JP4707862B2 - Production of plant sterols - Google Patents
Production of plant sterols Download PDFInfo
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- JP4707862B2 JP4707862B2 JP2001116328A JP2001116328A JP4707862B2 JP 4707862 B2 JP4707862 B2 JP 4707862B2 JP 2001116328 A JP2001116328 A JP 2001116328A JP 2001116328 A JP2001116328 A JP 2001116328A JP 4707862 B2 JP4707862 B2 JP 4707862B2
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Description
【０００１】
【発明の属する技術分野】
本発明は、粗植物ステロールから、高純度の植物ステロールを製造する方法に関する。
【０００２】
【従来の技術及び発明が解決しようとする課題】
植物ステロールは、血中コレステロール低減効果を期待した臨床投与等に使用されるだけでなく、コレステロール代替物として医薬品原料、又は乳化剤や乳化安定剤として化粧品や食品に利用されている。
【０００３】
植物ステロールは、大豆油、ナタネ油、米糠油、パーム油、パーム核油、椰子油等の植物油中に含まれ、油脂精製時に発生する脱臭濃縮物等から抽出・精製して製造する方法が実用化されている。その抽出法として、油脂類の脱臭留出物に低級アルコールを加えて酸触媒でエステル化処理した後に、水洗し触媒除去を行い、新たに低級アルコールとアルカリ触媒を加えてエステル交換反応を行い、反応終了液を一夜静置し、析出した結晶を濾過により分離し、少量のヘキサンで洗浄し、更に再結晶を行う方法が知られている（特公昭５２−８３０９号）。
【０００４】
しかしこのような方法で得られる植物ステロールや市販の植物ステロールの一部では、純度がまだ十分に満足できるものではなく、このままでは医薬用、食品添加物としては使用できず、更に再結晶等の精製を行っている。しかし、再結晶等の精製法では、加熱溶解が必要であったり、大量の溶媒が必要であり、また結晶が析出するまでに時間がかかり、更に植物ステロールの回収率も悪く経済的ではない。
【０００５】
本発明の課題は、粗植物ステロールから、実用的かつ収率よく高純度の植物ステロールを得る方法を提供することにある。
【０００６】
【課題を解決するための手段】
本発明は、粗植物ステロールを有機溶媒に浸漬させた後、有機溶媒を分離することで精製を行う、植物ステロールの製法を提供する。
【０００７】
【発明の実施の形態】
本発明において植物ステロールとは、植物油脂中に含まれるステロールを指し、具体的には、β−シトステロール、スチグマステロール、カンペステロール、ブラシカステロールが挙げられる。また粗植物ステロールとは、不純物として、高炭素数（Ｃ27〜Ｃ31）の炭化水素、トコフェロール、脂肪酸エステル等を含有する植物ステロールであり、植物ステロールを８０重量％以上含有するものが好ましい。このような粗植物ステロールとして、市販の粉体状あるいはペレット状の植物ステロールを用いるのが好ましく、濾過等による有機溶剤の分離が容易であることから、ペレット状の植物ステロールを用いるのが更に好ましい。これらの植物ステロールの大きさは、粉体状の場合、粒径１０μｍ〜１mmが好ましく、１０μｍ〜０．５mmが更に好ましい。また、ペレット状の場合、粒径１〜５mmが好ましく、２〜５mmが更に好ましい。
【０００８】
本発明においては、まず粗植物ステロールを有機溶媒に浸漬させる。有機溶媒としては、ブタン、ペンタン、ヘキサン、ヘプタン、オクタン、ノナン、デカン等の炭化水素系溶媒、アセトン、メチルエチルケトン等のケトン系溶媒から選ばれる１種以上が好ましく、炭化水素系溶媒を含有するものが更に好ましい。有機溶媒は、粗植物ステロールに対して、好ましくは１〜１０重量倍、更に好ましくは１〜５重量倍、特に好ましくは１〜３重量倍用いる。
【０００９】
本発明における有機溶媒中への粗植物ステロールの浸漬は、有機溶媒が粗植物ステロールの固体内部に浸透するまで、静置あるいは撹拌することが好ましく、粗植物ステロールが膨潤するまで浸漬させるのが更に好ましい。本発明においては、有機溶媒を植物ステロールの固体内部まで浸透させて、植物ステロールの固体内部に存在する炭化水素、トコフェロール、脂肪酸エステル等の有機系の不純物を有機溶媒中に溶解させる。浸漬条件は、温度が好ましくは０〜５０℃、更に好ましくは２０〜４０℃、圧力が好ましくは常圧〜１Mpaで、１５分以上静置あるいは撹拌を行うのが好ましい。また、加圧濾過機等を用いて、濾過循環を行うことにより浸漬してもよい。
