solvent mixture,
b) treating the suspension of the xanthophyll in the organic solvent or solvent mixture at elevated temperature, and
c) subsequent separation off of the xanthophyll from the solvent by a solid-liquid separation,
wherein the organic solvent is selected from ketones of the formula (I) and mixtures of ketones of the formula (I)

where R 1 is C 1 -C 4 alkyl and R 2 is selected from C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, phenyl and benzyl, wherein the phenyl rings in the two last-mentioned radicals are unsubstituted, or R 1 and R 2 together are linear C 4 -C 6 alkanediyl, which can hear 1, 2 or 3 methyl groups as substituents,
wherein the ketone of the formula (I) makes up at least 95% by weight of the organic solvents used for suspending the xanthophyll, and
wherein the suspension of the xanthophyll is treated at a temperature of at least 60° C. and for at least 1 h, and
wherein the xanthophyll used comprises halogenated hydrocarbons and/or phosphorus compounds as contaminants which are depleted.

2. The process according to claim 1 , wherein the ketone of the formula (I) makes up at least 99% by weight of the organic solvents used for the suspension.

3. The process according to claim 1 , wherein the concentration of water in the solvent used to produce the suspension does not exceed 20% by weight.

4. The process according to claim 1 , wherein the suspension is treated at a temperature in the range from 60 to 150° C.

5. The process according to claim 1 , wherein the treatment time of treating the suspension is in the range from 6 to 144 h.

6. The process according to claim 1 , wherein the suspension has a xanthophyll concentration in the range from 2 to 50% by weight.

7. The process according to claim 1 , wherein, in the course of the treatment, at least some of the ketone of the formula (I) is distilled off and replaced by fresh ketone of the formula (I).

8. The process according to claim 1 , wherein the suspension is cooled to a temperature below 20° C. before separating off the xanthophyll from the organic solvent.

9. The process according to claim 1 , wherein the ketone is selected from compounds of the general formula (I) and mixtures thereof, where R 1 is methyl or ethyl and R 2 is C 1 -C 4 alkyl.

10. The process according to claim 1 , wherein a suspension of the xanthophyll in a ketone of the formula (I), where R 1 is methyl or ethyl and R 2 is C 2 -C 4 alkyl, is first treated at elevated temperature and the xanthophyll thus obtained is treated with acetone.

11. The process according to claim 1 , wherein the treatment of the suspension of the xanthophyll in the organic solvent and the subsequent separation off of the xanthophyll from the solvent is repeated at least once.

12. The process according to claim 1 , wherein the xanthophyll used contains one or more halogenated hydrocarbons as contaminant.

13. The process according to claim 1 , wherein the xanthophyll used comprises at least one organic phosphorus compound, as contaminant.

14. The process according claim 1 , wherein the xanthophyll used is astaxanthin.

15. The process according to claim 14 , wherein the astaxanthin used is an astaxanthin produced by Wittig reaction of [5-(4-hydroxy-2,6,6-trimethyl-3-oxo-1-cyclohexyl)-3-methyl-2,4-pentadienyl]triphenylphosphonium bromide or 3-[5-(arylsulfonyl)-4-methylpenta-1,3-dienyl]-6-hydroxy-2,4,4-trimethylcyclohex-2-en-1-one with 2,7-dimethyloctatrienedial.

16. The process according to claim 1 , wherein the xanthophyll used is canthaxanthin.

17. The process according to claim 16 , wherein the canthaxanthin used is a canthaxanthin produced by Wittig reaction of [5-(2,6,6-trimethyl-3-oxo-1-cyclohexyl)-3-methyl-2,4-pentadienyl]triphenylphosphonium bromide or 3-[5-(arylsulfonyl)-4-methylpenta-1,3-dienyl]-2,4,4-trimethylcyclohex-2-en-1-one with 2,7-dimethyloctatrienedial.

18. The process according to claim 1 wherein halogenated hydrocarbons and/or phosphorus compounds are depleted from xanthophylls selected from astaxanthin and canthaxanthin which comprise halogenated hydrocarbons and/or phosphorus compounds as contaminants.

19. The process according claim 1 wherein at least one of the following impurities is depleted from xanthophylls; canthaxanthin isomers, echinenone and other colored carotenoid impurities.

20. The process according to claim 1 , wherein the xanthophyll used comprises triphenylphosphine or triphenylphosphine oxide, as contaminant.

21. The process according to claim 1 wherein the suspension of the xanthophyll is treated at a temperature of at least 80° C.

Assignees

• Basf Se

Inventors

• Schäfer Bernd
• Siegel Wolfgang

Classifications

• C07C403/24 Primary

  having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene · CPC title

• C09B61/00

  Dyes of natural origin prepared from natural sources {, e.g. vegetable sources} · CPC title

• C09B67/0096

  Purification; Precipitation; Filtration · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title