Processes for preparing phytosterols and substantially citrostadienol-free phytosterols prepared thereby
View Patent ↗Processes for preparing substantially citrostadienol-free phytosterols are disclosed. The processes described include dissolving a liquid phytosterol in a hydrocarbon solvent, optionally with added methanol, and crystallizing the phytosterol compounds. Also described are the resulting phytosterols which are substantially citrostadienol-free, and preferably contain less than 0.5% by weight citrostadienol.
1. A process for preparing phytosterols, said process comprising:
(a) providing a liquid phytosterol starting material obtained by transesterification of a distillation residue with an alkanol;
(b) dissolving the liquid phytosterol starting material in a hydrocarbon solvent; and
(c) crystallizing a phytosterol product, wherein the phytosterol product is substantially citrostadienol-free.
2. The process according to claim 1 , wherein the distillation residue comprises a deodorizer condensate obtained from fatty acid methyl ester production.
3. The process according to claim 2 , wherein the deodorizer condensate is derived from an oil selected from the group consisting of rapeseed oil and sunflower oil.
4. The process according to claim 3 , wherein the oil comprises sunflower oil.
5. The process according to claim 1 , wherein the distillation residue comprises tall oil pitch.
6. The process according to claim 1 , wherein the alkanol comprises methanol.
7. The process according to claim 3 , wherein the alkanol comprises methanol.
8. The process according to claim 1 , wherein the liquid phytosterol starting material is maintained at a temperature of from 60° C. to 80° C. prior to and during dissolution in the hydrocarbon solvent.
9. The process according to claim 3 , wherein the liquid phytosterol starting material is maintained at a temperature of from 60° C. to 80° C. prior to and during dissolution in the hydrocarbon solvent.
10. The process according to claim 8 , wherein the liquid phytosterol starting material is maintained at a temperature of from 65° C. to 70° C.
11. The process according to claim 9 , wherein the liquid phytosterol starting material is maintained at a temperature of from 65° C. to 70° C.
12. The process according to claim 1 , wherein the hydrocarbon solvent comprises a linear or branched alkane isomer selected from the group consisting of pentane, hexane, heptane, octane, nonane, decane, and mixtures thereof.
13. The process according to claim 1 , wherein the hydrocarbon solvent comprises a linear or branched alkane isomer selected from the group consisting of hexane, heptane, and mixtures thereof.
14. The process according to claim 1 , wherein methanol is combined with the hydrocarbon solvent prior to crystallization.
15. The process according to claim 14 , wherein the methanol is present in an amount of from 1 to 15% by weight, based on the hydrocarbon solvent.
16. The process according to claim 3 , wherein methanol is combined with the hydrocarbon solvent prior to crystallization.
17. The process according to claim 16 , wherein the methanol is present in an amount of from 1 to 15% by weight, based on the hydrocarbon solvent.
18. The process according to claim 8 , wherein methanol is combined with the hydrocarbon solvent prior to crystallization.
19. The process according to claim 18 , wherein the methanol is present in an amount of from 1 to 15% by weight, based on the hydrocarbon solvent.
20. The process according to claim 1 , wherein crystallizing the phytosterol product comprises cooling the liquid phytosterol starting material in the hydrocarbon solvent to a temperature of below about 30° C.
21. The process according to claim 1 , wherein crystallizing the phytosterol product comprises cooling the liquid phytosterol starting material in the hydrocarbon solvent to a temperature of from about 25° C. to about 30° C.
22. The process according to claim 3 , wherein crystallizing the phytosterol product comprises cooling the liquid phytosterol starting material in the hydrocarbon solvent to a temperature of below about 30° C.
23. The process according to claim 3 , wherein crystallizing the phytosterol product comprises cooling the liquid phytosterol starting material in the hydrocarbon solvent to a temperature of from about 25° C. to about 30° C.
24. The process according to claim 1 , wherein the phytosterol product has a citrostadienol content of less than 0.5% by weight.
25. The process according to claim 1 , wherein the phytosterol product has a citrostadienol content of less than 0.2% by weight.
26. A process for preparing phytosterols, said process comprising:
(a) providing a liquid phytosterol starting material obtained by transesterification of a distillation residue with methanol, wherein the distillation residue comprises a deodorizer condensate derived from sunflower oil;
(b) dissolving the liquid phytosterol starting material in a hydrocarbon solvent, the hydrocarbon solvent comprising a linear or branched alkane isomer selected from the group consisting of hexane, heptane, and mixtures thereof, wherein the liquid phytosterol starting material is maintained at a temperature of from 60° C. to 80° C. prior to and during dissolution in the hydrocarbon solvent; and
(c) crystallizing a phytosterol product via cooling the liquid phytosterol starting material in the hydrocarbon solvent to a temperature of below about 30° C., wherein methanol is combined with the hydrocarbon solvent prior to crystallization in an amount of from 1 to 15% by weight, based on the hydrocarbon solvent, and wherein the phytosterol product has a citrostadienol content of less than 0.5% by weight.