【００１０】
本発明においては、粗植物ステロールを有機溶媒に浸漬させた後、有機溶媒を分離する。有機溶媒の分離法としては、濾過による分離が好ましい。またこの濾過の際に、濾液の流量をコントロールすることにより、不純物の除去性を上げることもできる。
【００１１】
本発明においては、有機溶媒の濾別後、更に有機溶媒で洗浄すると、更に高純度の植物ステロールを得ることができ、好ましい。ここで用いる有機溶媒としては、上記の浸漬に用いた有機溶媒が挙げられる。また、濾別及び洗浄により得られた有機溶媒を繰り返し使用することもできる。
【００１２】
【実施例】
各例において、植物ステロールの純度は、以下の方法で測定した。
【００１３】
＜植物ステロールの純度の測定法＞
(1) 標準サンプルとしてスチグマステロールを用い、これをヘキサンに溶解後、シリル化処理して検量線を作成する。
(2) 原料粗植物ステロール又は各例で得られた精製植物ステロールをヘキサンに溶解後、シリル化処理を行い、分析用サンプルを調製する。
(3) 上記分析用サンプルについて、下記条件のガスクロマトグラフィー（ＧＬＣ）を行い、分析結果から、上記検量線により、４種（β−シトステロール、スチグマステロール、カンペステロール、ブラシカステロール）の合計ステロール含量を算出する。
【００１４】
・ＧＬＣ条件
カラム：ＤＢ-1 ＨＴ（Ｊ＆Ｗ社） ０．２５mm×１５ｍ
カラム流量：１．３ml／min
ＩＮＪ：２５０℃、ＤＥＴ：２６０℃（ＦＩＤ）
スプリット比：１／５０
カラム条件：２５０℃→２６０℃（０．５℃／min）
ＩＮＪ量：２μｌ
比較例１
カーギル製植物ステロール（粉体状／Lot911031）１２０ｇを処理槽に仕込み、２０℃のヘキサン６００ｇを仕込んだ。６８℃まで加熱し完全に溶解後２時間かけて冷却し晶析を行った後、濾過（濾過面積５５．４ｃｍ2、濾過圧力０．３ＭＰａ、濾紙No.2）を行った（濾過時間４７分）。回収したケークを減圧乾燥機で乾燥を行い、精製植物ステロールを得た。
【００１５】
実施例１
比較例１と同じカーギル製植物ステロール１２０ｇを処理槽に仕込み、２０℃のヘキサン６００ｇを仕込んだ。２０℃で１時間攪拌を行った後、濾過（濾過面積５５．４ｃｍ2、濾過圧力０．３ＭＰａ、濾紙No.2）を行った（濾過時間３７分）。回収したケークを減圧乾燥機で乾燥を行い、精製植物ステロールを得た。
【００１６】
実施例２
比較例１と同じカーギル製植物ステロール１００ｇを処理槽に仕込み、２０℃の実施例１で回収した濾液とヘキサンを合わせて６００ｇとし、仕込んだ。２０℃で１時間攪拌を行った後、濾過（濾過面積５５．４ｃｍ2、濾過圧力０．３ＭＰａ、濾紙No.2）を行った（濾過時間４２分）。回収したケークを減圧乾燥機で乾燥を行い、精製植物ステロールを得た。
【００１７】
実施例３
比較例１と同じカーギル製植物ステロール１００ｇを処理槽に仕込み、２０℃のヘキサン６００ｇを仕込んだ。２０℃で１時間攪拌を行った後、濾過（濾過面積５５．４ｃｍ2、濾過圧力０．３ＭＰａ、濾紙No.2）を行い、濾過後ヘキサン１００ｇでケークを洗浄した（濾過時間合計９０分）。回収したケークを減圧乾燥機で乾燥を行い、精製植物ステロールを得た。
【００１８】
実施例４
比較例１と同じカーギル製植物ステロール１００ｇを処理槽に仕込み、２０℃の実施例３で回収し濾液とヘキサンを合わせて６００ｇとし、仕込んだ。２０℃で１時間攪拌を行った後、濾過（濾過面積５５．４ｃｍ2、濾過圧力０．３ＭＰａ、濾紙No.2）を行い、濾過後ヘキサン１００ｇでケークを洗浄した（濾過時間合計６０分）。回収したケークを減圧乾燥機で乾燥を行い、精製植物ステロールを得た。
【００１９】
実施例５
比較例１と同じカーギル製植物ステロール１００ｇを処理槽に仕込み、２０℃の実施例４で回収した濾液とヘキサンを合わせて６００ｇとし、仕込んだ。２０℃で１時間攪拌を行った後、濾過（濾過面積５５．４ｃｍ2、濾過圧力０．３ＭＰａ、濾紙No.2）を行い、濾過後ヘキサン１００ｇでケークを洗浄した（濾過時間合計６０分）。回収したケークを減圧乾燥機で乾燥を行い、精製植物ステロールを得た。
【００２０】
実施例６
比較例１と同じカーギル製植物ステロール１００ｇを処理槽に仕込み、２０℃の実施例５で回収した濾液とヘキサンを合わせて６００ｇとし、仕込んだ。２０℃で１時間攪拌を行った後、濾過（濾過面積５５．４ｃｍ2、濾過圧力０．３ＭＰａ、濾紙No.2）を行い、濾過後ヘキサン１００ｇでケークを洗浄した（濾過時間合計７５分）。回収したケークを減圧乾燥機で乾燥を行い、精製植物ステロールを得た。
【００２１】
原料粗植物ステロール、比較例１及び実施例１〜６で得られた精製植物ステロールの純度、及びＣ27〜Ｃ31の炭化水素含量、並びに各例の操作時間、仕込み時のヘキサン使用量（濾過後の洗浄ヘキサンの量は除く）、及び植物ステロールの回収率をまとめて表１に示す。
