Organic compounds -- part of the class 532-570 series – Organic compounds – Cyclopentanohydrophenanthrene ring system containing
Reexamination Certificate
2002-05-03
2004-07-13
Badio, Barbara P. (Department: 1616)
Organic compounds -- part of the class 532-570 series
Organic compounds
Cyclopentanohydrophenanthrene ring system containing
Reexamination Certificate
active
06762312
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a process for producing a phytosterol (or plant sterol) from a crude fatty acid ester derived from a vegetable (or plant) fat and/or oil.
BACKGROUND ART
Phytosterols are not only used in clinical administration etc. expected to have an effect of reducing cholesterols in blood but also utilized generally as a raw or starting material for pharmaceutical agents as substitutes for cholesterols or as emulsifiers or emulsion-stabilizers in cosmetics and foods.
As the process for producing phytosterols, a method in which sterols contained in vegetable oils such as a soybean oil, a rapeseed oil, a rice bran oil, a palm oil, a palm kernel oil and a coconut oil are extracted and purified from a deodorized concentrate etc. is practically used. There is known the extracting method which comprises adding a lower alcohol to a deodorized distillate of fats and oils to esterify with an acid catalyst, then washing with water to remove the catalyst, transesterifying by adding an additional lower alcohol and alkali catalyst, calmly laying overnight the resultant solution after the reaction to precipitate crystals, separating the crystals by the filtration, washing with a small amount of hexane to further re-crystallize (JP-B 52-8309).
In this method, however, it is necessary to repeatedly re-crystallize in order to obtain highly pure sterols. Then, it is difficult to more easily obtain highly pure phytosterols.
DISCLOSURE OF INVENTION
The object of the present invention is to provide a process for producing a highly pure phytosterol, at a high yield in particular, by a simple and easy treatment from a crude fatty acid ester derived from a vegetable fat and/or oil.
The invention a process for producing phytosterol, which comprises (A) bringing a crude fatty acid product derived from a vegetable fat and/or oil including phytosterol into contact with a mixed solvent (or solvent mixture) of an organic solvent and water to crystallize the phytosterol and separating the crystals from the mixed solvent; or (B) mixing a crude fatty acid ester derived from a vegetable fat and/or oil including the phytosterol and a fatty acid ester with a lower alcohol, allowing the mixture to stand at a temperature of 1 to 40° C. to precipitate crystals including the fatty acid ester and separating the crystals to take the lower alcohol solution including the phytosterol.
In the method (A), part or all of the treated phytosterol is crystallized. The invention process can be obtained by either the method (step) (A) or (B). Alternatively (A) and (B) may be used in combination with each other.
The present invention provides preferably the above-mentioned process which comprises Steps of (A) and which further comprises allowing a mixture of the crude fatty acid ester with a lower alcohol to stand at a temperature of 1 to 40° C. in order to precipitate crystals including the fatty acid ester.
In the above shown method (A), phytosterol existing in crude fatty acid esters of vegetable fats and/or oils can be concentrated by crystallizing the phytosterol in a solvent mixture of an organic solvent and water. A concentrated phytosterol-including product can be obtained this way.
In the method (B), phytosterol existing in crude fatty acid esters of vegetable fats and/or oils can be concentrated by crystallizing the fatty acid esters in a lower alcohol at a temperature of 1 to 40° C., separating the crystals out and taking the lower alcohol solution including phytosterol. The lower alcohol solution may include remaining fatty acid esters in addition to concentrated phytosterol. A concentrated phytosterol product can be obtained this way.
The invention provides a process for preparing a concentrated phytosterol product, comprising the above shown (A) or (B). (A) and (B) may be continuously repeated to obtained a very concentrated product of phytosterol. (A) and (B) may be used in combination with each other.
The starting material for (A) or (B) may be a natural source of fats and/or oils including phytosterol. It includes phytosterol, fatty acid esters of phytosterol and other fatty acid esters. Alternatively the natural source may be processed in advance to (A) or (B), for example, by treating fatty acid esters by saponification. The saponification may be effected with an alkali and a mixed solvent of a lower alcohol and water. The product of the invention may be saponified this way to obtain a more concentrated phytosterol product.
MODES FOR CARRYING OUT THE INVENTION
The phytosterols in the present invention refer to sterols, contained in vegetable fats and oils, such as sitosterol, stigmasterol, campesterol and brassicasterol.
The vegetable fats and oils used here may be one member of a soybean oil, a rapeseed oil, a rice bran oil, a palm oil, a palm kernel oil and a coconut oil or a mixture of two or more members selected therefrom. Among them, a palm kernel oil, a coconut oil or a palm oil is preferable.
As the crude fatty acid ester derived from vegetable fats and oils in the present invention, there may be preferably used a mixture of various compounds including mainly esters of higher fatty acids with lower alcohols such as esters of C
6-28
fatty acids with lower alcohols in particular. The composition thereof cannot be specified because the composition is varied depending on the vegetable fats and oils used as the raw material but the composition may also contain monoglycerides, diglycerides, triglycerides, glycerol etc. That is, the crude fatty acid ester is not particularly limited so far as it contains fatty acid esters and phytosterols. For example, there can also be used a crude fatty acid ester obtained by esterifying the above-mentioned deodorized distillate of a vegetable fat and/or oil and then, if necessary, transesterifying with a lower alcohol such as methanol or a raw material obtained by further distilling the said fatty acid ester product according to the technique described in JP-A 8-500598 and increasing the concentration of the phytosterols by distilling a part of the fatty acid ester product formed by the transesterification reaction.
Alternatively, the above-described vegetable fat and/or oil is esterified and then transesterified with a lower alcohol such as methanol, and the fatty ester product thus obtained is distilled to remove distillates, whereby the concentration of the phytosterols can be increased. The raw material concentrated in this manner can also be used. This concentrate contains not only the phytosterols and fatty ester acids but also unreacted monoglycerides, diglycerides and triglycerides having not reacted in the previous transesterification reaction. There can also be used a crude fatty acid ester obtained by further transesterifying the said concentrate.
In general, these raw materials often contain not less than 20% by weight of the esters of the C
6-28
fatty acids with the lower alcohols. In the present invention, fatty acid esters at such concentrations are also preferably used.
As the fatty acid in the present invention, there can be utilized any one selected from a member and a mixture of two or more members of linear or branched saturated or unsaturated ones. The lower alcohols include C
1-4
alcohols such as methanol, ethanol, isopropanol, n-propanol and a linear or branched butanol. As the lower alcohol, there can be used a member or a mixture of two or more members thereof. Among them, methanol, ethanol or a mixture thereof is preferable and a methanol-containing member is particularly preferable.
Although the content of the phytosterols in the crude fatty acid ester used in the present invention is not particularly limited, the content is preferably not less than 1% by weight (as compared with the mixture thereof excluding lower alcohols such as methanol) and, in order to exhibit an advantageous effect of the present invention, more preferably 3 to 40% by weight.
In Step A in the present invention, the crude fatty acid ester described above are brought into contact with a mixed solvent comprising an organic solvent and wa
Hattori Yasuyuki
Horio Masamitsu
Kono Jun
Badio Barbara P.
Kao Corporation
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