【００２２】
【表１】
実施例７
カーギル製植物ステロール（ペレット状／Lot001061）１２０ｇを加圧濾過機に仕込み、４０℃のヘキサンを４００ｇ仕込んだ。４０℃で３０分濾過循環（８０ｍＬ／ｍｉｎ）を行った後、濾過（濾過面積５５．４ｃｍ2、濾過圧力０．１３ＭＰａ、２００メッシュの金網）を行い、濾過後ヘキサン５０ｇでケークを洗浄した（濾過時間合計５分）。回収したケークを減圧乾燥機で乾燥を行い、精製植物ステロールを得た。
【００２４】
原料粗植物ステロール及び得られた精製植物ステロールの純度、及びＣ27〜Ｃ31の炭化水素含量、並びに操作時間、仕込み時のヘキサン使用量（濾過後の洗浄ヘキサンの量は除く）、及び植物ステロールの回収率を表２に示す。
【００２５】
【表２】
実施例８
カーギル製植物ステロール（ペレット状／Lot006194）１００ｇを加圧濾過機に仕込み、２０℃のヘキサンを５００ｇ仕込んだ。２０℃で６０分静置し、ケークの膨潤を行った後、濾液の流量を絞り２４分かけて濾過（濾過面積５５．４ｃｍ2、濾過圧力０．１３ＭＰａ、２００メッシュの金網）を行い、濾過後ヘキサン７０ｇでケークを洗浄した（濾過時間５分）。回収したケークを減圧乾燥機で乾燥を行い、精製植物ステロールを得た。
【００２７】
実施例９
実施例８と同じカーギル製植物ステロール１００ｇを加圧濾過機に仕込み、２０℃のヘキサンを２００ｇ仕込んだ。２０℃で６０分静置しケークの膨潤を行った後、濾液の流量を絞り３１分かけて濾過（濾過面積５５．４ｃｍ2、濾過圧力０．１３ＭＰａ、２００メッシュの金網）を行い、濾過後ヘキサン７０ｇでケークを洗浄した（濾過時間１６分）。回収したケークを減圧乾燥機で乾燥を行い、精製植物ステロールを得た。
【００２８】
原料粗植物ステロール、実施例８及び９で得られた精製植物ステロールの純度、及びＣ27〜Ｃ31の炭化水素含量、並びに各例の操作時間、仕込み時のヘキサン使用量（濾過後の洗浄ヘキサンの量は除く）、及び植物ステロールの回収率を表３に示す。
【００２９】
【表３】
【発明の効果】
本発明の方法によると、粗植物ステロールの固体内部にまで有機溶媒が浸透し、固体内部の不純物まで除去することができ、植物ステロール含有量９０重量％以上の高純度の植物ステロールを得ることができ、食品添加物自主規格を満足させることができる。また、晶析法で必要な加熱溶解、晶析工程が不要となり、処理時間の低減が可能となる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a method for producing high-purity plant sterols from crude plant sterols.
[0002]
[Prior art and problems to be solved by the invention]
Plant sterols are used not only for clinical administration and the like that are expected to reduce blood cholesterol, but are also used as raw materials for pharmaceuticals as cholesterol substitutes, or in cosmetics and foods as emulsifiers and emulsion stabilizers.
[0003]
Plant sterols are contained in vegetable oils such as soybean oil, rapeseed oil, rice bran oil, palm oil, palm kernel oil, coconut oil, etc., and a method of producing by extracting and refining from deodorized concentrates etc. generated during oil purification is practical It has become. As the extraction method, after adding a lower alcohol to the deodorized distillate of fats and oils and esterifying with an acid catalyst, washing with water to remove the catalyst, newly adding a lower alcohol and an alkali catalyst to perform a transesterification reaction, A method is known in which the reaction-terminated liquid is allowed to stand overnight, the precipitated crystals are separated by filtration, washed with a small amount of hexane, and further recrystallized (Japanese Patent Publication No. 52-8309).
[0004]
However, some of the plant sterols obtained by such a method and commercially available plant sterols are still not sufficiently satisfactory, and as they are, they cannot be used as pharmaceutical or food additives, and further, such as recrystallization. Purification is performed. However, purification methods such as recrystallization require heating and dissolution, a large amount of solvent is required, and it takes time until crystals are precipitated, and the recovery rate of plant sterols is also poor and not economical.
[0005]
An object of the present invention is to provide a method for obtaining a highly pure plant sterol from a crude plant sterol in a practical and high yield.
[0006]
[Means for Solving the Problems]
This invention provides the manufacturing method of a plant sterol which refine | purifies by immersing a crude plant sterol in the organic solvent, and isolate | separating an organic solvent.
[0007]
DETAILED DESCRIPTION OF THE INVENTION
In the present invention, the plant sterol refers to a sterol contained in a vegetable oil and fat, and specifically includes β-sitosterol, stigmasterol, campesterol, and brush casterol. The crude plant sterol is a plant sterol containing a high carbon number (C 27 -C 31 ) hydrocarbon, tocopherol, fatty acid ester or the like as an impurity, and preferably contains 80% by weight or more of the plant sterol. As such a crude plant sterol, it is preferable to use a commercially available powdered or pelleted plant sterol, and since it is easy to separate the organic solvent by filtration or the like, it is more preferable to use a pelleted plant sterol. . The size of these plant sterols is preferably 10 μm to 1 mm, more preferably 10 μm to 0.5 mm, in the case of powder. In the case of a pellet, the particle size is preferably 1 to 5 mm, more preferably 2 to 5 mm.
[0008]
In the present invention, the crude plant sterol is first immersed in an organic solvent. The organic solvent is preferably one or more selected from hydrocarbon solvents such as butane, pentane, hexane, heptane, octane, nonane and decane, and ketone solvents such as acetone and methyl ethyl ketone, and contains a hydrocarbon solvent. Is more preferable. The organic solvent is preferably used in an amount of 1 to 10 times, more preferably 1 to 5 times, particularly preferably 1 to 3 times the weight of the crude plant sterol.
[0009]
The immersion of the crude plant sterol in the organic solvent in the present invention is preferably allowed to stand or stir until the organic solvent penetrates into the solid interior of the crude plant sterol, and is further immersed until the crude plant sterol swells. preferable. In the present invention, an organic solvent is infiltrated into the solids of the plant sterol, and organic impurities such as hydrocarbons, tocopherols, fatty acid esters and the like existing in the solids of the plant sterol are dissolved in the organic solvent. The immersion conditions are preferably a temperature of 0 to 50 ° C., more preferably 20 to 40 ° C., a pressure of preferably normal pressure to 1 MPa, and standing or stirring for 15 minutes or more. Moreover, you may immerse by performing filtration circulation using a pressure filter.
[0010]
In the present invention, the crude plant sterol is immersed in an organic solvent, and then the organic solvent is separated. As a method for separating the organic solvent, separation by filtration is preferable. Further, during this filtration, the removability of impurities can be improved by controlling the flow rate of the filtrate.
[0011]
In the present invention, after the organic solvent is filtered off, washing with an organic solvent is preferable because a higher-purity plant sterol can be obtained. As an organic solvent used here, the organic solvent used for said immersion is mentioned. Moreover, the organic solvent obtained by filtration and washing | cleaning can also be used repeatedly.
[0012]
【Example】
In each example, the purity of the plant sterol was measured by the following method.
[0013]
<Measurement of plant sterol purity>
(1) Using stigmasterol as a standard sample, dissolve it in hexane and silylate it to create a calibration curve.
(2) The raw material crude plant sterol or the purified plant sterol obtained in each example is dissolved in hexane and then subjected to silylation treatment to prepare a sample for analysis.
(3) The above sample for analysis is subjected to gas chromatography (GLC) under the following conditions. From the analysis results, the total sterols of 4 types (β-sitosterol, stigmasterol, campesterol, and brassicasterol) are analyzed using the calibration curve Calculate the content.
[0014]
GLC condition column: DB-1 HT (J & W) 0.25 mm × 15 m
Column flow rate: 1.3ml / min
INJ: 250 ° C., DET: 260 ° C. (FID)
Split ratio: 1/50
Column conditions: 250 ° C. → 260 ° C. (0.5 ° C./min)
INJ volume: 2 μl
Comparative Example 1
120 g of Cargill plant sterol (powder / Lot911031) was charged into a treatment tank, and 600 g of hexane at 20 ° C. was charged. After heating to 68 ° C. and completely dissolving, cooling was performed over 2 hours and crystallization was performed, followed by filtration (filtration area 55.4 cm 2 , filtration pressure 0.3 MPa, filter paper No. 2) (filtration time 47 minutes) ). The recovered cake was dried with a vacuum dryer to obtain purified plant sterols.
[0015]
Example 1
The same Cargill plant sterol as in Comparative Example 1 was charged in a treatment tank, and 600 g of hexane at 20 ° C. was charged. After stirring at 20 ° C. for 1 hour, filtration (filtration area 55.4 cm 2 , filtration pressure 0.3 MPa, filter paper No. 2) was carried out (filtration time 37 minutes). The recovered cake was dried with a vacuum dryer to obtain purified plant sterols.
[0016]
Example 2
The same Cargill plant sterol as in Comparative Example 1 was charged into a treatment tank, and the filtrate collected in Example 1 at 20 ° C. and hexane were combined to make 600 g. After stirring at 20 ° C. for 1 hour, filtration (filtration area 55.4 cm 2 , filtration pressure 0.3 MPa, filter paper No. 2) was carried out (filtration time 42 minutes). The recovered cake was dried with a vacuum dryer to obtain purified plant sterols.
[0017]
Example 3
The same Cargill plant sterol as Comparative Example 1 was charged into a treatment tank, and 600 g of hexane at 20 ° C. was charged. After stirring at 20 ° C. for 1 hour, filtration (filtration area 55.4 cm 2 , filtration pressure 0.3 MPa, filter paper No. 2) was performed, and after filtration, the cake was washed with 100 g of hexane (total filtration time of 90 minutes). . The recovered cake was dried with a vacuum dryer to obtain purified plant sterols.
[0018]
Example 4
100 g of the same Cargill plant sterol as in Comparative Example 1 was charged into the treatment tank, recovered in Example 3 at 20 ° C., and the filtrate and hexane were combined to make 600 g. After stirring at 20 ° C. for 1 hour, filtration (filtration area 55.4 cm 2 , filtration pressure 0.3 MPa, filter paper No. 2) was performed, and after filtration, the cake was washed with 100 g of hexane (total filtration time 60 minutes). . The recovered cake was dried with a vacuum dryer to obtain purified plant sterols.
[0019]
Example 5
The same Cargill plant sterol as in Comparative Example 1 was charged into a treatment tank, and the filtrate collected in Example 4 at 20 ° C. and hexane were combined to make 600 g. After stirring at 20 ° C. for 1 hour, filtration (filtration area 55.4 cm 2 , filtration pressure 0.3 MPa, filter paper No. 2) was performed, and after filtration, the cake was washed with 100 g of hexane (total filtration time 60 minutes). . The recovered cake was dried with a vacuum dryer to obtain purified plant sterols.
[0020]
Example 6
The same Cargill plant sterol as in Comparative Example 1 was charged into a treatment tank, and the filtrate collected in Example 5 at 20 ° C. and hexane were combined to 600 g, and charged. After stirring at 20 ° C. for 1 hour, filtration (filtration area 55.4 cm 2 , filtration pressure 0.3 MPa, filter paper No. 2) was performed, and after filtration, the cake was washed with 100 g of hexane (total filtration time of 75 minutes). . The recovered cake was dried with a vacuum dryer to obtain purified plant sterols.
[0021]
Raw material crude plant sterol, purity of purified plant sterol obtained in Comparative Example 1 and Examples 1 to 6, hydrocarbon content of C 27 to C 31 , operation time of each example, amount of hexane used in charging (filtration Table 1 summarizes the recovery rate of plant sterols, excluding the amount of subsequent washing hexane.
[0022]
[Table 1]
Example 7
120 g of Cargill plant sterol (pellet / Lot001061) was charged into a pressure filter, and 400 g of hexane at 40 ° C. was charged. Filtration (80 mL / min) was performed at 40 ° C. for 30 minutes, followed by filtration (filtration area 55.4 cm 2 , filtration pressure 0.13 MPa, 200 mesh wire mesh). After filtration, the cake was washed with 50 g of hexane ( Filtration time total 5 minutes). The recovered cake was dried with a vacuum dryer to obtain purified plant sterols.
[0024]
Raw material crude plant sterol and purity of purified plant sterol obtained, hydrocarbon content of C 27 to C 31 , operation time, amount of hexane used in charging (excluding amount of washed hexane after filtration), and plant sterol Table 2 shows the recovery rate.
[0025]
[Table 2]
Example 8
100 g of Cargill plant sterol (pellet / Lot006194) was charged into a pressure filter, and 500 g of hexane at 20 ° C. was charged. After allowing to stand for 60 minutes at 20 ° C. to swell the cake, the flow rate of the filtrate was squeezed and filtered (filtering area 55.4 cm 2 , filtration pressure 0.13 MPa, 200 mesh wire mesh) for filtration. Thereafter, the cake was washed with 70 g of hexane (filtration time: 5 minutes). The recovered cake was dried with a vacuum dryer to obtain purified plant sterols.
[0027]
Example 9
The same Cargill plant sterol as in Example 8 was charged into a pressure filter, and 200 g of hexane at 20 ° C. was charged. After allowing the cake to swell by standing at 20 ° C. for 60 minutes, the flow rate of the filtrate was squeezed for 31 minutes and filtered (filtration area 55.4 cm 2 , filtration pressure 0.13 MPa, 200 mesh wire mesh) and after filtration The cake was washed with 70 g of hexane (filtration time 16 minutes). The recovered cake was dried with a vacuum dryer to obtain purified plant sterols.
[0028]
Raw material crude plant sterol, purity of purified plant sterol obtained in Examples 8 and 9, and hydrocarbon content of C 27 to C 31 , operation time of each example, hexane usage at the time of charging (washed hexane after filtration Table 3 shows the recovery rate of plant sterols.
[0029]
[Table 3]
【The invention's effect】
According to the method of the present invention, the organic solvent can penetrate into the solid of the solid plant sterol, and impurities inside the solid can be removed, thereby obtaining a high-purity plant sterol having a plant sterol content of 90% by weight or more. Yes, it can satisfy the voluntary standards for food additives. In addition, the heat dissolution and crystallization steps required in the crystallization method are unnecessary, and the processing time can be reduced.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| JP2001116328A JP4707862B2 (en) | 2001-04-16 | 2001-04-16 | Production of plant sterols |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001116328A JP4707862B2 (en) | 2001-04-16 | 2001-04-16 | Production of plant sterols |
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| Publication Number | Publication Date |
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| JP2002316996A JP2002316996A (en) | 2002-10-31 |
| JP4707862B2 true JP4707862B2 (en) | 2011-06-22 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2001116328A Expired - Fee Related JP4707862B2 (en) | 2001-04-16 | 2001-04-16 | Production of plant sterols |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS528309B2 (en) * | 1972-05-10 | 1977-03-08 | ||
| JPH10506394A (en) * | 1994-09-29 | 1998-06-23 | ザ ユニヴァシティ オブ ブリティッシュ コロンビア | Sterol composition from pulping soap |
| WO1999042471A1 (en) * | 1998-02-20 | 1999-08-26 | B.C. Chemicals Ltd. | Method for the preparation of phytosterols from tall oil pitch |
| WO2000064924A1 (en) * | 1999-04-27 | 2000-11-02 | Sterol Technologies Ltd. | Process for the purification of sterols from hydrocarbon extracts using evaporative fractionation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1173464T1 (en) * | 1999-04-27 | 2009-02-28 | Forbes Medi Tech Inc | Process for preparing a phytosterol composition |
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2001
- 2001-04-16 JP JP2001116328A patent/JP4707862B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS528309B2 (en) * | 1972-05-10 | 1977-03-08 | ||
| JPH10506394A (en) * | 1994-09-29 | 1998-06-23 | ザ ユニヴァシティ オブ ブリティッシュ コロンビア | Sterol composition from pulping soap |
| WO1999042471A1 (en) * | 1998-02-20 | 1999-08-26 | B.C. Chemicals Ltd. | Method for the preparation of phytosterols from tall oil pitch |
| WO2000064924A1 (en) * | 1999-04-27 | 2000-11-02 | Sterol Technologies Ltd. | Process for the purification of sterols from hydrocarbon extracts using evaporative fractionation |
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